Protecting What Matters Most: October’s Guide to Keeping Your Tech Team Focused

It’s the second week of October, and I’m sitting in my fifth “urgent” meeting of the day. The agenda: Should we pivot our Q4 roadmap to accommodate a new initiative that came up yesterday? The executives are excited. The sales team is pushing for it. And I’m watching my engineering team – who’s been heads-down on critical projects for weeks – start to get that glazed look that says “here we go again.”

This is the moment that defines a Chief of Staff’s value: Do you let the shiny new thing derail months of careful planning? Or do you protect your team’s focus, even when it’s uncomfortable?

I chose protection. And that decision – repeated hundreds of times in small and large ways – is what separates high-performing teams from teams that are constantly in chaos, always reacting, never delivering.

October is a critical month for tech teams. Q4 is in full swing, year-end goals are looming, everyone’s starting to think about next year’s planning, and the pressure to do more, faster, with less is at its peak. This is when teams either execute brilliantly or collapse under competing priorities.

As Chiefs of Staff, our job isn’t just to manage the chaos; it’s to prevent it. Let me show you how.

Why October Is the Breaking Point

October isn’t just another month. It’s when everything converges:

The Q4 Crunch: Teams are trying to deliver on annual commitments. There’s no more “we’ll catch up next quarter.” This is it.

The Planning Paradox: While executing Q4, you’re also planning for next year. Your team needs to be in two places at once—delivering now and thinking strategically about the future.

The Urgency Spiral: Everything suddenly becomes urgent. That project that’s been on the backlog for months? Urgent now. That customer request? Critical. That new idea from the CEO? Top priority.

The Energy Dip: Your team has been going hard for nine months. They’re tired. Morale fluctuates. The initial enthusiasm of January is a distant memory.

The Distraction Storm: Conference season, holiday planning starting early, people thinking about year-end bonuses and next year’s goals. Focus becomes harder to maintain.

This is when teams need protection most—and when they’re most vulnerable to getting derailed.

What We’re Protecting Against

Let me be specific about the threats to your team’s focus, because “distractions” is too vague:

1. The Bright Shiny Object Syndrome

Every week, someone has a brilliant new idea. A competitor launched something. A customer asked for something. An executive read an article. And suddenly there’s pressure to drop everything and chase the new thing.

Each individual idea might be good. But the cumulative effect is chaos. Your roadmap becomes meaningless. Your team never finishes anything. You’re always starting, never shipping.

2. Death by a Thousand Meetings

I audited my team’s calendars last month. On average, engineers were spending 20 hours per week in meetings. Twenty hours! That leaves 20 hours for actual work, except nobody can focus in 30-minute blocks between meetings.

Meetings multiply because:

  • Nobody says no to meeting invites
  • Everything is “collaborative” so everyone needs to be included
  • Meetings create more meetings (action items that need follow-ups)
  • There’s no meeting hygiene or discipline

3. Context Switching Costs

Your engineer is working on Feature A. Then they get pulled into a quick call about Project B. Then someone Slacks about a bug in System C. Then they’re back to Feature A, except now they need to remember where they were.

Research shows it takes 23 minutes on average to fully regain focus after an interruption. Your team isn’t losing minutes to interruptions—they’re losing hours.

4. Unclear Priorities

When everything is a priority, nothing is. I’ve seen roadmaps with 15 “P0” items. That’s not prioritization; that’s abdication of decision-making.

Without clear priorities, your team:

  • Wastes time asking “what should I work on?”
  • Works on the wrong things (usually the loudest, not the most important)
  • Gets frustrated because their work keeps getting deprioritized
  • Experiences decision fatigue

5. The Urgency Addiction

Some organizations operate in permanent crisis mode. Everything is urgent. Everything is a fire. Everyone’s in reactive mode all the time.

This feels productive (so much activity!) but it’s actually killing your ability to do strategic work. You’re always fighting fires instead of fireproofing the building.

6. Well-Meaning Stakeholders

Sometimes the threat isn’t malicious; it’s just people trying to do their jobs. Sales needs a custom feature for a deal. Customer success needs a bug fixed now. Marketing needs something for a launch. Leadership needs data for a board presentation.

Each request is legitimate. But if you say yes to all of them, your team’s calendar is owned by everyone except themselves.

The Protection Framework I Use

After years of doing this, I’ve developed a framework for protecting my team’s focus. It’s not magic; it’s discipline. Here’s how it works:

Layer 1: Ruthless Prioritization

This is the foundation. If you don’t have clear priorities, you can’t protect anything because you don’t know what you’re protecting.

My quarterly prioritization process:

  1. Start with strategic objectives (what must we accomplish this quarter?)
  2. Force rank everything (not tiers, actual ranks: 1, 2, 3…)
  3. Draw a line: Everything above the line gets resourced, everything below doesn’t happen
  4. Get explicit buy-in from leadership
  5. Make it visible to everyone

I use a simple framework: P0 (do now), P1 (do if we have time), P2 (not this quarter). Only 3-5 items can be P0. Everything else falls below.

When someone comes with a new request, I ask: “Where does this rank relative to our current P0s?” If they say “higher,” I ask: “Which P0 are you willing to drop?” Usually, that ends the conversation.

Layer 2: Calendar Protection

Protecting your team’s calendar is protecting their ability to do deep work.

My calendar rules:

  • No meetings Monday mornings or Friday afternoons (focus time)
  • All recurring meetings get audited quarterly (do we still need this?)
  • Default meeting length is 25 or 50 minutes (not 30 or 60—gives people buffer)
  • Every meeting must have an agenda and clear decision-making authority
  • If you can’t articulate why someone needs to be in a meeting, they don’t

I also institute “No Meeting Days” once a month—usually mid-month when everyone’s overwhelmed. The first time I did this, I got pushback (“but how will we collaborate?”). After people experienced the productivity of eight uninterrupted hours, they became zealots about protecting these days.

Layer 3: The Filter Role

This is where Chiefs of Staff earn their keep. I position myself as the filter between the team and the chaos.

How this works in practice:

  • All requests for engineering time come through me first
  • I triage: Is this aligned with priorities? Is this urgent? Can this wait?
  • I say no to 80% of requests (or I redirect them, defer them, or find alternative solutions)
  • For the 20% that are legitimate, I batch them and slot them appropriately

My team doesn’t see most of the noise. They don’t get random Slack messages from other departments. They don’t get pulled into every ad-hoc meeting. They trust that if something truly needs their attention, I’ll bring it to them.

Am I making friends with this approach? Not always. But I’m not trying to win popularity contests; I’m trying to help my team deliver exceptional work.

Layer 4: Communication Boundaries

Constant communication feels collaborative but it’s actually fragmenting. So I set communication boundaries:

Synchronous communication (meetings, calls):

  • Reserved for decision-making, complex problem-solving, or relationship-building
  • Time-boxed and structured
  • Action-oriented (we’re here to decide/solve X)

Asynchronous communication (email, docs, Slack):

  • Default for updates, information sharing, non-urgent questions
  • Expectation: Responses within 24 hours, not immediately
  • Use threads and documentation, not DMs

Focus mode:

  • Encourage team to set “Do Not Disturb” for focused work time
  • No expectation of immediate responses during focus blocks
  • Model this behavior myself

I also fight against the “we need to be available 24/7” culture. My team knows: If it’s not on fire, it can wait until tomorrow. If it is on fire, there’s an escalation path. Everything else is noise.

Layer 5: Scope Protection

Feature creep kills projects. Scope creep kills roadmaps. My job is to protect scope.

My scope protection tactics:

  • Clear definition of done for every project (in writing, agreed upon upfront)
  • Change control process (anything that changes scope goes through approval)
  • Pushing back on “just one more thing” (the answer is almost always “great idea for v2”)
  • Timeboxing (if we can’t ship in X weeks, we’re cutting scope, not extending timeline)

When someone says “can we just add…?” I respond with: “Sure! What should we remove to make room for that?” This forces real prioritization.

Layer 6: Energy Management

This is the layer most people miss. Protecting focus isn’t just about time and priorities—it’s about energy.

How I manage team energy:

  • Mix high-intensity projects with lower-intensity work
  • Build in recovery time after crunch periods
  • Watch for burnout signals (irritability, disengagement, quality drops)
  • Celebrate wins regularly (don’t just move to the next thing)
  • Protect vacation time (nobody works on vacation, period)
  • Encourage sustainable pace (sprints, not marathons)

A burned-out team can’t focus, no matter how much you protect their calendar. Energy management is focus management.

Practical Tactics for October

Let’s get tactical. Here are specific things you can do this month to protect your team’s focus:

Week 1: The Focus Audit

Spend this week assessing where focus is breaking down:

  • Review team calendars (how much meeting time vs. focus time?)
  • Track interruptions (how often is the team context-switching?)
  • Survey the team (what’s preventing them from doing their best work?)
  • Identify the biggest drains on focus

Document everything. You need data to make changes.

Week 2: The Priority Reset

Get crystal clear on priorities:

  • Review Q4 goals with leadership
  • Force rank current projects
  • Identify what’s slipping and why
  • Make hard decisions about what to defer
  • Communicate priorities clearly to the entire team

Create a visible artifact (dashboard, poster, document) that everyone can reference. When in doubt about what to work on, the priority list is the answer.

Week 3: The Calendar Cleanse

Attack the meeting problem:

  • Cancel all recurring meetings for one week (seriously)
  • Only reinstate ones that are truly necessary
  • Audit every meeting: agenda, decision-maker, required attendees
  • Block focus time for your team
  • Set up “No Meeting Days” for the rest of Q4

You’ll get resistance. Push through it. Most meetings are habits, not necessities.

Week 4: The Communication Cleanup

Fix your communication patterns:

  • Set expectations about response times
  • Create channels for different types of communication
  • Train people on when to use sync vs. async
  • Shut down channels that are just noise
  • Model good communication behavior

This might mean having uncomfortable conversations with stakeholders who expect immediate responses. Have them anyway.

Scripts for the Hard Conversations

Protecting focus means saying no. A lot. Here are scripts I use:

When someone wants to add to your roadmap:

“I appreciate you thinking of us for this. Help me understand: Is this more important than [current P0 project]? Because if we take this on, something else has to give. What would you suggest we deprioritize?”

When someone wants your engineer in yet another meeting:

“I want to make sure we’re being respectful of [engineer]’s time. Can you help me understand what decision you need from them? And have we provided all the context they need to make that decision async? If they truly need to be in the meeting, let’s timebox their participation to the exact 15 minutes when their input is needed.”

When everything is suddenly urgent:

“I’m seeing multiple P0s. Let’s get aligned on what P0 actually means; it should be ‘if we don’t do this, there’s significant business impact this quarter.’ Using that definition, which of these is truly P0? And for the others, what’s a reasonable timeline?”

When leadership wants a status update right now:

“I can get you a high-level summary now, or a thorough update tomorrow morning. Which would be more useful? [Pause] Great, I’ll send the detailed update first thing tomorrow. This lets the team stay focused on execution instead of context-switching to create reports.”

When someone pushes back on your filtering:

“I understand you’d prefer direct access to the engineering team. Here’s why we route through me: Our engineers are working on critical Q4 deliverables, and context-switching costs us 20-30% productivity. I’m here to triage and protect their focus so we actually ship what we’ve committed to. If something truly needs their immediate attention, I’ll make it happen. But I need us to be disciplined about what qualifies as ‘immediate.'”

The Signs You’re Succeeding

How do you know if your focus protection is working? Look for these signs:

Your team is shipping consistently. Not starting lots of things, but finishing and shipping them.

People report feeling less overwhelmed. In your 1:1s, you hear “I actually got deep work done this week” instead of “I’m drowning in meetings.”

Meetings are productive. They start on time, have clear outcomes, and people leave with clarity about next steps.

Priorities are clear. When you ask anyone on the team what the top priority is, they give you the same answer.

Quality is high. When people have focus time, quality improves because they’re not rushing or context-switching.

Morale improves. People feel empowered, not scattered. They see their work having impact.

Stakeholders trust the process. Even if they don’t always get what they want when they want it, they trust that you’re making good decisions.

When You Can’t Protect Everything

Real talk: Sometimes you can’t protect everything. There are legitimate crises, real urgencies, and unavoidable trade-offs.

Here’s how to handle those situations:

1. Be transparent about the cost.

“If we take on this urgent project, here’s what we’re not going to deliver. I want to make sure leadership understands that trade-off and is explicitly choosing it.”

2. Make it temporary.

“We’re going into crisis mode for the next two weeks. After that, we’re going back to our roadmap. No exceptions.”

3. Build in recovery.

“After this crunch period, the team gets a week of low-intensity work to recover. That’s non-negotiable.”

4. Don’t let it become the new normal.

“This is the third ‘one-time emergency’ this quarter. We need to talk about why we keep having emergencies and how to prevent them, because this isn’t sustainable.”

5. Protect what you can.

Even in chaos, protect something. Maybe you can’t save the whole roadmap, but you can protect Friday afternoons. Maybe you can’t prevent all meetings, but you can limit them to 25 minutes. Small protections matter.

The Mistakes I’ve Made (So You Don’t Have To)

I’ve been doing this for years, and I’ve absolutely screwed up. Here are my biggest mistakes:

Mistake #1: Protecting Too Much

Early in my career, I was so zealous about protecting my team that I became a bottleneck. I said no to everything, filtered out things that actually needed their input, and created frustration.

The lesson: Protection isn’t isolation. Your team needs to be connected to the business, to customers, to stakeholders. You’re filtering noise, not building walls.

Mistake #2: Not Building Relationships

I initially approached filtering as purely tactical; “does this meet my criteria for team time?” But I didn’t invest in relationships with other departments, so my “no” felt arbitrary and created resentment.

The lesson: Build relationships first. When people trust you, they’re more willing to accept your filtering. They know you’re not just saying no; you’re optimizing for the business.

Mistake #3: Not Explaining the Why

I would say no without explaining my reasoning. People felt dismissed.

The lesson: Always explain why. “No, because we’re focused on X and this doesn’t align” is so much better than just “no.” People might not agree, but they understand.

Mistake #4: Not Creating Alternatives

“No” is easier to accept when paired with “yes, but differently.” I wasn’t creative enough about finding alternative solutions.

The lesson: Before saying no, ask: “What problem are you trying to solve?” Often there’s a way to solve the problem without consuming your team’s focus.

Mistake #5: Burning Out Myself

I was so focused on protecting my team that I didn’t protect my own energy. I became the release valve for all the pressure, and I nearly burned out.

The lesson: You can’t pour from an empty cup. Protecting your team includes protecting yourself.

The Long Game: Building a Focus-Friendly Culture

Protecting focus in October is good. Building an organization that values focus year-round is better.

Here’s how to play the long game:

Make Focus a Value

Talk about it explicitly. “We value deep work and focus” should be as clear as “we value innovation” or “we value customers.”

In every all-hands, in performance reviews, in how you recognize people—reinforce that focus and depth matter more than activity and responsiveness.

Measure What Matters

Stop measuring “hours worked” or “availability” and start measuring outcomes. Did we ship what we committed to? Was it high quality? Did we make meaningful progress on strategic goals?

When you measure focus-friendly metrics, you get focus-friendly behavior.

Model It from the Top

If executives are constantly in back-to-back meetings, always responsive on Slack, working nights and weekends, that’s your culture. Period.

Leaders need to model focus: Blocking deep work time, not responding immediately to everything, being thoughtful about their calendar, taking real time off.

Create Systems That Support Focus

Don’t rely on individual discipline. Create systems:

  • Default meeting lengths of 25/50 minutes (not 30/60)
  • Core hours when everyone’s available, plus flex time for focus
  • Documentation culture (write it down instead of meetings)
  • Clear escalation paths (so people know when something’s truly urgent)
  • Regular calendar audits (where teams review and eliminate unnecessary meetings)

Celebrate Focus Wins

When a team protects their focus and ships something great, celebrate it publicly. Tell the story of how focus enabled quality. Make heroes of the teams that say no to distractions.

Be Willing to Lose People Who Don’t Get It

This is the hardest one. Some people will never value focus. They’ll always create chaos, always have urgent requests, always push for immediate responses.

At some point, you need to be willing to say: This person isn’t a fit for how we work. Not because they’re bad, but because they’re misaligned with our values.

Your October Challenge

Here’s my challenge to you: Pick one thing from this article and implement it this month.

Maybe it’s:

  • Doing a calendar cleanse
  • Setting up No Meeting Days
  • Forcing rank on your priorities
  • Having a hard conversation about focus with leadership
  • Building focus time into your team’s calendar

Just one thing. Do it well. See the impact. Then expand.

Because here’s what I know after years of this work: Small changes in focus create exponential changes in outcomes. A team that’s 20% more focused doesn’t just deliver 20% more; they deliver 2x or 3x more because they’re doing deep, high-quality work instead of scattered, fragmented work.

And in October – when the pressure is highest and the distractions are everywhere – that focus is the difference between teams that thrive and teams that just survive.

The Real Job of a Chief of Staff

Let me close with this: People think the Chief of Staff’s job is to facilitate, coordinate, and execute. And yes, we do all that.

But the real job – the job that actually matters – is protection.

We protect:

  • Strategy from being diluted by every new idea
  • Priorities from being hijacked by urgency
  • Focus from being shattered by constant interruptions
  • Quality from being sacrificed for speed
  • People from burning out
  • Outcomes from being drowned in activity

We’re not just keeping things running. We’re creating the conditions for excellence.

And in October – when everything is competing for your team’s attention, when the pressure to do more is overwhelming, when focus is hardest to maintain – that protection is everything.

So here’s to all of us protecting what matters most. Here’s to saying no when everyone wants us to say yes. Here’s to putting up walls when the world wants open doors. Here’s to defending our team’s focus against all the well-meaning, urgent, seemingly-important distractions that would otherwise derail everything.

Your team might not always see the battles you fight on their behalf. But they’ll see the results: consistent delivery, high-quality work, sustainable pace, and the satisfaction of actually finishing what they start.

That’s the job. That’s what we protect. That’s why it matters.

Now go forth and be the shield your team needs. October is counting on you.

Why “Just an Admin” Is the Most Outdated Phrase of 2025

Let me tell you about the moment I knew something had to change. I was in an executive meeting- you know, the kind where important decisions get made and strategies get set – when someone said, “We need Sarah on this, but she’s just an admin so she probably can’t help with the technical parts.”

I was Sarah. And I’d spent the morning:

  • Troubleshooting the CEO’s security settings because IT was backlogged
  • Coordinating a cross-functional project involving five departments
  • Analyzing budget data to prep for the CFO’s board presentation
  • Managing our contractor onboarding system
  • And yes, also booking some travel and scheduling some meetings

“Just an admin.” Those three words stung, but more than that, they were wildly inaccurate. And they represent a mindset that’s so outdated it belongs in a museum next to fax machines and BlackBerrys.

I’ve been a technology administrative professional for twelve years – note that title, we’re going to come back to it – and I’m here to tell you: If your organization still thinks of admins as “just” anything, you’re not only disrespecting crucial team members, you’re also leaving enormous value on the table.

Let’s talk about why the “just an admin” mindset is dead (or should be), and what the role actually looks like in 2025.

The Evolution Nobody Talks About

First, let’s get historical for a second, because understanding how we got here matters.

Twenty years ago, administrative roles were largely about execution: Take dictation, type letters, file paperwork, answer phones, book travel. Important work, absolutely, but primarily execution-focused and fairly standardized.

Then technology happened.

Slowly, then all at once, administrative roles absorbed:

  • Technology troubleshooting and training
  • Project coordination across teams
  • Data management and analysis
  • Process design and optimization
  • Vendor management and negotiation
  • Budget tracking and financial analysis
  • HR functions (onboarding, benefits, culture initiatives)
  • Operations management
  • Security compliance
  • Strategic planning support

The job title stayed the same. The compensation mostly stayed the same. But the actual work? Completely transformed.

And yet, the perception lagged by about fifteen years. People still think “admin” means what it meant in 1995, and that disconnect is the root of the problem.

What Technology Admins Actually Do (And Why It Matters)

Let me get specific about what my role actually entails, because I suspect many admins reading this will recognize themselves, and many executives reading this will be surprised.

We’re the Operating System of the Organization

If your company is a computer, executives are the high-level applications, teams are the programs, and admins? We’re the operating system. We’re the layer that makes everything else work, that connects different parts, that manages resources, that handles the background processes nobody thinks about until they break.

I manage:

  • Executive calendars (which is actually strategic prioritization)
  • Information flow across teams (which is knowledge management)
  • Cross-functional projects (which is program management)
  • Vendor relationships (which is stakeholder management)
  • Office systems and tools (which is operations and tech support)

None of this is “just” anything. It’s organizational infrastructure.

We’re Translators and Connectors

I speak engineer, product manager, executive, finance, HR, and customer. I can translate technical concepts for non-technical leaders and business priorities for engineers. I connect people who need to talk but don’t realize it. I spot patterns across different parts of the org because I see everything.

This is not a skill you can automate or outsource. It requires institutional knowledge, emotional intelligence, and systems thinking.

We’re Security and Compliance Gatekeepers

Who has access to what? Who can see sensitive information? What’s our process for onboarding and offboarding? How do we ensure we’re compliant with regulations?

In many tech companies, admins are on the front lines of security and compliance. I’ve caught security breaches, flagged compliance issues, and prevented data leaks. Not because that’s explicitly in my job description, but because I’m paying attention and I understand the stakes.

We’re Project Managers (Without the Title)

I’m currently managing:

  • Our office move (coordinating with 10+ vendors, managing budget, timeline, and communications)
  • Our Q4 off-site (venue, travel, agenda, materials, dietary restrictions for 50 people)
  • Implementation of a new HR system (requirements gathering, vendor evaluation, rollout planning)
  • Three board meetings with different compliance and documentation requirements

Each of these is essentially a project with budget, timeline, stakeholders, and success criteria. But because it’s admin work, it gets minimized as “logistics.”

We’re Data Analysts

I track and analyze:

  • Travel spend patterns to negotiate better rates
  • Meeting effectiveness to optimize executive time
  • Tool usage to eliminate unused licenses
  • Process efficiency to identify bottlenecks

I use Excel, SQL, and visualization tools. I create dashboards and reports. I provide insights that drive decisions. But again, because it’s admin-adjacent, it’s not seen as “real” analysis.

We’re Culture Carriers

Want to know the health of your organization? Ask your admins. We see everything. We hear everything. We know when morale is dropping, when there’s conflict brewing, when people are checking out.

We also shape culture actively planning events, facilitating connections, creating rituals, modeling values. We’re not HR, but we’re absolutely culture workers.

The Skills Gap Nobody Acknowledges

Here’s something that frustrates me: The gap between the skills required for modern admin work and what companies are willing to pay for or even acknowledge.

To be effective as a technology admin in 2025, you need:

Technical Skills:

  • Proficiency with dozens of software tools
  • Basic coding/scripting (yes, really—I write scripts to automate workflows)
  • Data analysis capabilities
  • Security awareness and best practices
  • Tech troubleshooting and support

Business Skills:

  • Financial acumen (budgeting, forecasting, analysis)
  • Project management
  • Process design
  • Strategic thinking
  • Vendor negotiation

Interpersonal Skills:

  • Stakeholder management
  • Conflict resolution
  • Change management
  • Communication across audiences
  • Emotional intelligence

Organizational Skills:

  • Systems thinking
  • Prioritization under ambiguity
  • Multi-tasking without dropping balls
  • Attention to detail at scale
  • Crisis management

This is not an entry-level skill set. This is not “just” anything. And yet, many companies treat admin roles as if they require only basic office skills.

The Compensation Problem We Need to Talk About

Let’s address the elephant in the room: Admins are dramatically underpaid for the value they provide and the skills they possess.

I’ve seen job postings for “Executive Assistant” at tech companies that require:

  • 5+ years experience
  • Project management experience
  • Technical proficiency
  • Budget management
  • Cross-functional coordination
  • Discretion with sensitive information

And offer $60K-$75K in markets where rent alone is $2,500/month.

Meanwhile, project managers with similar skill sets are making $100K+. Operations managers are making $120K+. Executive assistants at finance companies are making $150K+.

Why the gap? Because tech companies still think of admin as “support staff” rather than strategic roles. Because there’s a historical legacy of admin work being undervalued (let’s be honest: it’s gendered). Because admins rarely advocate for themselves (we’re too busy keeping everything running).

This needs to change. Not just for fairness (though that’s reason enough), but because you cannot attract and retain top talent at these compensation levels. The best admins leave tech for industries that pay them what they’re worth. And tech companies suffer for it.

What Great Companies Get Right

I’ve worked at companies that get it and companies that don’t. Here’s what the good ones do differently:

They Use Better Titles

“Executive Assistant” undersells the role. Companies that understand this use titles like:

  • Chief of Staff (for senior admin roles supporting executives)
  • Operations Manager
  • Technical Program Coordinator
  • Business Operations Specialist

These titles better reflect the actual work and signal that these are strategic roles.

They Pay Competitively

They benchmark admin compensation against project managers and operations roles, not against historical admin rates. They recognize that retaining a great admin is worth paying for.

They Include Admins in Strategic Conversations

Admins attend leadership meetings not to take notes, but to contribute. They’re consulted on decisions. They have a voice in planning. They’re treated as partners, not servants.

They Invest in Development

Training budget, conference attendance, skill development, career pathing—all the things other roles get, admins get too. They’re not stuck in the role forever unless they want to be.

They Measure and Recognize Impact

Great companies track the impact of admin work-time saved, costs reduced, projects delivered, crises averted. They recognize that this work has measurable value.

One company I worked with calculated that their executive admin saved the CEO 15 hours per week through calendar optimization and meeting efficiency. At the CEO’s hourly rate, that was $500K+ in annual value. Suddenly, paying the admin $120K seemed like a bargain.

How to Advocate for Yourself (Because You Have To)

If you’re an admin reading this and nodding along, you’re probably wondering: How do I change this in my organization?

Here’s my playbook:

Document Your Impact

Start tracking:

  • Projects you manage (scope, budget, impact)
  • Time you save others
  • Costs you reduce or avoid
  • Problems you solve
  • Processes you improve

Create a quarterly “impact report” even if nobody asks for it. Show your value in concrete terms.

Stop Diminishing Your Work

When someone asks what you do, don’t say “I’m just an admin.” Say:

  • “I manage operations for the executive team”
  • “I coordinate cross-functional projects and handle strategic logistics”
  • “I’m the Chief of Staff to the VP of Engineering”

Language matters. Own your value.

Ask for What You Deserve

Research comparable roles at other companies. Prepare your case based on your impact. Ask for the raise, the title change, the budget for training.

Will you always get it? No. But you definitely won’t get it if you don’t ask. And if you ask well (with data and impact) and they still say no, that tells you something about whether this is the right place for you.

Build Your Skills Strategically

You’re probably already doing work adjacent to project management, operations, or program management. Get certifications in those areas. Take courses. Build the resume that matches the work you’re actually doing.

This does two things: It gives you leverage in negotiations, and it makes you more marketable if you decide to leave.

Network with Other Admins

The best career advice I ever got came from other admins. We share strategies, support each other, celebrate wins, and commiserate about the frustrations. Find your people; there are admin communities in tech that are gold mines of wisdom.

Know When to Leave

Sometimes the organization just won’t recognize your value. You can do everything right and still hit a ceiling. If that’s the case, don’t stay out of loyalty or fear. There are companies that will value you appropriately. Go find them.

For Managers and Executives: How to Not Suck

If you manage or work with admins, here’s how to not be part of the problem:

Stop Using “Just an Admin”

Ever. Not in meetings, not in casual conversation, not in your head. The language signals disrespect and limits how people think about the role.

Include Them Strategically

If your admin is in the room only to take notes, you’re doing it wrong. They should contribute to discussions, be consulted on decisions, and have a seat at the table.

Pay Them Appropriately

Benchmark against operations and project management roles, not historical admin rates. And be transparent about compensation and advancement paths.

Invest in Their Development

Training budget, conference attendance, stretch assignments, mentorship; all of it. Invest in their growth the way you would any other strategic role.

Measure and Recognize Their Impact

Make their contributions visible. When they save your ass (and they will), acknowledge it publicly. When they deliver a major project, celebrate it the way you would any other project delivery.

Listen to Them

Your admin knows things you don’t. They see patterns you miss. They understand people dynamics you’re blind to. When they raise concerns or make suggestions, listen.

Create Career Pathways

Admin shouldn’t be a dead-end role. Create paths to project management, operations, program management, chief of staff roles. Make it possible to grow without leaving the organization.

The Future of Technology Administration

Where is this role headed? Based on what I’m seeing, here are my predictions:

Increasing Specialization

We’re already seeing admins specialize; technical project coordination, operations management, executive business partnering. This trend will continue, with clearer career paths in each direction.

More Tech-Forward Roles

Admins who can code, automate, and leverage AI will be increasingly valuable. The role is becoming more technical, not less.

Recognition as Strategic

Companies are slowly (very slowly) recognizing that great admins are strategic assets. This will accelerate as competition for talent increases.

Better Compensation

As admins advocate for themselves and companies compete for talent, compensation will (hopefully) start to reflect actual value. We’re already seeing this at companies that get it.

Hybrid Roles

The line between admin, operations, project management, and chief of staff is blurring. Future roles will likely be more fluid and adaptable.

My Message to Other Admins

If you’re reading this and you’re an admin in tech, here’s what I want you to know:

You are not “just” anything. You are critical infrastructure. You are strategic partners. You are the reason things work.

If your organization doesn’t recognize that, the problem is with them, not with you.

You deserve:

  • To be paid fairly for your skills and impact
  • To be included in strategic conversations
  • To have a voice in decisions
  • To grow in your career
  • To be respected as a professional

If you’re not getting those things, it’s okay to advocate for them. And if you advocate and it falls on deaf ears, it’s okay to leave.

There are companies out there that will value you. There are managers who will treat you as the strategic partner you are. There are roles where you can use all your skills and be compensated fairly for them.

Don’t settle for less because you think this is just how it is. It’s not. It’s how it’s been, but it doesn’t have to be how it continues.

My Message to Everyone Else

If you work with admins, manage them, or benefit from their work (which is basically everyone in tech), here’s my ask:

Stop using “just an admin.” Stop undervaluing their contributions. Stop treating them as invisible or interchangeable.

Start recognizing their strategic value. Start paying them appropriately. Start including them in decision-making. Start investing in their growth.

It’s not just the right thing to do (though it is). It’s also the smart thing. Great admins are force multipliers. They make entire teams more effective. They save you from disasters you don’t even know were coming. They’re the glue that holds organizations together.

Treat them like it.

The Bottom Line

“Just an admin” is an insult to the complexity, skill, and strategic value that modern technology administrative professionals bring to their organizations.

We’re not “just” anything. We’re:

  • Operations managers
  • Project coordinators
  • Strategic partners
  • Problem solvers
  • Culture carriers
  • Technical specialists
  • Crisis managers
  • And yes, occasionally we also book your travel and schedule your meetings

The next time you hear someone say “just an admin,” correct them. The next time you think it, catch yourself. The next time you’re budgeting or planning or making decisions, include your admins and value their input.

Because here’s the truth: If you lose a great admin, you’ll feel it immediately and dramatically. Your calendar will be chaos. Your projects will stall. Your costs will rise. Your crises will multiply. Your meetings will be disasters.

That’s not the impact of “just” anything. That’s the impact of strategic infrastructure.

It’s 2025. Let’s finally retire the most outdated phrase in tech and start treating administrative professionals like the strategic powerhouses they actually are.

When Work Invades Home: Setting Boundaries That Actually Stick

It’s 9:47 PM on a Wednesday. You’re on the couch, theoretically watching TV with your partner, but your laptop is open “just to check one thing.” Your phone buzzes with a Slack notification. Then another. Your partner gives you That Look; the one that says “you said you were done with work two hours ago.” You feel guilty, but also defensive because this project is important and how are you supposed to just ignore urgent messages?

If this scene feels familiar, welcome to the club nobody wanted to join: Tech professionals whose work has completely invaded their home life.

I’ve been coaching people through work-life integration (we’ll get to why I don’t say “balance”) for eight years, and here’s what I know: The pandemic didn’t create this problem, but it made it exponentially worse. When your office is also your bedroom, your dining room, your living room—when your coworkers can reach you 24/7 through ten different channels—boundaries don’t just blur. They disappear.

And here’s the part that makes this especially tricky for those of us in tech: We’ve been sold the “always on” culture as a feature, not a bug. Working at 11 PM is “dedication.” Responding to Slack on weekends is being a “team player.” Never fully disconnecting is “passion for your work.”

Except it’s killing us. Slowly, invisibly, but definitely killing us.

So let’s talk about how to set boundaries that actually stick—not theoretical boundaries that look good on paper but crumble the first time a “quick emergency” comes up, but real, sustainable boundaries that protect your wellbeing without torpedoing your career.

Why Boundaries Fail (And It’s Not Because You’re Weak)

Before we talk about what works, let’s talk about why boundary-setting fails for most people. Because if you’ve tried and failed to establish work-life boundaries before, it’s probably not because you lack willpower or discipline. It’s because you’re fighting against some powerful forces.

The Psychological Trap of Accessibility

Our brains are not wired for the level of accessibility that technology enables. Historically, when you left the office, work stayed there. Now, work is literally in your pocket 24/7. And every time you check your phone “just to see if anything urgent came up,” you’re creating a psychological pattern.

Your brain learns: Work never ends. There might be something urgent. I need to check. Just in case.

This isn’t weakness—it’s operant conditioning. You’ve been trained, through a thousand small repetitions, to always be available. Breaking this pattern requires more than willpower; it requires deliberately retraining your brain.

The Culture of Urgency

Tech companies love to operate in permanent crisis mode. Everything is urgent. Everything is a priority. Everything needs to happen now. And if you’re the person who says “I’ll look at this tomorrow morning,” you worry you’ll be seen as not committed or not a team player.

Here’s the uncomfortable truth: Some of that urgency is real. Most of it isn’t. But distinguishing between real urgency and manufactured urgency requires confidence and experience that not everyone has.

The Identity Trap

For many of us in tech, work isn’t just what we do; it’s who we are. We’re engineers, product managers, designers. We take pride in our work. We find meaning in it. We’ve built careers and identities around being good at what we do.

So when we set boundaries around work, it feels like we’re rejecting a part of ourselves. If I’m not checking Slack at 10 PM, am I still a dedicated engineer? If I take a real vacation, am I still committed to my team?

The answer is yes, but getting there emotionally is harder than it sounds.

The Fear of Missing Out (Professional Edition)

In fast-moving tech companies, a lot happens outside of traditional working hours. Decisions get made in Slack threads at 8 PM. Strategy gets discussed over late-night video calls. The people who are there have influence; the people who aren’t, don’t.

Setting boundaries means sometimes missing those moments. And that feels risky, especially if you’re ambitious and want to advance in your career.

The Inadequate Tools and Practices

Most companies say they value work-life balance but provide no actual support for it. No clear policies about after-hours communication. No modeling of healthy boundaries from leadership. No tools or practices that make it easy to disconnect.

You’re expected to figure it out yourself, which usually means you don’t figure it out at all.

The Shift from Balance to Harmony (And Why It Matters)

I deliberately avoid the term “work-life balance” because it sets up an impossible standard. Balance implies 50/50, equal weight, perfect equilibrium. That’s not realistic for most people in tech.

Some weeks, work will demand more. Launch weeks, crisis response, critical projects; there will be periods of imbalance. And that’s okay.

What we’re aiming for is harmony: The ability to flex between work and personal life in a way that feels sustainable over time. Some weeks you give more to work. Some weeks you protect your personal time fiercely. The key is that you’re making these choices consciously, not defaulting to “always work.”

Harmony means:

  • Intentional choices about when and how you engage with work
  • Recovery periods after intense work periods
  • Core boundaries that you maintain even during busy times
  • Flexibility without completely losing yourself to work

With that framing, let’s talk about how to actually create this harmony.

The Four Layers of Effective Boundaries

After years of coaching people through this, I’ve developed a framework with four layers of boundaries. You need all four for boundaries that actually stick.

Layer 1: Physical Boundaries

These are the easiest to understand but often the hardest to maintain, especially if you work from home.

Create spatial separation:

  • If possible, have a dedicated workspace that isn’t your bedroom or main living area
  • If that’s not possible, create a “work zone” that you only use during work hours
  • When work is done, physically close the laptop and put it away
  • Don’t bring your work laptop to your relaxation spaces (couch, bed, etc.)

I had one client who worked from a one-bedroom apartment. She couldn’t have a separate office, but she created a rule: Work happens at the dining table. When she was done, she put the laptop in a cabinet. The dining table became neutral territory again. That physical act of closing and storing the laptop became her boundary ritual.

Control your physical environment:

  • Turn off notifications on your phone after work hours
  • Use separate devices for work and personal life if possible
  • Put your work phone in another room during off-hours
  • Create visual cues that signal “work time” vs. “personal time” (different lighting, closing doors, etc.)

The goal is to make it harder to accidentally engage with work and easier to be fully present in your personal life.

Layer 2: Temporal Boundaries

These are about time; when you work and when you don’t.

Define your core work hours:

  • Be explicit about when you’re available
  • Communicate these hours to your team
  • Protect them as your “focused work time”
  • Build your schedule around them

Notice I didn’t say 9-5. Your core hours might be 7 AM-3 PM or 11 AM-7 PM. The point is defining them and being consistent.

Create hard stops:

  • Set an alarm for when work should end
  • Have commitments after work that force you to stop (gym class, dinner plans, picking up kids)
  • Don’t just rely on willpower; create external accountability

I have one client who enrolled in an evening class specifically to force herself to stop working. It worked because she’d paid for it and couldn’t skip without losing money.

Protect your weekends (or whatever your equivalent is):

  • Decide in advance what your policy is for weekend work
  • If you need to work weekends sometimes, make it the exception not the rule
  • When you do work weekends, take comp time during the week

This isn’t about being rigid—it’s about being intentional.

Layer 3: Digital Boundaries

This is where most people struggle because our work is inherently digital.

Manage your notifications ruthlessly:

  • Turn off all work notifications outside of work hours
  • Use “Do Not Disturb” modes
  • Uninstall Slack from your phone (yes, really) or at minimum turn off its notifications
  • Set up email filters so only true emergencies reach you after hours

“But what if there’s an emergency?” you ask. Which brings me to…

Define what actually constitutes an emergency:

  • Work with your team to establish what truly requires after-hours response
  • Create an actual escalation path for real emergencies (not just “message everyone on Slack”)
  • For most roles, true emergencies are rare; everything else can wait until morning

One company I worked with created a “pager system” for actual emergencies. If you’re not on call, you don’t respond. This eliminated the ambient anxiety of “what if something breaks?”

Use technology to support your boundaries:

  • Email delay send (compose at night if you must, but schedule to send during work hours)
  • Slack status (“out of office until morning” with notifications off)
  • Calendar blocking (including personal time, so people can see you’re not available)
  • Separate browsers or browser profiles for work vs. personal

Batch check work communications:

  • Instead of constantly monitoring, check at defined times
  • When you do check, actually respond; don’t just skim and create anxiety
  • Then close it and move on

Layer 4: Psychological Boundaries

This is the deepest and most important layer, and the one most people skip.

Separate your identity from your work:

  • You are not your job title
  • Your worth is not determined by your productivity
  • You can be excellent at your job AND have a life outside of it
  • Remind yourself regularly why you work (to fund your life, not to replace it)

This sounds simple but requires ongoing psychological work, especially if you’ve built your identity around career achievement.

Develop a mindset of “good enough”:

  • Not everything needs to be perfect
  • Some things can wait until tomorrow
  • Done is often better than perfect
  • Your best work doesn’t come from working 80 hours a week; it comes from working sustainably

I had a perfectionist client who was burning out because every email, every presentation, every line of code had to be flawless. We worked on “tiered effort”; deciding what truly deserves your A-game and what can be B+ work. That shift saved her career and her health.

Practice letting go:

  • When work time ends, practice consciously releasing work thoughts
  • Use a ritual to mark the transition (change clothes, go for a walk, close your laptop)
  • If work thoughts intrude, acknowledge them and set them aside (“I’ll think about that tomorrow”)
  • Don’t catastrophize about what might happen if you’re not available

Cultivate non-work sources of meaning and identity:

  • Hobbies that have nothing to do with tech
  • Relationships that aren’t work-related
  • Community involvement, creative pursuits, physical activities
  • Parts of yourself that exist entirely separately from your career

The stronger your non-work identity, the easier it is to set work boundaries.

The Conversation Template That Works

One of the hardest parts of boundary-setting is communicating your boundaries to your team, your manager, and your organization. Here’s a template I use with coaching clients:

For your manager:

“I want to talk about my work hours and availability. I’m committed to doing excellent work and meeting my commitments, and I’ve realized I need to be more intentional about when I’m working to be sustainable and effective. Here’s what I’m thinking: [your proposed boundaries]. This means [concrete implications]. I wanted to share this with you and make sure you’re comfortable with this approach. Do you have concerns?”

Key elements:

  • Lead with commitment to excellent work
  • Frame it as about sustainability and effectiveness (which benefits them)
  • Be specific about what you’re proposing
  • Invite conversation, don’t present it as a demand
  • Address concerns proactively

For your team:

“Hey team, I’m adjusting my work hours to be more sustainable. Going forward, I’ll be online and responsive from [X to Y]. Outside those hours, I won’t be monitoring Slack/email except for true emergencies. If something truly urgent comes up, here’s how to reach me: [escalation path]. This helps me do my best work during the day. Thanks for respecting these boundaries.”

Key elements:

  • Clear about your availability
  • Define what constitutes an emergency and how to reach you
  • Frame it positively (helps you do better work)
  • Respectful but firm tone

For yourself:

This is the internal conversation that matters most:

“My boundaries are not negotiable except in true emergencies. Setting these boundaries doesn’t make me less dedicated—it makes me more sustainable. I’m making a choice to be excellent at work AND have a life outside of work. That’s not only okay, it’s necessary. I will not apologize for taking care of myself.”

Repeat as needed until you believe it.

Real Scenarios and How to Handle Them

Let me get practical with real scenarios I see all the time in coaching:

Scenario 1: Your Manager Slacks You at 10 PM

What usually happens: You respond immediately because they’re your manager and you want to be seen as responsive.

What to do instead:

  • Don’t respond (unless it’s a true emergency)
  • If you see it and it’s stressing you out, use delay send to respond in the morning
  • In your next 1:1, address it: “I noticed you sent me a message at 10 PM last night. I want to make sure; do you expect responses outside of work hours? I’m trying to be more boundaried about when I’m available.”
  • Often managers don’t expect immediate responses; they’re just working late and offloading thoughts

Scenario 2: You’re on Vacation and Someone Keeps @-mentioning You

What usually happens: You log in “just to handle this one thing” and end up working half your vacation.

What to do instead:

  • Before vacation, set crystal clear out-of-office messages everywhere
  • Designate a backup person for anything urgent
  • Actually don’t log in (yes, really)
  • If someone reaches you anyway: “I’m on vacation and offline. [Backup person] can help with urgent matters. I’ll follow up when I’m back on [date].”
  • Resist the urge to “just check quickly”; that’s how vacations die

Scenario 3: There’s a Launch/Crisis and Everyone’s Working Late

What usually happens: You feel obligated to match everyone else’s hours even if you don’t need to be there.

What to do instead:

  • Ask yourself: Is my presence actually needed or is this performative?
  • If you need to be there, be there fully; then take comp time after
  • If you don’t need to be there: “I’m going to head out now. I’ll be back online at [time] tomorrow to pick up anything that came up.”
  • Don’t apologize for not working 24/7 during a crisis that requires some people to work long hours but not everyone

Scenario 4: You’re Worried About Career Impact

What usually happens: You sacrifice your boundaries because you’re afraid setting them will hurt your advancement opportunities.

What to do instead:

  • Document your impact and results (which are not correlated with hours worked)
  • Have explicit conversations with your manager about what success looks like
  • Look for managers and companies that actually value sustainability
  • Know that if a company only promotes people who work 80-hour weeks, you probably don’t want to advance there anyway

Scenario 5: You Work with Global Teams Across Time Zones

What usually happens: Someone is always working somewhere, so you feel like you should always be available.

What to do instead:

  • Establish clear overlapping hours for synchronous communication
  • Use async communication for everything else
  • Rotate who takes early/late meetings so it’s not always the same people sacrificing
  • Be explicit: “I’m available [X to Y in my timezone]. Outside that, I’ll respond within 24 hours but not immediately.”

The 30-Day Boundary-Building Plan

Okay, enough theory and scenarios. Here’s your practical 30-day plan for actually implementing boundaries:

Week 1: Assess and Design

  • Track when you’re actually working (including evenings, weekends, “just checking” Slack)
  • Identify your biggest boundary violations (what’s invading your personal time most?)
  • Design your ideal boundaries (work hours, availability, device usage)
  • Identify obstacles (cultural, personal, practical)

Week 2: Start Small and Communicate

  • Pick ONE boundary to implement (start with the easiest)
  • Communicate it to your team and manager
  • Set up the tools/systems to support it (notifications off, calendar blocks, etc.)
  • Practice saying no or “I’ll handle that tomorrow”

Week 3: Expand and Reinforce

  • Add another boundary
  • Notice what’s working and what’s not
  • Adjust as needed
  • Handle pushback or challenges that come up

Week 4: Make It Sustainable

  • Implement your full boundary system
  • Create rituals and habits that reinforce it
  • Review and adjust
  • Plan for how you’ll maintain it going forward

The key is starting small and building gradually. Don’t try to go from “always available” to “completely boundaried” overnight. You’ll fail, feel bad, and give up. Build incrementally.

When Boundaries Aren’t Enough (And What to Do)

Here’s the hard truth: Sometimes the problem isn’t your boundaries—it’s your job or your company.

Signs your job is the problem:

  • You’ve set reasonable boundaries and get punished for them
  • The workload is genuinely unsustainable even with perfect boundary-setting
  • Leadership says they value balance but model the opposite
  • Setting boundaries actively hurts your career trajectory
  • You’re in constant crisis mode with no relief

If this is you:

  • Have an honest conversation with your manager about sustainability
  • Look for examples of people at your company who have boundaries AND successful careers (if they don’t exist, that’s your answer)
  • Consider whether this is the right environment for you
  • Know that leaving isn’t failure; it’s recognizing a mismatch

Some companies and roles are genuinely incompatible with healthy boundaries. You can’t boundary-set your way out of a toxic culture or an impossible workload. Sometimes the answer is to leave.

The Maintenance Plan (Because Boundaries Are Not Set-It-and-Forget-It)

Here’s what nobody tells you: Boundaries require ongoing maintenance. They’re not something you set once and then they’re done. They need regular attention and reinforcement.

Monthly boundary audit:

  • Are my boundaries still serving me?
  • Where am I letting them slip?
  • What needs to be adjusted?
  • What new boundaries do I need?

Seasonal adjustments:

  • Your boundaries might need to flex based on work demands
  • Plan for intensive periods and recovery periods
  • Don’t let temporary boundary relaxation become permanent

Ongoing practices:

  • Daily end-of-work ritual
  • Weekly reflection on work-life harmony
  • Regular check-ins with your support system
  • Continuous learning about what works for you

My Final Wisdom After Years of This Work

I’ve coached hundreds of people through setting work-life boundaries, and here’s what I know for sure:

Nobody is coming to save you. Your company won’t suddenly decide to protect your boundaries. Your manager won’t tell you to work less (even if they say they want you to). You have to do this for yourself.

Perfect boundaries don’t exist. Some weeks will be messy. Some boundaries will get violated. That’s okay. What matters is the overall pattern, not each individual day.

Guilt is part of the process. You’re going to feel guilty when you set boundaries, especially at first. That guilt doesn’t mean you’re doing something wrong; it means you’re changing a pattern, and change feels uncomfortable.

It gets easier. The first time you don’t respond to a Slack at 9 PM will feel terrifying. The tenth time will feel normal. The hundredth time won’t even register.

The people who matter will respect your boundaries. The ones who don’t either don’t matter or aren’t worth working with.

You cannot pour from an empty cup. Every boundary you set is an investment in your sustainability, your health, and your ability to do excellent work over the long term.

Your future self is counting on you. The boundaries you set today are gifts to yourself six months, a year, five years from now. You’re not just protecting today; you’re protecting your entire career.

Your Next Steps

Close this article. Look at your calendar for tomorrow. Find one place where you can practice a boundary. Maybe it’s not checking Slack after 7 PM. Maybe it’s taking a real lunch break. Maybe it’s closing your laptop at 6 PM even though there’s more you could do.

Do that one thing. Then do it again the next day. And the next.

That’s how boundaries that actually stick get built; not through grand declarations or perfect plans, but through small, consistent choices that add up over time.

Your work will not fall apart if you set boundaries. Your career will not end. Your team will not collapse. In fact, the opposite is more likely: You’ll be more focused, more creative, more sustainable, and ultimately more valuable when you’re not running on empty.

The work will always be there. There will always be one more email, one more Slack thread, one more thing you could do. The question is: Will you be there? Will you be healthy, present, and sustainable?

That’s entirely up to you.

Now close the laptop. Go be a human who happens to work in tech, not a tech worker who’s forgotten how to be human.

You’ve got this.

How OKRs Can Keep Your Tech Strategy from Becoming a Pumpkin Patch

You know what a pumpkin patch and most tech strategies have in common? They both start with grand intentions, lots of seeds get planted, and by the end you have a sprawling mess where you can’t quite remember which pumpkin (project) was supposed to be the prize winner and which ones were just taking up space.

I’ve been leading technology strategy and planning for the better part of a decade, and I’ve seen it all: strategies that look beautiful in PowerPoint but fall apart in execution, roadmaps that are obsolete three months after you create them, initiatives that multiply like rabbits until nobody can remember what we’re even trying to accomplish anymore.

And then there are OKRs (Objectives and Key Results) which sound like yet another framework that consultants invented to sell books and workshops. Except here’s the thing: When done right, OKRs are the difference between a strategic pumpkin patch (chaos) and an actual strategy (aligned, measurable, achievable).

Let me show you how to use OKRs to keep your tech strategy from becoming a sprawling mess of good intentions and competing priorities.

Why Most Tech Strategies Fail (Spoiler: It’s Not the Strategy Part)

Before we dive into OKRs, let’s talk about why tech strategies so often fail to deliver. And I don’t mean “fail” in the dramatic flame-out sense. I mean the more common “we spent six months on a strategy and now nobody follows it” sense.

Problem #1: The strategy is too vague

“Modernize our technology stack.” Great. What does that mean? Which parts? By when? How do we know if we’re successful? Vague strategies invite vague execution, which leads to everyone doing their own interpretation of what “modernize” means.

Problem #2: Everything is a priority

I once inherited a strategic plan that listed 27 initiatives as “P0 – Critical.” Twenty-seven. That’s not prioritization; that’s a wishlist. When everything is a priority, nothing is.

Problem #3: No clear connection between strategy and execution

Your engineering team is executing on their quarterly roadmap. Your product team is chasing their OKRs. Your infrastructure team is working through their backlog. And somehow none of it clearly connects to the strategic objectives you spent all that time defining. Everyone’s busy, but are they busy with the right things?

Problem #4: No feedback loop

You set a strategy in January. Check in on it maybe in July (if you remember). Discover in December that half the initiatives never launched and the other half are delivering value nobody wanted. There’s no mechanism for learning and adjusting as you go.

Problem #5: Leadership doesn’t actually commit

This is the big one. Leadership approves the strategy, maybe even gets excited about it, and then goes right back to operating the way they always have. New requests that aren’t in the strategy get approved. Resources get pulled for “urgent” projects. Nobody actually makes the hard choices required to stick to the plan.

Sound familiar? Yeah, me too. That’s where OKRs come in.

What OKRs Actually Are (And What They’re Not)

Let’s get definitional for a second, because there’s a lot of confusion about what OKRs are versus what they’re supposed to do.

Objectives are qualitative, aspirational goals. They answer “what do we want to achieve?” They should be inspiring, directional, and time-bound (usually quarterly or annually).

Example: “Establish our platform as the most reliable in our category”

Key Results are quantitative measures that tell you whether you’re achieving your objective. They answer “how will we know we’re successful?” They should be specific, measurable, and ambitious but achievable.

Example Key Results for the above objective:

  • Achieve 99.95% uptime (from current 99.8%)
  • Reduce P0 incidents by 50%
  • Reach NPS of 50+ for platform reliability

That’s it. That’s the framework. Simple, right?

And yet, here’s what OKRs are NOT:

  • Not a task list. “Launch feature X” is not a key result. It’s an output, not an outcome.
  • Not a performance review. OKRs should be ambitious. You should expect to hit 60-70% of them. If you’re hitting 100%, they weren’t ambitious enough.
  • Not set in stone. Markets change. Priorities shift. OKRs can and should be adjusted if circumstances change dramatically.
  • Not a replacement for strategy. OKRs are how you execute strategy, not the strategy itself.

Clear? Good. Now let’s talk about how to actually use them to keep your tech strategy from becoming chaos.

How OKRs Keep Your Strategy from Becoming a Pumpkin Patch

Here’s the magic of OKRs: They force clarity, alignment, and measurement. Let me break down how:

1. They Force You to Choose

You can’t have 27 objectives. Well, you can, but then they’re meaningless. Most organizations should have 3-5 company-level objectives per quarter, maybe 3-5 more at the team level.

This constraint forces you to answer hard questions:

  • What matters most right now?
  • What are we NOT going to do?
  • What can wait until next quarter?

When I implemented OKRs at my last company, the executive team spent two full days arguing about priorities. It was uncomfortable. People had to let go of their pet projects. But at the end, we had clarity: These three things are what matter. Everything else is secondary.

That clarity eliminated so much noise. Teams could make decisions independently because they understood the priorities. Resources went to initiatives that mattered. The pumpkin patch became a garden.

2. They Create Alignment

One of the biggest problems in tech organizations is that everyone’s working hard on stuff that doesn’t connect. Engineering is building features that product didn’t prioritize. Infrastructure is optimizing systems that aren’t business-critical. Everyone’s rowing, but in different directions.

OKRs create alignment through cascading objectives. Company OKRs inform departmental OKRs, which inform team OKRs. Everyone can see how their work connects to the broader strategy.

Example cascade:

  • Company OKR: Establish our platform as the most reliable in our category
  • Engineering OKR: Reduce system complexity and improve observability
  • Team OKR: Implement distributed tracing across all services

See how each level connects? The team knows exactly why their work matters and how it contributes to the bigger picture. That’s alignment.

3. They Make Success Measurable

“Improve reliability” is fuzzy. “Achieve 99.95% uptime” is measurable. This matters because:

  • You know whether you’re succeeding (no more vague “I think we’re making progress”)
  • You can adjust course if you’re not hitting targets
  • You can celebrate wins when you do hit them
  • You can have objective conversations about performance without it being political

I can’t tell you how many strategic planning sessions I’ve been in where people argue about whether we’re succeeding because there’s no clear measure. OKRs eliminate that ambiguity.

4. They Create a Rhythm for Strategy Review

With OKRs, you have natural checkpoints. Weekly or bi-weekly check-ins on key results. Monthly reviews of progress. Quarterly retrospectives and planning for the next cycle.

This rhythm means your strategy doesn’t sit in a deck gathering dust. It’s a living thing that gets reviewed, adjusted, and acted upon regularly. You catch problems early instead of discovering in December that you’re way off track.

5. They Enable Transparency

When OKRs are visible across the organization (and they should be), everyone knows what everyone else is working toward. This reduces duplication, enables collaboration, and creates accountability.

It also empowers teams to self-organize. If they can see the objectives, they can figure out how to contribute without needing top-down direction for everything.

My Framework for Setting OKRs That Actually Work

Okay, enough theory. Here’s my practical framework for setting OKRs that don’t just sit in a spreadsheet but actually drive behavior and results.

Step 1: Start with Strategy

OKRs should flow from your strategy, not create it. Before you set objectives, be clear on:

  • What’s our strategic direction?
  • What are the big bets we’re making?
  • What capabilities do we need to build?
  • What problems do we need to solve?

If you don’t have a clear strategy, stop. Fix that first. OKRs won’t save a bad strategy; they’ll just help you execute it faster (which is not what you want).

Step 2: Draft Company-Level Objectives

Get your leadership team together and ask: “Given our strategy, what are the 3-5 most important things we need to achieve in the next quarter/year?”

These should be:

  • Qualitative: “Enable rapid product innovation”
  • Inspirational: Something people can rally around
  • Time-bound: Clear timeframe (usually quarterly for tactical, annually for strategic)
  • Achievable but ambitious: Stretch goals, not layups

Common mistake: Making objectives too tactical. “Migrate to Kubernetes” is not an objective. “Achieve platform flexibility that enables sub-24-hour deployments” might be.

Step 3: Define Key Results

For each objective, identify 2-4 key results that will tell you whether you’re achieving it. Ask:

  • How will we know we’re successful?
  • What metrics will change?
  • What outcomes are we driving toward?

Key results should be:

  • Quantitative: Numbers, percentages, metrics
  • Specific: “Increase by 20%” not “increase significantly”
  • Outcome-focused: Not “ship feature X” but “increase user engagement by Y”
  • Ambitious: 60-70% achievement is good

Pro tip: Include a mix of leading indicators (things you can control) and lagging indicators (outcomes you’re driving toward). This gives you early signals about whether you’re on track.

Step 4: Cascade to Teams

Once you have company-level OKRs, each team should create their own OKRs that support the company objectives. The question they’re answering is: “Given our company’s objectives, what’s our team’s contribution?”

This is not a top-down dictation. Teams should have autonomy in how they contribute. Your job as a strategy leader is to:

  • Ensure alignment (their OKRs ladder up to company OKRs)
  • Catch conflicts (two teams going after the same thing or working at cross-purposes)
  • Challenge them to be ambitious

I usually spend time with each team during this process, asking questions, pushing back on mediocrity, helping them think bigger.

Step 5: Socialize and Commit

OKRs don’t work if they’re secret. Once they’re set, make them visible:

  • All-hands presentations
  • Shared in a central location (wiki, dashboard, wherever)
  • Regular references in meetings and communications

And here’s the critical part: Leadership has to commit. That means:

  • Saying no to initiatives that don’t support OKRs
  • Allocating resources to what matters
  • Talking about OKRs in every strategic conversation
  • Modeling the behavior you want to see

If leadership doesn’t walk the talk, OKRs become just another framework that people ignore.

Step 6: Review and Adjust

Set a rhythm for reviewing progress:

  • Weekly/Bi-weekly: Team check-ins on key results
  • Monthly: Cross-functional reviews with leadership
  • Quarterly: Retrospective and planning for next quarter

In these reviews, ask:

  • Are we on track?
  • What’s blocking us?
  • Do we need to adjust course?
  • Do we need to adjust the OKRs themselves?

Remember: OKRs are a tool, not a religion. If circumstances change dramatically, it’s okay to adjust. But you should be thoughtful about it—don’t change OKRs just because they’re hard.

Common OKR Mistakes (And How to Avoid Them)

I’ve seen OKRs implemented dozens of times, and the failure patterns are remarkably consistent. Here are the biggest mistakes and how to avoid them:

Mistake #1: Confusing Outputs with Outcomes

Bad Key Result: “Launch the new API by Q2” Good Key Result: “Enable 50% of enterprise customers to integrate via API, reducing time-to-value by 30%”

See the difference? The first is an output; something you ship. The second is an outcome; the impact you’re trying to create. OKRs should focus on outcomes. If you launch the API and nobody uses it, did you really succeed?

Mistake #2: Setting Too Many OKRs

More is not better. Every objective you add dilutes focus. Every key result you add makes measurement harder. I recommend:

  • 3-5 company objectives max
  • 3-5 department/team objectives max
  • 2-4 key results per objective

If you can’t fit your priorities into this structure, you don’t have a priority problem—you have a strategy problem.

Mistake #3: Making Them Too Easy

If you’re hitting 100% of your OKRs, they’re not ambitious enough. OKRs should stretch you. Hitting 60-70% is actually good performance; it means you set ambitious goals and made significant progress.

I’ve seen teams game this by setting easy OKRs they know they can hit. Don’t do this. You’re only hurting yourself. The point is to reach for something meaningful, not to check boxes.

Mistake #4: Not Connecting to Day-to-Day Work

OKRs fail when they exist separately from how teams actually work. Your sprint planning, your roadmap, your project portfolio; all of it should connect to your OKRs.

In planning meetings, the question should be: “How does this support our OKRs?” If the answer is “it doesn’t,” you need to either reconsider the work or reconsider your OKRs.

Mistake #5: Using Them for Performance Reviews

This kills OKRs faster than anything. If people know their bonus or promotion depends on hitting OKRs, they’ll set safe goals. They’ll sandbag. They’ll game the system.

OKRs are about ambitious goal-setting and alignment. Performance reviews are about evaluating individual performance. These are separate things and should stay that way.

Mistake #6: Not Reviewing Progress

Setting OKRs and then ignoring them until the end of the quarter is pointless. You need regular check-ins to:

  • Track progress
  • Identify blockers
  • Make adjustments
  • Keep them top of mind

If you’re not reviewing OKRs at least monthly (ideally more often), don’t bother setting them.

Mistake #7: Lack of Leadership Buy-In

This is the fatal one. If your CEO says “OKRs are important” but then approves every pet project that comes their way regardless of alignment, OKRs are dead on arrival.

Leadership commitment means:

  • Being willing to say no to good ideas that don’t support OKRs
  • Asking “how does this connect to our OKRs?” in every decision
  • Holding themselves accountable to the framework
  • Being visible about their own OKRs and progress

Without this, you’re just going through the motions.

Real Examples from My Experience

Let me make this concrete with some real examples from companies I’ve worked with (details changed to protect the innocent).

Example 1: SaaS Company Scaling Challenges

Context: Mid-sized SaaS company, growing fast, infrastructure barely keeping up, customer complaints about performance increasing.

Objective: Deliver enterprise-grade reliability and performance

Key Results:

  • Achieve 99.95% uptime across all services (from 99.7%)
  • Reduce P1 incidents from 12/month to 3/month
  • Decrease average API response time from 300ms to 100ms
  • Reach infrastructure cost per customer of $50 (from $85)

What happened: They hit 99.9% uptime (not quite 99.95%, but massive improvement), reduced P1 incidents to 4/month, hit the API response time goal, and got cost per customer to $60. Overall grade: 75% achievement, which is actually excellent.

Why it worked: The objective was clear and aligned with the biggest business risk (losing customers due to reliability issues). The key results were specific enough to drive concrete work but outcomes-focused (not “migrate to X infrastructure”). Everyone could see how their work contributed.

Example 2: Tech Company Trying to Move Upmarket

Context: Product was designed for small businesses, now trying to land enterprise customers, but enterprise buyers kept saying “you’re not ready for us.”

Objective: Become enterprise-ready

Key Results:

  • Achieve SOC 2 Type II certification
  • Enable SSO and advanced role-based access controls
  • Reduce onboarding time for 1000+ seat customers from 90 days to 30 days
  • Close 5 deals with companies >$1B revenue

What happened: They got SOC 2, implemented the security features, got onboarding time down to 45 days (not 30, but significant improvement), and closed 3 enterprise deals (not 5, but these were $2M+ deals that changed the trajectory of the company).

Why it worked: The objective captured what they really needed (credibility with enterprise buyers), and the key results were a mix of capabilities (certifications, features) and outcomes (faster onboarding, actual deals). It focused the entire company on a single strategic priority for two quarters.

Example 3: Engineering Team Drowning in Technical Debt

Context: Fast-growing startup, moved incredibly fast for three years, now the codebase was a mess and slowing them down.

Objective: Build a sustainable engineering foundation

Key Results:

  • Reduce deployment frequency from weekly to daily
  • Decrease production bugs by 40%
  • Achieve 80% code test coverage (from 45%)
  • Reduce average time to onboard new engineers from 6 weeks to 3 weeks

What happened: This one was harder. They got to 3x weekly deployments (not daily), reduced bugs by 25%, got test coverage to 65%, and onboarding time to 4 weeks. Overall achievement: about 60%.

Why it worked anyway: Even though they didn’t hit all targets, the progress was significant and the direction was right. More importantly, the OKRs gave them permission to invest in technical debt instead of just features. They could say “this refactoring supports our OKR” and get executive buy-in.

How to Get Started (Even If Your Organization Has Never Done OKRs)

If you’re reading this thinking “this sounds great but my organization doesn’t do OKRs,” here’s how to start:

Option 1: Start with Your Team

You don’t need company-wide adoption to get value from OKRs. Start with your own team:

  • Set 2-3 objectives for your team for the quarter
  • Define key results
  • Review weekly in your team meetings
  • Share results with stakeholders

Once people see the clarity and focus it creates, they’ll want it too. Then you can expand.

Option 2: Pilot with Leadership

Get your executive team together for a half-day session. Walk them through the framework. Set company-level OKRs for one quarter as an experiment.

Frame it as: “Let’s try this for 90 days and see if it helps us execute more effectively.” Most leaders will agree to a time-boxed experiment.

Option 3: Tie It to Strategy Planning

If you’re doing annual or quarterly strategic planning anyway, introduce OKRs as the framework for executing the strategy. This feels less like “new process” and more like “better way to do what we’re already doing.”

Start Simple

Don’t try to implement the perfect OKR process on day one. Start with:

  • Clear objectives
  • Measurable key results
  • Regular check-ins
  • Retrospective at the end

That’s it. You can add sophistication later (cascading OKRs, more formal review processes, tools and dashboards). But the basics will get you 80% of the value.

Tools and Resources (What Actually Helps)

You don’t need fancy tools to do OKRs, but some things make it easier:

For tracking:

  • Spreadsheets work fine for small teams
  • Notion, Asana, or similar for more structure
  • Dedicated OKR tools (Lattice, 7Geese, Perdoo) if you’re at scale

For learning:

  • “Measure What Matters” by John Doerr (the OG OKR book)
  • Google’s OKR playbook (free online, very practical)
  • Re:Work guide from Google (also free, excellent)

For workshops:

  • Bring in a facilitator for your first OKR-setting session if budget allows
  • The framework is simple, but having someone guide the conversation helps
  • Once you’ve done it once, you can run it yourself

The Quarterly Rhythm That Keeps It Working

Here’s the rhythm I recommend for keeping OKRs alive and effective:

Week 1 of Quarter:

  • Leadership sets/reviews company OKRs
  • Teams draft their OKRs aligned to company objectives
  • Feedback and iteration

Week 2:

  • Finalize all OKRs
  • All-hands presentation of company OKRs
  • Team presentations of how they’re contributing

Weeks 3-11:

  • Weekly team check-ins on key results
  • Monthly cross-functional reviews
  • Adjust course as needed

Week 12:

  • Retrospective: What did we achieve? What did we learn?
  • Scoring: Grade your OKRs (I use 0.0-1.0 scale)
  • Celebrate wins
  • Identify what to carry forward vs. what’s done

Week 13 (or last week of previous quarter):

  • Start planning next quarter’s OKRs
  • Use learnings from retrospective
  • Align with annual strategy

This rhythm creates predictability and keeps OKRs from becoming a “set it and forget it” exercise.

When OKRs Aren’t the Answer

Real talk: OKRs aren’t always the solution. They work best when:

  • You have reasonable strategic clarity
  • Leadership is bought in
  • You have capacity to review and adjust regularly
  • You’re willing to say no to things that don’t align

OKRs might not be right if:

  • You’re in crisis mode (sometimes you just need to survive)
  • Your strategy is completely unclear (fix that first)
  • Leadership isn’t willing to commit (don’t waste the effort)
  • You don’t have the discipline for regular reviews (they’ll just become noise)

It’s okay to acknowledge OKRs aren’t right for your situation right now. Better to do something simpler that you’ll actually maintain than implement OKRs halfheartedly.

The Bottom Line: From Pumpkin Patch to Garden

Here’s what I’ve learned after years of using OKRs to execute tech strategy: The framework itself is less important than the discipline it creates.

OKRs force you to:

  • Choose what matters most
  • Define success clearly
  • Review progress regularly
  • Adjust based on what you learn

Without this discipline, your tech strategy becomes a pumpkin patch—lots of stuff growing in different directions, some of it useful, much of it not, and nobody quite sure which pumpkins (projects) you were actually trying to grow in the first place.

With OKRs, you transform that patch into a garden. Still complex, still requiring constant attention, but organized. Intentional. With clear paths between the rows and a harvest plan that everyone understands.

Your strategy stops being a document that people reference twice a year and becomes a living framework that guides daily decisions. Your teams stop wondering if their work matters and start seeing exactly how they contribute. Your leadership stops having circular debates about priorities and starts having concrete conversations about progress.

Is it perfect? No. Does it solve every problem? Definitely not. But it’s the difference between strategic chaos and strategic execution. And in tech, where the pace of change is relentless and the pressure to deliver is constant, that difference is everything.

So take a look at your tech strategy. Is it a pumpkin patch or a garden? If it’s the former, maybe it’s time to give OKRs a shot. Your October harvest (and every harvest after) will thank you.

Now if you’ll excuse me, I have Q4 OKR planning to do. These objectives won’t define themselves.

Why Cybersecurity Should Be Your October Obsession (Besides Pumpkin Spice)

October is here, which means three things are inevitable: pumpkin spice everything, premature holiday marketing, and – if you’re a tech leader paying attention – Cybersecurity Awareness Month. I know, I know. The first two are way more fun. But stick with me, because if you think cybersecurity is just for your IT security team, I have some uncomfortable news for you.

As someone who’s led tech teams through two ransomware scares (one of which was very, very real), multiple phishing attacks that almost took down our CEO, and the constant barrage of “your password has been found in a data breach” notifications, I can tell you this: October isn’t just about celebrating cybersecurity awareness. It’s about getting ahead of the nightmare scenarios that keep me up at night more than any horror movie ever could.

So pour yourself that pumpkin spice latte, get comfortable, and let’s talk about why cybersecurity should be your obsession this month—and every month after.

The Wake-Up Call I Had (So You Don’t Have To)

Two years ago, on a perfectly ordinary Tuesday morning, I walked into the office and our VP of Engineering met me at the door with three words that made my stomach drop: “We’ve been breached.”

For context, I was leading a mid-sized SaaS company. We had security measures. We did annual training. We had a security team. We thought we were reasonably protected. We were wrong.

A senior engineer – smart, experienced, should-have-known-better – clicked on a very sophisticated phishing email that appeared to come from our CEO. Within 20 minutes, attackers had access to our internal systems. Within an hour, they’d started moving laterally through our network. By the time we caught it (thanks to an alert security engineer who noticed unusual activity), they’d accessed customer data and internal documents.

The next 72 hours were a blur of incident response, customer notifications, legal calls, PR management, and existential dread. The financial cost was significant—six figures for remediation, legal fees, credit monitoring for affected customers, and security upgrades. The reputational cost was worse. We lost three major customers and spent the next year rebuilding trust.

But here’s what really haunted me: It was completely preventable. Not through some expensive, enterprise-level security solution we couldn’t afford. Through better awareness, better processes, and better leadership around security.

That was my wake-up call. Don’t wait for yours.

Why October Matters (Beyond the Marketing)

October is Cybersecurity Awareness Month, which sounds like one of those made-up awareness months that nobody actually cares about. But there’s a reason it exists, and a reason smart tech leaders lean into it.

First, it’s a forcing function. We’re all busy. Security often falls into the “important but not urgent” category until it becomes urgently important (usually at the worst possible time). Having a designated month gives you permission—no, an obligation—to prioritize it.

Second, it’s a cultural moment. Everyone’s talking about cybersecurity in October. There are campaigns, resources, training materials. It’s easier to get buy-in from your team when the broader tech community is already having the conversation.

Third, it aligns with year-end planning. Q4 is when you’re planning budgets, priorities, and initiatives for next year. If you use October to assess your security posture, you can make informed decisions about where to invest in 2026.

But honestly? The real reason October matters is that cybersecurity threats don’t take breaks. They’re happening right now, as you read this. And if you’re not actively thinking about security, you’re passively accepting risk.

The Biggest Cybersecurity Myths Tech Leaders Believe

Before we talk about what to do, let’s bust some myths that I hear constantly from otherwise smart tech leaders:

Myth 1: “We’re too small to be a target”

This is the most dangerous myth out there. Attackers don’t just go after Fortune 500 companies. In fact, small and mid-sized companies are often easier targets because they have weaker defenses. Ransomware attacks are increasingly automated; attackers cast a wide net and hit whoever they can.

I’ve seen attacks on companies with 20 employees. Size doesn’t matter. If you have data that’s valuable (and you do), you’re a target.

Myth 2: “Security is IT’s job”

Security is everyone’s job, starting with leadership. Your security team can build the best technical defenses in the world, but if your employees are clicking on phishing emails, using “Password123” for everything, and sharing credentials, your defenses mean nothing.

As a leader, your job is to create a culture where security is part of how everyone works, not an afterthought or an IT problem.

Myth 3: “We have insurance, so we’re covered”

Cyber insurance is great. You should have it. But it doesn’t prevent attacks, and it doesn’t cover everything. It won’t cover your reputational damage. It won’t prevent customer churn. It won’t undo the operational chaos of responding to an incident.

Insurance is your safety net, not your strategy.

Myth 4: “Our security is fine; we haven’t been attacked”

That you know of. Many breaches go undetected for months. Some companies only find out they’ve been compromised when their data shows up on the dark web or when ransomware finally activates.

The absence of evidence isn’t evidence of absence. Get an assessment done if you haven’t recently.

Myth 5: “Security slows us down”

Bad security slows you down. Good security is invisible and enables you to move fast with confidence. When you have strong security practices, you don’t have to stop every project to assess risk from scratch. You don’t have to slow down product releases for security reviews at the last minute. You build security in from the start, and it becomes part of your velocity.

What Actually Keeps Tech Leaders Up at Night (Security Edition)

Let me get specific about the security threats that should be on your radar as a tech leader:

1. Phishing and Social Engineering

This is still the #1 attack vector, and it’s getting scarily sophisticated. We’re talking emails that perfectly mimic your CEO’s writing style, fake video calls using deepfakes, text messages that look exactly like they’re from your bank.

The attack that almost got us? The email was nearly perfect. Right tone, right signature, plausible request. The only tell was a slightly off email address that the engineer didn’t notice because he was in a hurry.

What to do: Regular training isn’t enough. You need simulated phishing campaigns, real-time feedback when someone clicks something they shouldn’t, and a culture where it’s okay to verify weird requests even if they seem to come from executives.

2. Ransomware

Ransomware attacks have become more targeted and more devastating. Attackers now exfiltrate your data before encrypting it, so even if you have backups, they can still threaten to release your sensitive data publicly.

The ransom amounts are also getting smarter. Attackers research your company’s revenue and set ransoms at amounts they think you can afford to pay. They’re running this like a business.

What to do: Offline backups (seriously, offline), incident response plans that you actually test, and endpoint protection. Also, make a decision now about your ransom payment policy so you’re not making that call under pressure.

3. Supply Chain Attacks

Remember the SolarWinds breach? That was a wake-up call about supply chain risk. You can have perfect security, but if your vendor gets compromised, you’re compromised.

Every third-party tool you use, every API you integrate, every vendor who has access to your systems; they’re all potential attack vectors.

What to do: Vendor security assessments, limited access (principle of least privilege), and monitoring for unusual activity from third-party integrations. Also, know what’s in your software supply chain—what open source dependencies you’re using, where they come from, who maintains them.

4. Insider Threats

Not everyone is malicious, but people make mistakes. They leave their laptop unlocked. They share credentials. They copy sensitive data to personal devices. And yes, occasionally, someone is actually malicious—a disgruntled employee exfiltrating data on their way out.

What to do: Access controls, monitoring for unusual data access patterns, offboarding processes that actually work, and background checks for roles with access to sensitive data. Also, treat your people well—most insider threats come from employees who feel wronged.

5. Cloud Misconfiguration

Moving to the cloud is great for so many reasons, but it introduces new security challenges. An S3 bucket set to public instead of private. A database without proper authentication. A misconfigured firewall rule that exposes your entire network.

These misconfigurations are embarrassingly common and often go unnoticed until someone (hopefully you, not an attacker) discovers them.

What to do: Regular security audits of your cloud infrastructure, infrastructure-as-code so security is standardized and reviewable, and tools that alert you to misconfigurations. Also, training for your engineers on cloud security best practices.

Your October Cybersecurity Action Plan

Okay, enough doom and gloom. Let’s talk about what you can actually do this month to level up your security posture. I’m breaking this into four weeks so it’s manageable alongside everything else you’re juggling.

Week 1: Assess Where You Actually Are

You can’t improve what you don’t measure. This week is about getting an honest picture of your current security posture.

Actions:

  • Conduct a security audit (bring in an outside firm if you can afford it, use a framework like CIS Controls if you can’t)
  • Review access controls (who has access to what? Is it appropriate? Are there former employees still in your systems?)
  • Check your backups (when was the last time you actually tested a restore?)
  • Inventory your data (what sensitive data do you have? Where is it? Who can access it?)
  • Review vendor security (have you actually read the security section of your vendor contracts?)

This isn’t fun work, but it’s essential. You’re looking for gaps, risks, and vulnerabilities. Document everything.

Week 2: Address Your Highest Risks

Based on your assessment, you probably found some things that made you uncomfortable. This week, triage and start addressing the highest risks.

Actions:

  • Fix critical vulnerabilities (unpatched systems, misconfigured access controls, obvious security gaps)
  • Implement MFA everywhere (if you haven’t already, this should be your #1 priority; Multi-factor authentication stops most attacks)
  • Review and update your incident response plan (you have one, right? If not, create a basic one)
  • Conduct a tabletop exercise (gather your leadership team and walk through what you’d do if you were breached tomorrow)
  • Update your password policies (require strong passwords, use a password manager, rotate credentials for sensitive systems)

Focus on quick wins that significantly reduce risk. You don’t have to solve everything this week, but you should address anything that could lead to a catastrophic breach.

Week 3: Invest in Your People

Technology is important, but people are your first and last line of defense. This week is about leveling up your team’s security awareness and capabilities.

Actions:

  • Launch security awareness training (make it engaging, not just a boring compliance video)
  • Run a simulated phishing campaign (see who clicks, provide immediate feedback, don’t shame people)
  • Create a security champions program (identify people across teams who can be security advocates)
  • Host a “security office hours” (let people ask questions without judgment)
  • Share real examples (talk about recent breaches in your industry, make it concrete)

The goal is to shift culture. Security should be something everyone thinks about, not just IT. And people need to feel safe reporting mistakes or suspicious activity without fear of punishment.

Week 4: Plan for Continuous Improvement

Security isn’t a one-month project. This week is about setting up systems for ongoing security management.

Actions:

  • Schedule regular security reviews (monthly or quarterly, depending on your size and risk)
  • Allocate budget for 2026 (security tools, training, assessments, insurance)
  • Establish security metrics (what will you track? Time to patch vulnerabilities? Phishing click rates? Incident response time?)
  • Create a roadmap (what security improvements will you make in the next 12 months?)
  • Document everything (policies, procedures, incident response plans—get it written down)

The companies that do security well don’t do one big initiative and then forget about it. They build security into their operational rhythm.

Quick Wins That Make a Big Difference

If you only have time to do a few things this month, do these. They’re high-impact, relatively easy to implement, and will significantly reduce your risk:

  1. Enable MFA on everything (email, cloud services, admin accounts, VPNs, everything)
  2. Implement a password manager (and require your team to use it)
  3. Patch your systems (yes, I know it’s annoying, but unpatched vulnerabilities are low-hanging fruit for attackers)
  4. Limit admin privileges (not everyone needs admin access; use the principle of least privilege)
  5. Encrypt sensitive data (at rest and in transit)
  6. Test your backups (actually restore something to make sure they work)
  7. Review who has access to what (remove access for people who’ve left or changed roles)
  8. Set up security alerts (unusual login activity, failed login attempts, large data transfers)

None of these are sexy. All of them work.

How to Talk to Your Board/Executives About Security

One challenge I hear constantly from tech leaders: “I know we need to invest in security, but I can’t get buy-in from leadership.”

Here’s how to frame it in a way that gets attention:

Don’t lead with technical details. Your board doesn’t care about firewalls and encryption protocols. They care about business risk.

Talk about business impact. “A ransomware attack would shut down our operations for days and could cost us $X million in lost revenue, remediation costs, and legal fees. We have customers who contractually require certain security standards. A breach could result in customer churn, regulatory fines, and reputational damage that takes years to recover from.”

Benchmark against competitors. “Companies our size in our industry are typically spending 3-5% of their IT budget on security. We’re at 1%. That gap is a business risk.”

Frame it as enabling growth. “Investing in security allows us to pursue enterprise customers who require SOC 2 compliance. It enables us to move faster because we’re not constantly putting out fires. It protects the business we’ve built.”

Show the math. “The cost of prevention is $X. The cost of a breach is $Y (typically 10-100x more). This is insurance we can’t afford not to have.”

Make it tangible. Share recent breach stories from companies similar to yours. Use real numbers. Make it clear that this isn’t hypothetical, it’s a when, not if scenario.

And if you’re really struggling to get buy-in? Bring in an outside expert for an hour. Sometimes leadership needs to hear it from someone external to take it seriously.

The Security-First Culture You’re Building

Here’s what I’ve learned: Great security isn’t about having the best tools or the biggest security team. It’s about culture.

In a security-first culture:

  • People feel comfortable reporting mistakes without fear of punishment
  • Security is part of the development process, not an afterthought
  • Employees understand their role in keeping the company safe
  • Leadership models good security behavior (yes, that means you need to use MFA and strong passwords too)
  • Security concerns are taken seriously and addressed promptly
  • There’s ongoing training and awareness, not just annual compliance checkboxes

Building this culture doesn’t happen overnight, but October is a great time to start. Use the momentum of Cybersecurity Awareness Month to kickstart conversations, initiatives, and changes that will outlast the month.

What to Do When (Not If) Something Goes Wrong

Despite your best efforts, something will go wrong at some point. Someone will click a phishing email. A vulnerability will be exploited. A vendor will be compromised. The question isn’t if you’ll face a security incident; it’s how you’ll respond when you do.

Here’s your basic incident response framework:

1. Contain the damage. Isolate affected systems immediately. Cut off the attacker’s access. Don’t worry about preserving evidence or understanding exactly what happened—first priority is stopping the bleeding.

2. Assess the impact. What systems were affected? What data was accessed? Who needs to be notified? What’s the business impact?

3. Notify the right people. Your incident response plan should have a clear escalation path. Who needs to know immediately? Your security team, your legal team, your PR team, potentially your customers and regulators.

4. Investigate. Once you’ve contained the damage, figure out what happened. How did they get in? What did they access? How long were they there? This informs both your immediate response and your long-term improvements.

5. Recover. Restore systems from clean backups, reset credentials, patch vulnerabilities, implement additional controls. Make sure you’re actually removing the attacker’s access, not just their initial entry point.

6. Learn. Conduct a post-incident review. What worked? What didn’t? What processes do you need to update? What technical controls do you need to add? How will you prevent this from happening again?

7. Communicate. Keep stakeholders informed throughout the process. Be transparent about what happened, what you’re doing about it, and what they should do. People appreciate honesty, even when it’s uncomfortable.

The teams that handle incidents well are the ones who’ve practiced. That’s why tabletop exercises matter—you’re building muscle memory for crisis response.

The ROI of Security (Because Someone Will Ask)

Security is often seen as a cost center, which makes it hard to justify investment. But here’s how I think about the ROI:

Direct cost avoidance: The average cost of a data breach in 2024 was $4.88 million. If you spend $100K on security and avoid one breach, that’s a 48x return. Even if you only reduce the impact of a breach by 50%, the ROI is clear.

Revenue enablement: Many enterprise customers won’t even talk to you without certain security certifications. SOC 2, ISO 27001, GDPR compliance—these aren’t just checkboxes, they’re requirements for accessing entire market segments.

Operational efficiency: Good security means fewer incidents, less downtime, less time spent on remediation. Your engineers can focus on building products instead of cleaning up security messes.

Risk reduction: This is harder to quantify but no less real. The value of not having your company’s name in headlines for a breach. The value of not losing customers. The value of sleeping at night.

Competitive advantage: In an industry where breaches are common, strong security is a differentiator. You can market it. You can use it in sales conversations. It builds trust.

I’ve never had a CEO regret investing in security. I’ve had plenty regret not investing enough, but usually only after they’ve learned that lesson the hard way.

Your October Challenge

Here’s my challenge to you: Make security your obsession for the rest of October. Not in an anxious, paranoid way, but in an intentional, proactive way.

Spend time learning about the threats your organization faces. Have conversations with your security team (or hire one if you don’t have one). Walk through scenarios. Ask uncomfortable questions. Look at your systems through an attacker’s eyes.

And then take action. Even if it’s small. Even if it’s not perfect. Every improvement matters.

Because here’s the truth: The pumpkin spice lattes will be gone by November. The Halloween decorations will come down. But the cybersecurity threats? They’ll still be here. And they’ll be here in November, and December, and every month after.

Make October the month you stop treating security as someone else’s problem and start treating it as the fundamental business imperative it is.

Your future self – the one who doesn’t have to deal with a catastrophic breach – will thank you.

Now go forth and obsess. Just maybe grab that pumpkin spice latte first. You’re going to need the caffeine.

Coaching Clients Through the Great Tech Pivot: Stay Ahead or Stay Behind

Let me tell you about three conversations I had last week. Client A: Ten years as a QA engineer, worried her manual testing skills are becoming obsolete. Client B: Mid-level product manager, paralyzed by whether to go deeper into product or pivot to AI/ML product management. Client C: Senior engineering manager, watching her peers get promoted into VP roles while she’s been passed over twice.

Three different people, three different situations, one common thread: They’re all at inflection points in tech careers that are shifting faster than anyone predicted. And honestly? These conversations are my entire week, every week, right now.

If you’re a career counselor in tech in 2025, you’re not just helping people polish their resumes or prep for interviews anymore. You’re helping them navigate an industry in the middle of the most dramatic transformation since the internet itself. The ground is moving under everyone’s feet, and the question isn’t “should I pivot?” It’s “how do I pivot before the platform I’m standing on disappears?”

Let me share what I’m seeing from the front lines of career coaching in tech, and more importantly, how I’m helping my clients not just survive but actually thrive through the chaos.

The Great Tech Pivot: What’s Actually Happening

First, let’s get clear on what we’re dealing with, because “tech is changing” is about as useful as saying “water is wet.” Here’s what I’m seeing:

The AI Reshuffling

This is the big one. AI isn’t just a new tool; it’s fundamentally reshaping what roles exist and what skills matter. Roles that were safe six months ago are now “at risk.” Skills that were valuable are becoming commoditized. And entirely new roles are emerging faster than universities can create programs for them.

I’ve got clients in their 40s who’ve been developers for 20 years asking me if they need to become AI engineers. I’ve got designers wondering if their entire profession is about to be automated. I’ve got project managers trying to figure out if they should lean into AI product management or double down on the human side of project leadership.

The truth? It’s both terrifying and full of opportunity, depending on how you approach it.

The Experience Paradox

Here’s something wild: I’m seeing senior people struggle to get jobs they’re overqualified for, while junior people with the right AI/ML skills are getting offers that would’ve gone to someone 10 years their senior. Experience matters less than adaptability right now, and a lot of experienced tech professionals don’t know how to translate their deep expertise into this new landscape.

The Remote/Hybrid Whiplash

Just when everyone adjusted to remote work, companies started pushing return-to-office. Then they partially backed off. Now it’s this weird hybrid situation where nobody’s sure what the rules are. My clients are constantly asking: “Should I only look at remote roles? Am I limiting myself? Will I be deprioritized if I’m remote?”

There’s no clear answer, which makes career planning even harder.

The Generational Tension

Gen Z is entering the workforce with AI-native skills and different expectations. Millennials are in their leadership years but feeling squeezed. Gen X is wondering if they’ll make it to retirement or get aged out. Boomers who stayed in tech longer than expected are finding fewer soft landing spots.

Every generation is dealing with its own version of “how do I stay relevant?”

The Pivot Mindset: What Separates Those Who Thrive from Those Who Get Left Behind

After coaching hundreds of tech professionals through career transitions, I’ve noticed patterns. The people who successfully pivot—who not only survive but come out ahead—share certain mindsets and behaviors. Here’s what I’ve learned:

1. They Act Before They Have To

The clients who struggle the most are the ones who wait until they’re laid off, passed over, or desperately unhappy before they start thinking about their next move. By then, they’re operating from fear and scarcity, which never leads to good decisions.

The ones who thrive? They’re what I call “proactive pivoters.” They see the writing on the wall and start positioning themselves six months to a year before they need to. They’re building new skills while they still have stable income. They’re expanding their network before they need to activate it. They’re exploring options while they still have leverage.

I had a client who was a senior iOS developer. She saw the market shifting and spent six months learning cross-platform development and cloud architecture; all while still employed. When her company started layoffs, she was already interviewing for roles that paid 20% more than what she was making. That’s not luck; that’s strategy.

2. They Embrace “And,” Not “Or”

One of the biggest mistakes I see is people thinking they have to completely abandon their expertise to stay relevant. A developer thinks they need to become a data scientist. A project manager thinks they need to become a product manager. A designer thinks they need to learn to code.

Sometimes that’s true, but more often, the opportunity is in the intersection. The clients who crush it are the ones who figure out how to be “X and Y”:

  • Developer AND AI implementation specialist
  • Project manager AND change management expert
  • Designer AND AI/UX researcher
  • QA engineer AND automation architect

You don’t have to throw away your expertise. You need to augment it with what’s emerging. That’s where the unique value is, because not many people have both.

3. They Get Comfortable Being Uncomfortable

This is the hardest one, especially for people who’ve been successful for years. Learning new things means being bad at them for a while. Pivoting means uncertainty. Adapting means admitting what you don’t know.

I’ve watched senior engineers nearly have breakdowns in coaching sessions because they’re used to being the expert, and now they’re asking junior people for help with AI tools. It’s humbling. It’s uncomfortable. And it’s absolutely necessary.

The clients who make it through are the ones who can reframe discomfort as growth. They don’t see “I don’t know” as failure—they see it as the starting point for learning.

4. They Build Anti-Fragile Careers

Nassim Taleb talks about anti-fragility; systems that don’t just survive shocks but actually get stronger from them. I’m coaching my clients to build anti-fragile careers.

What does that look like?

  • Multiple income streams (full-time job plus consulting, side projects, or passive income)
  • Transferable skills that work across industries
  • Networks that span companies and sectors
  • Personal brands that exist independently of their current employer
  • Learning habits that keep them perpetually current

When you’re anti-fragile, layoffs aren’t catastrophic; they’re redirections. Market shifts aren’t threats; they’re opportunities to deploy different parts of your skillset. You’re not dependent on one company, one role, or one version of the tech industry.

My Framework for Coaching Through Pivots

Every client is different, but I use a consistent framework to help people navigate career pivots. Here’s the playbook:

Phase 1: Reality Check (Weeks 1-2)

Before we talk about where you’re going, we need to get brutally honest about where you are. I ask:

Market Reality:

  • How in-demand is your current role/skillset?
  • What’s the trajectory? Growing, stable, or declining?
  • What are comparable roles paying?
  • What skills are employers actually asking for?

I have clients do market research; real research, not just vibes. Look at 50 job postings for your role. What shows up in requirements again and again? What’s listed as “nice to have” that’s actually becoming required?

Personal Reality:

  • What do you actually enjoy doing? (Not what you’re good at, what you enjoy)
  • What are your non-negotiables? (Salary, flexibility, impact, etc.)
  • What are you willing to invest? (Time, money, discomfort)
  • What’s your runway? (How long can you afford to make this transition?)

This phase is uncomfortable because it often reveals that what you thought was true about your career isn’t. But you can’t navigate to a destination if you don’t know where you’re starting from.

Phase 2: Exploration (Weeks 3-6)

Now we explore options. Not committing to anything yet, just opening up possibilities. This includes:

Informational interviews: I have clients reach out to 10-15 people in roles they’re curious about. Not to ask for jobs, but to understand what the day-to-day looks like, what skills matter, what the path forward is.

Skills assessment: What do you have? What do you need? What’s the gap? Be specific. “I need to learn AI” is too vague. “I need to understand how to integrate LLMs into existing products” is actionable.

Experimentation: Can you do a small project in the direction you’re considering? Can you volunteer for a cross-functional initiative? Can you take a course or build something to test your interest and aptitude?

The goal here is to move from “I think I might want to do X” to “I’ve tested X enough to know if it’s right for me.”

Phase 3: Strategy (Weeks 7-10)

Based on reality and exploration, we build a concrete strategy. This includes:

The target: What role/company/opportunity are you aiming for? Be specific.

The gaps: What’s standing between you and that target? Skills, experience, network, credibility?

The plan: How will you close those gaps? What’s the timeline? What are the milestones?

The story: How will you talk about this pivot in interviews? Your narrative needs to make sense; not as “I’m desperate and will take anything” but as “this is a strategic evolution of my career.”

This is where I push clients to be realistic but ambitious. You don’t have to start over from scratch, but you also can’t just update your LinkedIn and hope something changes.

Phase 4: Execution (Weeks 11+)

Now we execute the plan. This is where most people fall off, because execution is hard and takes sustained effort. My job is to be the accountability partner and coach through the obstacles.

This phase includes:

  • Building new skills (courses, projects, certifications)
  • Updating your brand (LinkedIn, portfolio, resume)
  • Activating your network (reaching out, sharing your pivot story)
  • Applying strategically (not spray-and-pray, but targeted outreach)
  • Interviewing and negotiating (practicing, getting feedback, improving)

I’m checking in weekly, reviewing progress, troubleshooting obstacles, and keeping momentum going. Because the difference between people who successfully pivot and people who stay stuck is usually just sustained action over time.

Common Pivot Scenarios I’m Seeing (And How to Navigate Them)

Let me get specific about the pivot scenarios I’m coaching through most often right now:

Scenario 1: “My Role is Being Automated”

The Panic: QA engineers, junior developers, customer support specialists, data entry roles; anywhere that involves repetitive tasks, people are worried AI is coming for their jobs.

The Reality: Some roles will be automated. Some will be augmented. Some will evolve. The question is which category yours falls into and how you position yourself.

The Strategy:

  • If augmented: Become the expert in using AI tools to do your job 10x better
  • If evolving: Identify the human elements that can’t be automated (judgment, strategy, relationships) and lean into those
  • If automated: Use your domain expertise to move into adjacent roles where human judgment is still critical

Example: I had a QA engineer who was terrified about AI-powered testing. Instead of fighting it, she became the go-to person for implementing and optimizing AI testing tools. Now she’s a QA automation architect making 40% more than she was before.

Scenario 2: “I’m Stuck at My Level”

The Panic: You’ve been a senior engineer/manager/IC for 3-5 years. You keep getting passed over for staff/principal/director roles. You’re not sure what you’re doing wrong.

The Reality: Getting to the next level requires different skills than what got you here. You need visibility, strategic thinking, influence, and often a sponsor.

The Strategy:

  • Identify what’s actually holding you back (ask for specific feedback)
  • Build the missing skills deliberately
  • Increase your visibility (share your work, speak up in meetings, document wins)
  • Find a sponsor (not a mentor, a sponsor—someone who advocates for you when you’re not in the room)
  • Sometimes, move companies (it’s often easier to level up by switching than by waiting)

I’ve had multiple clients get promoted within 6 months of implementing this strategy because they finally understood the game they were playing.

Scenario 3: “Should I Go Into Management?”

The Panic: You’re a senior IC. People keep suggesting management. You’re not sure if you want it, but you’re worried you’ll hit a ceiling if you don’t take it.

The Reality: Management is a career change, not a promotion. It requires different skills, different work, and different energy. And there are now IC tracks that go just as high in many companies.

The Strategy:

  • Get clear on what you actually want your day-to-day to look like
  • If you’re genuinely interested in management, test it (lead a project, mentor interns, manage a small initiative)
  • If you’re not interested, actively pursue the IC track and get explicit about career progression
  • Don’t let fear of a ceiling push you into a role you’ll hate

I’ve coached people in both directions, and the ones who are happy are the ones who chose based on what they want to do, not what they think they’re “supposed” to do.

Scenario 4: “I Want Out of Tech (But I’m Scared)”

The Panic: You’ve been in tech for years, you’re burned out, you’re not excited anymore, but the money is good and you’re not sure what else you’d do.

The Reality: Your tech skills are transferable to tons of non-tech roles and industries. But you need to figure out what you’re moving toward, not just what you’re running from.

The Strategy:

  • Explore what actually lights you up (coaching, teaching, consulting, creative work, social impact?)
  • Look for bridge roles (tech-adjacent but different enough to scratch the itch)
  • Build a financial runway (save aggressively so you can afford to take a pay cut if needed)
  • Test your new direction while still employed (side projects, volunteer work)

I worked with a client who left a $300K engineering role to become a technical consultant for nonprofits. She took a pay cut but is happier than she’s been in years. But she didn’t just quit—she spent a year exploring, testing, and setting up her finances to make it work.

The Skills That Matter Most in 2025 (Regardless of Your Pivot)

No matter what direction my clients are pivoting, there are certain skills I’m encouraging everyone to build:

AI Literacy (not expertise, literacy): You need to understand what AI can and can’t do, how to work with AI tools, and how to think about AI in your domain. This doesn’t mean you need to build neural networks. It means you need to not be intimidated by AI and know how to leverage it.

Systems Thinking: Tech is increasingly complex and interconnected. The ability to see how pieces fit together, how changes ripple through systems, and how to solve problems holistically is incredibly valuable.

Communication Across Contexts: The ability to translate between technical and non-technical, between different functions, between strategy and execution. This has always been valuable; it’s now essential.

Strategic Thinking: Moving from “how do I execute this?” to “what should we be doing and why?” is what separates senior people from everyone else. Practice thinking strategically, even if it’s not your job yet.

Learning Agility: The meta-skill. Can you learn new things quickly? Can you adapt to new contexts? Can you unlearn old patterns that no longer serve you? This is the skill that makes all other skills possible.

What I Tell Every Client (My Real-Talk Moment)

At some point in our coaching relationship, usually when someone is in the valley of despair between starting a pivot and seeing results, I give them this speech:

“The tech industry owes you nothing. Your company owes you nothing. Your past success guarantees nothing about your future success. That sounds harsh, but it’s liberating. Because it means your career is entirely in your hands. You can wait for someone to take care of you, or you can take care of yourself. You can hope the world doesn’t change, or you can change with it. You can see this as a threat, or you can see it as the biggest opportunity of your career to reinvent yourself on your terms.

The people who are thriving right now aren’t necessarily the smartest or most talented. They’re the ones who saw change coming and got ahead of it. They’re the ones who invested in themselves before they had to. They’re the ones who weren’t afraid to look stupid while learning something new.

You can do this. But only if you start now.”

Some clients cry during this speech. Some get angry. Some sit quietly and nod. But they all start taking action after, because sometimes you need someone to tell you the truth with love.

Your Action Plan: What to Do This Month

Okay, enough theory. Here’s what you should do in the next 30 days if you’re contemplating a pivot:

Week 1: Assess

  • Research 25 job postings in your current role. What skills keep showing up?
  • Research 25 job postings in roles you’re interested in. What’s different?
  • Talk to three people in your network about what they’re seeing in the market
  • Write down your current market value (be honest)

Week 2: Explore

  • Identify three possible directions for your pivot
  • Reach out to one person in each direction for an informational interview
  • Take one course or complete one tutorial in a skill you’re curious about
  • Journal about what excites you and what drains you in your current work

Week 3: Plan

  • Based on your exploration, pick one direction to focus on
  • Identify the top three gaps between where you are and where you want to be
  • Create a 90-day plan to start closing one of those gaps
  • Find one accountability partner (friend, colleague, or hire a coach)

Week 4: Start

  • Take the first action on your 90-day plan
  • Update your LinkedIn with one thing that points toward your pivot
  • Join one community related to your target direction
  • Schedule your next three months of consistent effort

Don’t try to do everything at once. Don’t wait until everything is perfect. Don’t let fear paralyze you into inaction. Just start.

The Uncomfortable Truth

I’m going to close with something I don’t say to my clients until I’ve built enough trust with them, but I’ll say it to you:

Most people won’t do this work. They’ll read articles like this, nod along, maybe bookmark it for later, and then go back to complaining about how hard the job market is or how unfair it is that their skills are becoming obsolete. They’ll wait until they’re forced to change, and then they’ll change reactively from a position of weakness.

Don’t be most people.

The tech professionals who will be successful five years from now are the ones making moves today. They’re the ones who are uncomfortable right now because they’re learning and growing and pushing themselves into new territories. They’re the ones who understand that career security doesn’t come from staying still; it comes from being perpetually adaptable.

The great tech pivot isn’t coming. It’s here. The question is whether you’re going to lead your own pivot or let it happen to you.

Stay ahead, or stay behind. Your choice.

The Rise of Change Resiliency Programs: How You Can Join the Cool Club

Remember when “change management” meant creating a communication plan, doing some training, and hoping for the best? Yeah, that was adorable. Welcome to 2025, where change isn’t a project with a start and end date; it’s the constant hum of organizational life. And if you’re still treating it like an event rather than a capability, we need to talk.

Change resiliency programs are having a moment, and for good reason. We’ve gone through a global pandemic, multiple waves of tech disruption, the rise of AI, hybrid work debates, economic uncertainty, and approximately 47 “transformation initiatives” per organization. The companies that are thriving aren’t the ones that managed change well once; the ones that built change into their DNA.

As someone who’s spent the last eight years helping tech organizations navigate everything from mergers to platform migrations to wholesale culture overhauls, I’ve watched change management evolve from a nice-to-have to a strategic imperative. And the newest evolution? Change resiliency programs that actually work. Let me show you how to build one (or join one, if you’re lucky enough to work somewhere that gets it).

What Even Is Change Resiliency? (And Why It’s Different From Change Management)

Let’s get our terms straight, because people love to use these interchangeably and then wonder why nothing works.

Change Management is what you do when a specific change is happening. You’re rolling out a new system, reorganizing a department, shifting strategy. You create a plan, you execute it, you measure adoption, you declare victory (or quietly move on and hope everyone forgets). It’s project-based, time-bound, and focused on getting people from Point A to Point B.

Change Resiliency is building your organization’s capacity to handle change as an ongoing reality. It’s not about managing one change; it’s about creating a culture, processes, and capabilities that make your organization inherently adaptable. It’s the difference between teaching someone to cross one specific river versus teaching them to swim.

Think of it this way: Change management is tactical. Change resiliency is strategic. Change management gets you through this quarter’s transformation. Change resiliency means you’re still thriving when the next six transformations hit.

Why Everyone Suddenly Cares About This

If you’re wondering why change resiliency programs are popping up everywhere like artisanal coffee shops, here’s your answer: Change velocity has outpaced traditional change management capacity.

Let me paint you a picture. In a typical tech company right now, you might have:

  • A cloud migration happening
  • A new AI strategy rolling out
  • Quarterly OKRs driving priority shifts
  • A reorganization because the last reorganization didn’t work
  • A new collaboration tool being implemented (RIP the old tool no one will miss)
  • Evolving compliance requirements
  • Market shifts requiring product pivots
  • And probably a handful of other initiatives I’m forgetting

Traditional change management says you assign a change manager to each initiative, create individual plans, and hope they don’t conflict too much. Change resiliency says you build a system that can absorb all of this without everyone having a collective breakdown.

Organizations are finally realizing that you can’t keep treating change like an exception. It’s the rule. And if your people aren’t resilient to change, you’re going to have an engagement, retention, and performance problem.

The Core Components of a Real Change Resiliency Program

I’ve built and advised on enough of these programs to know what actually works versus what looks good in a deck. Here are the must-haves:

1. Leadership Capability Building (Not Optional)

Your leaders are either your biggest asset or your biggest liability when it comes to change. There’s no middle ground. A middle manager who doesn’t know how to lead through ambiguity will create a pocket of resistance that torpedoes even your best initiatives.

A real change resiliency program includes ongoing leadership development focused on:

  • Leading through ambiguity (because we’re never going to have all the answers)
  • Change communication (which is different from regular communication)
  • Managing resistance (without being defensive or punitive)
  • Modeling adaptability (because people watch what you do, not what you say)

This isn’t a one-time workshop. It’s quarterly check-ins, peer learning sessions, coaching, and real-time feedback. The best programs I’ve seen include “change labs” where leaders can practice navigating difficult scenarios in a low-stakes environment before they face them for real.

2. A Change Network (Your Secret Weapon)

Here’s something most organizations miss: You can’t centralize all change expertise in one team. You need distributed capacity across the organization. Enter the change network.

A change network is a group of people across different departments who are trained in change principles and serve as advocates, coaches, and early warning systems. They’re not full-time change managers; they’re engineers, product managers, designers, and other individual contributors who have change capabilities.

These are your people on the ground who can:

  • Spot resistance early and help address it
  • Translate change initiatives into language their teams understand
  • Provide feedback to leadership about what’s working and what’s not
  • Model positive change behaviors in their spheres of influence

I helped build a change network at my last company that started with 15 people and grew to 60 within a year. Why? Because being part of the change network was seen as cool. These folks got special training, access to leadership, and visibility. It became something people wanted to join, not something they were forced into.

Pro tip: Recruit your informal influencers for this, not just your high performers. The person everyone goes to for advice? That’s who you want. The person who sets the tone in their team? That’s your target. You want culture carriers, not just people with good resumes.

3. Psychological Safety Infrastructure

You cannot build change resiliency in an environment where people are afraid to speak up. Full stop. If your culture punishes failure, questions, or dissent, your change resiliency program is doomed before it starts.

This means you need:

  • Regular mechanisms for upward feedback (surveys, town halls, skip-level meetings)
  • Visible responses to that feedback (not just “thanks for sharing,” but “here’s what we’re changing”)
  • Leaders who model vulnerability (admitting when they don’t have answers, acknowledging mistakes)
  • Celebrating productive failure (the kind where you learned something valuable)

One company I worked with created a “learning wall” where people posted initiatives that didn’t work and what they learned. The CEO was the first to post. That single act did more for psychological safety than a thousand all-hands speeches about “it’s okay to fail.”

4. Change Readiness Assessments (Know Before You Launch)

Flying blind into change is how you end up with 30% adoption rates and a bunch of frustrated people. Change resiliency programs include standardized assessments before major initiatives to gauge:

  • How saturated is this team/organization with change right now?
  • What’s their historical experience with change? (Positive or negative?)
  • Do they have the capacity to take on something new?
  • What competing priorities exist?
  • What’s the trust level between leadership and teams?

I use a simple red/yellow/green framework. Red means “do not launch anything new here without addressing serious issues first.” Yellow means “proceed with caution and extra support.” Green means “ready to go.”

Here’s the kicker: You need executive buy-in that red means NO. Not “we’ll do it anyway and hope for the best,” but actually NO. I’ve seen too many organizations do assessments and then ignore the results because the timeline is “set.” That’s not change resiliency; that’s change theater.

5. Adaptive Planning Processes

Traditional change management loves a good linear plan. Phase 1, Phase 2, Phase 3. Check the boxes. Declare victory. Change resiliency says “that’s cute, but reality is messy.”

Adaptive planning means:

  • Regular checkpoints (not just at the end) to assess what’s working
  • Permission to pivot based on what you’re learning
  • Transparent communication about changes to the plan
  • Built-in experimentation where you test approaches before going all-in

One of my favorite techniques is the “pilot and iterate” model. Instead of rolling out a change to 5,000 people at once, you pilot with 50, learn fast, adjust, pilot with 200, learn more, adjust, and then scale. It takes longer upfront but saves you from massive failures later.

6. Skills Development at Scale

Change resiliency requires specific skills that most people don’t naturally have:

  • Comfort with ambiguity
  • Growth mindset
  • Emotional regulation
  • Problem-solving under pressure
  • Effective communication during uncertainty

Your program needs to build these skills systematically, not just assume people will figure it out. This can look like:

  • Micro-learning modules people can do in 10 minutes
  • Lunch-and-learns on specific topics
  • Peer coaching circles
  • Access to resources (books, articles, tools)

Make it easy and make it practical. Nobody has time for three-day workshops anymore. Give people bite-sized learning they can apply immediately.

How to Build Your Business Case (Because Someone’s Going to Ask)

Let’s be real: Most executives aren’t going to fund a change resiliency program because it’s the right thing to do. You need to show ROI. Here’s how to make the case:

Cost of Failed Change Initiatives Pull data on change initiatives from the last two years. What was invested? What was the adoption rate? If you spent $2M on a platform migration that only 40% of people use, that’s $1.2M of wasted investment. Now multiply that across all your failed or underperforming initiatives. That number gets big fast.

Employee Turnover and Engagement Change fatigue is a real driver of turnover. If you can show that employee engagement drops during major changes (it does) and that correlates with turnover (it does), you can estimate the cost. Replacing an employee costs 1.5-2x their salary on average. If a change resiliency program reduces turnover by even 5%, that’s probably hundreds of thousands of dollars saved.

Speed to Value Organizations with high change resilience get to value faster. They don’t spend six months in resistance and confusion—they adapt quickly and start seeing returns. If you can show that building change capability would accelerate time-to-value by even 20%, the business case often makes itself.

Competitive Advantage This one’s harder to quantify but powerful for strategic leaders. Companies that can adapt quickly outperform those that can’t. If your competitors are launching new capabilities every quarter and you’re still debating whether to adopt the last trend, you’re going to lose market share. Change resiliency is a competitive moat.

Red Flags That Your Organization Needs This (Like, Yesterday)

Not sure if you need a formal change resiliency program? Here are the warning signs:

  • People talk about “change fatigue” in every meeting
  • There’s open cynicism about new initiatives (“here we go again”)
  • Adoption rates for new tools/processes are consistently low
  • Middle managers are overwhelmed and asking for relief
  • You’re seeing turnover in roles that were previously stable
  • Projects keep getting delayed due to “change management issues”
  • Leadership keeps saying “we need better communication” but nothing changes
  • You’ve had multiple reorgs in the past two years
  • Employee survey scores on items related to clarity and direction are dropping

If you’re nodding along to more than three of these, it’s time to have a serious conversation about building change capacity.

How to Get Started (Even If You’re Not the CEO)

Good news: You don’t have to be a C-suite executive to start building change resiliency. Here’s how to start where you are:

If you’re an individual contributor:

  • Develop your own change resilience skills (there are great resources out there)
  • Model adaptability in your team
  • Volunteer to help with change initiatives
  • Build relationships with people in change management or learning & development

If you’re a manager:

  • Invest in your team’s change capabilities through coaching and development
  • Create psychological safety on your team
  • Be transparent about changes and why they’re happening
  • Give people space to process and adapt
  • Share what you’re learning with peer managers

If you’re a senior leader:

  • Assess where your organization is on change capability
  • Start building a business case for a formal program
  • Invest in your own leadership development around change
  • Model the behaviors you want to see
  • Create space in the budget for change capability building

If you’re in change management/OD:

  • Document the current state (costs of failed changes, engagement data, etc.)
  • Find an executive sponsor who gets it
  • Start small, maybe a pilot change network or leadership cohort
  • Show quick wins to build momentum
  • Connect with other change professionals who’ve done this (we love to share war stories)

What “Good” Looks Like (So You Know You’re On Track)

You’ll know your change resiliency program is working when:

  • People stop asking “why is this changing?” and start asking “how can I help?”
  • Resistance becomes productive conversation rather than entrenched opposition
  • Leaders proactively think about change impact, not just execution
  • Teams can absorb new initiatives without burnout or breakdown
  • You’re seeing higher adoption rates on changes
  • Employee engagement scores are stable or improving even during major changes
  • People are actually using the language and tools of change resilience
  • You hear stories of teams self-organizing to address change challenges
  • The change network has a waiting list to join

The ultimate sign? When change just becomes “how we work” rather than something that happens to people.

The Cool Club Part (Why You Actually Want to Be Here)

Here’s why being part of a change resiliency program – whether building it or participating in it – is genuinely valuable for your career:

You’re developing the #1 skill for the future of work. Adaptability isn’t a nice-to-have anymore; it’s the skill that determines who thrives and who gets left behind. If you can navigate ambiguity and lead through change, you’re valuable anywhere.

You get visibility. People who are part of change networks or leading change capability building get exposure to senior leaders, cross-functional projects, and strategic initiatives. It’s a career accelerator.

You’re building a differentiator. Most people have “change management” on their resume. How many have “built organizational change resiliency at scale”? That’s the kind of thing that gets you interesting opportunities.

You’re making work better. For real. Organizations with strong change resilience are better places to work. People feel more empowered, less anxious, more engaged. You’re not just helping the company; you’re making life better for everyone.

You join a community. The change resiliency community is growing, and we’re a supportive bunch. There are conferences, Slack groups, monthly meetups. You’re plugging into a network of people who get it and who are happy to share resources and advice.

Real Talk: The Challenges You’ll Face

I’m not going to pretend this is easy. Here are the challenges you’ll definitely encounter:

Executive attention span. Leaders love the idea of change resiliency until it requires sustained investment and attention. You’ll need to keep making the case and showing value.

Measuring impact. Some of this is hard to quantify. You’ll need to get comfortable with qualitative data alongside quantitative metrics.

Competing priorities. There’s always a fire to fight, a deadline to hit, a crisis to manage. Change resiliency can feel like “we’ll get to that later.” Your job is to make it urgent enough to prioritize.

Resistance from unexpected places. Sometimes the biggest resistance comes from change managers who are threatened by a distributed model, or from leaders who think they already know how to do this. Navigate carefully.

Sustainability. Starting a program is easier than sustaining it. You’ll need governance, ongoing funding, and champions who stick around.

But here’s the thing: All of those challenges are manageable if you’re strategic, patient, and persistent. And the payoff is worth it.

Your Action Plan for the Next 30 Days

Okay, you’re convinced. Now what? Here’s your 30-day plan to get started:

Week 1: Assess and Learn

  • Document three recent changes in your organization and their outcomes
  • Survey 10 people about their change experience
  • Read up on change resiliency best practices (I’ve got resources if you need them)
  • Identify one person in your organization who “gets it” about change

Week 2: Build the Case

  • Calculate the cost of underperforming change initiatives
  • Gather employee engagement data related to change
  • Create a one-page business case draft
  • Identify your potential executive sponsor

Week 3: Start Small

  • Pilot one element (maybe a change network or leadership session)
  • Test your assumptions about what people need
  • Gather feedback and iterate
  • Document what you’re learning

Week 4: Socialize and Plan

  • Share your findings with key stakeholders
  • Refine your business case based on feedback
  • Create a six-month roadmap
  • Start recruiting your early adopters

Final Thoughts: Change Isn’t Going Anywhere

Look, I’m going to level with you. The pace of change in tech isn’t slowing down. If anything, it’s accelerating. AI is going to disrupt workflows we haven’t even thought about yet. Market conditions are going to continue shifting. Organizations are going to keep reorganizing, pivoting, and transforming.

You have two choices: Get reactive and exhausted, or build capability and get resilient.

Change resiliency programs aren’t about making change easy (spoiler: it’s always going to be hard). They’re about making your organization capable of handling hard things without breaking. They’re about turning your people from victims of change into agents of change.

And honestly? This work is some of the most meaningful you can do. You’re not just managing projects or implementing systems—you’re building human capability at scale. You’re making it possible for people to not just survive but actually thrive in uncertain times.

So yeah, change resiliency programs are having a moment. And it’s a moment worth joining. The cool club is building something that actually matters. Come join us.

Now if you’ll excuse me, I have to go convince another executive that investing in change capability is more important than launching another initiative without it. Wish me luck.

AI Assistants: Project Management’s New (Sometimes Annoying) Best Friend

Look, I’m just going to say it: AI assistants are like that overenthusiastic coworker who shows up to every meeting with 47 suggestions, half of which are brilliant and half of which make you wonder if they’ve ever actually worked in your industry. They’re helpful. They’re annoying. They’re sometimes weirdly accurate and other times completely out of touch. And yet, here I am, six months into my AI-assisted project management journey, and I can’t imagine going back.

Let me be clear; I was a skeptic. When our CTO announced we’d be piloting AI tools for project management, I did the internal eye roll that every PM perfects over years of sitting through “this will change everything” presentations. I’ve seen too many silver bullets turn into lead balloons. But I’m also pragmatic, and if there’s a tool that can help me stop drowning in status updates and actually do strategic work, I’m listening.

So here’s my honest, no-BS take on using AI assistants as a project manager in 2025: the good, the bad, and the “did the AI just suggest we have a meeting about having a meeting?”

The Honeymoon Phase (Where I Fell in Love)

The first week with my AI assistant was magical. I’m talking “where have you been all my life” magical. I fed it my project documentation, my team’s chat history, and my roadmap, and within minutes it had:

  • Identified three critical path risks I hadn’t fully articulated
  • Suggested more realistic timelines based on our team’s historical velocity
  • Caught a resource conflict between two projects that would have blown up in two weeks

I felt like I’d hired an analyst who worked 24/7 and never needed coffee breaks. I was that person in the team Slack going “You guys, the AI just…” followed by some mind-blowing insight. My teammates were impressed. I was impressed. The AI was probably impressed with itself.

Then reality set in.

The Reality Check (Where I Learned Its Limits)

Here’s what they don’t tell you in the sales demos: AI assistants are incredibly literal. They don’t understand context the way humans do, and they definitely don’t understand the political landmines that make up 50% of project management.

Case in point: I asked my AI assistant to “identify stakeholders who aren’t engaged enough with the project.” It came back with a list that included our VP of Engineering, who happened to be on parental leave. Technically accurate? Sure. Socially aware? Not even a little bit.

Or the time I asked it to summarize blockers from our standup notes, and it flagged “Sarah is blocked on feedback from Mark” for 15 consecutive days. Yes, AI, we all know Sarah is blocked on feedback from Mark. We’re all painfully aware. What you don’t understand is that Mark is a senior director who responds to escalation very poorly, and there’s a whole dance I’m doing behind the scenes to get Sarah what she needs without making Mark defensive. Your helpful “suggestion to escalate immediately” would have set my project back three weeks.

This is when I learned the most important lesson: AI assistants are tools, not replacements. They’re phenomenally good at pattern recognition and data processing. They’re terrible at nuance, politics, and reading the room (since, you know, they’re not in the room).

What AI Assistants Actually Excel At (The Good Stuff)

Once I got over my initial disillusionment and learned to use my AI assistant for what it’s actually good at, things got much better. Here’s where I’ve found genuine value:

1. Meeting Prep and Notes (My Favorite Use Case)

I now have my AI assistant join every project meeting. It takes notes, identifies action items, and creates a summary that I review and edit before sending out. This has saved me hours every week; I used to spend 20-30 minutes after each meeting crafting summaries. Now I spend 5 minutes editing what the AI produces.

The key word there is “editing.” The AI captures everything, but it doesn’t know that when Jake said “yeah, I can probably look at that” it was really “no, and I’m annoyed you even asked.” I do. So I adjust the notes accordingly. The AI does the heavy lifting; I do the translation.

2. Status Report Generation (Goodbye, Weekly Drudgery)

I used to spend every Friday afternoon pulling together status reports from five different sources; Jira, Slack, meeting notes, direct messages, and whatever random updates people had sent me throughout the week. It was tedious, mind-numbing work that sucked up 2-3 hours.

Now? My AI assistant does a first pass. It pulls data from all our connected tools, identifies what’s changed since last week, and creates a draft. I review it, add the human context (like “we’re behind on the API integration, but that’s because the vendor dropped the ball, not our team”), and send it out. Friday afternoons are now for actual strategic work instead of copy-paste gymnastics.

3. Risk Identification (When It’s Actually Smart)

This is where AI assistants genuinely shine. They can spot patterns in historical data that I would never catch. Mine flagged that we were consistently underestimating QA time for features that involved third-party integrations. Looking back at six months of data, it was right; we were off by an average of 30%. I adjusted our estimation model, and our delivery predictability improved immediately.

It also caught a staffing risk I hadn’t fully appreciated: Three of our five senior engineers were scheduled to take time off during the same two-week period in November. Individually, none of them seemed like a big deal. Collectively? Potential disaster. The AI connected those dots before I did, and I was able to have proactive conversations about staggering time off.

4. Dependency Mapping (For Complex Projects)

On large projects with multiple teams, tracking dependencies manually is a nightmare. My AI assistant creates visual dependency maps that update in real-time based on what’s happening in Jira and our planning docs. When a dependency is at risk, it flags it automatically.

Is it perfect? No. It occasionally identifies “dependencies” that are really just “these two things exist in the same project.” But 80% of the time, it’s catching things that would have slipped through the cracks, and that’s valuable enough to deal with the occasional false positive.

What AI Assistants Are Terrible At (Let’s Be Honest)

1. Understanding Human Dynamics

AI has no idea that your lead developer and your designer haven’t spoken directly in three weeks because of an argument about button placement. It doesn’t know that your product manager is conflict-averse and will say “yes” in meetings but drag their feet on implementation. It can’t read body language in video calls or pick up on the tension when someone’s video is off and they’re typing aggressively in the chat.

All of that? That’s still our job. The AI can tell you that a task is overdue. It can’t tell you why, and the why is usually the most important part.

2. Creative Problem-Solving

When I hit a truly gnarly project problem – like how to deliver a feature when we’ve lost a key engineer, the scope has crept by 40%, and the deadline is immovable because of a contractual commitment – my AI assistant’s suggestions are… not helpful.

It will suggest things like “add more resources” (not in the budget), “reduce scope” (already tried, got shot down), or “extend the timeline” (literally not an option). What it can’t do is help me brainstorm creative solutions like “what if we partner with the services team to deliver part of this as professional services instead of product” or “what if we ship a 70% solution now and a polish pass in the next sprint?”

That kind of creative, contextual problem-solving is still firmly in the human domain, and I don’t see that changing anytime soon.

3. Stakeholder Management

My AI assistant once suggested I send a project update to our board because “the project timeline has changed by more than 15%.” Technically true; we had accelerated delivery by three weeks because the team crushed it. But sending unsolicited updates to board members about an internal project that’s ahead of schedule is a great way to create unnecessary questions and panic.

Stakeholder management is all about timing, tone, and knowing your audience. AI doesn’t have the social intelligence to navigate that minefield. It can draft the communication, but you need to decide if, when, and how to send it.

My Practical Framework for Working with AI Assistants

After six months of trial, error, and occasional frustration, here’s the framework I’ve developed for making AI assistants actually useful:

Use AI for Pattern Recognition, Humans for Context

Let the AI surface trends, anomalies, and patterns in your data. Then apply your human brain to figure out what those patterns mean and what to do about them. The AI can tell you that velocity has dropped 20% in the last sprint. You know it’s because your tech lead was out sick and the team was nervous to make decisions without them. The AI gives you the what; you provide the why and the how.

Treat AI Output as a First Draft, Not Final

Everything – and I mean everything – that comes from my AI assistant gets a human review before it goes anywhere. Meeting notes? I edit them. Status reports? I add context. Risk assessments? I validate them against what I actually know about the team and project.

The AI saves me time by doing the grunt work, but I’m still the editor-in-chief. This is not optional. I made the mistake early on of sending AI-generated notes without reviewing them, and I had to issue a correction because the AI had completely misunderstood a decision we’d made. Lesson learned.

Be Specific in Your Prompts

The more specific I am with my AI assistant, the better the output. “Summarize the project status” gives me generic garbage. “Summarize the project status focusing on timeline risks, resource constraints, and blocker resolution” gives me something useful.

I’ve started keeping a document of “prompts that work” for common tasks. It’s made my interactions with the AI much more efficient because I’m not spending time rephrasing and clarifying what I need.

Know When to Ignore It

This sounds obvious, but it’s worth saying: Sometimes the AI is just wrong. It might be confident, it might seem like it’s based on data, but it’s wrong. Trust your gut. You have context, relationships, and experience that the AI doesn’t have. If something the AI suggests feels off, dig deeper. More often than not, your instinct is right.

The Unexpected Benefits (Things I Didn’t See Coming)

1. It Forced Me to Document Better

To get useful output from my AI assistant, I had to make sure all our project information was actually documented and up to date. This was painful at first but has paid massive dividends. Our documentation is now the source of truth, not Janet’s memory or that Slack thread from three months ago.

2. It Made Me a Better Communicator

Because I’m editing AI-generated content regularly, I’ve become much more aware of clarity in communication. When I see the AI misunderstand something, I realize my original communication was probably ambiguous. It’s made me more precise in how I document decisions and action items.

3. It Gave Me Time Back for Strategic Work

This was the big one. By offloading routine administrative tasks to my AI assistant, I’ve reclaimed probably 5-7 hours a week. That’s time I now spend on actual project management; talking to my team, thinking through risks, building relationships with stakeholders, and doing the strategic work that actually moves projects forward.

The Things That Still Annoy Me

Let’s be real; it’s not all sunshine and efficiency gains. Here are the things that still drive me nuts:

The overconfidence. AI assistants present everything with the same level of certainty, whether they’re telling you something obvious (the project started last month) or something they’re completely guessing at (this risk will materialize in two weeks). There’s no “I’m not sure, but…” It’s all stated as fact, and you have to develop your own sense of when to trust it.

The inability to understand “not now.” My AI assistant has no sense of priority or timing. It will flag something as urgent at 4:45 PM on a Friday with the same enthusiasm it flags something at 9 AM on a Monday. Everything is always urgent in AI world. I’ve learned to adjust, but I wish there was a better way to teach it “yes, this matters, but not right this second.”

The occasional hallucination. Sometimes my AI assistant just makes stuff up. It will reference meetings that didn’t happen or decisions that were never made. This is rare, but when it happens, it’s spectacular. I’ve learned to always verify anything that seems off, because sometimes it’s just… invented.

Advice for PMs Considering AI Assistants

If your organization is considering AI tools for project management, here’s what I’d tell you:

Start small. Don’t try to AI-ify your entire workflow at once. Pick one or two use cases where you spend a lot of time on repetitive tasks (meeting notes, status reports) and start there. Learn what works before expanding.

Set clear boundaries. Be explicit with your team about what the AI is being used for. I told my team upfront that an AI would be taking meeting notes and that I’d review them before sending. Transparency prevents weird reactions later.

Keep the human in the loop. This cannot be overstated. AI tools should augment your work, not replace your judgment. You’re still the PM. The AI is your assistant, not your boss.

Give it time. There’s a learning curve, both for you and for the AI (if it has any learning capability). The first month was frustrating. By month three, I’d figured out the rhythms. By month six, I couldn’t imagine going back.

Stay skeptical. Just because it’s AI doesn’t mean it’s magic. Verify important information, especially anything that will be shared with stakeholders or used for decision-making. Trust, but verify.

The Bottom Line

Are AI assistants going to replace project managers? Absolutely not. Anyone who tells you that doesn’t understand what project management actually is. The job is not just tracking tasks and sending status updates; it’s navigating ambiguity, managing personalities, making judgment calls with incomplete information, and occasionally performing miracles when things go sideways.

AI can’t do that. What it can do is handle a lot of the tedious, repetitive work that takes up time we’d rather spend on the actual art of project management.

So yes, my AI assistant is sometimes annoying. It’s occasionally overconfident, often literal to a fault, and completely oblivious to office politics. But it’s also saved me hours every week, caught risks I would have missed, and made me better at my job by forcing me to be more structured and clear in my processes.

Is it a best friend? Maybe more like a very efficient intern who needs constant supervision but does great work when properly directed. And honestly? That’s exactly what I need.

Now if you’ll excuse me, I need to go review the meeting notes my AI just generated and add the part where everyone agreed to something but nobody actually meant it. Some things, AI will never understand.

Chief of Staff Hacks: Managing Cross-Functional Chaos with a Smile

Listen, if you’ve ever described your job to someone at a party and watched their eyes glaze over before you finished the second sentence, welcome to the Chief of Staff club. We’re the people who make things happen without anyone really understanding how we make things happen. We’re part therapist, part air traffic controller, part fortune teller, and part professional cat herder—except the cats have engineering degrees and very strong opinions about architecture decisions.

After five years of managing cross-functional chaos in tech companies ranging from scrappy startups to enterprise behemoths, I’ve learned that surviving (and dare I say, thriving) as a Chief of Staff requires equal parts strategy, diplomacy, and the ability to smile while your Slack is on fire. Here are my hard-won hacks for keeping your sanity while everyone else is losing theirs.

Hack #1: Become a Master Translator (No Rosetta Stone Required)

The single most valuable skill in my arsenal isn’t project management or strategic planning; it’s translation. Not the Google Translate kind, but the ability to translate between the many languages spoken within your organization.

Engineering speaks in sprints, technical debt, and “that’s not how the API works.” Marketing speaks in campaigns, brand alignment, and “what’s our narrative here?” Finance speaks in burn rate, ROI, and “show me the numbers.” Your job? Be the Babel fish that makes everyone understand each other without anyone feeling like they’re being dumbed down or talked over.

Here’s how I do it: I keep a running document (yes, I’m that person) of common phrases from each department and their translations. When Product says “we need to validate the use case,” Engineering hears “they don’t trust our technical judgment.” When Engineering says “that’s technically feasible but not architecturally sound,” Product hears “they’re being difficult again.” My job is to reframe these conversations so everyone hears what was actually meant, not what their departmental bias tells them was meant.

Pro tip: Learn the sacred cows of each department. Engineering’s sacred cow might be code quality. Marketing’s might be brand consistency. Finance’s is definitely the budget. When you know what people will go to war over, you can navigate around it: or intentionally invoke it when you need to light a fire.

Hack #2: The “Reply All” is Your Enemy (Use It Wisely)

Hot take: 90% of organizational chaos is caused by email threads that should have died five replies ago. I have a strict personal policy about Reply All, and it goes like this: If more than four people are on the thread and the conversation has gone beyond three rounds, it’s time for a meeting.

I know, I know. “Another meeting that could have been an email.” But here’s the thing, when you’re the Chief of Staff, you’re not adding another meeting. You’re preventing the 47 fragmented conversations that happen when everyone interprets that email thread differently and runs off in their own direction.

My hack? I swoop in with what I call the “Clarity Call.” I’ll literally Reply All (one of the few acceptable uses) with: “Lots of great input here! Let’s align synchronously. I’m setting up 30 minutes tomorrow at 2 PM to make some decisions. Come with your top three priorities.” This does two things: it shows leadership that you’re taking control of the chaos, and it forces people to think critically about what they actually need versus what they’re just debating for sport.

Also, for the love of all that is holy, use the BCC function when you’re communicating decisions that don’t need feedback. Your executives don’t need to see 47 people chiming in with “+1” or “agreed.” Just tell them what was decided and move on.

Hack #3: Build Your Intelligence Network (Spy Skills Optional)

The best Chiefs of Staff I know aren’t the ones in every meeting; they’re the ones who know what happened in every meeting without being there. How? A carefully cultivated intelligence network.

This isn’t about being shady or playing politics. It’s about recognizing that you cannot physically be everywhere, so you need trusted allies who will give you the real story. Not the sanitized version that ends up in the meeting notes, but the “here’s what was actually said when the VP got heated” version.

I have what I call my “Coffee Cabinet”, a rotating group of five to seven people across different functions who I grab for casual coffee chats every week. These aren’t formal check-ins. There’s no agenda. But in those 15-minute conversations, I learn more about what’s actually happening in the organization than I do in four hours of status meetings.

The key is reciprocity. I share information too (appropriately, of course). When they tell me that the product roadmap is about to get blown up, I might share that I heard finance is nervous about next quarter’s projections. Everyone benefits from the information flow, and I become the central node in the network, which is exactly where a Chief of Staff should be.

Hack #4: Perfect the Art of the Pre-Meeting

If you’re going into important cross-functional meetings cold, you’re doing it wrong. The real work of a Chief of Staff happens before the meeting, in what I call “temperature checks” and “alignment sessions.”

Before any major decision meeting with executives or cross-functional leaders, I spend 30 minutes to an hour doing individual check-ins. I want to know: What’s their position? What are they worried about? Where are they willing to compromise? What’s their walk-away point?

This might sound exhausting (it is), but it saves hours of circular debate and “I wish we had discussed this offline” moments. By the time we’re in the actual meeting, I’ve already identified the landmines, brokered some pre-agreements, and know exactly where the real friction points are.

Here’s my secret weapon: I frame these pre-meetings as “I want to make sure your perspective is fully represented.” Nobody can resist that. Everyone wants to feel heard, especially when they’re about to walk into a room full of strong personalities. By giving them that space beforehand, they’re calmer, more collaborative, and less likely to dig their heels in just to make a point.

Hack #5: Master the Follow-Up (Because Memory is a Myth)

Real talk: Nobody remembers what was decided in meetings. Not your CEO, not your VP of Engineering, not even the person who said “yes, I’ll own that action item” with full eye contact.

My hack for this is what I call the “Accountability Framework,” which is a fancy way of saying I follow up on literally everything. Within two hours of any meeting, I send out a summary that includes:

  • What was decided
  • Who owns what
  • When it’s due
  • What happens next

But here’s the key: I don’t just send it and forget it. I have a tracking system (I use a hybrid of Notion and Google Sheets, because I’m a chaos-loving organized person) where I track every commitment made in every meeting. One week before something is due, they get a friendly nudge. Three days before, they get a “just checking in” message. On the day it’s due, I’m knocking on their virtual door.

Does this make me annoying? Sometimes. Do things actually get done? Always. And here’s the secret: people start coming more prepared to meetings with me because they know I’m going to follow up. The accountability creates better behavior.

Hack #6: Protect Your Executive’s Time Like It’s Your Own (Because It Basically Is)

One of the most underrated parts of being a Chief of Staff is gatekeeping. And I don’t mean that in the toxic way; I mean it in the “your CEO has 47 meeting requests and 12 of them are absolutely unnecessary” way.

I’ve developed a framework I call “The Five Questions Test.” Before anything gets on my executive’s calendar, I ask:

  1. Does this require executive-level decision-making, or can it be decided at a lower level?
  2. Is this time-sensitive, or is someone just marking it urgent to get attention?
  3. Are the right people prepared with the right information?
  4. Is this a conversation or a presentation? (Presentations can be async)
  5. What’s the decision we’re trying to make, and is this meeting the right format?

If a meeting request can’t pass at least four of these five tests, I’m sending it back with “helpful suggestions” about how to make it more effective. Sometimes that means a different format. Sometimes it means including different people. Sometimes it means “why don’t you align with Sarah first and then we’ll circle back.”

Am I making friends with this approach? Not always. Am I protecting my executive from death by a thousand meetings? Absolutely. And here’s the thing: once people realize you’re the gatekeeper, they start coming to you first with better-thought-out requests. The quality of meeting requests goes up dramatically when people know they have to pass the Chief of Staff test first.

Hack #7: Create Rituals, Not Just Routines

In the chaos of cross-functional work, rituals are your anchor. I’m not talking about the daily standup that everyone hates—I’m talking about intentional practices that create rhythm and predictability in an otherwise unpredictable environment.

For example, I have “Focus Fridays” where I block the first three hours for deep work only: no meetings, no Slack, just strategic thinking time. I also have “Monday Minute” where I send a quick voice memo to my executive with the three things I’m focused on this week. It takes 60 seconds but creates alignment and visibility.

My favorite ritual is what I call “Win Wednesday.” Every Wednesday at 3 PM, I post in our team Slack channel one win from the past week; big or small. It could be “we shipped the new feature” or “Janet finally fixed the printer and we’re all grateful.” This does two things: it creates positive momentum, and it models celebration in a culture that’s often too busy for recognition.

Rituals create predictability, and predictability creates calm. In a role where you’re constantly responding to fires, having these anchors keeps you from becoming purely reactive.

Hack #9: Know When to Escalate (and When to De-Escalate)

This is the skill that separates good Chiefs of Staff from great ones: judgment about escalation. Escalate too much, and you become “the person who cries wolf.” Escalate too little, and small problems become organizational crises.

My rule of thumb: Escalate when there’s a decision only your executive can make, when there’s a risk that could impact business outcomes, or when there’s a people issue that’s festering. Everything else? Handle it at your level.

But here’s the counterintuitive part: Sometimes your job is to de-escalate. When tensions are high and people are treating a product launch delay like a five-alarm fire, I’m the person who comes in with perspective. “Yes, this is frustrating. No, it’s not the end of the world. Here’s how we fix it.” Your ability to modulate the emotional temperature of a situation is just as important as your ability to manage the tactical work.

The Smile Part (Yes, I’m Serious)

You’ve probably noticed I mentioned “with a smile” in the title. Here’s why that matters: Your demeanor sets the tone for how chaos is handled. If you’re frantic and stressed, everyone around you will be frantic and stressed. If you’re calm and collected (even when you’re internally screaming), it creates permission for others to stay calm too.

I’m not saying toxic positivity or “good vibes only.” I’m saying that your ability to project confidence and capability – even in the midst of chaos – is a strategic tool. People look to the Chief of Staff to gauge how worried they should be. If you’re smiling (or at least not spiraling), they can breathe a little easier.

Plus, honestly? Sometimes you have to laugh at the absurdity of it all. The day I had three different executives give me three completely contradictory directives within a 45-minute span, I could either cry or laugh. I chose laughter, called a quick alignment meeting, and we sorted it out. The smile isn’t about being fake; it’s about maintaining perspective when everything feels like it’s on fire.

Final Thoughts: Chaos is the Job

Here’s what I wish someone had told me when I first stepped into the Chief of Staff role: The chaos isn’t a bug; it’s a feature. Cross-functional work is inherently messy because you’re bringing together people with different goals, different languages, and different ideas of success. Your job isn’t to eliminate the chaos; it’s to orchestrate it into something productive.

You’re not going to get it right every time. You’ll miss things. You’ll make calls that, in hindsight, you’d make differently. But if you build your translation skills, master the pre-game, follow up relentlessly, and keep your sense of humor intact, you’ll not only survive; you’ll actually enjoy the ride.

And on the days when you question everything? Remember: You’re the person who makes the impossible happen every single day. Even if nobody fully understands how you do it, they know they can’t do it without you.

Now go forth and herd those cats. With a smile, of course.

The Introvert’s Guide to Networking in a Post-Pandemic Professional World

I need to start with a confession: I’m an introvert who built a successful career coaching practice by completely ignoring every piece of traditional networking advice I ever received. “Work the room!” they said. “Always have your elevator pitch ready!” they insisted. “Follow up within 24 hours!” they demanded. And after years of forcing myself to follow this advice and feeling exhausted, inauthentic, and ultimately unsuccessful, I finally realized something crucial: traditional networking advice is written by and for extroverts.

The post-pandemic professional world has accidentally created the perfect environment for introverted networking. Remote work, virtual events, asynchronous communication, and digital communities have made it possible to build meaningful professional relationships without the energy-draining performance that traditional networking requires. As someone who’s helped hundreds of introverted tech professionals build strong career networks, I can tell you that the future of professional relationship building actually favors introvert strengths.

Understanding Introvert Networking Challenges

Before we dive into solutions, let’s be honest about why traditional networking is particularly challenging for introverts:

Energy Drain vs. Energy Gain: Extroverts gain energy from social interaction, while introverts expend energy in social situations. Traditional networking events can leave introverts feeling depleted rather than energized, making it hard to maintain the consistency that relationship building requires.

Depth vs. Breadth Preference: Introverts typically prefer deeper conversations with fewer people, while traditional networking emphasizes meeting as many people as possible. This mismatch makes networking events feel superficial and unsatisfying for introverts.

Processing Time Requirements: Introverts often need time to process information and formulate thoughtful responses. The quick-thinking, immediate-response expectations of networking events can make introverts feel like they’re not representing themselves well.

Authenticity vs. Performance: Traditional networking often requires a level of self-promotion and performance that can feel inauthentic to introverts who prefer to let their work speak for itself.

Small Talk Struggle: Many introverts find small talk draining and prefer conversations that have substance and purpose. Traditional networking events often prioritize breadth of contact over depth of conversation.

The Post-Pandemic Networking Landscape

The shift to remote work and virtual events has fundamentally changed how professional networking works. These changes have created new opportunities that play to introvert strengths:

The Rise of Asynchronous Communication: Professional relationships can now be built through thoughtful written communication rather than just face-to-face interaction. This gives introverts time to process and respond thoughtfully.

Digital Community Building: Online communities around professional interests create opportunities for ongoing relationship building rather than one-time networking events.

Quality Over Quantity: The focus has shifted from collecting business cards to building meaningful digital relationships, which aligns with introvert preferences for deeper connections.

Content-Based Networking: Sharing insights through writing, commenting thoughtfully on others’ content, and contributing to professional discussions online allows introverts to network through expertise sharing rather than personality promotion.

Virtual Event Options: While virtual networking events still exist, the format often allows for more structured, purposeful interactions that work better for introverts than unstructured “mingling.”

The Introvert’s Networking Advantages

Instead of trying to overcome introvert traits, successful introvert networking leverages these traits as advantages:

Deep Listening Skills: Introverts are typically excellent listeners who ask thoughtful questions and remember details about other people. These skills create more meaningful connections than surface-level networking charm.

Thoughtful Communication: The tendency to think before speaking often results in more meaningful, valuable contributions to professional conversations.

Quality Relationship Focus: The preference for fewer, deeper relationships often leads to stronger professional support networks than broad but shallow networking approaches.

Content Creation Strength: Many introverts excel at written communication and content creation, which are powerful networking tools in the digital age.

Research and Preparation Skills: Introverts often research people and topics before meetings, leading to more productive and valuable professional interactions.

One-on-One Excellence: While introverts might struggle in group networking settings, they often excel in one-on-one professional conversations where deeper connection is possible.

Digital-First Networking Strategies

Build your professional network online first, then selectively move to in-person interactions:

LinkedIn as a Primary Platform: Instead of treating LinkedIn as a digital business card, use it as a relationship-building tool. Comment thoughtfully on posts, share valuable insights, and engage in meaningful conversations in comment threads.

Content Creation Networking: Write articles, create posts, or contribute to discussions about topics you’re passionate about professionally. This attracts like-minded professionals and creates natural conversation starters.

Community Participation: Join online communities related to your field or interests. Slack communities, Discord servers, Reddit communities, and specialized platforms provide ongoing networking opportunities without the pressure of formal events.

Virtual Coffee Chats: Suggest one-on-one virtual coffee conversations with people you’d like to know better. These focused interactions play to introvert strengths and create stronger connections than group events.

Asynchronous Networking: Use tools like email, LinkedIn messages, and community forums to build relationships over time through thoughtful, ongoing communication rather than single networking events.

The Authentic Relationship Building Approach

Focus on building genuine relationships rather than strategic networking contacts:

Shared Interest Connection: Connect with people around shared professional interests, challenges, or goals rather than trying to network broadly. Join book clubs, study groups, or discussion forums related to topics you care about.

Helper’s Network Strategy: Position yourself as someone who helps others rather than someone seeking help. Share resources, make introductions, offer expertise. This approach feels more authentic and creates stronger relationships.

Learning-Based Networking: Attend workshops, training sessions, or educational events where the focus is on learning together rather than networking. Relationships that develop around shared learning often feel more natural.

Problem-Solving Communities: Connect with people who are working on similar challenges or problems. Working parent groups, remote work communities, career transition support groups—these communities provide both practical value and relationship building opportunities.

Leveraging Written Communication

Introverts often excel at written communication, which is a significant advantage in digital networking:

Thoughtful Follow-Up: After meeting someone (virtually or in person), send thoughtful follow-up messages that reference specific parts of your conversation and offer genuine value.

Email Relationship Building: Build relationships through regular, valuable email communication. Share interesting articles, ask thoughtful questions, or offer relevant opportunities.

Content Commenting Strategy: Instead of creating your own content (though that’s valuable too), become known for thoughtful, valuable comments on other people’s content. This builds relationships with content creators and other commenters.

Newsletter Participation: Subscribe to newsletters from people in your field and respond with thoughtful comments or questions. Many newsletter authors appreciate engaged readers and this can lead to meaningful professional relationships.

The Strategic In-Person Approach

When you do attend in-person events, approach them strategically:

Preparation Strategy: Research attendees and speakers in advance. Identify a few specific people you’d like to meet and plan conversation starters based on their work or interests.

Quality Over Quantity Goals: Instead of trying to meet everyone, set goals like “have three meaningful conversations” or “learn something new from two different people.”

Structured Interaction Events: Choose networking events with structure—panel discussions, workshops, or presentations followed by Q&A. These formats provide natural conversation starters and reduce small talk requirements.

Buddy System Approach: Attend events with a colleague or friend who can help facilitate introductions and provide social energy support.

Energy Management: Plan recovery time after networking events. Schedule downtime to recharge rather than trying to push through energy depletion.

Building Professional Relationships Through Service

One of the most effective networking strategies for introverts is building relationships through service:

Mentorship Opportunities: Offer to mentor people earlier in their careers. Mentoring relationships often develop naturally into broader professional networks as mentees advance and become colleagues.

Volunteer Leadership: Volunteer for professional organizations, conferences, or community initiatives. Working together on meaningful projects creates strong professional relationships.

Knowledge Sharing: Organize or participate in knowledge-sharing initiatives like lunch-and-learns, study groups, or skill-sharing sessions. Teaching others creates natural relationship-building opportunities.

Industry Contribution: Contribute to open source projects, write for industry publications, or participate in research initiatives. These contributions create visibility and attract like-minded professionals.

The Long-Term Relationship Investment Strategy

Introverts often excel at maintaining long-term relationships, which is a significant networking advantage:

Consistent Check-Ins: Develop systems for staying in touch with professional contacts over time. Regular, brief check-ins often build stronger relationships than sporadic intensive contact.

Relationship Maintenance Systems: Use tools like CRM systems or simple spreadsheets to track professional relationships and ensure regular contact.

Milestone Recognition: Remember and acknowledge important milestones in your professional contacts’ careers—promotions, job changes, achievements. This personal attention strengthens relationships over time.

Value-First Communication: When you do reach out to professional contacts, lead with value—sharing an interesting opportunity, making a useful introduction, or offering relevant expertise—rather than asking for something.

Managing Introvert Networking Energy

Energy management is crucial for sustainable introvert networking:

The Energy Audit: Track which networking activities energize you versus which ones drain you. Focus more time on energizing activities and limit draining ones to what’s absolutely necessary.

The Recharge Strategy: Build recovery time into your schedule after social professional activities. This might mean blocking calendar time after virtual networking events or scheduling quiet work time after in-person meetings.

The Batch Processing Approach: Instead of spreading networking activities throughout the week, batch them together and plan recovery time afterward. This prevents constant energy drain and allows for more effective recharging.

The Boundary Setting: Be clear about your availability and energy limits. It’s better to participate authentically in fewer activities than to spread yourself too thin across too many networking commitments.

Leveraging Introvert-Friendly Technology

Use technology tools that support your natural communication preferences:

Scheduling Tools: Use calendar scheduling tools that reduce back-and-forth communication and allow people to book time with you when you’re mentally prepared for interaction.

Video Call Strategies: For virtual meetings, use features like chat functions to contribute thoughts in writing when verbal participation feels overwhelming.

Asynchronous Collaboration: Use tools like Slack, Microsoft Teams, or project management platforms that allow for thoughtful, asynchronous communication rather than requiring immediate responses.

Content Planning Tools: Use social media scheduling tools to maintain consistent professional visibility without requiring real-time social media engagement.

The Niche Expertise Strategy

Instead of trying to be known by everyone, focus on being well-known within specific professional niches:

Deep Specialization: Become known as an expert in specific areas rather than trying to network broadly. Deep expertise creates more valuable professional relationships than broad visibility.

Niche Community Leadership: Lead or actively participate in specialized communities related to your expertise. Being a big fish in a smaller pond often provides more valuable networking than being invisible in large general communities.

Thought Leadership in Specific Areas: Develop a reputation for insights in specific professional areas. This attracts people who need your expertise and creates more meaningful professional relationships.

Industry Vertical Focus: Instead of networking across all of technology, focus on specific industries or applications where your expertise is most valuable.

Building Confidence in Professional Relationships

Many introverts struggle with confidence in networking situations, but there are specific strategies to build networking confidence:

Preparation Builds Confidence: The more prepared you are for professional interactions, the more confident you’ll feel. Research people you’re meeting, prepare conversation topics, and have specific goals for each interaction.

Success Documentation: Keep track of successful professional interactions and relationship-building wins. Reviewing these successes builds confidence for future networking activities.

Strength Focus: Instead of trying to fix introvert “weaknesses,” focus on leveraging introvert strengths in professional relationship building.

Progress Measurement: Set small, achievable networking goals and track progress. Building momentum through small wins creates confidence for larger networking challenges.

The Remote Work Networking Opportunity

Remote work has created unprecedented opportunities for introvert networking:

Global Relationship Building: Remote work removes geographic constraints, allowing you to build professional relationships with people anywhere in the world who share your interests or expertise.

Flexible Interaction Timing: You can schedule professional interactions when your energy levels are highest rather than being constrained by traditional business hours or event schedules.

Comfortable Environment Control: Virtual interactions allow you to participate from environments where you feel comfortable and confident, which often improves interaction quality.

Multiple Communication Channels: Remote work provides various ways to connect—video calls, phone calls, instant messaging, email—allowing you to choose communication methods that work best for your style.

Measuring Networking Success

Traditional networking success metrics (number of business cards, events attended, people met) don’t work well for introvert networking. Use different success measures:

Relationship Quality: Measure the depth and meaningfulness of professional relationships rather than the quantity.

Mutual Value Creation: Track how much value you’re creating for others in your professional network, not just what you’re receiving.

Energy Sustainability: Assess whether your networking activities are sustainable over time or burning you out.

Career Impact: Measure how your networking activities are actually contributing to your career goals rather than just activity levels.

Personal Satisfaction: Evaluate whether your professional relationship building feels authentic and satisfying rather than performative and draining.

Creating Your Introvert Networking Plan

Develop a networking approach that works with your introvert traits rather than against them:

Week 1-2: Self-Assessment

  • Identify your introvert networking strengths and challenges
  • Audit current professional relationships for quality and value
  • Assess which networking activities energize versus drain you

Week 3-4: Digital Foundation Building

  • Optimize LinkedIn profile and begin consistent, thoughtful engagement
  • Identify 2-3 online communities relevant to your professional interests
  • Plan content creation or community participation strategy

Week 5-6: Relationship Mapping

  • Map existing professional relationships and identify gaps
  • Identify 5-10 specific people you’d like to build stronger relationships with
  • Plan systematic approaches for deepening these relationships

Week 7-8: Energy Management System

  • Design systems for managing networking energy and recovery time
  • Create boundaries and sustainable practices for professional relationship building
  • Plan batch processing approaches for networking activities

Week 9-12: Implementation and Iteration

  • Begin executing networking plan with focus on sustainability
  • Track what works and what doesn’t for your specific introvert style
  • Adjust approach based on energy levels and relationship building success

The Future of Introvert-Friendly Networking

The professional world is evolving in ways that favor introvert networking approaches:

Authenticity Over Performance: There’s growing recognition that authentic professional relationships are more valuable than performative networking.

Digital-First Relationship Building: The shift toward digital communication creates more opportunities for thoughtful, asynchronous relationship building.

Niche Community Growth: Specialized online communities are creating opportunities for deep expertise-based networking rather than broad relationship building.

Remote Work Normalization: Continued remote work adoption means more professionals are comfortable with virtual relationship building.

The Mindset Shift

The most important change for successful introvert networking is shifting from “how can I force myself to network like an extrovert” to “how can I build professional relationships in ways that work with my natural traits.”

From Networking to Relationship Building: Focus on building meaningful professional relationships rather than “networking” as a separate activity.

From Performance to Authenticity: Be genuinely yourself in professional interactions rather than trying to adopt an extroverted networking persona.

From Quantity to Quality: Build fewer, stronger professional relationships rather than trying to meet everyone.

From Energy Drain to Energy Management: Accept that professional relationship building requires energy management and plan accordingly.

From Weakness to Strength: Leverage introvert traits as networking advantages rather than trying to overcome them.

The post-pandemic professional world has accidentally created the perfect environment for introvert networking success. Remote work, digital communities, asynchronous communication, and the shift toward authentic relationship building all favor introvert strengths.

Stop trying to network like an extrovert and start building professional relationships like an introvert. The future of work needs the deep thinking, careful listening, and thoughtful communication that introverts bring to professional relationships. Your networking approach should reflect and leverage these strengths, not fight against them.

Remember: the goal isn’t to become an extroverted networker. The goal is to build a professional support network that provides career value while feeling authentic and sustainable for your introvert personality. The best professional relationships are built on mutual respect, shared interests, and genuine connection—all things that introverts can excel at when they stop trying to be someone else.

The future belongs to professionals who can build authentic relationships, think deeply about complex problems, and communicate thoughtfully—all classic introvert strengths. Your networking approach should reflect and celebrate these capabilities, not hide them.