Your New Project Team: 3 Humans, 5 AI Agents, and One Terrified Stakeholder

Congratulations. You’re now managing a project team that would make a sci-fi writer raise an eyebrow: three humans, five AI agents, a stakeholder who keeps forwarding LinkedIn articles about “the power of automation,” and an executive sponsor who still doesn’t know the difference between “training” and “inference.”

This is not your grandmother’s project plan. It’s also not your typical tech team. It’s the weird, wonderful reality of 2026, where managing people is only half the job. The other half is managing models, prompts, and expectations that corporate enthusiasm has wildly overinflated.

Welcome to hybrid human-AI project management. The good news? You’re in charge of something no one fully understands, which means you get to write the playbook. The bad news? You’re also the first one blamed when the “smart system” hallucinates a budget forecast that looks like a fever dream.

Welcome to the Age of the AI Coworker

If you haven’t been introduced to your new AI colleagues yet, you will be soon. They are fast, competent, occasionally moody, and just as prone to gossip as any slack thread.

You’ll meet:

  • CodeCore, your engineering AI, which for some reason writes better documentation than half your dev team.
  • InsightBot, the analytics model that loves to surface “interesting anomalies” at 4:59 p.m. on Fridays.
  • Draftly, your writing assistant who has an ego about grammar and thinks “synergy” should be in every mission statement.
  • RiskEye, the compliance bot who treats every new feature as a potential SEC headline.
  • Prompta, the conversational AI project assistant who says “Happy Monday!” like she really means it.

Each tool is branded as your new productivity partner. But here’s the truth most whitepapers skip: these systems don’t reduce your workload, they redistribute it.

Instead of chasing human misalignment, you’re now chasing prompt optimization, hallucination mitigation, and whatever “trust calibration” is this week.

You’re Still Managing People. They Just Have Silicone Assistants Now.

The three humans on your team? They’re looking at you like you’ve invited robots to steal their lunch.

The first human is your engineer, who swears the AI-generated code is “fine” but refuses to ship it without line-by-line review.

The second is your product designer, skeptical that any chatbot understands “vibe consistency.”

And the third is your data analyst, who is simultaneously training, fine-tuning, and side-eyeing the machine that might replace her someday.

Your job? Keep them all productive, confident, and collaborating, while the models hum quietly in the background doing 90% of the grunt work but 0% of the relational glue.

Make no mistake: emotional management is now strategic leadership. AI doesn’t get anxious about deadlines. People do. And as PMs, you’re the interpreter between speed and sanity.

Setting Expectations in the Post-Hype Hangover

Let’s get one thing straight: nothing in tech is as dangerous as optimistic marketing.

The AI tools you’ve deployed were demonstrated in carefully curated demos under ideal lighting. In the real world, their performance depends on data quality, configuration, and the all-powerful human variable known as “context.”

Your actual job now includes playing translator between those contexts.

Here’s what that looks like in daily practice:

  • Exec: “Can we use AI to spin up the first draft of our customer migration plan?”
  • You: “Yes, though it will need human review for tone, accuracy, and risk.”
  • Exec: “So AI will do it automatically?”
  • You: “Not unless you define ‘automatically’ as ‘after I spend six hours rewriting it.’”

This is the modern PM’s dilemma: keeping enthusiasm alive without letting it drift into delusion. You have to defend reality without killing optimism. It’s boundary-setting with project timelines attached.

The New Hybrid Workflow

Managing mixed teams means thinking beyond traditional project frameworks.

Agile sprint planning now includes two entirely new cycles:

  1. Prompt sprints, where you tune requests to get usable AI output.
  2. Validation sprints, where humans check that the output isn’t subtly undermining your company’s ethics policy.

You’re orchestrating collaboration between people and systems that don’t share instincts, humor, or caffeine dependencies.

A typical day might look like this:

  • 9:00 a.m. Standup. Humans vent about last week. AI agents post metrics.
  • 11:30 a.m. Quick debugging session after CodeCore “creatively reinterprets” a user requirement into a recursion loop.
  • 2:00 p.m. Stakeholder meeting, featuring both genuine progress and a carefully curated illusion of predictability.
  • 4:00 p.m. You gently remind InsightBot to stop flagging anomalies that are “user behavior during lunch.”

This is the new normal: part conductor, part therapist, part algorithmic babysitter.

Managing the Terrified Stakeholder

Ah yes, your most unpredictable variable. The stakeholder who agreed to “try out AI” during last quarter’s innovation summit and now spends every meeting oscillating between excitement and existential dread.

They have questions. So many questions.

“Can the AI be liable for delays?” No.
“If the AI deletes something, who do we sue?” Not the AI.
“Can we have it generate our status updates automatically?” Please don’t.

Your role here is to maintain confidence without committing career suicide through overpromising. Stakeholders want magic; you’re offering math.

The smartest move? Turn data into story. Every update should explain what the human oversight achieved, not just what the machines spit out. That’s how you protect trust and budget at the same time.

Boundaries, Bottlenecks, and Burnout

Let’s talk about boundaries. Because right now, a lot of organizations are blurring them.

Executives hear “AI assistant” and assume “endless capacity.” They forget those assistants need supervision, validation, and the occasional moral compass adjustment. Who provides all that? You do.

And if you don’t draw clear rules of engagement, you’ll find yourself in a 24/7 Slack channel answering messages like, “Hey, Prompta just rewrote our OKRs, can you review?” at midnight.

Here’s what boundaries look like in this era:

  • “AI-generated output is a draft, not a decision.”
  • “Human review is mandatory for external comms.”
  • “We do not measure team success by the number of prompts submitted.”

You are not anti-innovation; you are pro-sanity. This balance is what keeps enthusiasm from becoming chaos.

Lessons Only Modern PMs Understand

The future of project management isn’t about replacing work. It’s about redefining what “done” means when your tools have opinions.

Here are a few new laws of hybrid PM physics:

  • Velocity is now exponential, but quality still linear. Someone has to reality-check output.
  • AI teams don’t suffer burnout, but their humans do. Rest cycles still matter.
  • Data drift is the new scope creep. What was “working fine” last month may now be 12% biased against your key user demographic.
  • The PM is the translator between logic and language. You are the only one fluent in both human nuance and prompt precision.

One day, you’ll look at a dashboard full of model performance metrics and realize you’re managing a team that half-exists in the cloud. And it’ll feel normal. And slightly terrifying.

The Feminine Superpower: Calibration

If there’s one thing women PMs bring to this hybrid landscape, it’s calibration. You already manage competing priorities, uncertain variables, and highly emotional environments with grace. AI just adds another layer of unpredictability to navigate.

While some leaders obsess over technical outputs, women often anchor in relational context — which turns out to be exactly what hybrid project management needs. You’re reading not just what the tools produce, but what the people are feeling, what the stakeholder isn’t saying, and what the project culture actually tolerates.

That kind of contextual intelligence doesn’t show up on your Gantt chart, but it’s what keeps the team functional and the AI outputs ethical.

The Future of the PM Role

By 2026, project management has evolved into something closer to systems diplomacy.

You negotiate between speed and safety, between automation and human dignity, between what leadership dreams and what actual humans can deliver without losing their will to live.

Your biggest asset isn’t Jira mastery or AI fluency. It’s discernment. You decide when to trust automation, when to call time-out, and when to tell the stakeholder their twelve-week timeline belongs in fan fiction.

Make no mistake: PMs who can manage both people and prompts are the new executives-in-waiting. Because when an entire industry is learning how to collaborate with machines, the person who understands both empathy and efficiency becomes indispensable.

How to Stay Sane through It All

  • Treat prompts like interns. Give clear instruction, double-check everything, and praise improvement.
  • Keep humor handy. When your AI-generated status report claims the team “achieved emotional resonance,” you’ll need the laugh.
  • Document relentlessly. It’s your only defense in a post-fact environment.
  • Celebrate human wins. Remind the team what value only people bring. Context, creativity, and conscience still matter.
  • Rest. You’re managing the weirdest, fastest-evolving workforce in history. That’s worth a genuine break.

The Bottom Line

Hybrid teams are not the future; they’re the present. And women project managers are uniquely positioned to lead them — not just because we can juggle, but because we’ve spent our careers translating chaos into deliverables.

You are not just coordinating people anymore. You’re coordinating realities. Every standup, every stakeholder update, every AI-driven surprise is a test of your adaptability and your humor.

And when it all works? When human intuition and machine precision align just right? That’s when you remember why you do this job. Because leadership isn’t about delegating tasks. It’s about syncing rhythm in a world that changes tempo every quarter.

The Silent Power Broker: How Women Chiefs of Staff Run the Company While Everyone Else Is on Stage

Let’s talk about power. Not the Instagrammable, TED-worthy kind, but the kind that shows up in your inbox at 11:47 p.m. with an urgent “Can you talk?” from your CEO who just watched a competitor make headlines. It’s the kind of power that looks invisible from the outside and feels like an ongoing political thriller from the inside.

If you’ve ever been the Chief of Staff in tech, you already know the job description is a polite fiction. Officially, you “ensure executive alignment and cross-org coordination.” In reality, you’re running the company from the shadows while making sure everyone else thinks it’s their idea.

Welcome to the strategic chaos of being a woman Chief of Staff in technology, where influence lives in the gaps between authority, charm doubles as a management tool, and half your emotional stamina goes into making sure your genius CEO doesn’t spontaneously announce a reorg before the product team’s morning standup.

The Myth of the “Invisible Fixer”

Here’s the tragicomedy of being a CoS: if you’re good, no one outside the senior circle knows you exist. You will have vendors emailing your VP to thank them for “their leadership” on a project you actually conceived, staffed, resourced, and dragged to completion through sheer strategic grit and caffeine.

And because the work looks effortless, people assume it is.

But women Chiefs of Staff have learned a powerful trick in this invisibility act. They treat invisibility not as erasure, but as camouflage. They see what’s happening without needing credit, building quiet power through relationships, trust, and cross-functional truth-telling.

One veteran CoS I spoke with compared her role to being “a ghostwriter for the company’s priorities.” You steer direction, prune chaos, and groom messaging while the executives on stage get the applause.

Except here’s the plot twist: every coherent company decision likely has your fingerprints all over it.

You’re Not a Fixer. You’re a Force Multiplier.

Let’s just retire the term “fixer.” It belongs in political thrillers and PR scandals.

A Chief of Staff in tech is not fixing things that are broken. You’re scaling things that work, translating vision into execution, mood swings into strategy decks, and executive brainstorms into deliverables with dates attached.

In a healthy organization, you’re the connective tissue. You’re the one person who knows the priorities, people, and possible landmines well enough to keep the CEO and their lieutenants moving as a coordinated organism.

Force multiplication isn’t glamorous, but it is pure power. You don’t chase visibility because you own velocity. You make the gears mesh faster, decisions land clearer, and meetings end in something resembling outcomes.

Here’s how the calculus works:

  • When leadership spends 90% of its time communicating and only 10% executing, you invert that ratio.
  • When engineers complain that they “don’t understand the strategy,” you condense 60 slides into three bullet points and a meme.
  • When a VP spirals after a rough board review, you offer a coffee, a plan, and a tactful reminder that “the issue isn’t our performance, it’s our narrative.”

The result: the company doesn’t just move, it glides.

The Political Reality: Influence > Authority

A woman Chief of Staff spends her days in a complex geopolitical game where every director, VP, and product lead is a small sovereign state with its own borders, currency (usually “budget”), and touchy pride.

Your job is diplomacy with a poker face.

You can’t issue decrees; you make things happen through trust, timing, and psychological triage. One conversation too early and you look presumptuous; one too late and the project derails.

It’s no accident that women often thrive in this role. The mix of strategic empathy, social intelligence, and long-term political memory is something women in tech have been honed to use for survival, and now we channel it professionally.

Your best tools as a CoS are often the softest ones: tone, presence, humor, and immaculate meeting notes disguised as informal chats.

Corporate Espionage of Feelings

Let’s be honest: most executive offsites are equal parts strategy and therapy.

You will hear a CTO mutter, “I just don’t think the engineers respect me anymore.” You’ll see a CMO trying to heal her bruised ego because her campaign budget got sliced again. And you’ll witness founders coming to terms with the company’s awkward adolescence when scrappy starts to look sloppy.

Women Chiefs of Staff often absorb those emotional tremors and convert them into action plans. We read tone faster than metrics, sensing when someone’s frustration isn’t about analytics but about meaning.

The downside? Emotional labor without credit is an ergonomic hazard.

That’s why part of your job, especially if you want longevity, is building boundaries that treat emotional intelligence like a professional tool, not a personal obligation. You can empathize without inheriting everyone’s angst.

Otherwise, you’ll find yourself crying over a reorganizational spreadsheet that isn’t even your department.

Meetings Are Your Natural Habitat, So Design Them Intelligently

You will attend at least 27% more meetings than any other executive. It’s practically in the job description. But the real trick is that you’re not just attending meetings, you’re orchestrating them.

Good Chiefs of Staff treat meetings as strategic choreography:

  • You seat the fragile ego next to the data-driven introvert so they balance each other out.
  • You give the CEO a crisp pre-brief: “We’re not problem-solving here; we’re aligning.”
  • You end at minute 49 instead of 60, just to build goodwill.

These are micro-plays of influence, the subtle power of context over content. And when done well, you don’t need to rehash conversations five times.

The Art of the Executive Whisper

If you ever want to understand influence, watch a CoS in the wild at an all-hands.

At 8:58 a.m., they’re walking the CEO through the slide deck, gently editing out the phrase “we’re killing it,” because the dev team is, in fact, not.

At 9:02, they’re sitting offstage, laptop half-open, calm expression, while executives improvise rehearsed authenticity.

At 9:45, they’re sending a follow-up note to HR, Finance, and the UX lead containing hidden context only three people in the company actually know, but which will determine whether the next quarter runs or combusts.

That’s orchestration, not assistance.

As one CoS put it: “My job is not to tell the CEO what to do. It’s to make sure when they do it, the timing, alignment, and narrative actually land.”

Survival Rules for Women Chiefs of Staff

After seeing dozens of women thrive (and flame out) in this space, here’s the collective cheat code:

  • Use your access wisely. You’ll have more contextual data than anyone in the company. Don’t hoard it, curate it.
  • Get your own narrative straight. Otherwise, you’ll always reflect someone else’s story.
  • Insist on credit in business terms. Frame successes as “our forecast landed because of decision alignment” because you were that alignment.
  • Cultivate patience as a political weapon. Most fights resolve themselves if you hold your nerve longer than the loudest person in the room.
  • Mentor the next woman behind you. Quiet power grows louder when shared intentionally.

The Legacy Question: Are You Building Systems or Just Saving People?

The day you realize you’ve built a system that continues to function even when you take PTO, that’s power.

The best Chiefs of Staff are architects, not paramedics. They design processes that make the executive team self-correcting. They document, predict, and human-proof chaos with quiet delight.

And when you leave, the next CoS finds a framework, not a crisis. That’s real leadership; it outlives your calendar access.

Final Thoughts: Visibility Is Overrated, Impact Isn’t

Being invisible used to mean being dismissed. Now it can mean being indispensable.

You don’t need a spotlight when you’re holding the fuse box. You don’t need applause when you’ve engineered the harmony.

The women Chiefs of Staff of 2026 are redefining what power looks like. Silent, strategic, emotionally literate, and deliciously unbothered by who gets the quote in the press release.

Because the truth is, sometimes the person most responsible for running the company isn’t on stage. She’s off to the side, sipping her coffee, watching everything run exactly as she designed it to.

Lessons from 2025: What This Year’s Tech Layoffs, Reorgs, and ‘Strategic Pivots’ Taught Women Project Managers

It’s been a hell of a year.

Maybe your company did layoffs. Maybe you survived them. Maybe you didn’t. Maybe you’ve watched colleagues you respected get walked out with two weeks’ severance and a hastily arranged farewell Zoom call. Maybe you’re the one who had to tell your team members they were being let go. Maybe you spent six months managing a project that got canceled overnight when someone upstairs decided it was no longer “strategically aligned.”

Maybe you sat through the all-hands where leadership talked about “rightsizing” and “focusing on core business” and “emerging stronger” while you mentally calculated how many people you just saw get their lives upended.

Welcome to 2025 in tech, where job security is a joke and “strategic pivot” is corporate-speak for “we made some bad bets and now you’re paying for it.”

As women project managers, we’ve had a front-row seat to all of it. We’re the ones who have to keep projects moving forward when half the team gets laid off. We’re the ones who absorb the emotional fallout while also dealing with our own anxiety about whether we’re next. We’re the ones who are expected to make sense of chaos that makes no sense.

So let’s talk about what this year’s brutal cycle of layoffs, reorgs, and strategic pivots actually taught us. Not the sanitized lessons from the leadership post-mortem, but the real lessons we learned in the trenches.

Lesson 1: You’re Not Safe, No Matter How Good You Are

Let’s start with the hardest lesson: competence doesn’t protect you.

You’ve probably known this intellectually, but 2025 made it visceral. You watched high performers get laid off. You watched people who just got promoted get laid off three months later. You watched people who’d been at the company for a decade get laid off. You watched people who were literally indispensable to critical projects get laid off, and then watched leadership scramble to figure out how to do the work they were doing.

The criteria for who stays and who goes in layoffs is often arbitrary, political, and disconnected from actual performance or value. Sometimes it’s just “this org is too expensive, cut 20%.” Sometimes it’s “we need to show investors we’re serious about costs.” Sometimes it’s “this VP wants to bring in their own people.”

As women, we’re especially vulnerable because we’re more likely to be in roles that get categorized as “nice to have” rather than “essential,” even when we’re absolutely essential. We’re more likely to be overlooked for the critical projects that provide protection. We’re more likely to lack the executive sponsorship that keeps people off the layoff list.

So what do you do with this lesson?

Stop over-functioning to prove your value. Working yourself to death won’t protect you, and it will leave you burned out if (when) you do get laid off.

Build your external network and reputation. Your value needs to extend beyond your current company. Make sure people outside your organization know what you’re capable of.

Keep your skills current and marketable. You should always be in a position to leave if you need to.

Have a financial runway. If possible, save enough to survive 3-6 months without income. I know that’s privileged advice and not everyone can do it, but if you can, do.

Don’t tie your identity to your job. You are not your job title. You are not this project. You are not this company. You’re a talented professional who happens to work here right now.

Lesson 2: The Project You’re Killing Yourself Over Might Get Canceled Tomorrow

You know that project you’ve been working nights and weekends on? The one where you sacrificed time with your family, pushed your team, and bent over backwards to hit deadlines? There’s a non-zero chance it’s going to get canceled, and nobody’s going to apologize for all the effort you put into it.

2025 was brutal for this. Massive projects got shut down overnight with no warning. Work that teams had invested months or years in got scrapped because of a “strategic pivot.” All that effort, all that sacrifice, all that stress, just gone.

Here’s what this teaches us: stop treating every project like it’s life or death.

Obviously, do good work. Hit your deadlines. Deliver quality. But recognize that in the current environment, no project is guaranteed to matter in six months. The company might pivot. Priorities might change. Leadership might decide this isn’t strategically important anymore.

So what does this mean practically?

Set boundaries. Don’t work unsustainable hours for projects that might evaporate. Your health and relationships are more permanent than any project.

Celebrate progress, not just outcomes. If the project gets canceled, you still learned things, built relationships, and developed skills. That matters even if the deliverable never ships.

Keep perspective. When you’re tempted to spiral about a deadline or a project setback, remember that none of this might matter in three months anyway. Do your best and then let it go.

Document your contributions. Even if the project gets canceled, you want credit for what you delivered while it existed.

Don’t let work consume your identity. You need sources of meaning and satisfaction outside of your projects, because projects are temporary and fragile.

Lesson 3: Reorgs Are Almost Never About What They Say They’re About

How many reorgs did your company go through in 2025? Two? Three? Are you even sure what org you’re in anymore?

Here’s what you’ve learned: when leadership says “we’re reorganizing to better align with strategic priorities” or “streamline decision-making” or “break down silos,” that’s rarely the whole story.

Sometimes reorgs are about:

New executives wanting to bring in their own people and push out the existing team.

Making it easier to do layoffs by moving people into roles where they’ll fail or quit.

Power plays between VPs who are fighting for headcount and budget.

Trying to fix a cultural or execution problem with a structural change (spoiler: doesn’t work).

Stalling for time because leadership doesn’t actually know what the strategy should be.

As a PM navigating reorgs, you learn to read between the lines. You learn to watch who’s gaining power and who’s losing it. You learn that what matters isn’t the org chart on the slide, it’s who actually has budget, headcount, and executive sponsorship.

Practical lessons from 2025’s reorgs:

Your project’s priority can change overnight based on whose org it’s in. If your project gets moved to a different org, immediately figure out whether the new leadership cares about it.

Relationships matter more than org charts. The people who actually help you get things done might not be anywhere near you on the official org chart.

Reorgs create opportunity and risk. They can be your chance to move into a better role or get visibility with new leadership. They can also be the thing that makes your job unbearable.

Don’t get too attached to any structure. It’ll change again in six months anyway.

Use reorg chaos to negotiate. When everything is in flux, there’s opportunity to redefine your role, your scope, or your compensation.

Lesson 4: Emotional Labor Falls on Women, and Nobody Compensates Us for It

When layoffs happen, when reorgs create chaos, when people are anxious and demoralized, who does the emotional labor?

Let me guess: you do.

You’re the one checking in on team members who are spiraling. You’re the one having the hard conversations. You’re the one trying to keep morale up while also managing your own anxiety. You’re the one expected to be empathetic, supportive, and strong simultaneously.

And you know what you get for it? Nothing. No extra comp. No recognition. Just the expectation that this is part of being a good team member, a good manager, a good woman.

Meanwhile, the men at your level are focused on their own careers, their own projects, their own advancement. They’re not expected to take care of everyone’s feelings. They’re not judged harshly if they prioritize their own needs.

What 2025 taught us about this:

You can’t fix everyone’s problems. You’re not responsible for managing everyone’s anxiety or making everyone feel okay about organizational chaos that you didn’t create.

Boundaries are essential. It’s okay to say “I care about you and I’m not in a place to process this with you right now.”

Name the dynamic. When you’re doing invisible emotional labor, make it visible. “I’ve noticed I’m doing a lot of emotional support work for the team. How can we distribute this more evenly?”

Take care of yourself first. You can’t support others from an empty tank. Your wellbeing matters as much as anyone else’s.

Don’t let empathy become exploitation. Being empathetic is a strength, but if your organization is exploiting that by expecting you to manage all the emotional fallout of their decisions, that’s a problem.

Lesson 5: The Skills That Matter in Chaos Are Different Than the Skills That Matter in Stability

When things are stable, being a good PM means planning well, managing timelines, coordinating stakeholders, delivering on commitments.

In 2025’s chaos, those skills still mattered, but other skills became more critical:

Adaptability: The ability to pivot quickly when priorities change.

Triage: The ability to figure out what actually matters when everything feels urgent.

Resilience: The ability to keep moving forward when things keep falling apart.

Political navigation: The ability to understand power dynamics and protect your projects and team.

Transparent communication: The ability to be honest with your team about uncertainty instead of pretending you have answers you don’t have.

The PMs who thrived in 2025 weren’t necessarily the ones with the best Gantt charts. They were the ones who could navigate ambiguity, manage up and down simultaneously, and keep teams focused despite chaos.

Skills to develop for ongoing uncertainty:

Scenario planning: Get comfortable with “if this happens, then we’ll do this” planning instead of fixed timelines.

Stakeholder management under stress: Learn to manage executives who are anxious, team members who are demoralized, and partners who are skeptical, all at the same time.

Quick decision-making with incomplete information: You won’t have perfect data. You need to be able to make good calls anyway.

Resilience practices: Whatever helps you personally recover from setbacks, build that into your routine. Therapy, exercise, meditation, hobbies, whatever works.

Lesson 6: Women Get Hit Harder by Uncertainty

Here’s the thing nobody says out loud: uncertainty hits women harder than it hits men, and not because we’re less resilient.

Women are more likely to be supporting families on our income or to be the primary earner. Women are more likely to be balancing caregiving responsibilities that make job loss catastrophic. Women have smaller financial cushions on average because of the wage gap. Women have fewer executive networks to catch us if we fall.

So when your company goes through layoffs and everyone’s anxious, women have additional layers of anxiety that our male peers might not fully understand.

And when the dust settles and your company is asking people to do more with less, women are more likely to say yes because we’re socialized to be helpful and because we’re more worried about being seen as difficult or uncommitted.

What this means:

Your anxiety about job security is not irrational. You’re not overreacting. You’re correctly assessing risk.

You don’t have to pretend to be fine. The toxic positivity around layoffs (“it’s actually an opportunity!”) is harmful. You’re allowed to acknowledge that this is hard.

Support other women. We need to build our own safety nets. Share job opportunities. Make introductions. Provide references. Hire each other.

Don’t sacrifice yourself to prove your commitment. When leadership asks you to take on the work of three people who got laid off, it’s okay to say “here’s what’s realistic with current resources.”

Lesson 7: Strategic Pivots Are Code for “We Don’t Know What We’re Doing”

Let’s be real about what “strategic pivot” usually means: leadership made bets that didn’t pay off, and now they’re scrambling to find a new story.

Sometimes it’s wrapped in compelling language about “focusing on core strengths” or “doubling down on what’s working.” Sometimes it’s legitimate strategy evolution. But often? It’s leadership throwing spaghetti at the wall to see what sticks.

The problem is, as a PM, you’re expected to execute these pivots with enthusiasm. You’re supposed to pretend this new direction is brilliant and well-thought-out, even when you can see the holes in the logic.

What 2025’s endless pivots taught us:

Ask clarifying questions. Don’t just nod and execute. Make sure you actually understand the strategy and the reasoning. If it doesn’t make sense, ask why.

Protect your team from whiplash. Your team doesn’t need to internalize every strategic shift. Buffer them from the chaos when you can.

Don’t internalize failure when strategies fail. If you executed well on a strategy that didn’t work, that’s not your failure. That’s a strategy problem.

Build skills that transfer across pivots. The more adaptable your skill set, the more valuable you are regardless of what direction leadership picks.

Know when to cut your losses. If your company is pivoting every quarter with no clear direction, that might be a sign that leadership doesn’t actually have a strategy, and you should consider whether you want to stick around for that.

Lesson 8: The Real Lesson Is That You Need a Plan B

Here’s the biggest lesson from 2025: you need a Plan B. Always.

Plan B might be another job. Plan B might be freelancing or consulting. Plan B might be a side business you’ve been building. Plan B might be skills you’re developing that make you more marketable. Plan B might be a financial cushion that gives you options.

But you need something. Because in the current tech environment, loyalty doesn’t pay, stability is an illusion, and any company can decide tomorrow that you’re no longer strategically aligned with their priorities.

This doesn’t mean you should be cynical or disengaged. It means you should be strategic about your own career in the same way you’re strategic about your projects.

Building your Plan B:

Network actively. Stay connected with recruiters. Keep your LinkedIn updated. Take coffee chats. Make yourself known outside your current company.

Build transferable skills. AI/ML, data analysis, strategic thinking, stakeholder management—these matter everywhere.

Create a portfolio. Document your wins. Quantify your impact. Build case studies. You want to be able to show what you’ve accomplished.

Stay interview-ready. Even if you’re not actively looking, periodically practice talking about your experience and accomplishments. Don’t wait until you’re desperate to figure out how to sell yourself.

Diversify your identity. Have interests and sources of meaning outside of work. It makes you more resilient and more interesting.

The Gratitude No One Wants to Hear (But That’s Real Anyway)

Here’s the paradox: 2025 was brutal, but it also made us better PMs and more resilient humans.

We learned to navigate impossible situations. We learned to lead through uncertainty. We learned to take care of ourselves and our teams when institutions failed us. We learned who we can trust and who we can’t. We learned that we’re more capable of handling hard things than we thought.

We also learned that the tech industry’s promises of meritocracy and stability were always somewhat fictional, and that’s actually liberating in a weird way. Once you stop believing the fairy tale, you can make clearer decisions about your career.

None of this makes the layoffs, the reorgs, or the strategic pivots okay. But it does mean that we’re entering 2026 with our eyes wide open, with better boundaries, and with a clearer understanding of what we’re willing to tolerate and what we’re not.

Moving Into 2026

So here’s what we’re taking into 2026:

We’re going to do good work, but we’re not going to kill ourselves for projects that might evaporate.

We’re going to support our teams, but we’re going to stop doing unpaid emotional labor that should be leadership’s responsibility.

We’re going to be strategic about our own careers, not just the projects we manage.

We’re going to build our skills, our networks, and our options.

We’re going to support other women because we’re all navigating the same chaos.

And we’re going to remember that we’re talented, capable professionals who happen to work in tech right now, not people whose entire identity and worth is tied to whether we’re currently employed.

2025 was hard. 2026 might be hard too. But we’ve learned how to survive hard things, and we’re going to be okay.

Year-End Review: How to Document Everything You Quietly Fixed in 2025 and Use It to Negotiate in 2026

Let me tell you what your year actually looked like:

You managed calendars for executives who couldn’t manage their own time. You rescheduled the same meeting seventeen times because nobody could commit to a time. You planned the offsite that everyone said was the best one yet. You coordinated the team celebration that built morale when everyone was burned out.

You onboarded the new hires and made sure they felt welcome. You fixed the expense report system that was driving everyone crazy. You knew exactly which vendor to call when the AV system failed five minutes before the board presentation. You were the one who remembered everyone’s dietary restrictions, personal preferences, and which executives couldn’t stand each other and shouldn’t be in the same room.

You kept the entire operation running smoothly, and most people didn’t even notice because that’s the point. When you do your job well, it’s invisible.

And now it’s year-end review season, and you’re supposed to somehow articulate your value to an organization that fundamentally undervalues administrative work. You’re supposed to negotiate for a raise when you know your role is seen as “support” rather than strategic. You’re supposed to advocate for yourself when you’ve spent the entire year advocating for everyone else.

So let’s talk about how to document everything you quietly fixed in 2025 and use it to negotiate in 2026. Because you deserve credit, compensation, and respect for the work you do.

The Visibility Problem

Here’s the fundamental challenge: the better you are at your job, the less visible your work becomes. When calendars flow smoothly, when meetings happen without a hitch, when problems get solved before they escalate, people assume it just happens.

They don’t see the hours you spent coordinating schedules across time zones. They don’t see you catching the error in the presentation the night before the board meeting. They don’t see you de-escalating the situation with the angry client or calming down the executive who was spiraling before the big pitch.

And because they don’t see it, they don’t value it appropriately. Or they think “anyone could do this” because they’ve never actually had to do it themselves.

As women in administrative roles, we face an additional layer of invisibility. The work we do gets gendered as “naturally” female, as though organizational magic and emotional labor are just things women instinctively know how to do rather than actual skills we’ve developed and honed.

So the first step in getting credit for your work is making it visible. And that starts with documentation.

The Running List You Should Have Been Keeping (And Will Start Today)

If you don’t have a running document of everything you’ve done this year, start one today. Right now. Open a document and start listing everything you can remember from 2025.

Here’s how to structure it:

Category 1: Things I Fixed or Improved

Did you overhaul a system that wasn’t working? Did you implement a new process that saved time? Did you find a better vendor or renegotiate a contract? Did you solve a problem that had been nagging the team for months?

For each item, document:

What was broken or inefficient?

What did you do to fix it?

What was the result? (time saved, money saved, problems eliminated, satisfaction increased)

Example: “Redesigned the meeting room booking system that was causing constant conflicts and complaints. Implemented a shared calendar with clear protocols. Result: booking conflicts dropped by 80%, complaints to IT about the system went to zero, teams reported higher satisfaction with ability to find meeting space.”

Category 2: Critical Moments I Handled

These are the fires you put out, the crises you managed, the situations that could have gone sideways but didn’t because of your intervention.

For each moment, document:

What was the situation?

What would have happened if you hadn’t intervened?

What did you do?

What was the outcome?

Example: “CTO’s flight was canceled day-before board presentation. Within two hours, found alternate routing through a different airport, arranged ground transportation, got him there with time to spare. Board presentation proceeded as scheduled with no delay.”

Category 3: Things I Manage That Nobody Thinks About

This is the ongoing, continuous work that people only notice when it doesn’t happen. Calendar management, expense processing, vendor relationships, supply ordering, event planning, onboarding coordination.

For each area of responsibility, document:

What’s the scope? (how many people’s calendars, how many events, how many vendors, etc.)

What’s the complexity? (international time zones, multiple stakeholder priorities, budget constraints, etc.)

What would happen if this wasn’t managed well?

Example: “Manage calendars for 5 executives with average of 45 meetings per week each, coordinating across 8 time zones with competing priorities and frequent changes. Maintain 98% meeting accuracy rate (meetings happen as scheduled with correct attendees and materials). Executives consistently report calendar management as one of their top productivity enablers.”

Category 4: Value I Added Beyond My Job Description

This is where you were doing project management, or ops work, or HR support, or communications, or literally anything that wasn’t technically your job but you did it because it needed doing.

For each area, document:

What was needed?

How did you step up?

What skills did you apply that go beyond typical administrative work?

What was the impact?

Example: “Led coordination of annual team summit for 120 people. Managed venue selection, agenda design, speaker coordination, budget management ($75K), logistics planning, and day-of execution. Event received 4.7/5 rating, highest in company history, and came in 8% under budget.”

Category 5: Relationships I Built and Maintained

This one often gets overlooked, but relationship management is valuable work. You’re the one who knows who to call for what. You’re the one who built rapport with vendors, clients, partners, cross-functional teams.

For each key relationship, document:

Who is the person/organization?

Why does this relationship matter to the business?

How have you cultivated it?

What has this relationship enabled?

Example: “Developed strong working relationship with facilities team at our co-working space. They now prioritize our requests, give us advance notice of changes, and have offered us first access to premium space when it opens. This relationship has directly enabled our team to secure better meeting spaces and resolve issues faster.”

Category 6: Emotional Labor and Culture Building

This is the hardest to quantify and the most undervalued, but it’s real work: You’re the one who remembers birthdays and makes people feel seen. You’re the one who notices when someone’s struggling and checks in. You’re the one who creates the culture of care on your team.

For each example, document:

What did you do?

Why did it matter?

What was the impact on morale, retention, or team culture?

Example: “Created and manage team recognition program where we celebrate wins, work anniversaries, and personal milestones. Program has increased participation in team events by 40% and multiple team members have cited feeling valued and recognized as reasons they chose to stay when considering outside offers.”

Translating Your Work Into Business Impact

Once you have your list, you need to translate it into language that business leaders understand: impact on time, money, productivity, retention, or risk.

Here’s how to reframe each type of work:

If you save time: Calculate how much. If you reduced the time executives spend on calendar management from 2 hours per week to 15 minutes, that’s 1.75 hours per week per executive. Multiply by number of executives and number of weeks. That’s hundreds of hours annually that they can spend on strategic work instead.

If you save money: Document it precisely. If you negotiated better rates with a vendor, if you found a more cost-effective solution, if you prevented waste, quantify it in dollars.

If you prevent problems: Estimate the cost of those problems if they had happened. A missed board presentation could have cost a funding round. A botched client event could have lost a contract. You can’t prove the counterfactual, but you can make a reasonable case.

If you improve productivity: Point to outcomes. Did the systems you implemented help the team ship faster? Did your coordination enable projects to stay on track? Connect your work to business results.

If you support retention: High-performing teams with good culture retain talent. Retention saves enormous money in recruiting and onboarding costs. If people specifically mention that you or the culture you help create is part of why they stay, that’s valuable.

Building Your Case for 2026 Negotiation

Now that you have your documented wins and business impact, it’s time to build your negotiation strategy for 2026.

Step 1: Research Your Market Value

Look up salary data for administrative roles at your level in your market. Sites like Glassdoor, Salary.com, and Payscale can give you data points.

But also recognize that your work might be beyond typical administrative scope. If you’re doing project management, operations coordination, or strategic support, look at those salary ranges too.

Step 2: Know Your Number

Based on your research and your impact, what do you believe you should be earning? Be specific. Not “more” or “a raise,” but “I believe my market value is $X based on my scope, impact, and market research.”

Have three numbers in mind:

Your ideal number (ambitious but justifiable)

Your acceptable number (fair and reasonable)

Your walk-away number (below this, you start looking elsewhere)

Step 3: Build Your Pitch Document

Create a document (2-3 pages max) that you’ll share with your manager before your review conversation. Include:

Overview of your role and scope: Make the breadth of what you do clear.

Key accomplishments from 2025: Pull from your documented list, focus on highest-impact items.

Business value delivered: Translate accomplishments into time saved, money saved, problems prevented, productivity improved.

Skills developed and applied: What have you learned? What certifications or training have you completed? How have you grown?

Request for 2026: “Based on this track record and market research, I’m requesting [specific compensation increase/title change/expanded responsibilities].”

Step 4: Practice Your Conversation

You need to be able to articulate your value out loud, not just on paper. Practice with a friend, a partner, or even just in front of a mirror.

Practice saying:

“I’ve delivered significant value this year, and I’d like to discuss compensation that reflects that.”

“Based on my research and the scope of my contributions, I believe $X is appropriate.”

“I’m committed to this team and want to continue growing here, and I need to know there’s a path for that.”

Practice until you can say these things without apologizing, without hedging, without minimizing your accomplishments.

Step 5: Have the Conversation

Request a specific meeting with your manager to discuss your performance and compensation for 2026. Don’t spring this on them during a routine check-in.

In the meeting:

Start with appreciation: “I’ve really valued working on this team this year.”

Share your document: “I put together an overview of my contributions this year that I wanted to walk through with you.”

Walk through your key accomplishments and impact: Don’t read the whole document, but hit the highlights.

Make your ask: “Given this track record and my research on market rates, I’m requesting [specific ask].”

Listen to their response without interrupting.

Handling Common Pushback

You’re going to get pushback. Here’s how to handle the most common responses:

“We don’t have budget for raises right now.”

Response: “I understand budget constraints are real. Can we discuss what’s possible within the budget, and also what would need to happen for this to be revisited? I want to continue growing here, and I need to understand the path forward.”

Also: Start looking at other opportunities. If they genuinely can’t or won’t pay you appropriately, you need to know that.

“Your role is at the top of the band already.”

Response: “I appreciate that context. Given that my work has expanded significantly beyond typical administrative scope, I’d like to discuss whether my title and role definition accurately reflect what I’m doing. Should we be looking at a different job category or level?”

“This is what we pay for this role.”

Response: “I understand that’s been the approach historically. What I’m bringing to your attention is that the scope of my work has evolved significantly. I’m handling project coordination, stakeholder management, and strategic support that goes beyond traditional administrative work. I’d like to discuss how we can align my compensation with the actual value I’m delivering.”

“You’re doing a great job but everyone’s in the same boat with raises.”

Response: “I appreciate the recognition of my contributions. If salary increase isn’t possible right now, can we discuss other forms of compensation? Additional PTO, professional development budget, title change, or a commitment to revisit compensation in Q2?”

“You should be grateful to have a job.”

Response: (Red flag, start looking elsewhere) “I am grateful to be part of the team. I’m also professionally advocating for compensation that reflects my contributions. These aren’t mutually exclusive.”

When to Walk Away

Here’s the hard truth: not every organization will value your work appropriately, no matter how well you document it or how skillfully you negotiate.

If you get clear signals that you’re not valued (consistent dismissal of your contributions, refusal to even discuss fair compensation, patterns of disrespect), it might be time to look elsewhere.

Signs you should start looking:

Your compensation hasn’t kept pace with inflation or market rates for multiple years.

Your scope has expanded significantly but your title and pay haven’t changed.

You’re consistently told you’re doing great work but that never translates to tangible recognition.

Your manager can’t or won’t advocate for you.

The organizational culture fundamentally devalues administrative work.

You’re burned out and nothing is changing.

You don’t have to stay somewhere that doesn’t value you. Your skills are transferable. Other organizations will appreciate what you do.

The Long Game: Positioning Yourself for 2027 and Beyond

Whether you stay in your current role or move on, here’s how to position yourself for long-term success:

Keep documenting: Don’t wait until next year’s review. Keep your running list updated quarterly.

Build your external brand: Connect with other administrative professionals. Join professional organizations. Share your expertise on LinkedIn. You’re not just “someone’s assistant,” you’re a professional with valuable skills.

Invest in your skills: Take courses in project management, operations, strategic communications, data analysis, whatever interests you and adds value. Make yourself more valuable and more marketable.

Build relationships outside your immediate team: Get known more broadly in your organization. Make sure more people understand the value you bring.

Have a career plan: Where do you want to be in 2-3 years? Operations management? Project management? Program coordination? Executive business partner? Chart the path and make intentional moves toward it.

The Recognition You Deserve

Here’s what I want you to hear: your work matters. The invisible work of keeping organizations running smoothly is not less valuable because it’s invisible. It’s actually more valuable because it’s the foundation everything else builds on.

You’re not “just” an administrative assistant. You’re an operational expert, a problem solver, a relationship manager, a culture builder, and probably about seven other things that aren’t in your job description.

You’ve earned the right to advocate for yourself. You’ve earned the right to be compensated fairly. You’ve earned the right to be seen, valued, and respected.

So document your wins. Know your worth. Make your ask. And if they don’t see your value, find somewhere that does.

2026 is your year to be recognized for everything you quietly fixed in 2025.

How to Take Time Off Without Secretly Working All Week

Let me tell you about the last “vacation” you took:

You spent the week before working late nights to clear your plate. You sent detailed handoff emails. You set up your out-of-office message. You told everyone you’d be disconnected. You were so organized, so prepared, so determined that this time, you’d actually unplug.

Day one of vacation: you checked Slack “just once” to make sure nothing was on fire. There were 47 unread messages. You told yourself you’d just skim them. Two hours later, you’d responded to six threads and joined a “quick” video call from the hotel bathroom.

By day three, you’d given up the pretense entirely. You were taking calls in the morning, working during your kid’s nap time, responding to emails after dinner. Your partner was annoyed. Your family was disappointed. And you felt guilty about all of it while also feeling like you had no choice.

You came back from vacation more exhausted than when you left.

Sound familiar?

Here’s the uncomfortable truth: you’re not bad at taking time off. You’re operating in a system that punishes disconnection and rewards constant availability. And until you understand that, you’re going to keep repeating the same pattern.

So let’s talk about how to actually take time off without secretly working all week. Not because you’re going to magically fix a broken system, but because you can learn to navigate it differently.

Why Women in Tech Can’t Disconnect

Let’s start by acknowledging the specific pressures that make this harder for women:

The Competence Trap: You’ve spent your entire career proving you’re reliable, responsive, and capable. You’re terrified that if you disconnect for a week, people will realize they don’t actually need you, or worse, that they’ll question your commitment.

The Coverage Gap: When men take vacation, someone usually covers for them. When women take vacation, we often end up covering for ourselves while also being gone. Nobody thought to redistribute our work because it wasn’t visible enough to begin with.

The Caretaker Conditioning: Women are socialized to be caretakers. We feel responsible for everyone and everything. The thought of our team struggling while we’re gone feels like we’re failing them.

The Flexibility Tax: Many women fought hard for flexible work arrangements. There’s this underlying fear that if we’re “too” unavailable, it will be used against us or against other women seeking flexibility.

The Penalty for Being Human: Men who take vacation are seen as successfully balancing work and life. Women who take vacation are sometimes perceived as less committed or less serious about their careers.

All of this combines into a perfect storm of guilt, anxiety, and compulsive email-checking that masquerades as a vacation.

The Real Cost of Not Disconnecting

Before we talk about solutions, let’s be honest about what’s at stake when you can’t actually take time off:

Burnout: You can’t sustain high performance without real recovery. Working through your vacation days means you never actually recharge, which means you’re running on fumes year-round.

Resentment: Toward your job, your boss, your team, your partner, yourself. Resentment corrodes everything.

Health Issues: Chronic stress leads to real physical and mental health problems. The occasional panic attack or stress headache is your body screaming that something needs to change.

Relationship Strain: Your family didn’t agree to share vacation time with your Slack account. The resentment goes both ways.

Modeling Terrible Behavior: If you’re a leader who works through vacation, you’re teaching your team that this is the expectation. You’re perpetuating exactly the culture you probably want to change.

Stunted Creativity: Your best ideas don’t come from grinding through another work session on vacation. They come from rest, boredom, new experiences, and space to think.

So yeah, the stakes are high. This matters.

The Before-Vacation Work That Actually Helps

Most advice about taking vacation focuses on the vacation itself. That’s too late. The work happens before you leave.

Two Weeks Before: The Ruthless Prioritization

Make a list of everything on your plate. Then categorize it:

Must happen while I’m gone: Critical operations, time-sensitive deadlines that can’t move.

Can happen while I’m gone with someone else doing it: Work that needs to happen but doesn’t require you specifically.

Can wait until I’m back: Everything else.

Most people drastically overestimate column one and underestimate column three. Your default should be that things can wait. Only move them to column one if there’s a genuine business reason they can’t.

10 Days Before: The Delegation Conversation

For everything in column two, you need to actually delegate it, not just hope someone picks it up.

This means:

Clear handoffs with documentation

Conversations with the people covering for you about what’s expected

Authority delegation (they can’t cover for you if they have to check with you on every decision)

Setting them up for success, not setting them up to fail and prove they need you

Women often struggle with this last part. We “delegate” in a way that ensures the person will need us, which gives us permission to stay involved. Stop it.

One Week Before: The Communication Blitz

Send a message to everyone who might need something from you. Not a vague “I’ll be out,” but:

I’m out from [dates] and fully disconnected.

For [category of issues], contact [person].

For [category of issues], contact [person].

If something urgent comes up that truly can’t wait, here’s the escalation path: [path that doesn’t end with you unless it’s literally a crisis].

Anything that’s not urgent will be addressed when I’m back on [date].

The more specific you are, the less people will “just check in real quick.”

Three Days Before: The Email Zero Project

This is controversial, but I’m a fan of getting to inbox zero before vacation. Not because you have to respond to everything, but because you need to know what you’re leaving behind.

For each email:

Respond if it’s quick.

Delegate if it’s someone else’s domain.

Add to your “first week back” list if it can wait.

Delete if it’s not actually important.

The goal is that when you leave, you’re not haunted by the nagging feeling that there’s something important you forgot.

The Day Before: The Pre-Vacation Shutdown Ritual

Your last day before vacation shouldn’t be a sprint to tie up loose ends. It should be a controlled handoff.

Morning: Final check-ins with people covering for you. Answer their questions. Reassure them they’ve got this.

Midday: Send your “I’m out” communications. Update your Slack status, set your out-of-office, put it on your calendar.

Afternoon: Close your laptop. Physically close it. Maybe even put it somewhere annoying to access, like the top shelf of a closet.

Evening: Do something fun and vacation-adjacent. Pack, make a playlist, plan your first day activity. Get yourself mentally into vacation mode.

The Vacation Itself: Strategies That Actually Work

Okay, you’re on vacation. Now how do you stay on vacation?

Strategy 1: The Complete Blackout

Delete work apps from your phone. Sign out of email. Go completely dark. Don’t check anything, don’t respond to anything, don’t even look.

This works if:

You have excellent coverage and clear escalation paths.

You trust your team and your systems.

Your leadership supports true disconnection.

This doesn’t work if:

You’re in a genuinely mission-critical role during a critical time.

Your organization culture will punish you for being unreachable.

Your anxiety about not knowing what’s happening is worse than the stress of checking.

Strategy 2: The Controlled Check-In

Set a specific time each day (I recommend morning) where you spend 30 minutes checking in. Skim for genuine emergencies. Respond only to things that truly can’t wait.

The rules:

One check-in per day, maximum.

Set a timer for 30 minutes.

Only respond to true emergencies, not “this would be helpful” requests.

Don’t get sucked into threads or projects.

Close the apps when the timer goes off.

This works if:

Total disconnection creates more anxiety than controlled connection.

You’re in a role where some availability is realistically required.

You have the discipline to stick to the boundaries.

This doesn’t work if:

You can’t stick to 30 minutes (be honest with yourself).

Your organization sees any availability as full availability.

It defeats the purpose of your vacation because you can’t mentally disconnect.

Strategy 3: The First/Last Day Compromise

You’re fully disconnected for the bulk of your vacation, but you check in on the first and last days to handle anything urgent on either end.

This gives you the psychological comfort of knowing nothing exploded while also giving you multiple full days of disconnection.

Strategy 4: The Buddy System

Before you go on vacation, make a pact with a colleague: they cover for you completely when you’re out, you cover for them completely when they’re out. No backsies, no checking in, no exceptions.

This works because it creates external accountability. You’re not just letting yourself down if you check work email, you’re violating an agreement with someone who’s holding up their end.

The Psychological Warfare of Vacation

Let’s talk about what actually happens in your head when you try to disconnect, because this is where the real battle is.

The Anxiety Spiral:

“What if something breaks and I’m not there to fix it?”

“What if people realize they don’t actually need me?”

“What if I miss something important and it reflects badly on me?”

“What if someone else does my job better than I do?”

Here’s the reality check you need: If your organization genuinely cannot function for one week without you, that’s a massive organizational failure, not a testament to your importance. Healthy organizations have redundancy and cross-training. If yours doesn’t, that’s a problem that predates your vacation.

As for people realizing they don’t need you? They won’t. One week is not enough time for anyone to conclude that your role is unnecessary. And if your organization is so dysfunctional that they would conclude that, you have bigger problems than vacation.

The Guilt Complex:

“My team is struggling and I’m not there to help.”

“I should be more available for them.”

“Taking time off is selfish when we’re so busy.”

Let’s reframe this: Taking care of yourself is not selfish. It’s essential. You can’t pour from an empty cup, and all those other cliches that are actually true. Your team is not helped by you being chronically exhausted and half-present.

Also, struggling is how people learn and grow. If you’re always there to solve every problem, you’re preventing your team from developing their own capabilities.

The FOMO (Fear of Missing Out):

“What if there’s a big decision and I’m not in the room?”

“What if something exciting happens and I miss it?”

“What if I’m not part of important conversations?”

Real talk: big decisions rarely happen in one week. Important conversations continue over time. You’re not missing as much as you think you are. And even if you are? That’s the price of taking time off, and it’s worth it.

Setting Boundaries with People Who Don’t Respect Them

Inevitably, someone is going to try to pull you back into work during your vacation. Here’s how to handle it:

The “Quick Question” Text:

Response: “I’m on vacation and fully disconnected. [Name] is covering for me, they can help with this.”

Then don’t engage further. Don’t answer the question. Don’t explain your boundary. Just redirect.

The “I Know You’re on Vacation But” Email:

Option 1: Don’t respond. Your out-of-office will reply for you.

Option 2: If you’re doing controlled check-ins and this truly can’t wait: “I have very limited availability this week. What’s the specific decision that needs to be made and what’s the deadline?” Force them to be specific, not vague.

The “Emergency” That Isn’t:

Someone’s definition of emergency is not necessarily your definition of emergency. Unless something is on fire, losing money, or violating regulations, it can probably wait.

If someone escalates something as an emergency that isn’t, you can say: “Thanks for flagging this. I’m reviewing our escalation protocols and will follow up when I’m back to make sure we’re aligned on what constitutes an emergency that requires pulling someone off vacation.”

Translation: stop crying wolf.

The Boss Who Doesn’t Respect Boundaries:

This is the hard one. If your boss routinely expects you to work through vacation, you have a few options:

Have a direct conversation before your vacation: “I’m planning to fully disconnect during my time off. If there’s a specific situation where you’d need me to be reachable, let’s discuss that now so I can plan accordingly.”

Document the pattern: If they routinely violate your vacation boundaries, document it. This is especially important if you’re ever in a position to raise concerns about workload or culture.

Vote with your feet: If you work for someone who fundamentally doesn’t respect your need to disconnect, that’s a massive red flag about that person’s leadership and the organization’s culture.

Coming Back Without Undoing All the Good

The vacation is over. You’re rested. Now how do you reintegrate without immediately spiraling back into the same patterns?

The First Day Back:

Do not try to catch up on everything immediately. You’ll fail and you’ll be miserable.

Instead:

First hour: Skim email and Slack for genuine emergencies. Handle anything that absolutely can’t wait another day.

Next two hours: Meet with your key team members or partners. Get downloaded on what happened. Let them tell you the story instead of trying to piece it together from message threads.

Afternoon: Start working through your backlog systematically. Prioritize ruthlessly.

The First Week Back:

Your goal is not to immediately return to your pre-vacation pace. Your goal is to maintain some of the perspective and space you gained on vacation.

Continue saying no to things that aren’t truly important.

Keep some of the boundaries you set for vacation (like not checking email after a certain hour).

Schedule your next time off before you get sucked back into the grind.

The Retrospective:

Within a week of returning, reflect:

What worked about how I took time off?

What didn’t work?

What do I need to change before my next vacation?

What did I learn about my team’s capabilities when I wasn’t there?

What can I permanently delegate based on what happened while I was gone?

This last question is key. Often you’ll discover that things you thought only you could do were successfully handled by others. That’s information you can use to lighten your load permanently.

The Organizational Change You Can (Maybe) Influence

Look, you can’t single-handedly fix a culture that expects constant availability. But if you’re in any kind of leadership position, you can influence it:

Model genuine disconnection when you take time off. Your team is watching.

Explicitly tell your team not to contact you when you’re on vacation. Mean it.

Don’t contact your team when they’re on vacation. Seriously, don’t.

Implement formal coverage plans so people aren’t covering for themselves.

Celebrate people who successfully disconnect instead of people who work through vacation.

Push back on timelines and expectations that require people to work through time off.

In performance reviews and one-on-ones, ask people about their ability to disconnect and address barriers.

Small actions compound over time. You might not change the entire organizational culture, but you can change the culture of your immediate team.

The Permission You’re Waiting For

Here’s what I know about you: you’re waiting for someone to give you permission to actually take time off. To disconnect. To prioritize your wellbeing over your inbox.

So here it is: You have permission.

You have permission to be unavailable for a week. You have permission to let things wait. You have permission to trust your team. You have permission to disappoint people who have unrealistic expectations. You have permission to take care of yourself.

Your worth is not measured by your responsiveness. Your value is not determined by your availability. Your importance is not proven by your inability to disconnect.

You’re allowed to rest. You’re allowed to have a life outside of work. You’re allowed to come back renewed instead of returning more exhausted than when you left.

Take the vacation. Actually take it. Your work will be there when you get back.

And so will you, if you let yourself rest.

The December Offsite That Actually Matters: Strategy Sessions Designed for Women’s Voices to Be Heard

Let me describe the December offsite you’ve probably attended:

A conference room (or worse, a “fun” offsite location that’s supposed to make everyone feel creative). A deck with 47 slides about strategic priorities. A facilitator who asks for input but somehow the same three people do all the talking. Breakout sessions where one person dominates while everyone else nods politely. A parking lot for issues that will never be addressed. Action items that no one is actually accountable for.

You leave feeling like you just spent two days achieving what could have been accomplished in a 45-minute meeting. The strategic “decisions” feel predetermined. The priorities coming out of it are suspiciously similar to the priorities going in. And your ideas, the ones you carefully prepared and tried multiple times to voice, somehow got attributed to the guy who repeated them with more confidence.

As a woman in strategy and planning, you’ve probably facilitated these sessions. You’ve definitely attended too many of them. You know they’re broken. You also know they’re critical, because December is when next year’s strategic direction actually gets set.

So let’s talk about how to design and run strategy sessions that don’t just extract input from women, they actually center women’s voices and create space for the kind of strategic thinking that moves organizations forward.

Why Traditional Strategy Sessions Fail Women

Before we talk about what works, let’s be honest about why the standard approach doesn’t.

Traditional strategy sessions favor a very specific communication style: confident, assertive, immediate, and loud. People who speak first, speak definitively, and speak often get heard. People who need time to think, who prefer to build on others’ ideas rather than dominate the conversation, who communicate with nuance rather than certainty, get overlooked.

Guess which communication style is disproportionately socialized in men versus women?

Then there’s the structural problem: most strategy sessions prioritize abstract, big-picture thinking over operational reality. The person who can paint the compelling vision gets airtime. The person who asks hard questions about feasibility, resource constraints, or implementation challenges gets labeled as “not strategic” or “too in the weeds.”

Women leaders, who are more likely to be held accountable for execution, are also more likely to raise these practical concerns. And then we’re dismissed as not being visionary enough.

The third problem is interruption and attribution. Research shows that women get interrupted more frequently in meetings, our ideas get credited to men who repeat them, and we’re less likely to get called on when we signal we want to speak.

In a standard strategy session where the loudest voice wins, women lose.

Designing for Inclusion from the Start

If you’re planning a December strategy session, inclusion can’t be an afterthought. It has to be baked into the design from the beginning.

Step 1: Be Intentional About Who’s in the Room

Look at your invite list. What’s the gender breakdown? What about race, age, tenure, functional background?

If your strategy session is predominantly senior white men, you’re going to get a very narrow set of perspectives. And here’s the uncomfortable truth: adding one or two women to a room full of men doesn’t actually create inclusion. It just creates pressure on those women to either assimilate to the dominant communication style or be ignored.

Aim for at least 30-40% women in your strategy sessions. Invite women at multiple levels, not just the most senior ones. Include individual contributors who are close to the actual work, not just executives who are three layers removed.

And if you can’t get to 30-40% women because your leadership team is that unbalanced? That’s a different problem that you should flag loudly.

Step 2: Send Pre-Read Materials That Level the Playing Field

One of the ways women get disadvantaged in strategy sessions is when decisions are made based on context that only a few people have. If you show up to a strategy session and the first hour is someone presenting information that you’ve never seen before, you’re immediately behind.

Send comprehensive pre-reads at least a week in advance:

Market analysis and competitive landscape

Current state assessment (honest, not sanitized)

Strategic options being considered

Key questions we need to

answer

Any relevant data or research

This does two things: it ensures everyone has the same context, and it gives people who process information by thinking and writing (rather than thinking out loud) time to develop their perspectives.

Step 3: Use Structured Facilitation Techniques

Free-form discussion might feel organic, but it consistently advantages people who are comfortable dominating conversations.

Instead, use structured techniques:

Round-robin sharing: Everyone gets two uninterrupted minutes to share their perspective before we open it up for discussion.

Silent brainstorming: Before we discuss, everyone writes down their ideas. Then we collect them all and discuss themes, not individual suggestions.

Breakout groups with clear roles: If you’re doing small group work, assign a facilitator, a note-taker, and a timekeeper. Rotate these roles. This prevents one person from controlling the conversation.

Parking lot with accountability: Yes, have a parking lot for topics that are off-agenda. But at the end, assign someone to actually follow up on each item. Otherwise it’s just a place where women’s concerns go to die.

The Pre-Work That Changes Everything

Here’s what I’ve learned: the quality of your strategy session is determined by the work you do before anyone walks in the room.

Two Weeks Before: Individual Reflection

Send everyone a brief reflection exercise:

What do you think is our biggest strategic opportunity right now? Why?

What’s our biggest strategic risk or blind spot?

If you could change one thing about our current strategy, what would it be?

What question should we be asking that we’re not asking?

Make this anonymous if you want truly honest responses. Compile the results and share themes with the group before the offsite.

This levels the playing field. Introverts and people who process through writing get to contribute meaningfully. You surface perspectives that might never come up in a meeting. You identify areas of alignment and areas of tension before you’re in the room.

One Week Before: Small Group Pre-Meetings

Before the big strategy session, convene small groups (4-5 people) to discuss specific strategic questions. Mix up the groups so people are working with colleagues they might not normally collaborate with.

These pre-meetings do a few things:

They build relationships and psychological safety before the high-stakes strategy session.

They let people test ideas in smaller settings where it’s less risky to be wrong.

They surface great thinking that might get lost in a larger group.

I specifically create some women-only pre-meeting groups. Not because women can’t hold their own in mixed groups, but because it creates space to discuss dynamics and concerns that might be gendered without having to constantly explain or justify them.

The Session Structure That Actually Works

Okay, you’ve done the pre-work. Now let’s talk about how to actually run the strategy session.

Opening: Set the Tone

In the first 15 minutes, you establish the culture of the session. I explicitly say:

“We’re here to make better decisions together than any of us could make alone. That requires us to hear from everyone, especially people who see things differently than the loudest voices in the room.”

“Great strategy comes from combining vision with operational reality. If your instinct is to raise implementation concerns, that’s strategic thinking, not negativity.”

“We will actively manage speaking time. If you’re someone who tends to think out loud, I’m going to ask you to pause and let others speak. If you’re someone who tends to process silently, I’m going to call on you and give you space.”

“Disagreement is not only welcome, it’s required. If we all leave here agreeing on everything, we probably didn’t push hard enough.”

Name the dynamics you’re trying to address without making it weird. People respect explicit facilitation more than they respect pretending these dynamics don’t exist.

Section 1: Where We Are (60 minutes)

Before you can talk about where you’re going, you need shared reality about where you are. Present the current state honestly. Not the story you tell the board, but the actual reality.

Then ask: What are we not seeing? What’s missing from this picture? What does this look like from your vantage point?

Use the round-robin technique here. Literally go around the room and give everyone two minutes. No interruptions.

You’ll learn more in this hour than in three hours of unstructured conversation.

Section 2: Where We Could Go (90 minutes)

This is where you explore strategic options. I use a structured framework:

Present 3-4 strategic directions the organization could take. Not one predetermined “right” answer, but genuinely different options with different tradeoffs.

For each option, discuss:

What would this enable us to do?

What would we have to stop doing or deprioritize?

What capabilities would we need that we don’t currently have?

What’s the risk if this is the wrong bet?

Who benefits most if we go this direction? Who loses?

That last question is the one that often doesn’t get asked. Every strategic choice creates winners and losers, both in the market and internally. If you don’t explicitly discuss this, you end up with strategy that benefits whoever had the most power in the room.

Break

Take a real break. Not a “let’s keep talking in small groups” break. A “go outside, clear your head, talk about anything other than work” break.

People need processing time. Women especially report needing time to think through complex issues before formulating their perspective. Give them that time.

Section 3: Making the Call (90 minutes)

This is where you actually decide on strategic direction.

Here’s my controversial opinion: not every decision needs to be consensus. Sometimes the leader needs to make a call. But the decision is better if it’s informed by diverse perspectives, and people are more bought-in if they understand why you made the choice you made.

So I structure this section as:

Round 1: Recommendation + Reasoning

Everyone shares which strategic direction they’d recommend and why. Focus on the reasoning, not just the conclusion.

Round 2: Concerns and Questions

For the direction that’s emerging as the likely choice, what are your concerns? What would you need to see to be comfortable with this direction?

Round 3: The Decision + Rationale

The decision-maker (usually the most senior leader) makes the call and explains the reasoning. Critically, they explain what input they heard that shaped the decision and what concerns they’re committing to address.

This structure ensures everyone gets heard, concerns get documented, and there’s clarity about how the decision got made.

Section 4: What This Means for Us (60 minutes)

This is where strategy becomes real. For the strategic direction you’ve chosen, what does it actually mean for how you operate?

What existing work do we stop or deprioritize?

What new capabilities do we need to build?

How do we need to reorganize or reallocate resources?

What’s the timeline for this transition?

What are the key dependencies and risks?

Who’s accountable for what?

I’m obsessed with this section because this is where so many strategy sessions fail. They make big strategic pronouncements but never translate them into operational reality. Then people leave confused about what actually changes.

Closing: Commitments and Follow-Up (30 minutes)

End with crystal clear commitments:

What did we decide?

What are the next steps, who owns them, and when are they due?

How will we communicate this strategy more broadly?

When are we reconvening to assess progress?

Document all of this and send it out within 24 hours.

Handling the Difficult Dynamics in Real Time

Even with the best structure, you’re going to face challenging dynamics. Here’s how to handle them:

When someone dominates the conversation:

“Thanks for that perspective. I want to make sure we’re hearing from everyone. Let’s pause here and get input from folks who haven’t spoken yet.”

Then literally call on people by name. Don’t ask “does anyone else have thoughts?” because the answer will be silence.

When a woman gets interrupted:

“Hold on, I want to hear the rest of what [name] was saying. [Name], please continue.”

Do this every single time. Interruptions are habitual. If you don’t actively counter them, they continue.

When a woman’s idea gets attributed to a man:

“Just to be clear, [woman’s name] raised that idea earlier. [Man’s name] is building on her point.”

This is uncomfortable. Do it anyway. Otherwise you’re complicit in the erasure.

When someone dismisses implementation concerns as “not strategic”:

“Actually, understanding implementation constraints is critical to strategy. A strategy that ignores operational reality isn’t strategic, it’s fantasy. Let’s dig into this concern.”

Reframe implementation thinking as strategic thinking. Because it is.

When you sense women are holding back:

“I notice we haven’t heard from several people. I specifically want to hear from [name women who haven’t spoken]. What’s your read on this?”

Direct invitations work better than general requests for input.

The Follow-Through That Determines Whether This Mattered

Your strategy session is only as good as what happens after it.

Within 48 Hours:

Send comprehensive notes including decisions made, rationale, concerns raised, and action items with owners and deadlines.

Within One Week:

Meet with each person who raised a significant concern. “You brought up X in the strategy session. I want to make sure I understand your concern fully and talk about how we’re addressing it.”

This signals that input actually mattered.

Within Two Weeks:

Begin communicating the strategy more broadly. But here’s the key: acknowledge that this strategy came from collective input, and specifically credit the diverse perspectives that shaped it.

“One of the insights that shaped our thinking was [specific point raised by a woman leader].”

When you explicitly credit women’s strategic contributions, you change the narrative about who drives strategy.

Ongoing:

In every leadership meeting going forward, reference the strategy and assess progress. Keep the strategy alive instead of letting it become a deck that sits on SharePoint.

The Meta-Strategy: Changing Who Gets Seen as Strategic

Here’s the deeper game you’re playing: by designing strategy sessions that center women’s voices, you’re not just making better strategy (though you are). You’re changing who gets perceived as a strategic thinker.

When a woman’s idea becomes part of the strategic direction and everyone knows it came from her, she becomes known as strategic.

When women are consistently invited to and centered in strategy conversations, they become seen as strategic leaders.

When implementation expertise is framed as strategic thinking (not just execution), women who carry that expertise get seen as strategic.

This matters because “not strategic enough” is one of the most common pieces of feedback that keeps women from advancing to senior leadership.

If you want to change that dynamic, you have to change how strategy gets made and who gets credit for it.

Your December Opportunity

It’s December. You’re probably planning strategy sessions right now. You have a choice: you can run them the way they’ve always been run, or you can design them intentionally to create different outcomes.

The women in your organization are watching. They’re noticing whether their ideas get heard or overlooked. Whether their concerns get addressed or dismissed. Whether they’re seen as strategic partners or just execution resources.

Design your strategy sessions to answer that question clearly: Women’s voices matter here. Women’s strategic thinking shapes our direction. Women are leaders in this organization.

Do that, and your strategy will be better. And so will your organization.

Holiday-Mode Leadership: Running a Tech Team When Half the Org Is Out and Everything Is On Fire

It’s December 18th. Your sprint planning meeting has three people on it instead of twelve. Your Slack channel is full of out-of-office auto-responders. Your production environment just threw an error that’s affecting customers, and the engineer who wrote that code is currently on a beach in Mexico with no intention of checking email.

Oh, and your VP just sent you a message: “Can we talk about Q1 planning? I know it’s the holidays but we need to get ahead of this.”

Welcome to holiday-mode leadership, where you’re simultaneously supposed to respect people’s time off, keep critical systems running, plan for next year, and also somehow not burn yourself out in the process.

Here’s what nobody tells you when you take on a leadership role: the holidays don’t mean you get to check out. They mean you get to juggle everyone else’s vacation schedules while making sure nothing catastrophic happens on your watch.

And if you’re a woman leader? You’re also probably managing the emotional labor of making sure people “feel okay” about taking time off, covering for team members who are out, and dealing with the subtle (or not so subtle) expectations that you’ll be available even when you shouldn’t be.

So let’s talk about how to actually lead through the holidays without losing your mind, compromising your team’s trust, or ending up as the person who sends Slack messages at 11pm on Christmas Eve because you don’t know how to set boundaries.

The Holiday Leadership Paradox

The fundamental tension of holiday leadership is this: you need to create space for people to actually disconnect and recharge, while also ensuring that critical work doesn’t fall apart. And you need to do both of these things simultaneously without making anyone feel guilty or unsupported.

This is especially fraught for women leaders because we’re socialized to be caretakers. You want everyone to have a great holiday. You want to be the “cool boss” who gives people freedom. You also don’t want to be the leader who let the system go down because you didn’t have adequate coverage.

So you end up taking on way too much yourself. You become the backstop for everything. You work through your own vacation days so your team doesn’t have to. You check Slack obsessively because what if something breaks and you’re not there to fix it?

And then January hits and you’re exhausted before the year even starts.

Let’s fix this pattern. Here’s how to lead effectively through the holidays without sacrificing yourself in the process.

Pre-Holiday Planning That Actually Matters

The key to surviving holiday mode is doing the work before the holidays actually hit. Waiting until December 23rd to figure out coverage is a recipe for disaster.

Step 1: Get Visibility on Who’s Out When

By early December, you should have a complete picture of when everyone on your team is taking time off. Not just approved PTO, but also people who are “planning to work but might not be super responsive.”

I create a simple shared calendar that shows:

Who’s completely out (no email, no Slack, actually on vacation)

Who’s nominally working but at reduced capacity (e.g., checking email once a day, available for emergencies only)

Who’s working normal hours

This isn’t about monitoring people. It’s about being realistic about capacity so you can plan accordingly.

Step 2: Identify Your Critical Functions and Single Points of Failure

What absolutely cannot break during the holidays? Customer-facing systems? Data pipelines? Security monitoring?

For each critical function, ask: who knows how this works? If that person is out, who’s the backup? If both of them are out, what’s the plan?

I’m a big fan of the “hit by a bus” test. If any single person on your team got hit by a bus (or, more likely, went on vacation), what would break? Those are your single points of failure, and you need to address them before everyone heads out.

This might mean:

Documenting processes that only live in someone’s head

Cross-training team members on critical systems

Bringing in contractors or other teams to provide coverage

Explicitly deciding that certain non-critical work will wait until January

Step 3: Set Clear Expectations About Availability

This is where a lot of leaders fail. They say “take the time off you need” but then continue to Slack people about non-urgent issues. Or they don’t say anything, leaving people to guess whether they’re expected to check in or not.

Be explicit. In a team meeting and in writing, communicate:

If you’re on PTO, you’re on PTO. Don’t check email or Slack unless you want to for your own reasons.

Here’s what constitutes an emergency that might require us to contact you: [very specific criteria, like “production down affecting customers” not “someone has a question about your project”]

Here’s who to contact for what: [clear escalation paths so people don’t feel like they have to be available]

For people who are working reduced hours, here are the expectations: [e.g., respond within 24 hours to non-urgent requests, join critical meetings only]

The more specific you are, the more permission you give people to actually disconnect.

Step 4: Create a War Room for Holiday Issues

Set up a dedicated channel (I call mine #holiday-war-room) where any issues that come up during the holiday period get triaged. Make it clear who’s monitoring this channel and when.

This does a few things:

It contains the chaos instead of letting it spill into every team channel

It makes it easy for people who are nominally available to see what actually needs attention

It creates a record of what happened during the holidays so you can do a retrospective later

Stock this channel with:

Runbooks for common issues

Contact info for critical vendors or partners

Escalation paths for different types of problems

A way to quickly pull in additional help if needed

Managing the Actual Holiday Chaos

Okay, so you’ve done all the pre-planning. Now it’s actually the holidays, half your team is out, and something inevitably breaks. Here’s how to handle it:

Triage Ruthlessly

Not everything is actually urgent. I know it feels urgent. But most things can wait until January.

When an issue comes up, ask:

Is this customer-impacting? If yes, how many customers and how severely?

Is this a security or compliance risk? If yes, what’s the actual risk level?

Is this blocking someone from doing critical work? If yes, is that work actually critical or just habitual?

What’s the worst that happens if we don’t address this until January 2nd?

You’ll find that 70% of the “urgent” things that come up during the holidays can actually wait. Give yourself permission to punt them.

Protect Your Team’s Boundaries Fiercely

This is where women leaders especially need to be vigilant. You will get pressure from other parts of the organization to “just check with your engineer real quick” or “I know they’re on vacation but can you Slack them about this?”

The answer is no, unless it meets your very specific criteria for an actual emergency.

I literally say: “They’re on PTO and unless this is a genuine emergency, I’m not going to interrupt their time off. Let’s figure out another solution or wait until they’re back.”

When you protect your team’s boundaries, you build enormous trust. They know you have their back. They know you mean it when you say they can actually disconnect.

Be Visible About Your Own Boundaries

Here’s the trap: you protect your team’s time off, but you work through your own. You respond to every Slack message immediately. You’re online at all hours. You don’t take any real time off yourself.

This does two things:

It burns you out.

It sets an impossible standard that makes your team feel guilty for taking time off.

Model the behavior you want to see. Take actual days off where you don’t check email. Set an out-of-office message. Let people know when you’ll be back online.

And here’s the thing that feels scary but is actually liberating: the organization will survive. Things might move slower. Some fires might burn a little longer. But it will be okay.

Have a Plan for When You Need to Escalate

Despite your best planning, something might happen that genuinely requires intervention from someone who’s out. Have a clear framework for when and how to escalate.

I use this three-tier system:

Tier 1 (Handle it ourselves): Issues that can be addressed by people who are working. No need to pull anyone off vacation.

Tier 2 (Brief interruption): Issues where we need someone’s expertise but it’s a quick fix. We send a message saying “if you happen to check your phone, we could use 15 minutes of your time, but if you don’t see this until you’re back, no worries.” We solve it another way if they don’t respond.

Tier 3 (Actual emergency): Production down, data breach, security incident, genuine crisis. We call the person directly and pull them in. This should happen rarely, maybe once a year if ever.

Having this framework means you’re not constantly second-guessing whether something is “bad enough” to interrupt someone’s vacation.

The Q1 Planning Pressure

Let’s talk about the special circle of hell that is being asked to do Q1 planning when half your team is out and you’re trying to keep systems running.

Executives love to use the “slow period” of the holidays to get strategic work done. What they forget is that it’s only slow for them because everyone else is working to keep things running.

When you get hit with “we need to finalize Q1 plans before the new year,” here are your options:

Option 1: Push back

“I want to make sure we have the right people in the room for this planning. Can we schedule this for the first week of January when everyone’s back? That way we get better input and more buy-in.”

This works surprisingly often. Most executives, when you frame it as “we’ll get better results if we wait,” are willing to wait.

Option 2: Do high-level planning only

“Happy to discuss strategic direction and high-level priorities this month. For detailed sprint planning and resource allocation, I’ll need my full team back in January.”

You can make progress on the big picture without getting into the weeds that require your full team.

Option 3: Be honest about constraints

“Here’s what I can commit to getting done before end of year with current capacity: X and Y. Z will have to wait until January. Let me know if that doesn’t work and we can discuss adjusting priorities.”

Setting clear expectations is better than agreeing to things you can’t actually deliver.

Handling the “Everything Is On Fire” Moments

Despite your best planning, you’re going to have moments where everything feels like it’s on fire simultaneously. The production incident happens while you’re dealing with a vendor issue while someone’s asking about next year’s budget while your own kid is home sick and needs attention.

Here’s your emergency protocol:

Step 1: Stop and Breathe

Literally. Take 60 seconds. When everything feels urgent, nothing is actually urgent until you get clear on what actually matters most.

Step 2: Triage Out Loud

If you’re dealing with multiple issues, literally say (in the relevant Slack channels or to your team): “We have three things happening right now: A, B, and C. Here’s the order we’re handling them and why: [reasoning]. If you disagree with these priorities, speak up now.”

This does two things: it gets everyone aligned, and it shares the cognitive load of decision-making.

Step 3: Delegate Decision-Making Authority

You don’t have to personally make every decision. Empower people to make calls within their domain.

“For this category of issues, you have authority to make decisions up to [scope]. Just document what you decided and why.”

This distributes the load and develops your team’s judgment.

Step 4: Know When to Call for Help

If things are genuinely out of control, escalate to your leadership. “We’re dealing with X, Y, and Z simultaneously with reduced capacity. Here’s what we’re doing, here’s what we might not be able to handle, and here’s what I need from you.”

Good leaders will either provide additional resources or help you prioritize. Bad leaders will just add more pressure, in which case you document what you flagged and handle what you can handle.

Taking Care of Yourself (Because You Matter Too)

Here’s the part that woman leaders especially need to hear: you don’t have to be a martyr.

You don’t have to work through every vacation day to prove you’re committed. You don’t have to respond to every message immediately to prove you’re on top of things. You don’t have to sacrifice your own wellbeing to take care of your team.

In fact, if you do those things, you’re modeling exactly the wrong behavior. You’re teaching your team that good leaders don’t take care of themselves. You’re perpetuating a culture where burnout is the price of leadership.

So here’s what you’re going to do:

Block time for actual rest. Put it on your calendar. Treat it like any other important commitment.

Set real boundaries. Out-of-office message. Turn off notifications. Actually disconnect.

Ask for support. From your partner, your family, your own manager, your peer leaders. You can’t do this alone.

Lower your standards temporarily. Your house doesn’t have to be perfect. The holiday doesn’t have to be Pinterest-worthy. Work doesn’t have to run flawlessly. Good enough is good enough right now.

Remember that January is coming. This is temporary. You will get through it. Your team will get through it.

The Recharge That Sets Up Your Year

Here’s the thing about holiday leadership: if you do it right, you enter January with a team that’s actually rested and ready to go. They trust you because you protected their time. They’re engaged because they had space to recharge. They’re aligned because you did the pre-planning work.

If you do it wrong, you enter January exhausted, resentful, and with a team that’s burned out before the year even starts.

The difference is boundaries, planning, and being willing to let some things be imperfect.

You’ve got this. Lead through the holidays with clarity, compassion, and the understanding that your wellbeing matters just as much as your team’s.

And when someone sends you a non-urgent Slack message on December 27th? Let it wait until January. I promise, it will still be there.

Building Your Personal Board of Directors Before the New Year Hits

You know what nobody tells you when you’re climbing the ladder in tech? That the higher you get, the lonelier it becomes. That the questions get harder and the stakes get higher, and the number of people you can actually trust to give you honest, strategic advice gets smaller and smaller.

So you do what most ambitious women in tech do: you figure it out yourself. You work harder, stay later, prove yourself over and over, and hope that someone notices. Maybe you have a mentor, someone who gives you occasional advice over coffee. Maybe you’re in a women in tech group where you commiserate about the challenges but rarely get concrete guidance on navigating them.

And it works, for a while. Until it doesn’t. Until you hit a career decision that you genuinely don’t know how to make. Until you’re stuck in a role that’s going nowhere and you don’t know whether to stay and fight or leave. Until you realize you’re reacting to your career instead of directing it.

That’s when you need what you should have built years ago: a personal board of directors.

Not a mentor. Not a sponsor. Not a networking contact you ping once a year to “grab coffee sometime.” An actual board. People who are invested in your success, who bring different perspectives and expertise, who will tell you the truth even when it’s uncomfortable, and who hold you accountable to your own ambitions.

It’s December. You have exactly a few weeks before the new year hits and everyone gets busy again. This is your window to build the infrastructure that’s going to shape your entire 2026.

Let’s talk about how to do it.

Why You Need a Personal Board of Directors

First, let’s be clear about what this is and isn’t.

A personal board of directors is a small group of people (I recommend 4-6) who agree to actively advise and support your career development. They meet with you individually throughout the year, they’re available for ad hoc advice when you’re facing specific challenges, and ideally, they occasionally convene as a group to discuss your career trajectory and push your thinking.

This is different from mentorship in a few key ways:

It’s reciprocal. You’re not just receiving advice. You’re offering something in return, whether that’s your perspective on their challenges, connections you can make for them, or simply the satisfaction of helping someone they believe in succeed.

It’s structured. You’re not waiting for them to reach out or hoping to grab time on their calendar. You have standing commitments, clear agendas, and specific asks.

It’s strategic. Each board member brings something different to the table. You’re not looking for six people who all think like you. You’re building a diverse advisory group that can help you see blind spots, challenge your assumptions, and open doors you didn’t know existed.

It’s active. Your board members aren’t passive observers. They’re actively advocating for you, making introductions, recommending you for opportunities, and pushing you to aim higher than you might on your own.

Now, here’s why you specifically need this as a woman in tech:

The informal networks that help men advance in tech (the golf outings, the after-work drinks, the buddy system) often exclude women, whether intentionally or not. You need to build your own formal network that’s just as powerful.

Women in tech face unique challenges that general career advice doesn’t address. You need advisors who understand the specific dynamics of being underestimated, interrupted, underpaid, and underrepresented.

You’re likely getting less sponsorship than your male peers. A personal board creates accountability structures for sponsorship instead of leaving it to chance.

You probably have fewer role models who look like you at senior levels. A well-constructed board fills that gap with people who’ve navigated similar paths or can help you create your own.

The Five Types of Board Members You Need

Here’s where most people go wrong when they think about building a personal board: they try to find one perfect mentor who can advise them on everything. That person doesn’t exist.

Instead, you want diversity of perspective and expertise. Here are the five types of board members I recommend:

The Navigator

This is someone who’s 10-15 years ahead of you in their career and has navigated the path you want to take. If you want to be a CTO, your Navigator is a current or former CTO. If you want to be a product leader, your Navigator has run large product organizations.

The Navigator helps you understand what skills and experiences you need to get to the next level. They can see patterns in your career that you can’t see yet. They know what challenges are coming before you hit them.

The Truth Teller

This is someone who knows you well enough to call you on your patterns. They’re the person who will say “you keep taking roles where you have to prove yourself from scratch, why do you think that is?” or “you’re consistently undervaluing yourself in negotiations, we need to fix that.”

The Truth Teller can be a peer, a former manager, a friend who works in tech. The key is that they have enough context on your career and enough trust with you to be radically honest.

The Insider

This is someone who understands the political and organizational dynamics of your current company or industry. They can help you navigate office politics, understand unwritten rules, and identify opportunities and landmines you might not see on your own.

The Insider might be someone senior in your organization (but not your direct manager), a former employee who left on good terms, or someone who’s worked with your leadership team in another context.

The Connector

This is someone with a broad network who can make introductions, open doors, and connect you to opportunities. They know everyone, they’re respected in their field, and they’re generous with their network.

The Connector is your shortcut to rooms you couldn’t access on your own. They recommend you for speaking opportunities, introduce you to hiring managers, connect you with clients or partners.

The Wildcard

This is someone outside your immediate field who brings a completely different perspective. Maybe they’re in tech but a different domain. Maybe they’re in a completely different industry. Maybe they’re an entrepreneur while you’re a corporate climber.

The Wildcard keeps you from getting myopic. They ask questions you haven’t thought of, suggest approaches that wouldn’t occur to you, and remind you that the path you’re on isn’t the only path.

How to Actually Recruit Your Board

Okay, so you know what types of board members you need. Now comes the hard part: actually asking people to serve on your board.

This is where I see so many talented women freeze up. You don’t want to be presumptuous. You don’t want to impose on busy people. You’re not even sure you deserve to have a personal board of directors (spoiler alert: you absolutely do).

Here’s exactly how to do it:

Step 1: Make a List

For each of the five board member types, write down 2-3 people who could potentially fill that role. Think about people you already have some relationship with, even if it’s not a close one. Former managers, colleagues you respected, people you met at conferences or through professional organizations, friends of friends who’ve offered to be helpful.

Don’t overthink this. You can always refine the list later.

Step 2: Start with a Specific Ask

Do not send an email that says “would you be willing to mentor me?” That’s vague and puts the burden on them to figure out what that means.

Instead, send something like this:

“I’m building a small advisory board to help guide my career over the next few years, and I’d love for you to be part of it. Specifically, I’m hoping you could meet with me quarterly to discuss [specific area where they have expertise]. I’d also love to be able to reach out between meetings when I’m facing decisions where your perspective would be invaluable. And if you’re open to it, I’d be happy to return the favor by [specific way you can add value to them].”

Notice what this does:

It’s specific about the commitment (quarterly meetings, ad hoc availability)

It’s clear about what you value about them specifically

It offers reciprocity

It uses the language of “advisory board” which frames this as a professional, structured relationship, not a favor

Step 3: Handle the “I’m too busy” Response

Some people will say yes immediately. Some will say they’re too busy. For the ones who say they’re too busy, try this:

“I completely understand. What if we started with just two 30-minute conversations in 2026? One in Q1 to discuss [specific challenge you’re facing] and one in Q3 to review how it went. If it’s valuable for both of us, we can continue. If not, no hard feelings.”

You’re lowering the barrier to entry. Once they say yes to two conversations and find them valuable, they’re much more likely to continue.

Step 4: Make the First Meeting Count

When you get that first meeting with a potential board member, come prepared:

Share a brief overview of your career trajectory and where you’re trying to go

Articulate 2-3 specific areas where you need guidance

Ask thoughtful questions about their experience and perspective

Be clear about what you’re hoping to get from the relationship

Take notes and follow up with a summary and action items

Your goal is to demonstrate that you’re serious, that you value their time, and that working with you will be rewarding, not a drain.

Step 5: Formalize the Relationship

If the first meeting goes well, send a follow-up that says:

“That conversation was incredibly valuable. I’d love to formalize this as a quarterly advisory relationship if you’re open to it. I’m thinking we meet every quarter for 30-45 minutes, and I can reach out between meetings if something urgent comes up where your advice would be helpful. Does that work for you?”

Get a commitment. Get it on the calendar. Make it real.

Running Your Board Effectively

Okay, so you’ve successfully recruited your board. Now what?

Here’s where most people drop the ball: they get the first meeting, maybe even the second, and then it fizzles because they don’t have a structure for maintaining the relationship.

Here’s how to run your board effectively:

Set standing meetings. Every quarter, every board member gets 30-45 minutes on your calendar. Non-negotiable. Schedule the whole year in January.

Come prepared. Before every meeting, send a brief agenda: “Here’s what I want to discuss: 1) my progress on X, 2) a decision I’m facing about Y, 3) your advice on Z.” This respects their time and makes the conversation more productive.

Follow through. If they make an introduction, send a thank-you note to them after the meeting happens. If they suggest a book or resource, read it and report back. If they give you advice, tell them how it worked out. Show them their investment in you is paying off.

Offer reciprocity. Look for ways to add value back. Make introductions for them. Share insights from your vantage point that might be useful to them. Offer to review their presentation or give feedback on their idea. The best board relationships are mutually beneficial.

Convene them strategically. Once or twice a year, consider bringing your board together for a group conversation. Maybe it’s a dinner where they can all weigh in on a big decision you’re facing. Maybe it’s a virtual roundtable where you present your career plan and get feedback. These group dynamics can surface insights that one-on-one conversations don’t.

The Questions Your Board Should Help You Answer

Your personal board isn’t just for warm fuzzy advice. They should be helping you answer hard, strategic questions:

Am I in the right role, or am I staying because it’s comfortable?

What skills or experiences am I missing that will limit my growth?

Am I being paid fairly, and if not, what’s my negotiation strategy?

Should I take this promotion, or is it a trap?

How do I navigate this difficult relationship with my manager/peer/executive?

What’s my personal brand, and is it working for or against me?

Where are my blind spots?

What opportunities am I not seeing?

When should I make my next career move, and what should that move be?

These aren’t questions you can Google. These aren’t questions your work friends can answer over lunch. These require perspective from people who have context, expertise, and a genuine investment in your success.

What to Do When Board Members Aren’t Working Out

Not every board relationship is going to be a great fit, and that’s okay.

If someone consistently cancels meetings, doesn’t follow through on commitments, or gives advice that feels off, it’s okay to let that relationship sunset. You don’t need to have an awkward conversation about “firing” them from your board. Just let the cadence slow down naturally.

Send an occasional update email instead of requesting meetings. When they do have availability, say you’re actually in a good place right now but you’ll reach out if something comes up. Eventually, they move out of your active advisory rotation.

Replace them with someone who’s a better fit. Your board should evolve as your career evolves. The person who was perfect to advise you as a senior engineer might not be the right person once you’re a director. That’s normal.

The Accountability Piece

Here’s the secret weapon of a personal board: accountability.

When you tell your board “I’m going to negotiate for a 20% raise in my next role” or “I’m going to position myself for a director promotion by Q3,” you’ve created accountability. You’re going to have to report back on whether you did it or not.

This is powerful. It’s the difference between having ambitious goals you tell yourself and having ambitious goals you’ve committed to out loud with people who are going to ask you about them.

At the end of every year, I do a board review where I assess:

What did I commit to at the beginning of the year?

What did I actually accomplish?

Where did I fall short and why?

What am I committing to for next year?

Then I share that assessment with my board and ask for their input. It’s uncomfortable. It’s also incredibly clarifying.

The Investment That Pays Dividends

Building a personal board of directors takes time. Recruiting members takes effort. Maintaining relationships takes consistency. But here’s what I’ve seen over and over with the women I counsel:

The women who have strong personal boards navigate their careers more strategically. They make better decisions because they’re getting diverse input. They recover from setbacks faster because they have people helping them reframe and regroup. They take bigger swings because they have people encouraging them to aim higher.

And critically, they’re less likely to stall out at the senior IC or middle management level because they have people actively opening doors and advocating for them.

Your career is too important to navigate alone. You need people in your corner who are as invested in your success as you are.

So here’s your December homework: Make your list. Draft your outreach emails. Send them before the holidays. Schedule your Q1 meetings in January.

By the time the new year hits, you’ll have something most women in tech don’t: a personal board of directors ready to help you make 2026 your best career year yet.

The December Storyline: How to Close the Year with a Compelling ‘Why’ for All the Chaos

It’s mid-December, and you know what that means: everyone is simultaneously checked out mentally while also panicking about Q4 deliverables, your Slack is full of messages that say “quick question” followed by paragraphs of anxiety, and someone just announced another reorganization that will be “fully implemented” by January 2nd. (Spoiler: it won’t be.)

Welcome to December in tech, where the chaos is the only constant and your job as an organizational change manager is to somehow make sense of it all.

Here’s the thing that no one tells you about change management: it’s not actually about managing change. Change is going to happen whether you manage it or not. Your job is to manage the narrative around change so that people understand why it’s happening, what it means for them, and how they’re supposed to show up differently starting January.

And the narrative you create in December? That’s what determines whether your organization enters 2026 energized and aligned or exhausted and cynical.

So let’s talk about how to close this year with a story that actually resonates, because I’m tired of watching talented change managers get crushed between executive “vision” that sounds like it came from a corporate buzzword generator and employees who just want someone to be honest about what’s actually happening.

The December Storyline Problem

Every December, the same pattern plays out in tech organizations:

Executives spend November in offsite strategy sessions where they decide on new priorities, new structures, new “strategic initiatives” that are going to define next year. They emerge excited, aligned, and ready to transform the organization.

Then they hand this vision to you, the change manager, and say “make everyone understand why this matters and get them excited about it.” Oh, and by the way, we’re announcing it December 20th, everyone needs to be onboard by January 6th, and we don’t have budget for any real change management activities. Good luck!

Meanwhile, the actual employees in your organization are tired. They’ve spent a year executing on this year’s priorities, which may or may not have been last year’s priorities rebranded. They’ve survived layoffs or at least layoff rumors. They’ve watched colleagues leave for better opportunities. They’re skeptical of grand announcements, and they’re really skeptical when those announcements come in late December.

Your job is to bridge that gap. And you can’t do it with a deck full of inspiring quotes and a vision statement that says absolutely nothing specific.

What Makes a Storyline Actually Compelling

Here’s what most executives get wrong about organizational narrative: they think compelling means aspirational and vague. “We’re going to be the industry leader in innovative solutions that empower our customers to achieve transformational outcomes.”

Cool. What does that actually mean for the engineer who’s debugging production issues at 2am? What does it mean for the product manager who’s trying to figure out whether to prioritize feature A or feature B? What does it mean for the team that just got told their entire project is being sunset?

A compelling storyline isn’t inspirational nonsense. It’s honest context plus clear direction plus respect for what people have already been through.

Let me break that down:

Honest context means you acknowledge reality. If this is the third reorganization in two years, you name that. If people are exhausted, you name that. If the market has changed and we need to change with it, you explain specifically how and why. Don’t gaslight people by pretending everything has been great and this is just “exciting growth.” People aren’t stupid. They know when they’re being managed.

Clear direction means you get specific about what’s changing and what’s not. Not “we’re shifting our focus to strategic priorities” but “we’re sunsetting these three product lines, doubling down on these two, and here’s exactly how that affects headcount, roadmap, and team structure.” Ambiguity breeds anxiety. Clarity breeds trust, even when the news isn’t what people wanted to hear.

Respect for what people have been through means you acknowledge the cost of change. Change management often focuses so much on the future state that it glosses over the fact that getting there is hard, exhausting work. People need to hear that their effort is seen and valued, not just that there’s more effort required ahead.

Building the Narrative Arc for 2025-2026

When I’m working on the December storyline for an organization, I structure it as an actual story arc, because humans are hardwired to understand narrative structure. We need a beginning, middle, and end. We need tension and resolution. We need characters we care about (hint: the characters are your employees).

Act One: Where We Were

This is where you acknowledge the reality of 2025. Not a sanitized highlight reel, but an honest assessment. What were we trying to do? What worked? What didn’t? What changed externally that we had to respond to?

I literally use language like “Remember when we started 2025 thinking X was our biggest priority? We learned that actually Y was the real challenge, and here’s how we responded.”

This section is critical because it validates people’s experience. If they felt like this year was chaotic, don’t tell them it was actually perfectly executed. Tell them why it felt chaotic and what you learned from that.

Act Two: Where We Are

This is the bridge. What’s the current state? Not aspirationally, but actually. What’s working that we want to keep? What’s not working that we need to change? What new information do we have about market, competition, technology, or customer needs that’s shaping our path forward?

This is where you introduce the tension that drives the story forward. “We’ve built incredible technology, but our go-to-market motion isn’t scaling. We have amazing talent, but our structure is creating silos that slow us down. We’re profitable, but we’re not positioned for the growth we need.”

Be specific. Use real examples that people will recognize. Don’t hide behind corporate speak.

Act Three: Where We’re Going and Why It Matters

This is where you introduce the change. But here’s the key: you frame it as a logical response to everything you just laid out in Acts One and Two. The change isn’t arbitrary. It’s not executives being bored and wanting to reshuffle the org chart. It’s a specific response to specific challenges and opportunities.

“Given that we learned X about our market and Y about our execution challenges, we’re making these specific changes: Z1, Z2, and Z3. Here’s what success looks like. Here’s how we’ll know we’re on track. Here’s what this means for you.”

And then, this is the part that most change managers skip: “Here’s what this is going to require from all of us. It’s going to be hard. You’re going to have to learn new ways of working. Some of you are going to have new roles or new teams. It’s going to be uncomfortable before it gets better.”

Don’t sugarcoat the transition. People respect honesty more than false optimism.

The “Why” That Actually Answers Employee Questions

When you’re crafting your December storyline, you need to answer the questions people are actually asking (even if they’re not asking them out loud):

“Why now?”

Don’t just say “the time is right.” Explain what changed that makes this the right moment. Is it market conditions? Competitive pressure? New technology capabilities? A specific insight from customer research? Be concrete.

“Why this specific approach?”

Employees are smart enough to know there are always multiple ways to solve a problem. If you’re doing a reorganization, why this structure instead of another? If you’re changing processes, why this process? You don’t have to justify every decision, but you should be able to articulate the reasoning.

“What does this mean for me specifically?”

This is where so many change narratives fall apart. They talk about organizational transformation in abstract terms without ever getting specific about what changes for individuals. You need to be able to say “if you’re an engineer on team X, here’s what changes for you” or “if you’re a manager, here’s what we need from you differently.”

“What if I don’t agree with this direction?”

Most change management approaches pretend everyone is going to enthusiastically support every decision. That’s fantasy. Acknowledge that some people might disagree with the direction, might wish resources were allocated differently, might be disappointed about how this affects their project or team. And then be clear: disagreement is fine, but we’re moving forward anyway, and here’s what constructive disagreement looks like versus destructive resistance.

“What happens if this doesn’t work?”

I love asking executives this question because it makes them deeply uncomfortable. But it’s a question employees are definitely thinking. You don’t have to have a perfect answer, but you should be able to say something like “we’re going to measure these specific indicators, review progress at these intervals, and be willing to course-correct if the data tells us we need to.”

Navigating the Politics of the December Narrative

Let’s be real: as a woman in organizational change management, you’re often in an impossible position. You’re expected to sell a vision that executives created without your input. You’re expected to make people feel heard while ultimately telling them they don’t get a vote. You’re expected to be both empathetic and tough, both transparent and diplomatic.

And if the change goes poorly? You’ll get blamed for not managing it well. If it goes well? The executives will get credit for their brilliant strategy.

I know. It’s infuriating.

But here’s what I’ve learned about navigating this: your power is in the narrative itself. When you control the story, you control how people make sense of the change. And that gives you more influence than you might think.

When the executive vision is vague or contradictory: I go back and ask clarifying questions until I get specificity. “When you say we’re focusing on customer experience, do you mean we’re reallocating engineering resources from feature development to reliability? Are we changing our quality metrics? What specific trade-offs are we making?” Don’t accept buzzwords. Push for concrete answers.

When the rationale doesn’t make sense: I play devil’s advocate in the room with executives before the messaging goes out. “Here’s what people are going to ask when they hear this. Here’s where the logic breaks down. Here’s what will feel like doublespeak.” Better to surface this before the announcement than after.

When the change is genuinely bad: This is the hardest one. Sometimes the change is short-sighted, poorly thought out, or actively harmful. You have three choices: try to influence it to be less bad, quit, or decide that you can still help employees navigate it even if you don’t agree with it. There’s no right answer here. Just know your own boundaries.

The Communication Cascade That Actually Works

The December storyline isn’t just one announcement. It’s a communication cascade that carries you from mid-December through January.

Mid-December: The Executive Announcement

This is where leadership shares the high-level vision and strategy. It should be honest, specific, and acknowledge both the opportunities and the challenges ahead. I always push for these to include Q&A time where leaders answer actual hard questions, not just softballs.

Late December: The Manager Enablement

Before managers communicate anything to their teams, they need to be enabled. I run sessions where I walk through the narrative, answer their questions, give them scripts and FAQs, and help them think through how this lands with their specific teams. Managers are your force multipliers. If they don’t understand it or don’t believe it, you’re sunk.

Early January: The Team Conversations

This is where managers cascade the message to their teams with team-specific context. Not just “here’s what leadership said” but “here’s what this means for our team specifically, here’s what’s changing in our day-to-day, here’s what I need from each of you.”

Mid-January: The Follow-Up and Course Correction

By mid-January, you’ll have learned what’s landing and what’s not. Do another round of communication that addresses the questions and concerns that surfaced. Adjust the narrative if you need to. Show that you’re listening and responsive.

Measuring Whether Your Storyline Worked

You can’t manage what you don’t measure, and that includes narrative effectiveness. Here’s what I track:

Qualitative feedback from managers: After they do their team cascades, I ask: What questions came up? What concerns did people raise? What didn’t make sense?

Employee survey data: I run a pulse survey in mid-January asking: Do you understand the direction for 2026? Do you know how your work connects to organizational priorities? Do you feel like leadership is being honest about challenges ahead?

Behavioral indicators: Are people showing up to town halls and asking questions, or are they checked out? Are they leaning into the new direction, or quietly continuing to do things the old way?

Executive feedback: Are executives hearing the same concerns bubbling up, or different ones? Are they surprised by employee reaction, or did the narrative prepare them for it?

The goal isn’t perfect alignment. Perfect alignment is a fantasy. The goal is informed, constructive engagement.

The Pep Talk You Need

Listen, I know December is exhausting. You’re managing other people’s anxiety while dealing with your own. You’re trying to spin straw into gold and make a mediocre strategy sound compelling. You’re probably underpaid and definitely underappreciated.

But here’s the thing: the work you do matters. When organizations go through change, people look for sense-making. They look for someone who can help them understand what’s happening and why. That’s you.

You’re not just writing communications and planning town halls. You’re shaping how people experience transformation. You’re building trust or eroding it. You’re creating clarity or confusion.

Do it well. Do it honestly. Do it in a way that respects people’s intelligence and honors their experience.

And when you get to January and someone inevitably says “that was the smoothest reorg we’ve ever had,” even though it wasn’t actually smooth at all, you’ll know it’s because you created a narrative that made the chaos feel purposeful.

That’s the power of a good December storyline.

Year-End Retrospectives That Don’t Suck (or Blame): PM Edition for Women Running the Show

Let me paint you a picture of every terrible year-end retrospective I’ve ever attended:

The team sits in a conference room (or on a Zoom call, bless us) while someone with access to the whiteboard (always suspicious) asks “what went well, what didn’t go well, and what should we do differently?” Cue 45 minutes of thinly veiled blame disguised as “learnings,” passive-aggressive comments about missed deadlines, and at least one person who dominates the conversation while everyone else checks Slack.

The output? A Confluence page of action items that no one will ever look at again, zero accountability, and a team that feels slightly worse about themselves than they did before the meeting.

Sound familiar?

As a PM, retrospectives are supposed to be your secret weapon. They’re where you extract real insights from the chaos, build psychological safety, and actually improve how your team works. But most of the time, they’re just performative exercises that check a box on someone’s Agile playbook.

Let’s fix that.

Why Most Retrospectives Are Terrible (Especially When You’re a Woman Running Them)

First, let’s talk about why retrospectives fail, because understanding the problem is half the battle.

Traditional retrospective formats assume everyone in the room has equal power and equal safety to speak honestly. That’s adorable. In reality, junior engineers are terrified to call out senior engineers, everyone’s worried about looking bad in front of leadership, and God forbid you’re a woman running a retrospective where you need to address issues with male team members who already don’t think you should be leading the project.

I’ve had retrospectives where I asked “what could we improve?” and got silence. Not because everything was perfect, but because no one trusted that honest feedback wouldn’t be used against them later. I’ve had retrospectives where one senior engineer decided to turn it into his personal TED Talk about everything everyone else did wrong. I’ve had retrospectives where the only feedback I got was that my “communication style” could be “softer” (translation: stop holding people accountable for deadlines).

The other problem? Most retrospective formats focus on problems without creating any psychological safety around failure. When you ask “what went wrong,” people hear “whose fault was it?” And when people are in defensive mode, you get nothing useful.

The Pre-Work That Actually Matters

Here’s what I learned after running approximately one million terrible retrospectives: the quality of your retrospective is determined before anyone enters the room.

Two weeks before your year-end retrospective, send a survey. Not a “please rate your satisfaction on a scale of 1-10” survey. A real one with open-ended questions that give people permission to be honest:

What’s one thing that frustrated you this year that you felt you couldn’t bring up in the moment?

What’s one process we have that actively makes your job harder?

If you could change one decision I made as PM this year, what would it be and why?

What support do you wish you’d gotten that you didn’t?

The key is asking questions that normalize criticism and assume there are problems worth discussing. Anonymous surveys get you more honest data than any in-person conversation ever will.

I also send a separate survey specifically asking people to reflect on wins: What’s something you’re genuinely proud of from this year? What’s something a teammate did that made your job easier? What’s a decision that worked out better than expected?

Why separate surveys? Because when you mix them, people focus on the negative and breeze through the positive. You want real reflection on both.

Creating Actual Psychological Safety (Not the Fake Kind)

Let’s be honest: psychological safety has become a buzzword that gets thrown around by people who have no idea what it actually means.

Real psychological safety isn’t about being nice or avoiding conflict. It’s about creating an environment where people can take interpersonal risks (like admitting mistakes or challenging ideas) without fear of punishment or humiliation.

As a woman PM, you’re already fighting an uphill battle on this. Women are socialized to be accommodating and to smooth over conflict. When we do hold people accountable or address problems directly, we’re often labeled as aggressive or difficult. It’s exhausting.

But here’s the thing: a retrospective without honesty is useless, and honesty requires safety. So you have to be intentional about creating it.

I start every year-end retrospective with a few ground rules, and I’m explicit about them:

This is a blameless space. We’re talking about systems and processes, not attacking individuals. If someone makes it personal, I will redirect.

Disagreement is expected and welcome. Silence is not consensus. If you disagree with something, say so.

Everything said here stays here unless we explicitly decide as a team to share something more broadly.

I will take notes on themes, not on who said what. No one is going to be punished for honest feedback.

Then I share my own failures first. Not in a self-deprecating way, but in an honest, reflective way. “Here’s something I tried this year that didn’t work, here’s why I think it didn’t work, and here’s what I’m going to do differently.”

When you model vulnerability, you give other people permission to be vulnerable. And vulnerability is where the real insights live.

The Format That Actually Works

Forget the standard “what went well, what didn’t, what should we change” framework. It’s boring and it produces surface-level insights.

Here’s the format I use for year-end retrospectives:

Part 1: The Highlight Reel (30 minutes)

Go around the room (or the virtual room) and have each person share one thing they’re genuinely proud of from this year. It can be a technical win, a process improvement, a moment they helped a teammate, whatever. The only rule is that it has to be specific.

This does a few things: it starts the meeting on a positive note, it reminds people of wins they might have forgotten, and it surfaces accomplishments that might not have been visible to the whole team.

I take notes on all of these and later compile them into a year-end wins document that I share with leadership. Your team members should get credit for their work, and it’s your job as PM to make sure they do.

Part 2: The Hard Stuff (45 minutes)

This is where you dig into the survey data. I pull out the themes (not individual responses) and present them to the team. “Here’s what I heard: people felt like there wasn’t enough clarity on priorities. People felt like they were context-switching too much. People felt like their feedback on the roadmap wasn’t being incorporated.”

Then I ask: “Does this resonate? What am I missing? What’s the real issue underneath this symptom?”

The magic happens when you treat problems as puzzles to solve together, not as indictments of anyone’s competence. When someone brings up a legitimate issue, I literally say “thank you for bringing this up, this is exactly the kind of thing we need to address.”

I also use this section to address things I saw as problems that might not have come up in the survey. “I noticed we had three major production incidents this year that all stemmed from unclear requirements handoffs. I take responsibility for not catching that pattern sooner. What do we think the root cause is?”

Part 3: The Commitments (30 minutes)

This is where most retrospectives go to die. Everyone agrees to “communicate better” or “improve documentation” and then nothing changes.

Instead, I focus on three specific, measurable changes we’re going to make in 2026. Not 10 things. Three. And for each one, we identify:

What exactly are we going to do differently?

Who owns making sure this happens?

How will we know if it’s working?

When will we check back on progress?

For example: Instead of “improve documentation,” we might commit to “every technical design doc must include a ‘how to test this’ section before it goes to engineering, PM owns enforcing this in the review process, we’ll know it’s working if QA reports fewer questions about test coverage, we’ll review in Q1 retro.”

Specificity is everything. Vague commitments produce vague results.

Part 4: The Meta-Retrospective (15 minutes)

This is my secret weapon: I end every retrospective by retrospecting on the retrospective itself.

“Was this useful? What would make these more valuable? What should we stop doing? What’s one thing you wish we’d talked about that we didn’t?”

It sounds meta (because it is), but it’s how you continuously improve your own process. And it signals to the team that you’re serious about making these meetings actually worthwhile.

Handling the Difficult Moments

Let’s talk about what happens when things get uncomfortable, because they will.

When someone dominates the conversation: I interrupt politely but firmly. “Thanks for that perspective, I want to make sure we hear from everyone. Let’s get some other voices in here.” Then I directly call on someone who hasn’t spoken. “What’s your take on this?”

When someone makes it personal: I redirect immediately. “Let’s focus on the process, not the person. What about the system made this outcome more likely?”

When you’re getting blamed for something: This is the hardest one, especially as a woman. Your instinct might be to defend yourself or deflect. Don’t. Acknowledge the feedback, ask clarifying questions to understand the real issue, and commit to addressing it if it’s valid. “I hear that the priority changes felt chaotic. Help me understand what would have made that better from your perspective.”

When you get silence: Don’t fill it. Silence is uncomfortable, but sometimes people need time to think. I count to 10 in my head before prompting again. If you still get silence, try a different approach: “Let me ask a more specific question…” or “What if I share what I observed and you tell me if I’m off base?”

The Follow-Through That Separates Great PMs from Everyone Else

Here’s where most retrospectives fall apart: nothing happens afterward.

Within 48 hours of your retrospective, send a summary email that includes:

The wins you celebrated (people love seeing their accomplishments documented)

The themes that came up in the “hard stuff” section

The three specific commitments you made as a team, with owners and timelines

A clear statement about what you personally are committing to doing differently

Then, in every sprint planning or team meeting for the next quarter, reference those commitments. “Remember we said we were going to improve our requirements handoff process? Here’s where we are on that.”

Accountability is what turns retrospectives from feel-good exercises into actual improvement mechanisms.

The Self-Retrospective You Need to Do

Before you facilitate your team’s retrospective, do your own. As a woman in tech leadership, you need to be honest with yourself about what worked, what didn’t, and what you’re going to do differently.

Ask yourself:

Where did I let my fear of being seen as difficult prevent me from holding people accountable?

Where did I overcompensate by being too accommodating?

What feedback did I get this year that I initially dismissed as sexist but might have had a kernel of truth? (This one is painful but important.)

What support did I fail to ask for because I was trying to prove I could do it all myself?

Where did I advocate effectively for my team, and where did I let them down?

Write this down. Not for anyone else. For you. Because you can’t improve your team’s processes if you’re not also improving your own leadership.

The Reality Check

Here’s the truth: even if you run the perfect retrospective, you’re still going to face resistance. You’re still going to have team members who don’t engage. You’re still going to have leadership that doesn’t prioritize the process improvements you’ve identified.

But you know what? You’re a PM. Navigating resistance and driving change despite obstacles is literally your job description. The question isn’t whether it’s going to be hard. The question is whether you’re going to do it anyway.

Your year-end retrospective isn’t just about closing out 2025. It’s about setting the foundation for how your team operates in 2026. It’s about building trust, creating accountability, and demonstrating that you’re serious about continuous improvement.

So make it count. Run a retrospective that doesn’t suck. Run a retrospective that doesn’t blame. Run a retrospective that actually moves the needle.

Your team deserves it. And so do you.