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.