🧭 LEADERSHIP

What Tech Leaders Do Before Going on Vacation

Early in my career, I worked on a team where the CEO decided to take two weeks off without much preparation. By the middle of the first week, people had “run out” of things to do. Not because there wasn’t work—there was plenty—but because no one knew what they were supposed to prioritize, who could make decisions, or how to move forward on anything that required input from leadership.

We spent those two weeks in a weird organizational limbo, working on whatever seemed important while bigger decisions piled up. Upon returning, the CEO was frustrated that so little had been accomplished, and the team was frustrated that they’d been left without clear direction. It was a perfect example of how taking time off as a leader requires completely different preparation than taking time off as an individual contributor.

The reality is that leadership vacation planning isn’t about finishing your own work—it’s about ensuring your team can function effectively without you. Done well, it’s actually a powerful way to develop your team’s autonomy and decision-making capabilities. Done poorly, it creates exactly the kind of organizational dysfunction I witnessed firsthand.

The Information Bottleneck Problem

Here’s what most leaders don’t realize: you’re probably a bigger bottleneck than you think. Not because you’re micromanaging, but because critical context lives in your head that your team needs access to in order to make good decisions. The challenge isn’t documenting everything you know—that’s impossible. The challenge is identifying what your team will actually need while you’re gone.

I’ve learned to approach this systematically. Instead of trying to dump all my knowledge, I focus on the specific work my team will be doing during my absence. What decisions might come up that I can provide context for? What blockers could they encounter and who could help in my absence? Who will take the lead on making decisions to help keep projects moving forward?

This exercise often reveals gaps in team communication that extend beyond vacation planning.

If people don’t know how to prioritize work when you’re gone for a week, they probably struggle with prioritization day-to-day more than you realize.

Vacation prep becomes a forcing function for better ongoing delegation.

The practical approach is straightforward: review your priority list and write down the context and contacts that your team will need to get work done while you’re away. But the deeper value is discovering where your team needs more autonomy and decision-making authority in general.

Decision-Making Without You

The most common mistake I see leaders make is trying to pre-decide everything that might come up while they’re away. This is both impossible and counterproductive. Instead, the goal should be empowering your team to make good decisions using the same framework you would use.

Before any significant time off, I have explicit conversations with my team about what kinds of decisions they can make independently and what should wait for my return. More importantly, I explain the reasoning behind those boundaries so they understand when to escalate and when to proceed.

More than just being on the same page, these boundaries help to build your team’s confidence in their own judgment.

When people understand your decision-making criteria and feel trusted to apply them, they’ll make better choices whether you’re away on vacation or away in a meeting.

The key is being specific about decision authority rather than vague about “checking with me first.” Instead of saying “let me know if anything important comes up,” try “you can approve any engineering changes that don’t affect the database schema, but flag anything that requires downtime for discussion when I’m back.”

Creating Clarity, Not Chaos

The difference between teams that thrive when their leader is away and teams that stagnate comes down to clarity of expectations. Your team needs to know not just what to work on, but how to make trade-offs when priorities conflict, who to go to for different types of help, and what success looks like in your absence.

I’ve found that internal communication about your time off is just as important as external auto-responders.

A quick message to your team explaining where to find information, who’s covering what responsibilities, and how to handle common scenarios prevents a lot of confusion and hesitation.

But the real test is whether your team feels empowered to act or feels like they’re in caretaker mode until you return. The goal is maintaining momentum, not just maintaining the status quo. This requires trusting your team with meaningful work and giving them the context they need to handle unexpected situations.

The Leadership Development Opportunity

Your vacation is actually a development opportunity for your team if you set it up intentionally.

When you step back temporarily, you create space for other people to step up, make decisions, and take on leadership responsibilities.

Instead of just hoping things will be fine while you’re gone, use your absence as a chance to test and develop your team’s capabilities. Give someone the opportunity to run meetings, handle stakeholder communication, or make technical decisions that they’re ready for but haven’t had the chance to practice.

The preparation for this kind of delegation is more involved than just finishing your own work, but the payoff is enormous. You return to a team that’s more capable and confident, and you’ve identified who’s ready for additional responsibilities. Plus, you’ve stress-tested your team’s ability to function without you, which is valuable information for organizational resilience.

Making Time Off Actually Restful

The irony of leadership is that taking time off can be stressful if you’re worried about what’s happening while you’re away. The best vacation preparation eliminates that anxiety by ensuring your team has everything they need to succeed without you.

This means being honest about your availability expectations and sticking to them. If you tell your team you’ll be completely offline, don’t check Slack “just once” and end up getting pulled into work discussions. If you’re going to check in periodically, be specific about when and how, so people know what to expect.

The teams that handle leadership time off best are the ones where this kind of preparation is routine, not exceptional. When delegation, clear communication, and decision-making authority are part of your regular management practice, preparing for vacation becomes straightforward rather than stressful.

Your time off should leave your team more capable, not less. When you return from vacation to find that your team tackled challenges, made good decisions, and maintained momentum without you, you’ll know you’ve built something sustainable. That’s not just good vacation planning—it’s good leadership.