What Tech Leaders Do Before Going on Vacation
What Tech Leaders Do Before Going on VacationEarly 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 ârun outâ of things to do. Not because there wasnât workâthere was plentyâbut 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 theyâd 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 isnât about finishing your own workâitâs about ensuring your team can function effectively without you. Done well, itâs actually a powerful way to develop your teamâs autonomy and decision-making capabilities. Done poorly, it creates exactly the kind of organizational dysfunction I witnessed firsthand.
The Information Bottleneck Problem
Hereâs what most leaders donât realize: youâre probably a bigger bottleneck than you think. Not because youâre micromanaging, but because critical context lives in your head that your team needs access to in order to make good decisions. The challenge isnât documenting everything you knowâthatâs impossible. The challenge is identifying what your team will actually need while youâre gone.
Iâve 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 donât know how to prioritize work when youâre 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 theyâre 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 teamâs confidence in their own judgment.
When people understand your decision-making criteria and feel trusted to apply them, theyâll make better choices whether youâre away on vacation or away in a meeting.
The key is being specific about decision authority rather than vague about âchecking with me first.â Instead of saying âlet me know if anything important comes up,â try âyou can approve any engineering changes that donât affect the database schema, but flag anything that requires downtime for discussion when Iâm back.â
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.
Iâve 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, whoâs 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 theyâre 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 youâre gone, use your absence as a chance to test and develop your teamâs capabilities. Give someone the opportunity to run meetings, handle stakeholder communication, or make technical decisions that theyâre ready for but havenât 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 thatâs more capable and confident, and youâve identified whoâs ready for additional responsibilities. Plus, youâve stress-tested your teamâs 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 youâre worried about whatâs happening while youâre 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 youâll be completely offline, donât check Slack âjust onceâ and end up getting pulled into work discussions. If youâre 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, youâll know youâve built something sustainable. Thatâs not just good vacation planningâitâs good leadership.