There is no good time to take vacation

A few years ago, I was managing a team during “crunch time”. There was lots of pressure from above, and unrealistic timelines. One of my developers had a vacation scheduled. I think he was going to Hawaii. It came up in a discussion with a VP of Engineering, who said I should ask him to postpone the vacation. I refused. I thought it was a completely unreasonable suggestion.

That VP was pissed that I refused to even consider the suggestion. I’m happy to take that as a measure of him, not of me.

Vacation policy often comes up in interviews. Or in 1–1 discussions with members of my team. People ask what are “good” times to take vacations. My response is pretty simple. There is no good time. There is no particularly convenient time. And that’s fine. Vacations aren’t for the company to define, they’re for the benefit of the employee.

Nobody knows better that they need or want a vacation than the person taking it. In the US in particular, vacation time is limited enough. Adding further restrictions on when someone can take that vacation is punitive.


Vacations are often presented as a favor from a company to an employee. That’s far from the truth. Vacations are a necessary part of ensuring people stay energized and enthusiastic. Feeling their work helps enable their life, rather than restricting it. Energized and enthusiastic employees are motivated and productive ones. Those are the kind of people I want on my team.

Refusing a vacation because it’s inconvenient is unproductive. The benefit I could get from having a team member available at a particular time is momentary. I want them to be feel invested in their work, and feel that they’re treated like adults. I trust them to make decisions that are right for them.

If someone is trying to find a “convenient” time to have a vacation, it’s impossible. In a busy company there’s always something more than needs doing. There’s always an upcoming release that needs work now. There’s no good time for me to have a member of my team unavailable for a week or two. Which means that any time is fine.


And it all works. People behave responsibly. If they’re booking a vacation far in advance then it’s easy to factor that into work planning. If there’s a big release next week, there aren’t many people who are going to ask for time off at the last minute. If they need to, chances are it’s an emergency.

Last week in a 1–1, a team member brought up a vacation request. The dates they want to go on vacation coincide with what I know will be a very busy week. We had a good discussion. I said that if they hadn’t booked it yet, and were flexible, it’d be great if they could push it back a week. I also made it clear that was only a request.

That’s the furthest I’ll ever go in suggesting any limitation to vacation. A week’s delay if it’s not time critical for the employee. The decision is still theirs. And no choice they make will make me look negatively at them.


People have lives outside work. They have other people whose lives interact with theirs. These don’t take second place to a short term need at work. Nor should they.

In building teams, in helping companies that I work for, I want sustainable success. Not reactive short term action at the expense of the long term good. Vacation planning is part of that. Of realizing that it’s something my team are entitled to.

Their vacations, taken at their convenience, will bring benefit to the company. Long term benefit. Benefit that outweighs any short term advantage to having them in the office that one extra-busy week.

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