Make It Easier for Your Boss to Say Yes to Vacation

by Holly Weeks

In an office where overworking is a badge of honor — if not a competitive sport — a request for vacation can be daunting, even if vacation time is part of your compensation package. The worry is not so much the request itself, but feeling judged for making it. What if your manager makes it seem like you’re not a team player? Not quite as committed to your work as you could be? Not as ambitious as others are? And what if she says no?

To set the stage for a positive conversation, work out your manager’s perspective first. It is likely that your vacation request is one piece of a larger puzzle that has to fit together. Your boss has competing needs, like meeting incremental deadlines and coordinating your time and your colleagues’ time simultaneously. She may be dealing with issues of precedence, such as a longer-term employee who has asked for vacation time that overlaps incompatibly with yours. In fact, she may be juggling multiple out-of-office requests, not just for vacations, but for professional development, conferences, and trade shows, too. Taking her perspective into account helps you plan a request that’s easier for her to grant.

For example, if you work with a team, ask your manager well in advance whether it’s easier for her to schedule vacation after a big deadline is met — which may seem obvious, but some deadlines are moving targets or are just plain fictional — or to stagger vacations, or to try to combine multi-party time off. This isn’t to say that your preference and your manager’s will match perfectly, but she will know that you are trying to be accommodating and she’ll appreciate not being taken by surprise.

Here’s how not to ask for vacation time: A woman who worked in a research office had waived enough vacation time to accrue four weeks’ worth in order to travel abroad for a long-planned family wedding. In her mind, this was fair; she had earned the vacation, which was strictly true. Her strategy was that by accruing the time quietly, she would be bulletproof when she told her manager, because, by the letter of the law, it was hers to take. But the fact that she kept quiet and then took her manager by surprise made it clear that she also knew the request would be unwelcome: it came at the worst time of year for the office, and such an extended vacation was utterly atypical in the organization. (Her family, however, would hear of nothing less.) Her manager was more than angry and indignant; she felt undermined and manipulated. In fact, the manager discussed the situation with her own senior managers and denied the request. Angry and upset herself, the staff member went anyway. And she did not return to the organization. It was a lose-lose situation all around.

vacastress_introIf you want a better outcome for a difficult vacation request, factor the rhythm of your work and customary vacation patterns into your strategy. If your own request is unusual, approach your manager with more openness than the staff member above did. Think less about how you justify your request to yourself and more about how it will appear to your manager and co-workers. Is your request problematic? If it might be, start by saying, “Let’s talk about any burden this creates, and what we’ll do about it,” with the emphasis on “what we’ll do about it.” Set the tone around how we can make this work out. You may be surprised by the amount of creative problem-solving you and a manager can bring to bear. Or maybe you won’t be surprised — it’s what your organization does most of the time with the conflicts of interest it faces.

Speak pro-actively about how your usual responsibilities will be handled in your absence: “My assistant is ready to spread his wings, the client knows and likes him, and one of my peers has agreed to backstop him while I’m gone.”

If it works for your family or others participating in your vacation, create an A plan and a B plan with a difference, for example, between length of vacation and particular dates, in order to give your manager some options. You might say, “My family is looking at two options to coordinate at my spouse’s firm and here in our company.” Your A plan might be two consecutive weeks, but maybe you’re willing to avoid the 4th of July. Your B plan may be three days off, including the 4th of July, and a week off during the kids’ winter break. This strategic how-can-we-make-it-work approach takes some planning even before you make your vacation request, but it improves the tone and content of the conversation so much that it’s worth it.

And this approach has another benefit — it protects you from stumbling into much weaker ways of making your request, like expressing guilt or apologizing over asking for a vacation at all, and talking yourself and your manager out of your own request even as you make it. It’s also worth noting that it does not help your working relationship with your manager to overshare details about how difficult it is to coordinate vacation schedules in the family, or how badly your spouse needs time off. Not because your manager doesn’t care about you and your loved ones, but simply because your manager’s task is a different one: to coordinate the players and the functions of the office. It is not wrong to take a manager who is your friend into your confidence, but at the point of making your vacation request, both of you may be better served if you realize that the best way to make an argument to your manager for time off is to give your manager a very good argument to use on your behalf if she needs to make your case to her own manager.

If you work where people don’t take their vacations, requesting one may raise an eyebrow. If it’s part of your compensation and you want to take it, be ready to speak positively about it, and frame it in terms your company values. You may find yourself spearheading a change.

The language you use may be less about the vacation itself and more about its results. You may want to talk about refreshing your mind, or opening up your thinking, changing your perspective, incubating some embryonic ideas, or letting some solutions percolate. You may want to be proactive, saying, “I never want to get in a rut. I don’t want to find myself working on auto-pilot.” There are, after all, organizations that encourage, if not require, vacation-taking for reasons like these.

Taking time away from the workplace is the flip side of taking a business trip away from friends, family, and home. If you talk through how to make it workable and comfortable for both sides, and plan how to minimize problems that might crop up while you’re away, it won’t be a case of attending to one side at the expense of the other, as it shouldn’t be. In fact, what you’ll really notice is that it’s great to be valuable, and to be missed.

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