TOT Tamer Advice Column: Boss-Friendly Vacation Planning

Dear Lynn:
My company president is a workaholic. He rarely leaves for vacations and when he does, he still sends a constant barrage of e-mail. My wife and I are planning a trip to Europe in a few months, and she is already nervous that he is either going to dump a lot of work on me before we leave or put the pressure on me to work while we are away. What is the best way to show that I’m committed while taking an extended vacation?

Hi Paul:
Technology has made the separation between work and leisure more blurry, but that doesn’t mean you can’t set boundaries! For example, have you used your “off” button on your cell phone lately? When it’s your valued leisure time, you hereby have permission to turn off the working world. So hold that power button firmly down – literally and figuratively!

The overall goal here is to humanize your workplace™, and the first step is to diplomatically “train” your TOT boss. You want to lead by example and let your boss know that balance is important to you.

First, you need to get inside your boss’s head. If you know he behaves like this with other subordinates during “off time,” then start with subtle hints, such as leaving your phone off at night, then progressing to statements like “I have another commitment,” to ultimately having a frank discussion where you politely set limits. If his behavior is limited to you, then find an opportune time to determine if he has trust issues with you and try to work them out in a calm, face-to-face meeting.

Once you both are communicating, you can better anticipate issues before they arise. You want to leave for your vacation in a relaxed state. You also want to leave your boss with a sense of peace: that your work will be handled while you’re gone.

TOTs not only need to be “managed up”…this one needs PLENTY of warning. If he doesn’t already know about your trip, tell him a couple months in advance. Then provide several reminders prior to your trip – along with that invaluable reassurance of how projects will be handled in your absence. Also let him know upfront that it will be extremely difficult to reach you while you are away – and that you’ve briefed another person for this reason. You need to establish this boundary in advance. Ask him to think of anything he may need to tell you or work he would like you to do before you leave.

Be patient and calm with him, and use humor when appropriate. A friend of mine used what I call a “levity lens” on this subject with his boss, who rarely took vacations herself. When requesting vacation time from her, he’d say, “I hate to ‘tee’ you off, but I’d like to take some time off!” So Paul, demonstrate that you have his best interests in mind, but be firm. Finally, have fun in Europe!

Best regards,


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