Traveling With Your Boss

How to make the trip turbulence free.

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The head honcho just asked you to join her on the next out-of-towner, and you can practically hear your proud father's voice: "Don't screw this up!" We asked Penelope Trunk, author of Brazen Careerist: The New Rules for Success, how to take a trip with the boss, turbulence-free. Q: I follow Brangelina as closely as I do marketing trends. Can I read Us Weekly on the plane if my seatmate's my boss? A: You don't have to read Barron's, but play it smart and save the tabloids about celebrity cellulite for later. Read a newspaper or bring some light work so your boss doesn't feel like she has to talk to you the whole flight. But definitely do not use it as a time to get organized--that will only make you look disorganized. Q: I just spent the day in soul-crushing meetings. Do I have to spend the night yukking it up with my boss at the hotel bar? A: Even if you'd rather be back in your room watching Entourage, if your boss wants to hang out, just do it. The one-on-one time is really a perk of the trip. If he wants to do team-building karaoke, you want to do team-building karaoke. Q: What's the best way to bend my boss's ear about my ideas without pestering her? A: Don't wait for a contrived, perfect moment that may never come. When your boss is relaxed, just say, "I have some ideas I want to run by you," and dive into your three best ones. Q: Between meetings, my boss asks me to spill the hot office gossip. What to do? A: It's OK to simply say you don't have any. You don't want her to count on you for gossip in the future, so set the boundaries now. Q: My male boss invited me to his hotel room to go over our presentation. Any chance he's using "PowerPoint" as a euphemism? A: Do what you will with the following: Research shows that coworkers who flirt do better work together, as long as lines aren't crossed. Use your judgment; if the situation feels at all unsafe, suggest a neutral locale.
(Image credit: Archives)

The head honcho just asked you to join her on the next out-of-towner, and you can practically hear your proud father's voice: "Don't screw this up!" We asked Penelope Trunk, author of Brazen Careerist: The New Rules for Success, how to take a trip with the boss, turbulence-free.

Q: I follow Brangelina as closely as I do marketing trends. Can I read Us Weekly on the plane if my seatmate's my boss?

A: You don't have to read Barron's, but play it smart and save the tabloids about celebrity cellulite for later. Read a newspaper or bring some light work so your boss doesn't feel like she has to talk to you the whole flight. But definitely do not use it as a time to get organized--that will only make you look disorganized.

Q: I just spent the day in soul-crushing meetings. Do I have to spend the night yukking it up with my boss at the hotel bar?

A: Even if you'd rather be back in your room watching Entourage, if your boss wants to hang out, just do it. The one-on-one time is really a perk of the trip. If he wants to do team-building karaoke, you want to do team-building karaoke.

Q: What's the best way to bend my boss's ear about my ideas without pestering her?

A: Don't wait for a contrived, perfect moment that may never come. When your boss is relaxed, just say, "I have some ideas I want to run by you," and dive into your three best ones.

Q: Between meetings, my boss asks me to spill the hot office gossip. What to do?

A: It's OK to simply say you don't have any. You don't want her to count on you for gossip in the future, so set the boundaries now.

Q: My male boss invited me to his hotel room to go over our presentation. Any chance he's using "PowerPoint" as a euphemism?

A: Do what you will with the following: Research shows that coworkers who flirt do better work together, as long as lines aren't crossed. Use your judgment; if the situation feels at all unsafe, suggest a neutral locale.