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Advice / Succeeding at Work / Break Room

The Do’s and Don’ts of Entertaining Your Boss

Whether you’ve invited your boss over for dinner or you’ve just been hand-picked to host an in-town company exec, you’re bound to be entertaining the higher-ups at some point in your career. Anxiety-inducing? Just a little bit. Hosting anyone can be tricky, but anytime co-workers and drinking are involved, there’s a fine line between putting your best foot forward and sticking your foot in your mouth.

But we’ve got you covered. Follow these hosting do's and don’ts to show off your skills and show your boss a great time—no stress required:

Do: Show Your Best Side

Even if you have a great relationship with your supervisor or the higher-up in question, it’s important to put a little thought into planning your engagement. Keep in mind that the same things that make you look good at the office will help you shine at home: Make sure your house is clean and in order. Think through your menu carefully. Shop and prepare as much as possible ahead of time to avoid last-minute stress. Also consider timing—nothing can ruin a good evening faster than having it go on too long (Michael Scott’s dinner party, anyone?). Things should move along steadily from cocktails to dinner to dessert, which signifies the end of a party.

Don’t: Worry About What You Can’t Fix

Sure, your boss may have a nicer house than you, but that's the natural order of things. So instead of worrying about what you can’t change, do the best with what you have. (And chances are, your boss knows you and will know what to expect!) If you can’t afford to host a high-end cocktail party, choose something more casual, like a backyard BBQ. Pick a theme and stick with it, weaving it consistently throughout your menu, set up, décor, and timing, and your event will come off as well-coordinated and classy, no matter what your budget.

Do: Cater to Your Guest

Before the big day, ask around and find out some of your boss’s likes and dislikes. What are her favorite and least favorite dishes? What does she drink? Any food or pet allergies? Then think through what else you know about her. If she loves being outdoors, plan to start the evening on the patio. If kids aren’t really her thing and you have toddlers, arrange for her to come over after their bedtime or get a sitter. Is she more charismatic or quiet? Plan the tenor of your event accordingly.

Don’t: Change Who You Are

If you’ve heard your boss doesn’t like dogs, keep your golden retriever in another room and vacuum up excess hair, but you don’t need to board him or pretend he doesn’t exist. More importantly, if your family has certain beliefs or traditions that you celebrate, like saying grace before dinner or (if you’re like my family) always making time for cocktail hour, continue them. It’s your house, your party, and your chance to let your manager see more of the real you. Just make sure your guest feels comfortable—i.e., don’t put her on the spot by designating her to lead the prayer, and keep your cocktail hour to just that, an hour.

Do: Get to Know Each Other Better

Hosting your boss is an opportunity to bond outside of work and let her in on more of who you are. So don’t be afraid to open up a little bit and share stories about your family and talk about your hobbies or what you like to do outside the office. Also, take this opportunity to find out more about what makes your boss tick. You never know, your common interests may take your relationship—and your job—to the next level!

Don’t: Get Too Personal

Of course, sharing more about who you are does not mean telling your supervisor all of your most embarrassing stories or intimate details. Relax and enjoy yourself, but be mindful not to drink too much and let your guard down. Remember, this is your boss you’re talking to, and though you want her to enjoy her evening, you also want her to continue to see you as the outstanding professional that you are.

Photo courtesy of Stephanie Wesolowski.

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