WORKPLACE / DEC. 20, 2014
version 3, draft 3

How to Take Your Boss to Lunch - And Why You Should

lunch at work
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If you thought inviting your boss out for lunch was somehow crossing the line, think again. Getting some one-on-one time outside the office setting has a number of benefits, including helping you develop and maintain good relations with your employer, as well as helping you keep your finger on the pulse of what’s happening around the office.

While it might seem awkward at first, since no one really does it, don’t hesitate to take this opportunity to get to know your boss a bit better, and to help your career along.


Find out when your boss is available

If you ask at the wrong time -- or at a time when it’s easy for your boss to decline -- you’ll be losing out on this opportunity. To avoid that, try to get any inside information you can about when she’s free or not dealing with difficult situations. Ask her secretary for help, or if your office maintains an open calendar, pick a day she doesn’t have much else going on.


Let him know you’re not quitting

When you ask for some one-on-one time, your boss might immediately think you’re either quitting, or that you have some serious problems at work that you want to discuss more privately. To allay those fears, let your employer know right away that this is a casual lunch and there won’t be any heavy conversations. Ideally, talk to your boss in person so you can discuss the details away from the sometimes-misconstrued constraints of email.


Pick a place you’ll both be comfortable

You might be in your element in a noise sports bar, while your boss might prefer an elegant white-tablecloth type place, but to make things easier for both of you, choose something more middle-of-the-road. You could ask your boss to suggest a place, but then again, if your budget is limited, that could set you up for an awkward denial. Once again, tap into any resources you might have, such as the boss’ secretary, to find out where the boss likes to eat. Then suggest a few places near the office and let her choose among them. Another thing to keep in mind: Don’t suggest a place with messy food, such as spaghetti, for example. 

Keep the conversation light

The point of this lunch engagement is not to bombard your boss with difficult subjects, and on the flip side, not to get overly familiar either. With that in mind, consider putting together a list of “safe” subjects you can talk about. Maybe you’ve been looking for ideas for a project you’ve been working on, or you’ve always wondered about how your boss got into your industry. Whatever you choose, keep the conversation light, with the idea that you’re there to develop a strong rapport with your employer.

Offer to pay

Since you invited your boss out, you should be the one to foot the bill. Then again, if the boss insists on picking up the tab after several attempts to the contrary, there’s probably no harm in letting her do so.

While it might seem like it was just lunch, this outing could pay other dividends in the future. Spending some time with your boss outside the walls of his office can be a way to get to know him better, to develop a good relationship, and to show that you’re willing to go the extra mile to succeed.

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