Pete the Planner's guide to when YOU should pick up the tab

Written by
Peter Dunn

The business lunch is an institution. Check that. A business lunch, that is handled appropriately, is an institution. I actually hate going to lunch for business unless at least one person benefits, hopefully both. I don't necessarily need to be the person who benefits. I just don't want the experience to be a waste of time or money.

All of that being said, the most awkward moment consistently occurs when the check arrives. Who pays? Knowing who pays, could be the key to advancing your career, or remaining in a position that you don't want.

You've been there. "One check or two?" Doh!!!! But with Pete the Planner's guide to when YOU should pick up the tab, you will never feel awkward again.

When you SHOULD pick up the tab:

  1. You ask a mentor-type to lunch- I owe my career to others. These others are men and women who took the time to go to a lunch with an absolute nobody in the financial world (not that I'm somebody now) just because I asked. Do you want to rise in your industry? Ask your "competitors" to lunch. Call the head of a competing firm, and ask him/her to lunch. Then pay for lunch. You aren't trying to learn trade secrets. You are trying to learn career secrets. Picking up the check confidently is a good career move. Act quickly, take the check firmly, give the person a firm nod, and say "I got this. Thank you." If they resist beyond the obligatory "no no no", then allow them to pick it up. You don't want to embarrass them.
  1. You dominate the lunch conversation- I believe that lunches should be productive for both people involved. If you clearly get more out of the lunchtime conversation, then pull an awesome move. "Hey Frank, I realize that I dominated the conversation today with my ______ issue. I've got the check. I really appreciate your willingness to listen." Baller.
  1. It's your turn- Step up and take your turn. If your normal lunch buddy always buys, then take your turn. I'm not talking about random lunches with your co-worker. I mean a real business lunch with a purpose.
  1. You're with someone that has made you a tremendous amount of money- If you are a vendor, a service provider, or a sales rep, and you are with someone that has referred you a ton of business or who consistently buys things from you or your company, then buy lunch...every time. This isn't negotiable.
  1. The other person is unemployed- I'm not going to explain this.
  1. You order a lunch beer and they don't- The lunch beer is one of life's true pleasures. If you are tipping one back, don't make the designated diner buy your lunch. Not cool.

When you SHOULD NOT pick up the tab

  1. You want to display your dominance- Believe it or not, I struggled with this for a very long time. Ask my friends. I always picked up the check. Was it an ego thing? Kinda. I'm working on it. Want to help me? I'll gladly let you buy me lunch. :)
  1. Because you make more money- Surprising, isn't it? The purpose of the lunch trumps financial status in my eyes.
  1. Based on gender- I can't think of anything more insulting then picking up a lunch tab based on gender. Chivalry is chivalry, but buying a business lunch because your co-diner is a lady-type, is ridiculous.

How/When to accept lunch from someone else:

  1. Graciously- Don't make a scene. You will look like a d-bag, especially to the server. The server doesn't want to stand there while you pound your chest like a weirdo. Make eye contact with the person offering to buy you lunch (nothing weird, don't lean in for a kiss), and say "Thank you. I really appreciate it." Your act of true graciousness will be remembered much more than you picking up the tab.
  1. If things get awkward- Have you ever seen two-man luge? Yeah, it's really awkward. If things get super awkward during the "no, I'll pay" debate, then retreat. The other person clearly didn't read Pete the Planner's guide to when YOU should pick up the tab.

When in doubt, go dutch. Pay for your own lunch. Sometimes requesting two checks is the best move. It's quite clear when this is the case. My default move used to be to buy lunch. I discovered that I bought lunch when I shouldn't have. The better move is to go dutch. That's my new move when the rules don't apply.

Have any rules to share? I'd love to hear them. Leave a comment. Happy dining!

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