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Dinner with the boss, how to enjoy the evening

Dinner with the Boss

Dinner with the boss is a GOOD thing!

Enjoy your dinner with the boss

Tis’ the season of dinner parties and if you have been invited to have dinner with the boss, you really shouldn’t worry. For the past week, I have been talking with friends and it amazes me how nervous folks become because they were invited to dinner with the boss. Just as nerve-wracking is when you are attending a dinner party with the significant other’s boss. I can honestly say that every day last week, I heard someone was nervous and worried about being invited to a party hosted by their boss or their S.O.’s boss.

It is easy to think about all the ways behavior can go badly, and when that happens in the presence of your boss, it is easy to think that your career will be in jeopardy. I understand that thinking, but if you have worked with your boss for any length of time and made a good impression, what makes you think that tonight will be any different?

There are plenty of articles on how NOT to act, what NOT to say, and what NOT to do. I am guilty of putting out a number of posts on how HR interprets holiday party behavior, but one thing I realized was that I didn’t say anything about what you SHOULD do, what you SHOULD say, and how you SHOULD act.

If you are attending a dinner party with your boss, be yourself and ENJOY!  It is your ability to be yourself at work that is probably what got you invited in the first place so don’t feel the need to act differently.     

It is a rare individual that can walk into a room full of strangers and be the life of the party.  You and your S.O. do not have to be the life of the party or re-create a scene from the Wedding Crashers. You just need to be a hair north of “interesting” and to the right of “upbeat”.

If you are fortunate enough to be invited out to dinner with the boss, your S.O.’s boss, or a big client of your significant other, remember the following and you will be successful.

  • Smile.  Anything less is a very visible cue.
  • Be yourself. You were hired because you proved you had social skills during the interview and you have only become more comfortable working in the company since that first interview.
  • As an exec, the last thing that I want when I invite someone to dinner is for the guest to be nervous, act differently, or be someone who they are not.  I am inviting you to dinner because I want to say “thank you”, or I want to celebrate an occasion and I like your company.

The very last thing I want is for anyone to be so nervous that they have a miserable time or worry about their behavior. I would hope that you act the same way around me as you would when you go out with your friends from work.

  • No exec made it to where they are by trying to put the people around them in awkward situations, or trying to you feel uncomfortable. This isn’t a scene from Dinner for Schmucks. If your boss wanted a stiff board, they would have gone to the lumber mill.  If you were really a schmuck, do you think your boss would have hired you and kept you on?

One person, I talked with this last week said: “I don’t want to get drunk when I have dinner with my boss”. I immediately asked them “Have you gotten drunk in front of your boss in the past”? Of course, the answer was “No”, to which I replied,

“If you had even given a hint of an indication that you might get drunk in front of the boss, do you think she would have invited you”? Their logic made no sense, but with a perception that so much is at stake, people can become irrational.

As an exec, if I thought you were going to embarrass me in front of our peers, I would not have invited you out or asked you to meet friends or clients.  You don’t have to be on your “best” behavior. I want you to demonstrate the same behavior you have always demonstrated at work.  It is behavior that I and your co-workers are comfortable being around.

We all have friends we invite to our parties and friends we do not invite.  We have colleagues we like to be around and those that we do not. Execs are no different, and if anything, most execs are NOT insecure when it comes to entertaining. For most people and especially execs, showing or verbalizing insecurity is a red flag.

Do not question or doubt why you were invited. The last thing I want to be asked when we are out is “why did you invite me?”.  I don’t mind explaining it to you, but really, I invited you because you have the confidence to accept the invitation and will be yourself versus an insecure baby.  Just roll with the evening and enjoy the moment.  If your boss passes you a blunt then make like Snoop and hand your Boo a 40.  (Sorry, got my blog posts mixed up there.)

Face time with the boss is a great thing. Don’t question it or think the worst. Look at it like the gift that it is.  This is an opportunity for them to learn more about you personally and professionally. It is an opportunity for you to ask for advice and learn more about them.

So, if you get invited this holiday season to by your boss to go out to dinner or close a big client, I have one piece of advice for you. “Enjoy yourself and don’t fuck it up.”

See you at the after party,


nasty: an unreal maneuver of incredible technique, something that is ridiculously good, tricky and manipulative but with a result that can’t help but be admired, a phrase used to describe someone who is good at something. “He has a nasty forkball”.

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