Ask LH: How Can I Have Interesting Conversations With My Boss?

Ask LH: How Can I Have Interesting Conversations With My Boss?

Dear Lifehacker, Every week after work we have informal drinks with the boss. I am the resident nerd and I want to find what topics of conversation are appropriate without pretending to like things that I don’t like or having to be false. I do have a decent sense of humor and can crack the boys up now and then, but I need more than that. I need to be interesting and respectful without acting like a fool or being a suck-up. What topics of conversation can I use that I am actually interested in that will engage and interest the boss and his cronies? Thanks, Conversation Starter

Office drinks picture from Shutterstock

Dear Conversation Starter,

Faking interest in an area is rarely a good conversational strategy, especially with your colleagues. I can’t suggest specific topics of conversation that you’ll be able to make interesting, because I don’t know what you personally find interesting. But I can suggest a few strategies to make the conversations you do have more interesting and engaging.

  • Don’t talk about yourself. This strategy works whether you’re the office underling or Prince Philip: ask people about themselves rather than trying to direct the conversation towards your own areas of interest. Sure, you know what your colleagues do, but everyone has a life outside of work.
  • Use the FORD technique. As we’ve noted before, the FORD technique is a good conversation starter: ask about family, occupation, relationship or dreams. Occupation is probably covered at a work event, but the others are all good.
  • Don’t always fight to be right. I’m a nerd, and I’ve been at plenty of nerd gatherings. The people that go over badly in that context? The ones who are utterly convinced that they are right and want to argue over every minor detail. Don’t be that guy. Let it go already.
  • Find out why people are enthusiastic. You might not share your co-worker’s interest in tapestry or The Hunger Games or bush dancing, but you can find out why they enjoy it to much. Tapping into the enthusiasm of others is easy: just ask “Why do you like _____ so much?”

If readers have additional suggestions, fire away and engage our interest in the comments.


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  • Check out their office. Typically most people with offices have personal items on display – the sporting trophies, photos of social events (like fishing) or family, books on certain topics, tourist trinkets, etc. Their office space is a minefield of talking topics, you can find plenty to talk about. This worked well when I was a consultant and visiting my client – you’d be surprised how much personal stuff is on display.

    But the most important thing to do is listen well – take topics from one week and remember them for the following week. It’s easier to continue a topic you know that your boss is interested in versus trying to find a new topic to discuss.

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