How to start good convos

I met some new colleagues for lunch this week and failed miserably. The others already knew each other and kept talking about that new company building in another city and contract details. So exciting, right? It was hard to step in and change topics, so I kept silent. Eventually, I asked the guy sitting opposite about his work. But he did not really seem to enjoy talking about it, so I gave up and went back to work.

What went wrong? They certainly did not show much interest or effort to integrate me into their group, but that’s outside my control and I could have certainly done better than mostly staying silent.

My approach to good talk is usually to explore interests and look for some common ground. Out of my curiosity, I usually find something interesting and start asking questions. Actually, this is what I enjoy about talking to strangers. It’s new territory - so much to explore (except for some boring exceptions).

I used to struggle how to start new conversations. It was a real eye-opener for me to realize just how blind I am to details. I learnt that great talkers are observant and watch for cues: the catchy T-shirt, their book, a particular behavior you share… These cues are super helpful, because they might indicate some common ground, letting you skip ahead the boring small talk right away. Curiosity is also key. Even behind simple questions about why someone did something this way might reveal something interesting. Recently on a friend’s birthday, a girl asked me why I would gift a todo-planner. The others were probably just thinking: “Oh he is german”. We discovered that her boyfriend is also a follower of the GTD philosophy and that we share many quirks. It was great to discover this, since it’s rare to find such people.

Besides asking questions, providing cues is also essential. Only if I reveal something about myself, can the other person take cues from it and ask good questions. This is still something I struggle with. I often only start talking when asked, but not out of own initiative. It’s a past behavior I need to unlearn. It’s a good thing, as long as I don’t go to deep into the weeds and just provide it as a cue. I want to become more thoughtful to share something from my day. I started last year to look for storyworthy moments every day, but I still have difficulties to find that moment. To often that short great moment succumbs to the more mundane but longer lasting / more recent events. I want to try to frame my day as a story. To capture these moments mentally as highlights of my story when they are happening and not just when asked or at the end of the day.

Another dimension of good conversations is humor. I admire humor in other people, but I used to believe that its just not a trait of me. Derek Sivers description of humor made me see it in new light.

Humor means using your mind beyond necessity, beyond reality, for both noticing and imagining. It shows you quickly looked at something from many angles, found the one that amused you the most, and considerately expressed it to someone else.

- How To Live, Derek Sivers

This is really much something that is learnable. I don’t want to be a comedian, but I can learn to be more observant and express things from an unusual perspective.