Nick Winter's Blog | Help Me Become a Better Conversationalist

Watch out: I use "I" 54 times in this post, so this will be boring if you, like me, aren't interested in hearing me talk about myself.

When I was in high school, I was so shy that I couldn't talk to almost anyone outside my family. Through a last-ditch effort when I went to college, I got better. I then got lucky and succeeded at a lot of things I tried after that, which rescued my general confidence, and I did some focused practice, rejection therapy, public speaking, and Beeminding to fix my social confidence.

But even though I'm no longer afraid to try, that doesn't mean that I can do it well. I still feel that I'm not usually a good conversationalist. I haven't had enough practice, especially since I have always spent most of my working time hacking in my lair instead of working socially. I started to practice things like this after the CFAR workshop in March, but put it on hold after getting married when I hurt my feet.

I'm finally recovered and can go outdoors again, so I spent this week practicing: three days of the hallway track at some conferences (plus moderating a discussion), two group classes, a social lunch, a party, hosting my cofounders for hacking, and a few video calls. I'm not completely socially exhausted--yeah, I threw the "introvert" label out of my identity a while ago--but I'm also not going to the second party tonight.

How did it go? I was trying to practice three things:


1. Be into others' stuff.
2. Smile.
3. Be vulnerable instead of safe.

In practice, I usually forgot about #2 and #3. I did much better at trying to focus on other peoples' interests in conversation than I usually do. I'm normally terrible at that, blathering on about my own stuff even as I'm bored of what I'm saying.

One thing I was doing a few months ago was explicitly asking people, right after I talked to them, how I could improve my conversation skills. I would send it in an email so that they could ponder it more and not be as nervous about telling me how I suck. It worked well. People said things like:


• I don't smile much, even when I'm engaged, and even when I'm talking about trying to remember to smile more.
• I'm not funny enough, and not as funny in person as in writing. (I'm funny in writing?)
• I use swearing and exaggerated enunciation as a crutch instead of finding better words.
• I talk too much instead of inviting others to speak.

Before I started asking people, this was what I thought I was missing:


• I mumble too much.
• I'm not very good at telling stories.
• I say "like" too much.

Notice: no overlap. Introspection failure again? Probably.

I didn't ask more than a handful of people, and it occurs to me that I should start doing this again when meeting new people. It also occurs to me to ask you, dear reader! If you have talked to me and have ideas for how I can become a better conversationalist, please tell me. Critical feedback is way better than me guessing. Then next time you talk to me, it'll be more fun for both of us.