SSD 11: Going Deeper

People sometimes measure their social skills by the number of great conversations they have. “I am capable of having a great conversation,” they think, “so therefore, I must have great social skills.” And when they have a bad conversation, they think “I’ve had so many successful conversations; clearly this person is awful.”

But the key question is – did great conversations happen because you had social skills? Or did they happen because your partners had social skills? I’ve always said that the true indicator of social skill isn’t connecting with people who are great communicators, but rather connecting with people who aren’t.

With that in mind, I want to focus on a situation where for once, I actually did something right. My friend, let’s call him F, was talking to me about his job and trying to downplay what he did, saying “I mean furniture’s been around for hundreds of years. Nothing new. I’m looking through 50 shades of gray to figure out which one’s the best.”

This was a tricky situation by any measure. I could’ve tried to disagree and come up with ways his job was interesting. OR I could’ve agreed, which is often the natural instinct in conversation (following the rule of “Yes… and”). But the former would’ve led to conflict in our conversation and come across as insincere (since I don’t know his industry) while the latter would’ve led us into a spiral of negativity. Maybe I would be tempted to demean my work as well to comfort him.

I needed to avoid disagreeing, but avoid negativity and be sincere. My read was that his comment came from a place of humility (meaning he doesn’t really, really believe furniture is boring) and insecurity (he wants to know that it’s okay to work in that industry). So I asked a simple follow-on, which was “Wait… so how do you pick which gray?”

And his answer was actually really interesting – he delved into detail about how furniture trends shift between gray and brown. Gray was currently in. And we looked around at the trendy restaurant we were in and indeed – all the furniture was gray. So I led us to a good place.

The beauty of what I did was – instead of trying to convince him that what he was doing was interesting, I showed him that I was interested in what he was doing by asking a deeper question. To do that, I had to veer off the path of either disagreeing or agreeing and instead probed deeper.

Perhaps in a different scenario, the follow on answer would’ve continued to be boring, but in that case, we would be working at least on factual bed rock if I were to agree and say “yes that’s boring.” Hopefully in a joking manner. But at least our conversation would be sincere.


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