I’m a good conversationalist. But I wouldn’t say I’m a natural at it. It’s something that I actively set out to get better at throughout my teens and twenties. I wouldn’t say I’m a master at it; there’s still a lot I have to learn. But I’m comfortable saying that I’m pretty good.
There are many things that can set you up to have better conversations. Knowing the other person well goes a long way, which is why good interviewers do their prep beforehand. It enables them to ask good questions. Knowing how to ask a good question is itself a valuable skill, and this requires having a sensitivity to what is interesting. You don’t really want to ask mundane ‘frequently asked’ questions, but you don’t necessarily want to ask overly profound or complex questions right away either, if your conversation partner isn’t sufficiently warmed up yet. (There are exceptions to all of these ‘rules’ depending on the context. Variables like your own reputation, and the expectations your partner brings to the conversation, can allow you to do things very differently and well.) There’s a sweet spot– a ‘question-space’ that we could describe as “moderately surprising, moderately detailed, moderately in-depth”. These are welcoming invitations that entice the other person to go deeper.
Ideally, broadly speaking, you wanna spend as much time as possible in this space. In this space, both parties can feel a sense of freedom, like they’re exploring and discovering together. You’ll notice in really great interviews that the interviewee is challenged to think and feel and remember and figure things out in the moment, but they enjoy it rather than feel annoyed or attacked, because they sense that the interviewer is ‘on their side’.
Everything I’ve said so far is just preamble to what I really want to be talking about. I had the realization recently– from some of my essays like a matryoshka of possibilities(look for interesting trapdoors)and straight outta tartarus(search for inner sanctums), that the breakthrough I’ve been looking for in my writing was something I had already actually understood about conversations years ago:
Re-read the above tweets and transpose them to the process of writing: the most powerful writing skill isn’t asking good questions nearly as much as asking good followup questions… this is the script of no script, the formula of no formula, you just pay really close attention to your writing in a curious, non-judgemental way without the burden of expectations, and look for anything surprising or interesting – and ask about that in a supportive way.”
It’s just so funny to me that I had this clear theory of good conversation, honed from years of practice, but I kinda lacked an equivalent clear theory of good writing… when essentially they’re the same thing. Of course, there’s a ton of nuance to get into on both counts. As I write all of this out, it weighs on me that I haven’t written about this in the most elegant way I theoretically could. That would take some tinkering and rework, which I don’t quite have the time and energy for these days.