Five Questions that Let You Watch What’s Going on in People’s Heads

A while back, when I was making Anki decks of the life concepts that I found most important, I wrote these two sentences:

“Communication is authentic when what we express externally corresponds to what’s going on internally.”

“Humans crave authentic communication.”

If you’re anything like me, you spend a big chunk of your waking hours talking to people. It’s important the time I spend communicating be fun, not unsatisfying. I don’t like it when I:

  • find myself planning what I’m going to say next instead of listening to the other person (Note: There is a level of listening beyond just being able to remember the words the other person said. That’s the type I’m referring to here.)
  • wonder whether the other person is really listening to me, or just being polite
  • discover that I’m completely off in my head somewhere else entirely, maybe thinking about what I’m going to eat for dinner
  • get the sense that the conversation is kind of dead, even if I couldn’t say why

Everything I listed above is a symptom of people not talking about what’s actually going on in their heads.

When what you’re saying is strongly connected to the pictures in your head, the feelings in your body, or the thoughts popping into your mind, you can bet I’m making eye contact, relaxing out of my own narrative to focus on you, letting my own emotions respond to your reality. It’s a lot like getting drawn into a good movie.

When what I’m talking about lines up with what I’m thinking about, and you’re listening, it feels like I’m the center of your universe. As I say things and see you respond in real-time, it helps me think. My default state is looking out at reality through my own distorted map, so having another human reacting to my thoughts and feelings is an excellent way to get perspective on the stories I’m constantly telling myself.

As Kenneth Folk, a meditation teacher who recommends dyad noting (where you note out loud with a partner) as a more reliable way to meditate, says, “Feedback is God”.

With that, I give you my best questions to steer your conversations towards authenticity.

1. What’s actually on your mind?

Sometimes, simple and direct is best. If you want to know what someone is really thinking about, you can just ask. I’m including it here because sometime last year, when Anna Salamon asked me this question, it caught me off guard in the best possible way. I remember I was sitting in the hot tub with her, feeling somewhat self-conscious because I didn’t know her very well. I asked her what she wanted to talk about and she asked me this question. I could tell she was sincere, and it was very disarming. There was a release of tension as the conflict between following my own train of thought and trying to make her happy dissolved.

2. As far as you can tell, am I getting what you’re saying?

When we say stuff out loud and we’re looking to have other people understand us, we look for clues to see if it’s working. Is the other person asking questions that show they understand? Does the other person seem to be feeling the same way I do about what I’m saying? Are they using metaphors that suggest that they have the same pictures in their head as I do? Usually, this checking to see if the other person is on the same page happens indirectly. We try to figure it out, but it’s not quite a shared effort. Give the other person a break by joining in this process. Ask if you seem to be getting it, and mean it. If the other person says ‘no’ or doesn’t seem sure, ask what it is that you’re not getting or what you’re doing that makes them suspect that you’re not getting it.

3. What’s your best guess about why I’m saying this?

This is another one that whoever it is that you’re talking to is probably already trying to figure out. We all have our own angles, biases, misconceptions, expertise, and values. And whenever we talk to anyone else, we need to know how much we can trust their information, so we ask ourselves why they’re telling it to us (sometimes consciously, sometimes not). If someone doesn’t believe you about something, chances are they already have a story about why you’d be saying it even though it isn’t true. Be curious. Ask what that story is.

4. How would you be able to tell whether…?

The first three questions were about getting the person you’re talking to share stuff that was already going on their head. This one is about helping the other person think. Say you’re talking to someone who just started learning how to paint, and they say, “I don’t think I could ever paint something truly awesome.” You could ask, “How would you be able to tell whether your painting were truly awesome?” For this to work, you have to ask in a curious way. Show that you’re genuinely interested in what goes on in their head to decide whether a painting they had made would be “truly awesome”. Often the person won’t know the answer right off the bat, so this question can get the wheels spinning.

5. What is your response to that?

This one comes from my friend, roommate, and life coach, Shannon Friedman. Sometimes what you want isn’t to follow someone’s train of thought about whatever happens to be on their mind, but to hear what’s going on inside in the other person in response to something you said. In which case, ask! Of course, be prepared for the other person’s response to be something that more about them and less about whatever it was you said. Be curious anyway, and you’ll go deeper.

If you have experience with any of these questions or ones you think should be added to the list, leave a comment!

(Note: When I went over this list with Will, he suggested taking out the qualifier for #2 and change it to “Do I understand you correctly?”. I went back and forth, but decided to leave the qualifier in because it can make people more comfortable answering honestly. I’d recommend experimenting with the wording on all of these and going with what flows. Tone will matter more than the exact words you use anyway.)

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