How to learn from conversations

Link post

(This is a post from a daily blogging experiment I did at, which I thought might also fit the tastes of LessWrong)

I’m currently in the middle of a virtual conference, so one thing heavily on my mind is how to get the most out of talking to people who know more than me. How to get as much information as I can, how to get it efficiently, and how to ensure I actually understand it and retain it! I think this is a very learnable skill, and one that I’ve cultivated a lot over the past 3 years. Having fascinating conversations with interesting people is one of my great joys in life, and I care a lot about being able to do this well! In this article I’ll try to convey some of the key tools I’ve developed!

Health warning: I get the feedback that I come across as fairly intense in conversations, and sometimes give the vibe that I’m judging whether the other person is worth my time. I try to minimise these, and to pay attention to the other person’s comfort level, but this seems like a pretty inescapable cost of this approach!

  • Ask questions

    • This one is pretty self-explanatory—ask a lot of questions! You want to make life as easy for the other person as possible. Shaping a conversation, and figuring out what to talk about takes a lot of cognitive work, and asking question makes life a lot easier for the other person

    • Technique: Notice curiosity

      • I find that often conversations, especially small talk, end up being about stuff that just isn’t that interesting. And this is terrible! If you’re talking about things you both find exciting, that’s a mutual win!

      • My main solution to this is to notice the hint of curiosity, or excitement, at what the other person is saying. Often someone’s statements have a lot of different points and information in them, some of which is much more exciting than others. I’ve found it valuable to practice introspecting on how excited I feel about each part, and asking questions about the bit that feels coolest

        • This often needs several layers of iteration, but is a pretty efficient way to move from small talk to something new and cool!

      • Introspection is a difficult skill, and generally Noticing emotions is something that I could talk at length about. But it’s something you can get better at with practice

        • Main points: You want to get as much surface area on the emotion as possible. Notice when you feel it, common trends, associated physical sensations. Flag to your mind that this matters and is important to you

          • Simulating historical examples mentally, and dissecting the feeling of curiousity can help to notice it in future

    • Technique: Noticing confusion!

      • If they mention something that feels a bit wrong, or off, ask about it!

      • Often it’s hard to formulate a precise question. In those cases, just saying “You said ___, I feel a bit confused about why that works, can you elaborate?” goes a pretty long way! And can be more effective than trying a specific question, when I’m confused about what I’m confused about

      • Variant: Notice when they refer to an aspect of the world that is super unfamiliar to me.

        • Prompt: “Could I talk about that for more than 30 seconds?” If not, ask about it!

      • The internal experience is that I’m trying to build a model in my head of what the other person is talking about. And every so often I notice a hole in it, or it throws an error. That is the feeling of confusion

  • Gain surface area on the conversation

    • Often the bottleneck for asking questions is not having the context to know what to ask about! This is super bad when I talk to a domain expert in a completely novel area—I lack the intuitions to know what to ask about, or what would be interesting

      • I call this context + intuitions surface area, and I think a key goal is figuring out how to get as much as possible

    • Technique: Using their intuitions

      • Conveniently, you’re talking to someone with a lot of surface area, and you can often access this with the right questions!

        • Eg “what surprised you when you got into X”, “what do people often misunderstand”, “what are most important problems in your field”

    • Technique: Asking for examples

      • Examples are an amazing way to learn things! So often, conversations turn into meanders through abstract terms and ideas, which loses its grounding in what I actually understand. If I can understand an example, that often conveys a ton of information

      • Having a specific example can often motivate questions, point to confusions or curiosities, because I can understand an example, even if I don’t get the overall idea

      • From an information theory point of view: We want to communicate concepts, but we have to translate them into words. This can lose a lot of information. Examples are another channel of communication, that can identify errors in translation

      • A key mental habit I’ve built is to always ask for an example, whenever anything feels confused in my head

  • Technique: Paraphrasing

    • Paraphrasing means repeating back what I think they’re saying, in my own words, and ask whether this is correct

      • Very important: Always ask rather than telling. Be humble, it’s easy to misunderstand! And easy to come across as annoying or arrogant or strawmanning if you misrepresent their point

    • This is an insanely key skill. I do this about every 5 minutes in most conversations, and this identifies a ton of misunderstandings.

      • If there’s one thing you get from this article, let it be paraphrasing!

    • Paraphrasing is my main error checking tool, because by translating things back into my words, I often identify errors. It’s much easier for the other person to correct something wrong, than to explain something clearly.

      • If you’re skeptical, I highly recommend just trying it. It’s disturbing just how many times I misunderstood something the first time

    • It’s also helps me retain the information, by giving me some processing time, and forcing me to check I actually got it

    • It’s easy to breeze through a conversation, zoning out a bit. Paraphrasing forces me to be active, and really engage

    • Another fun bonus: I think the ability to put complex ideas into words is a really useful one. A habit of paraphrasing forces me to get a lot of regular practice, and I’ve become dramatically better at this skill over the past few years.

      • This has noticeably improved my learning and teaching skills