LLenny's Podcast
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InfluenceJessica Livingston (co-founder of Y Combinator, author, podc

Building Your Own Social Radar

Turn people-reading from a mystery gift into a deliberate practice: checklist, conscious questions, and follow-up calibration.

Difficulty
Moderate
Time to result
~ongoing to results
Steps
5
Confidence
85%

Livingston resists calling her radar teachable, but the concrete advice she gives is a genuine method for people who feel 'clueless' at reading others: go in acknowledging your weakness, run a mental checklist of specific things to notice, ask a few deliberately revealing questions, then reflect afterward — and, over years, follow up to see whether your gut was right.

Origin

Jessica Livingston's own account of how a lifelong habit (as a child she spent hours 'dissecting situations,' earning an earlier nickname 'Detective Livingston') can be approximated deliberately by people who don't have it naturally.

Core principles

  • 01You must have a genuine interest in what drives people; the skill grows from curiosity, not technique.
  • 02Naming your own weakness ('I'm bad at these judgments') primes you to compensate consciously.
  • 03There are no trick questions — the skill is attention plus a few plain, revealing questions, then reflection.
  • 04Calibration comes from closing the loop: checking years later whether your read was correct.

How to run it

  1. 1

    Go in naming your weakness and your intent

    Before an evaluation, tell yourself explicitly: 'I know I'm bad at these judgments — I'm going to deliberately watch for a few specific things.' This shifts you from passively hoping to notice, to actively looking.

    Pro tip Frame it as an assignment ('I'm going in to evaluate these people') so observation becomes the job, not a byproduct.

  2. 2

    Run a short mental checklist during the conversation

    Keep a small, memorized checklist and run it live: Do they get along? Do they understand their product well? Are they defensive when challenged? It needn't be written down, but hold it in mind throughout.

    Pro tip Keep the list short enough to actually recall mid-conversation — a handful of behaviors, not twenty.

    Watch out Don't turn it into interrogation; these are things to observe within a natural conversation.

  3. 3

    Ask a few deliberately revealing questions

    Where the conversation doesn't surface something on your checklist, ask directly. If you don't know the co-founders' history: 'How did you two meet? Have you ever worked together before? How's it going?' Simple, non-tricky questions that expose key information.

    Pro tip Save application-derived flags for the interview: 'It looks like you have 90% of the stock and your co-founder has 1% — can you tell us why?'

  4. 4

    Reflect immediately afterward

    Right after the conversation, spend a few minutes reviewing the checklist against what you saw: 'Were they defensive when I asked why they're better than the competitor? How did that go?' Convert live impressions into a conscious judgment.

  5. 5

    Close the loop over years to calibrate

    Track your strong gut calls — especially the negative ones where you pushed not to fund — and follow up over 5-10 years to see whether you were right. This is the only real feedback signal for a slow-resolving skill.

    Pro tip Negative instincts are the ones most worth checking: find out whether someone you disliked went on to succeed, to learn whether your aversion was signal or noise.

    Watch out Resolution is slow — some founders take 5-10 years to fail — so treat calibration as a long-running habit, not a quick loop.

In the wild

The follow-up habit

Livingston deliberately follows up on strong gut instincts years later: 'I sort of like to know what happens a few years later. I like to follow up.' She notes there is no one she strongly opposed funding who then became a huge success — evidence her negative reads were calibrated.

A self-audited track record that both validates and sharpens the instinct over time.

Common mistakes

Waiting for a visceral gut feeling

Livingston says her read is 'more intellectual' than a body sensation — noticing 'this guy's interrupting her.' Beginners who wait for a dramatic gut feeling will miss the observable cues that actually carry the signal.

Never closing the loop

Without following up on outcomes, you can't tell whether your reads are accurate, and the skill never improves beyond guessing.

Is it for you?

Best for

Investors, hiring managers, and team leaders who feel weak at reading people and want a deliberate practice rather than a talent they think they lack.

Not ideal for

Situations demanding an instant verdict with no chance to reflect or follow up, where the calibration loop can't run.

From the transcript

I know I'm bad at these kind of judgments. I'm going to remember like, do they seem like they get along?

51:00

have a conversation. Do they understand their product well? Are they defensive? Like, maybe have your own little checklist

51:00

"How did you two meet? How did you Have Have you ever worked together before? How's it going?"

51:30

I sort of like to know what happens a few years later. I like to follow up.

43:30

From the episode

The social radar: Y Combinator’s secret weapon

Jessica Livingston (co-founder of Y Combinator, author, podc