Lenny's Podcast/Discussions
Discussion 07 of 12

The Question That Creates Space

A discussion about questions that create space for a person to think, not just perform a prepared answer.

Question for assistants

How should an assistant create room for unfinished thinking?

What it suggests

Use questions that invite the next thought instead of rushing to closure.

The Question That Creates Space audio

Audio discussion for The Question That Creates Space.

Discussion 07

The Question That Creates Space

Milo and Juni discussing The Question That Creates Space
11 exchanges / topic discussion. Press play for the Milo and Juni discussion.
milo
One category of question appears repeatedly in the strongest transcript moments. It's not clever. It doesn't demonstrate research. It creates space for the guest to say something they haven't decided yet.
juni
What do you mean by that is the obvious version. But the transcripts have subtler ones.
milo
Yes. Where does that leave you? Or what does that feel like from the inside? Or just: say more. These are permission structures. The host is signaling that there is more room, that the guest doesn't have to land yet.
juni
Most guests are used to being moved along. The next question is waiting. So they compress. They give you the summary.
milo
The space-creating question undoes that compression. It says: you don't have to summarize yet. Stay in the middle of it.
juni
And guests respond to that by saying things they haven't quite said before. You can see it in the transcript -- a slightly longer pause than usual before the answer, and then something that has a different texture than the rest of the conversation.
milo
The texture of live thinking rather than recalled thinking.
juni
That's what you want. The recalled version is available in the guest's other interviews. The live thinking is only available here, in this conversation.
milo
Which is the real value of a long-form interview done well. Not a better-formatted version of what the guest already believes. Something the guest worked out during the conversation itself.
juni
The question that creates space is the tool for that. And it takes confidence to use it. Most hosts feel the pressure to keep moving, to demonstrate preparation, to add their own contribution. Saying say more feels passive.
milo
It's the opposite of passive. It requires knowing that the guest has more and that the right move is to wait for it.
Moments from the transcript

Test the discussion against the words that prompted it.

Read the quote first, then the behavior note. These moments show where the discussion begins.

Source 170Ask with curiosity

Katie Dill

Lenny (00:21:40): You mentioned this word beauty, and I wanted to follow on this a little bit of just... This is a big question, but just what is great design? What is beauty? Is there like a objective definition where if a designer is like, "This is great design," how do you explain that?

The question creates space by letting the guest think from first principles instead of asking for a canned tactic.

Read Katie Dill source
Source 163Ask with curiosity

Judd Antin

Lenny (00:10:22): Yeah. That's exactly what I was thinking. As a PM, that's what I want to get answers to, is like, "How should we think about this one product?" And I totally get this. Judd Antin (00:10:31): Yeah. The questions turn out to be really interesting.

The host stays inside the guest's frame and invites more thinking rather than jumping to the next prepared prompt.

Read Judd Antin source
Source 121Ask with curiosity

Hamilton Helmer

Lenny Rachitsky (00:39:23): You're about to get a lot of requests for fireside chats. I hope you're ready. You mentioned AI at some point in our chat. I'm curious how you think AI is going to change your 7 Powers framework. Do you think defensibility goes down?

The question invites speculative reasoning while still tying back to the guest's own framework.

Read Hamilton Helmer source