a guest told me i asked too many questions

the most useful feedback i got this month came from a guest who liked the show.

on thursday i debriefed a founder who runs a software agency. she'd enjoyed the taping. she said so. and then she told me the truth anyway.

too many questions. not enough depth.

we'd covered about five questions in twenty minutes and she felt rushed through every one. her suggestion was simple.

"maybe shorten it and focus on like 3 questions, but go deeper."

she wanted it to feel more like a conversation and less like an interview.

i didn't argue. i couldn't. two or three other guests had told me some version of the same thing and i'd filed it away. when the fourth person says it, it's not a preference anymore. it's a pattern.

so here's how it happened, because i think the mistake is common.

the show used to be long form. ninety minutes. you can ask fifteen questions in ninety minutes and still go deep on half of them.

then we compressed it to about twenty minutes, because guests are busy and short episodes travel further. smart move. but i kept the question list. i cut the time and kept the count.

that's like taking a two hour dinner menu and serving every course in twenty minutes. same food. nobody tastes anything.

and my style made it worse. i described myself on that call as a bit robotic. i walk in with predefined questions and i want to get through them. charles is the opposite. zero prep. shoots from the hip.

the goal is somewhere in the middle. know the three things worth asking. then get out of the way.

everyone thinks a better interviewer asks better questions. i think a better interviewer asks fewer questions and stays on each one longer. the second follow up is where the real answer lives. the first answer is the one they've given a hundred times.

if you ask five, you only ever get the rehearsed version of each. if you ask three, you have room for why, and then what happened, and then what would you do differently. that's where a guest says something they've never said on camera.

and the guest feels it. depth is a form of respect. it tells them you came for their thinking, not to fill a slot.

this goes way past podcasting. a sales call with twelve discovery questions feels like an audit. an investor meeting where you rush through every slide leaves nothing anyone remembers. three questions, done properly, beat five done in a hurry... in any room.

the part i liked best is that this has a natural fix built in. part two episodes are more spontaneous by design. you already know each other. you already covered the basics. so i invited her back for one, and i'm going in with three questions.

long term, the show only works if guests walk away feeling heard. that's the whole reason they say yes, share it and send their friends. if the format makes people feel rushed, it doesn't matter how good the list was.

if you run a show, or any recurring conversation with customers or investors, ask for this kind of feedback on purpose. not did you enjoy it. ask what felt rushed. ask what you wanted to say and didn't get to. the polite answer is useless. the specific one is gold.

owning that is part of the job. a guest who tells you what's wrong is giving you something most people won't bother to.

if you want to see whether we got it right, come sit in the chair. you can apply on the show page... and tell me after if i asked too much.

so think about your last important conversation. how many questions did you ask... and how many answers did you go back for a second time?