5 insane user interview questions for a startup founder

How to get the most value out of talking to humans to uncover deep insights about users’ behaviors

çınar fidan
3 min readApr 27, 2021
From “Talking to Humans”

I have conducted 50+ user interviews in the past 8 months for ScribeUp.

I promise, none of them were relatives of mine.

I knew one thing.

When you are building a startup, you can outsource almost everything, except for the task of finding product-market fit.

That’s the founder’s job.

The most powerful tool of the founder is customer interviews.

It’s not the number that counts, it’s the quality of interviews.

So, here are my Top 5 questions to get the most value out of them.

Here we go!

Question 1: Tell me about your most recent purchase of [product X]?

Given the opportunity, people like to share opinions and hypothetical decisions.

But that’s not enough.

None of this is as insightful as the actual actions the customer performed. So, ask about a past action.

Question 2: What is difficult about this?

The customer might not have mentioned that it’s difficult.

But asking this way, you ensure to get an answer.

No existing product/process is without problems.

Bonus: Follow up with “Why is that difficult?” to dig deeper.

Question 3: How do you work around [problem]?

This leads to direct answers (which is what we’re after in the end).

But even if the customer has no workarounds, they will share their level of frustration.

Question 4:Why is [existing solution/workaround] not cool?

This leads to limitations of existing solutions.

Gold mine question!

Question 5: If you had a magic wand, how would you solve some of the problems you mentioned with [medium]?

This is my favorite for a reason.

It invites the user to problem-solve with you.

You unlock the user’s imagination.

Without constraints, they bring amazing insights for you.

Summary

User interviews are key to a startup’s success. We all understand this. But it’s not the number of interviews, it’s the quality of interviews that matters.

Summary table of my top 5 user interview questions

Bonus

If you have read until this point, let me reward you with a bonus question.

“What did I not ask?”

This does not work all the time, but when it does, it works big time.

The user emphasizes with you and shares the one big story that they have been waiting anxiously to share since the beginning of the interview.

Quick disclaimer: Most of these are based on learnings from Giff Constable and Frank Rimalovski‘s “Talking to Humans.” If you are a student/non-profit, the book is free! https://talkingtohumans.com

Let’s connect, follow me on Twitter!

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çınar fidan

MBA candidate at MIT Sloan, ex-McKinsey consultant. Interested in understanding consumer behavior, entrepreneurship and startups