Why I Love Customer Interviews (Even When They Prove Me Wrong)

Customer interviews are one of my favorite things to do.

Not because they prove I’m right. In fact, most of the time they prove me or my team wrong. That’s what makes them so valuable.

These interviews help me learn how people live, what matters to them, how they think and work, and what they’re actually trying to solve. If we’re building anything, especially early, we have to start there.

This is how I do it and hopefully it will help you develop a style that works for you that you can adapt to the person you’re interview. 

A Casual, Human, Flexible Style

My approach is very conversational. I don’t use a script. I try to keep things loose and friendly so the person I’m talking to doesn’t feel like they’re in a lab experiment or being evaluated. I want them to feel comfortable taking the conversation in the direction that matters to them, not just to me.

The less it feels like a formal research session, the more honest and useful the conversation becomes.

Most of my interviews happen over the phone or on video, but I’ve done them on bike rides, chairlifts, and in busy public places. I adapt to what works best for the person I’m talking to. My goal is to learn as much as possible, and that starts by meeting people where they are.

A lot of this comes from my background in journalism. Big thanks to Ms. Fall, my high school journalism teacher, and to my professors at American University. I’ve also been inspired by Cindy Alvarez, Indi Young and former FBI hostage negotiator Chris Voss. 

Preparing for an Interview

I don’t start with a list of questions. I start with two things.

What do I want to learn?

This is the most important part of preparation. I ask myself: what are the things I actually need to understand to move this product or idea forward?

That list can include things like:

• What’s painful for this person? Why?

• What are they trying to achieve?

• What else have they tried?

• How are they solving this today?

• How do they make buying decisions?

• How can we reach them?

• What do they care about?

• What motivates them?

• How familiar or sophisticated are they with this kind of problem?

Usually, I want to learn more than I can cover in 30 minutes. So I prioritize based on what matters most at this stage in the project.

What do I think I know?

Then I list out my assumptions. This helps me clarify what I think is true, so I can be more intentional about testing it.

Which assumptions are foundational? Which ones, if wrong, would make the entire idea fall apart?

That’s where I focus.

But once the interview starts, I try to set those assumptions aside. I want to be present and don’t want to bias the conversation or steer them toward confirming my beliefs. I want to learn from them, not lead them to what I want to hear.

A quick note on scripts

I don’t use them. They feel stiff and unnatural, and they make it harder to build trust. Instead, I create a list of topics I want to cover. As the conversation unfolds, I check off what we’ve hit and loop back to anything we missed.

Is it more work afterward to make sense of the insights? Yes. But it’s more real. And it’s always worth it.

What I Do in the Interview

Start with a little chit chat

Right away, I try to get a read on the person. Do they want to jump right in or warm up first? I’m naturally someone who likes to get to the point, but this part isn’t about me. If they want to connect first, I give space for that.

If they’re expecting a sales pitch (this happens), I pause and explain that I’m here to learn about them, not sell anything. That usually helps them reset and relax.

Ease in with an open question

My first question is always something gentle, personal, and a little bit open-ended. Things like:

• “How did you get involved in [the product or project]?”

• “What was [that experience] like?”

I want them to start telling their story. Often, they’ll share details that aren’t directly related to the problem I’m exploring but that context and rapport are essential. It helps me understand what matters to them and where their energy is.

Explore their past behavior

Instead of asking what they would do, I focus on what they have done. That’s a better predictor of future behavior.

Some of my favorite prompts:

• “Tell me how you do [this thing] today.”

• “What tools, tricks, or workarounds do you use?”

• “If you could wave a magic wand and do anything here, what would it be?”

• “What happened right before you started doing [the thing]?”

• “What did you do right after?”

• “Is there anything else I should have asked about this?”

Throughout the conversation, I listen for anything surprising, emotional, or revealing. If it touches on one of my risky assumptions, I go deeper. I ask follow-ups and try to understand what’s underneath.

Share the idea (briefly)

Toward the end, I often share a very rough version of the idea we’re exploring. I do this casually. Something like:

“So here’s what we’re thinking…” [quick description]

Then I shut up and listen.

I do this for two reasons. First, it signals that I’m open to feedback. Second, I want to see how they interpret the idea based on their experience not how well they can critique a pitch.

I’m not looking for a yes or no. I’m looking for insight.

Always ask for referrals

At the end of every interview, I ask:

“Is there anyone else you think I should talk to?”

This question has two benefits. First, it helps me line up the next interviews. Second, it tells me something about how they view the product, the problem, or the audience. If they refer me to someone totally outside our assumed customer segment, that’s a signal worth paying attention to.

This is the same mindset good hiring managers have: always be recruiting. A conversation today might become a great source, a future hire, a collaborator, or a customer advocate. 

Wrapping Up

Customer development interviews are not about proving your idea is right.

They’re about listening, learning, and staying open to where the truth takes you. The most powerful insights often come from the moments that surprise you, contradict your assumptions, or challenge your plans.

Let yourself be wrong. Let your customer teach you. And keep going.

Whether you’re validating a startup idea, rethinking a product, or just trying to understand your market, real conversations with real people are the best way to move forward.

And if you ever find yourself on a chairlift or climbing with me, you might just find yourself in one of these.

Image: a mixed media experiment