Asking Great Questions

A Guideline To Uncovering Insights From Customers

Last weekend, I rewatched Season 2 of Mindhunter.

It’s not just a show about serial killers. It’s about the process of uncovering patterns, starting with nothing but a few assumptions and a lot of uncertainty. Two FBI agents began asking new kinds of questions. Their work, at the time seen as unconventional, later became the foundation for one of the FBI’s most important units.

What really struck me wasn’t how they caught killers. It was how they asked questions.

They brought different perspectives, challenged each other’s biases, and knew how to make conversations open. So open that they didn’t just find answers. They found better questions.

This post isn’t about serial killers.
It’s about something product people rarely talk about, yet deeply rely on:
The skill of asking great questions.

Product is full of uncertainty. Sometimes, you don’t even know the right question to ask to get to the insight you’re looking for.

Take this common scenario:
Your website converts only 5% of users.
You benchmark against similar companies and find the standard is closer to 15%. You invest in SEO, design, and better copy. Two sprints later, you’re at 6%.

Now the real questioning begins:

• Who is converting?

• Where are they coming from?

• Who isn’t converting?

• Can we talk to both groups?

• How did the ones who converted make their decision?

At this point, many of us start with blogs, articles, competitor audits. That’s secondary research.

But we forget something more important: primary research — going straight to the source: the customer.

And let’s be honest, most people don’t do it.
They can’t find the customer, or they can’t find the time.

But if you can’t find time to speak with the people you’re building for, what exactly are you building?

Asking Great Questions Is a Skill. Here's How to Get Better:

• Start a conversation, not an interview.
  People put up a guard when they know they’re being interviewed. Ease them in. Ask how their day is going. Make it feel like a chat.

• Know your objective.
  What’s the big thing you’re trying to learn? For example: Why are users churning?

• Ask broad, open-ended questions.
  Instead of “Why did you stop using our product?”, try:
  “Can you walk me through your experience with us?”

• Use specifics as follow-ups.
  When someone says, “The pricing didn’t work for me,” follow up with:
  “What pricing model would work better for you?”
  or
  “How does the new provider’s pricing compare?”

• Don’t defend your product.
  People may spend the first few minutes ranting. Let them. Don’t correct them or explain. Just listen. You're here to learn.

• Not all interviews will be useful.
  Some might be messy, scattered, or inconclusive. That’s okay. Insight is a pattern game. You just need to talk to more people.

• Be aware of your own bias.
  You’re coming in with goals and assumptions. That’s fine. Just make sure you don’t cut people off when they go in another direction. Sometimes, that’s where the gold is.

Great PMs are great pattern seekers.
Whether it’s in dashboards, feedback forms, or interviews, we’re always looking for signals in the noise.

But the first step to finding those signals is asking better questions.

And the best ones aren’t about having the smartest wording.
They’re about starting with curiosity, staying open, and creating the space for something real to come out.

In my next post, I’ll break down how to actually analyze those responses using a simple thematic analysis process.

Till then, ask better questions.