Customer Interviews That Don’t Suck: Asking Questions That Actually Reveal Behavior

In partnership with

Customer interviews are one of the most powerful tools in a startup’s arsenal. Done right, they give you insights that no dashboard or survey can match. Done wrong, they lead to false confidence, wasted effort, and products built on shaky assumptions.

Too often, founders fall into the trap of running interviews that collect opinions instead of behaviors. They ask leading questions, chase validation, or accept polite lies. The result? A false sense of product-market fit.

In this edition of Startup Stoic, we’ll explore how to design customer interviews that cut through the noise, reveal real behavior, and help you make decisions with clarity.

Why Customer Interviews Fail

The problem isn’t that customers lie—it’s that humans are wired to be agreeable. If someone asks, “Would you use this?” the polite answer is almost always “Yes.” But yes doesn’t mean commitment. It means they want to end the conversation without conflict.

Other common reasons interviews fail include:

• Leading questions: “Wouldn’t it be great if…?” practically forces agreement.

• Hypotheticals: People are terrible at predicting their future actions.

• Over-indexing on features: Founders want feedback on their idea, but customers don’t live in features—they live in problems.

• Ego-driven listening: Interviewers look for validation, not truth.

A Stoic Approach to Customer Discovery

The Stoics believed in observing reality as it is, not as we wish it to be. Customer interviews work best when they follow that principle. Instead of chasing approval, you seek truth. Instead of asking for predictions, you dig into past behavior. Instead of being swayed by flattery, you look for patterns in evidence.

The mindset shift is this: you are not trying to sell your idea during an interview. You are trying to learn.

How to Ask Questions That Reveal Behavior

Here are practical guidelines:

1. Anchor in the past, not the future

Bad: “Would you use an app that automates your finances?”
Better: “Tell me about the last time you managed your finances. What tools did you use? What frustrated you?”

Past behavior predicts future action far better than guesses about hypotheticals.

2. Dig into specifics

Bad: “Do you care about saving time?”
Better: “Walk me through the last time you felt like you wasted time at work. What did you do?”

Details uncover patterns, while generalities create fluff.

3. Listen more, talk less

Your job is to create space for the customer’s story, not to pitch yours. Silence can be uncomfortable, but often that’s when the real truth emerges.

4. Don’t be afraid of negative feedback

Negative feedback isn’t rejection—it’s clarity. Every “this doesn’t matter to me” is a gift that saves you months of wasted building.

5. Look for emotion

If someone’s voice changes, they sigh, or they rant about a pain point—that’s gold. Emotion is a clue that the problem really matters.

Practical Structure for a Good Interview

A reliable interview framework looks like this:

1. Warm-up: Build rapport. Ask about their role, context, and day-to-day.

2. Problem exploration: “Tell me about the last time you faced [problem area].”

3. Current solutions: “How did you try to solve it? What tools did you use?”

4. Workarounds and hacks: “What did you do when those solutions didn’t work?”

5. Emotional cues: Note moments where frustration, delight, or urgency appear.

6. Closing: Thank them and don’t pitch. Save your idea for later.

Lessons for Startups

Customer interviews are not about collecting compliments. They’re about uncovering truths that will save your startup time, money, and effort. Done right, they help you:

• Identify urgent problems worth solving.

• Spot competitors and alternatives customers already use.

• Understand the real language customers use to describe pain.

• Build conviction in the right direction—and kill bad ideas faster.

Startups that master this discipline build products rooted in reality, not fantasy. They move with confidence, not blind optimism.

Closing Thought

The Stoics taught that clarity comes from stripping away illusions. For founders, illusions are the sweet lies customers tell when asked bad questions. Real clarity comes from asking about behavior, not opinions; listening without ego; and noticing where the story doesn’t line up with the pitch in your head.

If your customer interviews feel like therapy sessions, you’re doing it right. If they feel like sales calls, you’re doing it wrong.

The better your questions, the clearer your path forward.

See you next time,

— Team Startup Stoic