The user interview questions that changed my roadmap

I do user interviews regularly. Here are the questions that always uncover something unexpected.

"Walk me through the last time you used this feature."

Not "Do you use this feature?" People say yes to sound engaged.

Asking for a specific recent instance reveals actual usage patterns. If they can't recall a recent time, they don't actually use it.

"What did you try before this?"

Reveals workarounds, competitors, and mental models.

Users who tried three other solutions before yours have different needs than first-time users. Their friction points are more refined.

"If you could wave a magic wand and change anything about this experience, what would it be?"

Frees users from present constraints and reveals deeper pain points and aspirational needs, not just quick fixes they think you can deliver.

"Have you ever recommended the product to someone? Why or why not?"

Surfaces barriers to advocacy and what truly delights or frustrates. If they haven’t recommended it, their reasons can show unseen flaws or gaps in value.

"What’s the most confusing part of using our product?"

Identifies unclear flows or overwhelming features that are rarely revealed with generic satisfaction surveys.

The Pattern

Ask for specifics, not generalities. Recent examples, actual behavior, concrete outcomes.

Layer interviews with support tickets and telemetry. Interviews explain the why behind the data.

The best insights come from triangulating methods, not relying on one.