Questions to get the most out of interviews

“Pain is uncomfortable. Sitting there watching them go through their pain is awkward and it hurts. Sit through it with them.” – Luke Ruffing, The Pro-Guide to Making Your SaaS Product More Than a Nice to Have

Go into each interview with 10-15 problem-focused, customer-centric questions. They should always be working down toward a personal experience, or strongly held opinion.

THE ALL-ROUNDER: OPEN-ENDED BUT HIGHLY SPECIFIC

Good for: Opening the conversation and finding other talking points to go into

Avoid: Asking questions with foregone conclusions like, “Don’t you like this?”

Examples:

  • How are you liking it?

  • Does that pose a problem for you?

  • What do you like best (or least) about this thing?

  • What kind of problems does that cause for you?

Pro Tip:

Tie it back to something specific to get additional information without much effort

THE NUDGE

Good for: Bringing the conversation back around to your point when it’s tangented too far to be valuable

Avoid: Leading the conversation directly, prolonging the tangent, or launching into anotherExamples:

  • For a story that’s gone off track:

So what happened with X in the end?How did Y turn out though?

  • To bring the conversation into “my solution might fall into this realm…” territory:

Have you ever tried a Z to deal with this?

Oh, have you had experience with Y?

THE “WHY, THOUGH?”

Good for: Getting to the root of a problem in record time, or figuring out what’s motivating a person — why they care about a problem

Avoid: Dropping your line of questioning too soon

Examples:

  • This is as literal as it gets. Just ask “Why?”

Pro Tip:

Drag it out for 5 rounds to get to maximum specificity levels

THE “TELL ME MORE” BACKGROUND-GATHERER

Good for: Getting to the root of a problem when asking “why” fails you

Examples:

  • Tell me more about what happened.

  • Can you walk me through that?

  • What did you mean by that?

Pro Tip:

If your interviewee doesn’t seem sure what you mean or what you want from them, it’s OK to hold their hand a bit. “Did you then do X, Y, or Z? Did that have any ramifications? So when you say X, is that meaning Y to you, or…?”

THE ALTERNATIVE SOLUTION FINDER

Good for: Pushing customer research toward market research

Avoid: Crossing completely into the solution space. This type of question naturally butts up against it

Examples:

  • What have you found for X?

  • What have you done about Y?

Pro tip:

If they’ve done nothing to tackle the problem, your problem might not be so valid after all. If they’ve tried multiple resolutions, what stopped those from being the right solution for them?​

THE TIME-TABLER

Good for: Determining how pressing, common, or important a problem is to someone

Avoid: Accepting answers that are too general (“pretty often!”)

Examples:

  • When was the last time that problem came up?

  • How often have you had to deal with that?

  • When did you last do X?

THE CLOSER

“Would you pay to solve this problem?”

Good for: True validation in our capitalist society

Avoid: Avoiding this

*inspired by Rob Fitzpatrick’s The Mom Test

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