Chapter 3: Ask what happened, not what people want, lesson 2 of 7

Spot the questions that get you nothing

Leading, "would you", three-in-one and the pitch: the interview questions that get you nothing. Mark up a real first interview, then rewrite the worst ones.

By 4 min read, 15 min of exercises

Warm-up

From last time, your interview with Ken. Did each question get facts, or guesses?

  1. Tell me about the last time you settled up.

    Right, it's a question that gets facts. It asks about one real day. Ken told you about an hour of arguing and $200.

    Not quite. It's a question that gets facts. It asks about one real day. Ken told you about an hour of arguing and $200.

  2. Would you use group ordering if Tiffin had it?

    Right, it's a question that gets guesses. It asks about a future Ken has never lived. He said yes to be kind.

    Not quite. It's a question that gets guesses. It asks about a future Ken has never lived. He said yes to be kind.

  3. Could I see last month's sheet?

    Right, it's a question that gets facts. It turns talk into something you can see.

    Not quite. It's a question that gets facts. It turns talk into something you can see.

Last time, you interviewed Ken. The questions about what already happened found his problem. The ones about the future got kindness.

On Friday, Ryan Brooks, the product manager, runs his first interview. He talks to Dana, who manages a design studio of 12 people. Mia sits in and writes down every question.

Think first

Ryan, product manager, his first real question to Dana: You’ve been with Tiffin a while, so you must really like it, right?

How would you ask it instead?

You

Which of these is closest to your answer?

Shirish

Better. It no longer tells her the answer. But it still asks for an opinion, and she’s talking to someone from Tiffin.

What could she tell you about, instead of how she feels?

Shirish

This one still decides for her that she likes it. She’ll find reasons, to be polite.

How could you ask without putting an answer in?

Shirish

Yes. One real day, in her own words. Whatever she likes or doesn’t will show up in the story.

What would you listen for, as she tells it?

You

What this means

Ryan’s question tells Dana the answer he wants: you must really like it, right? She’ll agree, to be nice. Here’s what she said: It’s fine. The food’s good. We use it less now, though.

Look at the end. We use it less now is the most important thing she says in the first minute. Ryan’s next question was about what she likes most.

The questions that get you nothing

Every question below is one Ryan asked Dana. Each gets you something that feels like an answer, but isn’t.

  1. Leading. It holds the answer you want. So the main problem was really the delivery times, right? People agree to be polite.
  2. Would you? (the future). It asks about a life they haven’t lived. If Tiffin had a way to split the bill, would you start ordering for everyone again? You get a guess, usually a kind one.
  3. Three in one. Several questions in one breath. Was it hot, and did everyone get what they ordered, and was the packaging okay? They answer the easiest one, and the rest are lost.
  4. The pitch. You describe your idea and wait. We’re working on group ordering. I think you’d love it. After a pitch, people stop telling you problems.
  5. The price question. Would you pay a dollar extra for it? It ties them to your idea before you know their problem.

And here are the ones that work:

  • Tell me about the last time…
  • Walk me through it.
  • What happened next?
  • Can you show me?
  • And one open question at the end: Is there anything I didn’t ask that I should have?

Mark up Ryan’s interview

Practice

Here are eight of Ryan's questions to Dana. What kind is each one?

  1. Tell me about the last time you ordered lunch for the whole studio.

    Right, it's a question that works. One real day in the past. Dana told him about twelve meals and $150 on her card.

    Not quite. It's a question that works. One real day in the past. Dana told him about twelve meals and $150 on her card.

  2. Was it hot, and did everyone get what they ordered, and was the packaging okay?

    Right, it's several questions in one. Three questions at once. She said "it was fine" and the rest were lost.

    Not quite. It's several questions in one. Three questions at once. She said "it was fine" and the rest were lost.

  3. If Tiffin had a way to split the bill, would you start ordering for everyone again?

    Right, it's a question about the future. She has to guess about a feature that doesn't exist. She said "Maybe? Probably."

    Not quite. It's a question about the future. She has to guess about a feature that doesn't exist. She said "Maybe? Probably."

  4. We're actually working on group ordering. I think you'd love it.

    Right, it's a pitch. Now he's selling. She said "Send it to me when it's ready", and nothing else.

    Not quite. It's a pitch. Now he's selling. She said "Send it to me when it's ready", and nothing else.

  5. What does lunch look like in the studio now, since August?

    Right, it's a question that works. It asks about what really happens today. She told him the kitchen table is empty most days.

    Not quite. It's a question that works. It asks about what really happens today. She told him the kitchen table is empty most days.

  6. So the main problem was really the delivery times, right?

    Right, it's a leading question. He put his own guess in her mouth, and it was wrong. She said, "It was the money."

    Not quite. It's a leading question. He put his own guess in her mouth, and it was wrong. She said, "It was the money."

  7. Would the team order together again if it was easier?

    Right, it's a question about the future. A guess about other people's future. She can only say "I don't know."

    Not quite. It's a question about the future. A guess about other people's future. She can only say "I don't know."

  8. Before we finish, could you show me the notebook?

    Right, it's a question that works. It turns talk into something he could see. Every line in it was crossed out.

    Not quite. It's a question that works. It turns talk into something he could see. Every line in it was crossed out.

So, your bet. Of Ryan’s 21 questions, 9 got something useful. That’s about half, and it’s normal for a first interview. The best one came last: he asked to see Dana’s notebook, and every debt in it was crossed out.

How to fix a bad question

Most bad questions can be fixed the same way. Turn the future into the past.

Think first

Ryan, to Dana: If Tiffin had a way to split the bill, would you start ordering for everyone again?

Which rewrite would get Dana to tell you something real?

You

Pick the answer closest to yours.

Shirish

It’s shorter, but it’s the same question. It still asks Dana to guess about her future.

What already happened that you could ask about?

Shirish

Yes. Dana has lived that. Her answer: a designer left owing her $90, and she messaged her twice.

What would you ask after that?

Shirish

It’s about her now, which is better. But it still names your fix, so she’ll say yes to it.

How could you let her name the problem herself?

You

What this means

Turn would you into what happened. Would you use it? becomes Tell me about the last time you had this problem. Would you pay? becomes What do you spend on this now?

I learned how much this one habit matters from my own role-play.

Shirishfrom my own practice

Four of my questions, rewritten

After my role-play, I sorted my own ten questions. Four of them asked for a guess or a general picture. How often? What if? Would it make you switch? How would you rate it?

Each could be rewritten as Tell me about the last time. Rewritten, they would have found the real problem by my third question, not my tenth.

Words from this lesson

Leading question
A question that holds the answer you want, so people agree to be polite. In this lessonSo the main problem was really the delivery times, right?
Compound question
Two or more questions in one. People answer the easiest one. In this lessonWas it hot, and did everyone get what they ordered?
Pitching
Describing your idea and asking what they think. You get kindness, not problems. In this lessonWe're working on group ordering. I think you'd love it.

Back to your first answer

Your first answer

Your answer

Your answer will show here after you write one at the top of this page.

You've read the lesson. Would you change your answer?
Good. Which part of this lesson backs your answer?

Your bet: what should Ryan have asked next?

Your bet

Early on, Dana says something that Ryan lets go by.

Dana, studio manager: I keep a notebook of who owes me. I’ve lost count of what I’m owed.

What’s the best thing to ask next? Make your bet, and say how sure you are.

Your guess
How sure are you?

You'll find the answer in Lesson 3.3: Follow the thread people hand you.

Try this during the week: find a survey or form you’ve been sent. Spot one leading or “would you” question in it, and rewrite it about the past.

Sources

  • Rob Fitzpatrick, The Mom Test, 2013. On pitching, and on questions about the future.
  • Steve Portigal, Interviewing Users, second edition, 2023. On question types and how to ask them.
  • The role-play is from my own practice. Tiffin, Ryan, Mia and Dana are made up for this course.
Portrait of Shirish Shikhrakar

Written by

Shirish Shikhrakar

Shirish is a Google-certified UX designer and UX engineer based in Kathmandu, Nepal. He started as a software developer, moved into product design for Silicon Valley startups, and has taught UX foundations to hundreds of designers since 2019.