Hard customer interview questions you should ask

You

Second round of calls is done. No compliments, no fluff, only past specifics. And somehow I learned almost nothing.

Alex Tutor

Read me a few of your questions.

You

“How old is your cat?”, “Which brand did you buy last?”, “How many bowls does he have?”

Alex Tutor

All honest, none biased. And not one of them could change a single decision at CatChow. You've swapped bad questions for trivial ones.

You

So what makes a question worth asking?

Alex Tutor

An important question is one where a surprising answer would change the plan, or kill it. Quick test: if the answer shocked you, would you do anything differently? If not, drop it.

Alex Tutor

Question 1

Which question passes the test “a surprising answer would change CatChow's plan for the subscription”?

Choose one answer“How old is Whiskers?”“Which bowl does he eat from?”“The last time you ran out of food, what did you do, and what did it cost you?”“How long have you been a CatChow customer?”

Alex Tutor

Now the uncomfortable part. Which question have you been avoiding?

You

Probably whether people would actually leave their pet shop. Olivia has bought from the same shop by her building for years.

And whether they'd pay for a month upfront. If the answer is no, the whole subscription falls apart.

Alex Tutor

That's a scary question: important, and you dodge it because the answer might hurt. Those are the ones worth asking most. In every conversation, at least one question should make you a little nervous.

You

What if I freeze when it's time to ask?

Alex Tutor

Imagine a friend's startup had your plan. What would you tell her to ask? You'd be blunt with her. Be just as blunt for yourself, and write the question down before the call.

Alex Tutor

Question 2

Sofia drafts questions for next week. Which of them are scary in the sense of this lesson? Select all that apply.

Choose all that apply“Have you ever changed where you buy cat food? What made you change?”“When did you last pay for something for your cat a month or more in advance?”“What's your cat's name?”“Who in your home decides which food to buy, and who pays for it?”“How did you first hear about CatChow?”

You

I did ask one scary thing yesterday. Here's what Olivia said:

Olivia

Pay a month ahead for food? Hm. I don't know… I walk past the pet shop on my way home anyway. It's fine as it is.

You

Then I spent ten minutes convincing her. In the end she said, “OK, maybe I'd try it.”

Alex Tutor

So you traded honest data for a polite maybe. Her first answer, that lukewarm “meh”, was the most valuable moment of the call.

You

It didn't feel valuable. It felt like failing.

Alex Tutor

Compare the costs. Hearing “meh” from ten people now costs two weeks of calls. Hearing it after launch costs four months of development and the marketing budget. A “meh” is usually more honest than a “wow”.

You

So next time I don't argue. I ask why?

Alex Tutor

Yes. Is the problem smaller than we thought? Is she the wrong customer? Does she dislike one detail, like paying ahead? And thank her. She helped you more than anyone who “loved it”.

Alex Tutor

Question 3

A customer hears about the subscription and says: “Hm, not sure I'd need that.” What's the best next move?

Choose one answerExplain the benefits again until they agree to try itAsk what makes it unnecessary for them: how they buy food now and whether anything about it bothers themOffer a bigger discount on the spotThank them and cross them off without asking anything else

Alex Tutor

Another pattern in your notes. How did you open each call?

You

“What's your biggest problem with buying cat food?”

Alex Tutor

That's a premature zoom: you dive into one narrow problem before checking she cares about that area at all. She'll name a problem because you asked for one. Often one she's never really thought about.

You

So where do I start?

Alex Tutor

Broad. “What's been taking your time and money with Whiskers lately?” If getting food home is a real pain, she'll bring it up herself.

You

And if she talks about the vet instead?

Alex Tutor

Then you've learned something true: buying food isn't near the top of her list. Zoom in only after a strong signal, when she raises the problem herself.

Alex Tutor

Question 4Short answer · AI-checked task

Kate, a marketer at an online bookshop, is testing a monthly book box. She opens every call with: “What's your biggest frustration when buying books online?” Rewrite the opening so it starts broad.

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You

Olivia did say she ran out of food twice this year. Isn't that a signal?

Alex Tutor

A signal of what size? What happened those two times?

You

She went down to the shop by her building. Ten minutes, she said.

Alex Tutor

Then for her a subscription is a vitamin: nice to have, easy to put off. A painkiller fixes something that hurts right now, and painkillers get paid for first.

You

How do I tell them apart in a conversation?

Alex Tutor

Look for cost. Is she already spending money or time on it? Has she searched for a fix? Is it among her top three worries? A cat on a prescription diet that's often out of stock locally, now that's a painkiller story.

Alex Tutor

Question 5

Olivia ran out of food twice this year and both times fixed it with a ten-minute walk to the shop. That makes the subscription a painkiller for her.

TrueFalse

Alex Tutor

One more trap: stepping around the obvious problem. Didn't you also call an animal shelter?

You

Yes, Sarah, the volunteer coordinator. The pain is huge: forty cats, and food runs out every single week.

Alex Tutor

And who pays for the food?

You

Mostly donations, bags people bring in… I didn't ask about money. It felt awkward, they're a charity.

Alex Tutor

That's the elephant. A real, urgent pain with no budget is a dead end for a paid subscription. Same if the person can't decide: find out who the decision maker is.

You

So I ask about money even when it feels rude.

Alex Tutor

Especially then. Politely, and about the past: how was food paid for last month, and who signed off on it?

Alex Tutor

Question 6Short answer · AI-checked task

Write one or two questions Sofia should ask Sarah, the shelter's volunteer coordinator, to face the obvious problem head-on.

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Megan

Good news from my side! Three customers told me they'd switch today if we deliver the same day and cost less than their shop.

You

Alex, that sounds like strong validation, doesn't it?

Alex Tutor

It says “give me more for less and I'll take it”. Who'd refuse? Whether CatChow can deliver same-day and cheaper than a shop is a product risk: can we build it and make it work at scale?

Conversations can't remove product risk; only building and piloting can. What conversations test well is market risk: do people want it, will they pay, and are there enough of them?

You

So Megan's customers told us about our logistics, not about demand.

Alex Tutor

Exactly. Keep both risks on your list. A business can die of either one.

Alex Tutor

Question 7

Which of these uncertainties about the CatChow subscription are market risks that conversations can test? Select all that apply.

Choose all that applyWill owners pay for a month of food in advance?Can couriers reach small towns within 24 hours and still make a profit?Are there enough owners who regularly run out of a specific food?Can the warehouse system forecast accurately how much food each cat needs?Do owners who shop in the store by their building actually want delivery?

You

Let me go through the rest of this week's notes with all this in mind. Four lines stand out.

Alex Tutor

Good. For each, ask two things: what does it really tell us, and what would I do next?

You

One isn't from a cat owner at all. Lucy, who runs a small cat hotel, said it when I asked how they buy food for their guests.

Alex Tutor

The traps are the same whoever's talking. Different segments just hide them in different places.

Alex Tutor

Question 8

Match each line from Sofia's notes to what it really tells her.

Pick an answer for each row. Choosing an answer that is already used moves it to this row.

“Fresh food on a schedule? Sure, that'd be nice someday.”
Choose an answer
“We'd love it, but the owner signs every purchase and the budget's gone till January.”
Choose an answer
“If you deliver the same day and cheaper than my shop, I'm in.”
Choose an answer
“Hm. Honestly, I'm not sure I'd use it.”
Choose an answer

You

Tomorrow I'm calling Andrew. He buys food at a pet shop near his office. I want to do it right this time.

Alex Tutor

Then plan before you dial: a broad opening, your scary questions written down, and a decision about how you'll react to a “meh”.

You

Decide that now? Why?

Alex Tutor

Because in the moment you'll want to argue. Deciding calmly the day before is much easier than being brave in the middle of a call.

Alex Tutor

Question 9Case · AI-checked task

Plan Sofia's call with Andrew.

Andrew, 34, has a two-year-old cat and buys food at a pet shop near his office, usually on Fridays. He has been a CatChow customer for a year, so the team already knows his order history from the CRM. Sofia wants to find out whether a paid monthly subscription makes sense for people like him.

Write:

How Sofia opens the call (1–2 questions).
Two or three important questions, at least one of them scary, phrased by the rules for honest answers.
What she does if Andrew says: “Meh, not sure I need it.”
One uncertainty about the subscription this call cannot answer, and why.

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You

Honestly, I'm a bit scared of tomorrow's call now.

Alex Tutor

Good. That usually means you're finally asking something that matters.

Alex Tutor

Next time: how to pick your three big questions before every conversation, so the scary ones never get lost.

Alex Tutor

That’s the lesson. You answered every task — nicely done.

Next lesson: Your 3 big questions before every conversation