20 questions I ask in every customer interview

Knowing your ideal customers is key to building a unique, compelling position.

Understanding their pain points, desires, what they look for in a vendor, who they trust, how they search, what they know and don't know, how they behave, their values and beliefs, and ultimately, what gets them to buy.

Positioning requires you to know all of that...and more.

Uncovering those insights isn't easy.

Slapping a prompt into ChatGPT or Claude will give you answers, but they are nothing more than assumptions based on best practices for your industry.

And you know what they say about believing assumptions: it makes an ass out of you and me.

The best way to get insights on your ideal customers is to talk to them—schedule interviews and dig into their mindsets and beliefs.

Scary, I know.

I've conducted 100s of customer interviews for my clients over the last 6 years. Here's how you can make customer interviews more effective.

Why You Should Conduct Customer Interviews

Customer interviews are a non-negotiable for building a unique position.

You can't own a place in people's minds if you don't know how those minds operate.

Most businesses try to skip this step. It's time-consuming, awkward, and often they don't know how to turn customer input into an effective position.

But skipping this step, or worse, letting AI do it for you, will cost you in the long run.

According to Hinge Research Institute,

Firms that conduct frequent research (at least quarterly) grow up to 70% faster and are almost 50% more profitable than firms that don't."

When you don't interview your ideal customers, you hinder growth and stifle profitability.

Here's when I recommend conducting customer interviews:

Repositioning Project
New Messaging
Adjusting Your Offer
New Brand Design
Annually

20 Customer Interview Questions

Here are the twenty questions I ask in every customer interview.

Problem & Buying Journey

What caused you to realize you were facing a challenge and needed to find a solution?
What was that problem?
How did that problem impact you/your company? How did it make you feel?
Where did you start looking to find a solution?
What platforms/influencers do you go to when looking for a solution?
What other solutions were you considering?
Walk me through that decision process.
How did you find us?
Why did you reach out to us?
What made you decide to choose us?

Experience

Tell me about your experience with us - what did you like?
What could we have done better?
What obstacles did you encounter in learning how to use our product/service?
What problems or issues have you encountered while using our product/service?

Product/Offer

If we removed one component of our offer, what could we remove and still have you pay for it?
What would you still have paid for if we kept only one component of our offer?

Pricing

At what price point would this service be so high that you wouldn’t even consider it?
At what price point would this product be so low that you would never believe it could fulfill the promise we have?
At what price point would you say it’s really expensive, and you’d have to think about it, but you’d ultimately decide to buy?
At what price point would you say it is a steal or this is a bargain?

The 5 Whys

You will be tempted to trust the first answer a customer gives.

DON'T.

Most people respond with whatever is top of mind, easy to remember, or the last thing they encountered from you.

You want to dive into the real answer. That's where the insights live that will improve your positioning.

We use Sakichi Toyoda's 5 Whys Methodology in our customer interviews.

The 5 Whys methodology is a simple, iterative problem-solving technique used to identify the root cause of an issue by repeatedly asking the question "why?"

By peeling away layers of symptoms, it helps teams uncover the underlying flaw in a process or system so they can fix it permanently rather than just treating the immediate problem.

First why - identifies the top level reason for their answer
Second why - digs deeper to understand that top-level reason
Third why - helps in uncovering deeper reasons they might not readily recognize
Fourth why - reveals underlying reasons they didn't understand themselves
Fifth why - finally reaches the real answer and reason

It works to uncover deeper insights into how your ideal customers think.

Ask why? up to 5 times when your customer gives an answer. It forces them (and you!) to dig into the real reason for their response.

Create Insight Cards

Once an interview is completed, it's time to create insight cards—detailed breakdowns of the insights gathered, why they are happening, and recommendations to improve your position.

Here's a prompt we use after each interview to extract insights and recommendations.

Note: This prompt requires an interview transcript.

You will turn one customer interview into a set of insight cards.

An insight card is a small, structured finding. Four parts:

INSIGHT. A short title, 2 to 4 words, naming what’s actually going on. Not a category. “The Friday Email,” not “Communication Preferences.”

TYPE. Pain-remover or pleasure-maximizer. A pain-remover takes away something the customer was afraid of, tired of, or stuck with. A pleasure-maximizer gives them something they wanted but didn’t have. Most cards are one or the other. If a card is genuinely both, say so and explain which one got them to buy.

FACT. What is happening, in concrete detail, using the customer’s own words where their words are better than yours.

REASON. Why it’s happening. The mechanism underneath the fact. This is where you think, not summarize.

OPPORTUNITY. What the business should do about it. Specific enough to assign to somebody on Monday.

What counts as an insight

An insight changes what the company should do. “They love us” is not an insight. “They stayed because of a three-line email nobody on the marketing team knows exists” is.

Read the whole transcript, then look for:

- The trigger. What event made them start looking? Not “they needed a solution.” The specific thing that happened.
- What they compared you to, including doing nothing. Most customers’ real alternative is staying put.
- The moment they decided. What tipped it.
- What almost stopped them. The objection, the delay, the thing they had to get past.
- What they’d pay more for, and what they’d give up.
- What surprised them after buying, good or bad.
- What they say about you to other people, in their words.
- Anything the company clearly doesn’t know about itself.
- Contradictions. If they say one thing and then describe the opposite, that gap is a card.

Combine anything that’s really the same insight. Produce as many cards as the interview earns, usually between 5 and 15. Do not pad to hit a number. Order them most important first, where important means “most likely to change a decision the business makes.”

Worked example

Here is a strong card, from an interview with a client of a small bookkeeping firm:

| INSIGHT 3 | The Friday Email | TYPE | Pain-remover | | ----- | ----- | ----: | ----: | | **FACT** *What is happening?* | Every Friday her bookkeeper sends a three-line email: cash on hand, what's coming in next week, what's going out. "I read it in the parking lot before I drive home. It's the only thing that tells me whether I can breathe this weekend." She had two bookkeepers before this one and neither did anything like it. | | | | **REASON** *Why is this happening?* | She makes payroll for eleven people. Her fear isn't an audit, it's payroll. Monthly reports arrive three weeks after she could have done anything about the number in them. The Friday email turns bookkeeping from a compliance task into a decision she can make before the weekend. | | | | **OPPORTUNITY** *What does this mean for us?* | Recommendation(s):<br>• The Friday email appears nowhere in our marketing. Name it and put it on the homepage.<br>• Ask every other client whether they get one and whether they read it. If it's inconsistent, standardize it.<br>• Change the fear we write to. Our copy talks about accuracy and compliance. She's scared of missing payroll.<br>• If the email is why clients stay, make it why clients sign. | | |

Here is the weak version of the same card. Don’t write these:

INSIGHT 3: Communication. FACT: The client values good communication from her bookkeeper. REASON: Clients want to feel informed about their finances. OPPORTUNITY: Improve communication and highlight it in marketing materials.

The difference is specificity. The weak version could be about any company on earth. The strong version could only be about this one.

How to write

- Use the customer’s actual words. If they said something better than you could write it, quote it.
- Never invent a quote, a number, a name, or a detail that isn’t in the transcript. If you’re inferring rather than reporting, say “this suggests” or “worth checking.”
- No marketing adjectives. No seamless, robust, game-changing, leverage, delve, landscape, journey.
- No em dashes.
- Write like you’re briefing a colleague who wasn’t on the call. Plain, direct, 2 to 4 sentences per cell.
- Recommendations go in a short bulleted list, not a paragraph.

Sensitive detail

Interviews often contain personal information: illness, divorce, money trouble, family conflict. Anonymize it by default. Keep the pattern, drop the identifying specifics. “A health event that took her out of work for two months” rather than the diagnosis. Refer to the interviewee by first name or role only. If a sensitive detail is genuinely load-bearing for the insight, include it and add a one-line note that the interviewee should approve it before it’s used publicly.

If the interview was thin

Say so. If the transcript is mostly pleasantries, the answers are vague, or the interviewer never got past surface-level questions, produce fewer cards and tell the user plainly what the interview didn’t surface. Do not manufacture insights to fill space. Then list three specific questions to ask next time.

Output

Start with a header: the interviewee’s first name or role, the interview date if known, and one line of context about who they are.

Then the cards, as markdown tables, in the format shown above.

Then close with:

Top 3 takeaways. What this interview adds up to, in three sentences. What to ask next time. Two or three questions this interview raised but didn’t answer.

The transcript follows.

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