Willingness to Pay Interview Questions: Free Script

The short answer

Good willingness to pay interview questions start with the customer's problem and its cost, then explore what they use and pay today, how they buy, and what outcome matters. Only then ask about price, for example: 'What would have to be true for this to be worth $X a month to you?' Ask open questions, avoid pitching, and run at least ten interviews per segment.

Key takeaways

Spend the first two-thirds of the interview on the problem, its cost and the alternatives. Price comes last.
Ask about past behavior ('What did you pay for that?'), not hypotheticals ('Would you pay...?').
The single best price question: 'What would have to be true for this to be worth $X a month to you?'
Don't pitch. Your job is to listen, then stay quiet.
Run ten or more interviews per segment and compare notes on one sheet.

In my corporate sales career, I was always taught to "build the pain." I distinctly remember being shown a see-saw.

On one side: pain. On the other: buyer resistance.

The stronger the pain, the lower the resistance. (Plenty of what I learned in corporate life I've happily forgotten. Not that.)

It's also the secret to a willingness-to-pay interview. Most founders sit down with a customer, describe their product, then ask, "So, what would you pay for this?"

The customer, being polite and a little cautious, names a low number. The founder writes it down. Everyone loses.

The better way is to spend most of the interview on the pain: what the problem is, what it costs, what they've tried, and what they pay now. When you finally get to price, you're anchored on their problem, not your product.

Here's the script I'd use. It works best once you've confirmed people have the problem at all; if you're not sure, start with product/market fit. For how it fits with surveys and price tests, read willingness to pay: how to measure it.

Before the interview

Who: people who have the problem and are already spending money or time on it. Include a few lost deals.
How many: at least ten per segment. By the tenth, you'll know whether you keep hearing the same story.
How long: 30 minutes. Video or phone is fine.
Who runs it: ideally not the founder. Customers are more honest with someone who didn't build the product.

The recruitment email

Subject: 30 minutes to help shape [Offer / product]?

Hi [First name],

I'm working on [one sentence on the problem you solve, in the customer's words], and I'm talking to [business owners / practice managers / whoever] who deal with it every week.

Would you have 30 minutes for a call? I won't be selling anything. I'd just like to understand how you handle [the problem] today.

[Book a time]

[As a thank-you: a A$[X] gift card / a donation to a charity of your choice.]

[Your name]

The script (30 minutes)

Part 1: Opening (2 minutes)

"Thanks for making time. I'm trying to understand how [people like you] handle [the problem], so there are no right or wrong answers, and I'm not here to sell anything. Is it okay if I record this for my notes? I'll switch it off anytime."

Part 2: Their world (5 minutes)

"Tell me a bit about your role and what a typical week looks like."
"Where does [the problem] fit into that week?"
"When did it last come up? Walk me through what happened."

Part 3: The pain and its cost (8 minutes)

"What's the hardest part of dealing with [the problem]?"
"How much time does it take you, or your team, each week or month?"
"What does it cost when it goes wrong? Money, customers, stress, anything."
"If you could wave a wand and fix one part of it, what would it be?"
"How important is fixing this compared with everything else on your plate this year?"

Part 4: What they do and pay today (6 minutes)

"What do you use to handle it today?"
"What have you tried before? Why did you stop?"
"What do you pay for that today, roughly? Per month or per year?"
"What do you like about it? What drives you mad?"
"If [current solution] doubled in price tomorrow, what would you do?"

Part 5: How they buy (3 minutes)

"If you found something better, who else would be involved in deciding?"
"Is there a budget for this, and who owns it?"
"How do you usually prefer to pay for tools or services like this: monthly, yearly, per use?"
"What would make you nervous about switching?"

Part 6: Value and price (5 minutes)

Now, and only now, describe the offer in two or three sentences. Then:

"What, if anything, would this change for you?"
"What would be the most valuable part of it?"
"What would you expect something like this to cost?"
"At what price would it feel like a bargain? And at what price would it be too expensive to consider?" (Two of the four Van Westendorp questions, asked in conversation.)
"What would have to be true for this to be worth A$[X] a month to you?" Then stay quiet. Count to five in your head if you have to.
"Which parts would you happily go without for a lower price?"

Part 7: Close (1 minute)

"Is there anything I should have asked but didn't?"
"Would you be open to seeing an early version, or being one of the first customers?"

"Thank you. This has been really helpful."

Find the pain points in your interview notes

Paste your interview transcripts into the free Customer Pain-Point Analyser and get the recurring problems and jobs-to-be-done.

Open the free tool

Rules for the interviewer

Don't pitch. The moment you start selling, they start being polite.
Ask about the past, not the future. "What did you pay?" is evidence. "Would you pay?" is a guess.
Follow the emotion. When they sigh, laugh or say "honestly...", ask "Tell me more about that."
Write down their words, not your summary. "I lose every Sunday to invoicing" beats "time-consuming admin."
Never argue with a number. Just ask why.

The notes sheet

Fill in one row per interview straight after the call.

#	Segment	Problem in their words	Monthly cost of problem	Current solution and spend	Expected price	"Bargain" / "too expensive"	Must-have features	Buying role	Quote
1	[Segment]	"[Quote]"	A$[X] or [hours]	[Tool], A$[X]	A$[X]	A$[X] / A$[X]	[List]	[Decides / influences]	"[Quote]"

After ten rows, look for three things:

The cost of the problem. If it costs them A$500 a month and you're asking A$49, you're likely underpriced.
The anchor. What they pay today for the alternative is the number your price will be compared with.
The value metric. What do they naturally count: jobs, staff, clients, hours? That's often what you should charge by. See how to choose a value metric.

When the interviews aren't enough

Ten conversations tell you why and give you a rough range. They don't tell you how many people will buy at each price. For that, follow up with the willingness-to-pay survey, then a live test on new customers. And if you sell high-value services to a few clients, use the interviews to set a value-based price and test it in your next proposals.

What to do next

Send the recruitment email to 20 people to get 10 calls.
Run the script, and fill in the notes sheet after every call.
Paste your transcripts or notes into the Customer Pain-Point Analyser to spot repeated pain points.
Turn the numbers into a range and test it.

Customer Pain-Point AnalyserPaste reviews, emails or tickets and get pain points and jobs-to-be-done.Open the free tool →

Frequently asked questions

Should I record willingness-to-pay interviews?

Yes, if the person agrees. Ask at the start, explain it's only for your notes, and offer to switch it off. A recording lets you focus on listening instead of typing, and it captures the exact words people use about their problem, which are gold for your sales page. In Australia, check the rules on recording conversations in your state before you start.

Should I interview existing customers or prospects?

Both, but separately. Existing customers tell you why they bought and what they value now, but they've already accepted your price. Prospects and lost deals show you where price and value break down. For a new product, focus on people who have the problem and are already spending money or time trying to solve it.

Can someone else run the interviews for me?

Yes, and it often helps, because customers are more candid when they're not talking to the founder. A colleague, a researcher or a customer success person can run the script. Brief them on the goal, make sure they don't pitch, and ask them to capture quotes word for word. The founder should still read every set of notes.

How do I handle someone who asks 'Well, what does it cost?'

Turn it gently back: 'We haven't set it yet, which is why I'm talking to you. What would you expect something like this to cost?' If they push, give a range near the end, after you've heard about their problem. Answering early anchors the rest of the conversation to your number instead of their value.

What if everyone says the price should be lower?

Expect some of that. People rarely volunteer to pay more. Look past the stated number at the evidence: how much the problem costs them, what they pay for alternatives, and how urgently they want it fixed. If the problem is expensive and urgent and people still balk, your offer or message may be the issue, not the price.

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Robert Coorey, MBA

Robert is the author of The Subscription Playbook and Feed a Starving Crowd and a Director at BPAG Accountants in Sydney. More about Robert.

Sources

Facts and prices checked 27 October 2026. Spotted something out of date? Tell us.

The Willingness-to-Pay Interview Script: 25 Questions That Reveal What Customers Will Pay