đź‘‹ Hi, I’m James. Thanks for checking out Building Momentum: a newsletter to help startup founders and marketers accelerate SaaS growth through product marketing.

Positioning-by-assumption doesn’t work. When we want to build momentum, supercharge growth, and increase sales, we need real customer insight to build powerful positioning.

Sure, assumptions – the result of our experiences – are useful, a form of internalized pattern matching. But our biases, limited exposure, and and a lack of subject matter expertise often prevent assumptions from being useful in the real world.

Sometimes we can go further. We can determine inferences; conclusions we draw based on our observations. While these may begin in good faith, these (again) can often be biased and pre-determined in nature. What may start as truthful observations can quickly become layered in opinion. There are always three truths: your truth, their truth, and the real truth.

So we should aim to build evidence. Direct from your customer.

But it’s difficult to know where to start. Who do you ask? What do you ask? How do you use that information?

I’m sharing my customer development cheatsheet – 19 high-value questions designed to extract maximum insight from customer research interviews.

Get started

How to use the template

These questions are designed to get information in five areas.


Purpose: understand the lay of the land, and who has responsibility for the problem area

  • Who handles [problem area] at your business? Why?

  • Tell me about your role at [company]?

  • How much time is spent by your team managing [problem area]?

Problem Discovery

Purpose: Understand your customer’s perception of their challenges, their responsibilities, and what they think it’s important. We want to understand what’s going on for them overall.

  • What’s the hardest part of your day?

  • What activities take up the most time in your day?

  • If you had a magic wand, what could be done to improve your experience with [problem area]?

  • What’s the hardest part about being a [job title]?

  • What are your biggest/most important professional responsibilities and goals?

  • What are your biggest/most important personal responsibilities and goals?

Problem Validation

Purpose: Start to dig into their relationship with your problem area, and understand how they would perceive success and failure

  • Tell me about your relationship with [problem area] – how much time/effort/energy is spent on it, and why?

  • How important is [solving the problem] to you?

  • What would winning at this look like?

  • What are your biggest obstacles to winning?

  • What does losing at this look like?

  • How have you attempted to solve this problem so far?

Product Validation

Purpose: After sharing a brief overview (e.g. a one-page PDF, a website mockup, or a short demo), start to understand how a customer resonates with your current product thinking.

  • What do you think of this product?

  • How would this product solve your problem?

  • How do you imagine this would change your life? / How has our product changed your life?

  • What has changed in the last 5 years that has made this much more valuable?

Using the template

You’ll see the questions down the left column.

The first two columns you’ll see are Assumptions and Confidence.

In Assumptions, take an hour and state your current assumptions for each question – and mark your confidence against it – high, medium, or low. This is a really quick exercise that will tease out how well you know your ICP.

Next, set up interviews with current customers, prospects, and friendly people in the market. I’ve left four columns, but ideally the more customers you speak to, the stronger the patterns (aim for 10-15). Record the calls, make transcripts, and make notes.

Then review all the notes to look for patterns – jot those down in the next column.

Extracting insights

Now we have evidence, so we need to turn it into usable information.

For each persona that’s apparent – key stakeholders in the buying process, discovered throughout your research and experience – review the evidence and refine into these four categories:

  • Key jobs – common activities that your customer does as part of their day-to-day

  • Top 3 gains – their personal, professional, or business goals they want to achieve

  • Top 3 pains – marks of failure and frustrations the customer must avoid,

  • Likely triggers – their motivations to search for a way to solve their problem and switch away from their current solution

Evidence over assumption

Momentum is an outcome of focus and confidence.

To build confidence, you need to really understand what’s going on for your customer – their view of the world, their challenges, and what they care about.

So set up some calls, and get started.

Thanks for reading! Let me know what you thought – find me on Twitter @jdomanpipe.

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12 Replies to “Template: 19 customer questions for powerful positioning”

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