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Musings and writings from How This Works co about product, strategy, design, workshop facilitation, team dynamics, and technology

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Customer interviews 101

Interviewing customers: the unsung superpower that your product company needs right now

6 min readMay 6, 2025

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First in a series of four articles

When was the last time you talked to a customer who wasn’t already complaining? If you’re struggling to remember, you’re not alone — and it explains part of why the decisions around your product or its feature set increasingly feels like guesswork or whack-a-mole.

(Nearly) every time I talk to a new or potential client, I hear the same thing: “We know exactly what our customers want.” And I’ve also heard the notes of doubt creep in or looks of concealed surprise when we share what we learned in our customer interviews, but rarely have I heard upfront, “We have no idea what our customers are looking for.” And yet, I can count on one hand the teams/companies who’ve actually talked to one real customer — and if they have, it was weeks or months ago. Too many times, it’s never.

I’ve spent over 12 years working with teams of all sizes, from scrappy startups to established businesses, and I’ve noticed a pattern: the further teams get from real customer conversations, and more than that the less frequently those conversations happen, the more their decisions float afield. This drift doesn’t happen overnight — it’s the slow slide from understanding that occurs when teams rely on proxies for customer insights (team opinions, news headlines, competitor features, support ticket metrics, etc.) rather than direct dialogue.

That’s why customer interviews are so very necessary — to understand the customer better than our competitors do, to know and feel the customer’s pain points, to see how our product impacts (or has the potential to impact) a customer’s life. That deep, nuanced customer empathy is how you create products customers are excited to use, keep using, and tell their friends and family about.

A comic showing three men in an office setting. One man in a red shirt confidently declares ‘If I were our teenage girl target, I would LOVE our new product.’ Another man asks ‘Have you actually talked to any to make sure?’ A third man responds ‘What? And leave this room?’ This illustrates   how product teams make assumptions about their target audience without actually speaking to them. Drawn by Tom Fishburne, this comic is featured in Giff Constable’s ‘Talking to Humans.’
Product team members often confidently assume they know what their target audience wants, teenage girl or otherwise, while avoiding actually talking to them. An example of why getting outside the building matters more than conference room certainty. From Giff Constable’s ‘Talking to Humans’ (www.talkingtohumans.com).

As

, creator of the customer development methodology, famously says, “There are no facts inside your building, so get outside.” This mantra has become fundamental to entrepreneurship today for good reason. Blank’s methodology, developed in the mid 1990s, is built on the insight that early ventures have untested hypotheses about their business model, and the only way to validate them is through a formal process of testing business hypotheses “outside the building.”

For best results, product teams should follow this same principle.

The gap between what we build and what people need

Let’s be honest about what happens when we stop talking to customers regularly:

  • Product teams, especially established ones, become echo chambers, amplifying internal assumptions rather than external realities
  • Features get built based on hypotheses, biases, and ideas that are formed in conference rooms, rather than customer needs, desires, or painpoints
  • Resources get poured into solutions nobody asked for or wants, a la ’s feature factory paradigm
  • Worst of all, teams lose grasp of the empathy that initially connected us to the problems we aimed to solve in the first place

Customer interviews are the catalyst for smart business decisions. You can use them to solve a specific usability problem, get a better idea of who your customer base is, or gauge interest in a new product.

Though it may seem daunting to get started with customer interviews, once you’ve got a formula for doing them efficiently and effectively, you can rinse and repeat again and again. This kind of continuous customer interview process is key if you want to iterate rapidly and stay ahead of the competition, achieving product market fit.

I once worked with a healthcare technology company that specialized in workforce management who’d come to us to update the look ’n’ feel of their flagship application. It looked like something out of a windows installation installed via CD-ROM. But their main problem was much more sinister: the onboarding team spent over two (2) hours with every new client. And then an hour or so every six months or so, following whatever application updates they’d implemented.

Their core problem wasn’t just an outdated interface layer, it was the features piled high on top of an app that wasn’t informed by user research or customer interviews. The group had built a product that made perfect sense internally but was bewildering to the people who needed to use it.

A project summary slide titled ‘What was done’ showing accomplishments from an 8-week engagement with a healthcare workforce management company. The slide is organized into three columns: Experience design (green), business analysis (green), and technical architecture (green).
A slide from one of the reporting decks for the healthcare workforce mgmt company, outlining the work that’d been done in eight (8) weeks by our team in the areas of experience design, business analysis, and technical architecture

That experience taught me something I keep coming back to: the most elegant solution to the wrong problem is still wrong.

Beyond “we already know what customers want”

There’s a peculiar confidence that develops in product teams over time — a belief that we’ve gathered enough insights, that we understand the market, that our experience gives us a special ability to understand what customers need without asking them.

I call this “proximity blindness.” Product team members can spend too much time focused on the trees (read: the details of making the solution) and not enough on the forest (read: our customers’ context). And you need both.

captures this perfectly in his book, “The Mom Test,” when he writes that the purpose of customer conversations isn’t to ask people what they want — it’s to learn how they work and what they struggle with. The distinction might seem subtle, but it’s key.

In the next three parts, I’ll guide you through the entire journey of making customer interviews a core part of your product practice:

  • In part 2, I’ll share a lightweight framework that actually works in the real world — one that can be implemented by teams of any size without massive resources or specialized researchers. You’ll learn who should be involved in customer conversations, how frequent they should be, what questions actually generate useful insights, and how to capture what you learn without drowning in data.
  • In part 3, I’ll take you inside a Fortune 100 healthcare financing company that discovered their entire understanding of customer barriers was wrong. You’ll see how just 10 customer conversations over two weeks unlocked more than $2 million in retained revenue — a concrete ROI that makes the business case for this practice impossible to ignore.
  • And in part 4, I’ll break down the simple customer interview approach we used at Sesame to launch a new product in just three months with minimal resources. You’ll get a practical blueprint for implementing what I call the “minimum effective dose” of customer research — just five conversations that can transform your product direction.

Customer interviews aren’t a luxury or a nice-to-have research activity. They’re the fundamental practice that separates companies that build what people want from those that build what they think people want.

Thanks for reading. My name is Skipper Chong Warson and I run a product strategy and design services practice called How This Works co. What challenges have you faced in recognizing when your team has drifted away from customer reality? Are you struggling with this disconnect? Let’s chat about it. Book a free 25-minute intro call to discuss how customer interviews might transform your product decisions and path.

Citations:

  • Giff Constable — “Talking to Humans: Success Starts with Understanding Your Customers” (2014), co-authored with Frank Rimalovski, https://www.talkingtohumans.com/
  • Steve Blank — “The Four Steps to the Epiphany” (2005)
  • Rob Fitzpatrick — “The Mom Test: How to Talk to Customers and Learn If Your Business is a Good Idea When Everyone is Lying to You” (2013)
  • Melissa Perri — “Escaping the Build Trap: How Effective Product Management Creates Real Value” (2018)
  • Teresa Torres — “Continuous Discovery Habits” (2021)
  • Erika Hall — “Just Enough Research” (newest edition, 2024), https://www.mulebooks.com/just-enough-research

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How This Works co
How This Works co

Published in How This Works co

Musings and writings from How This Works co about product, strategy, design, workshop facilitation, team dynamics, and technology

Skipper Chong Warson
Skipper Chong Warson

Written by Skipper Chong Warson

Product strategist, designer, and facilitator at How This Works co, host of the How This Works show. Fjord, thoughtbot, SoftServe, and Shep (acquired) alumni.

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