How to Talk with Customers 📞
The full playbook of a master interviewer.
A few weeks ago we published an article about typical workflows and practices of product engineers. It was a hit: as of today it is the most popular Refactoring piece of the year.
Still, a lot of people had additional questions and reached out for advice.
The most common question I received was about talking with customers. In fact, in the article we advise engineers to sit in customer calls — but what happens in those calls, exactly?!
How do you talk with customers in a way that you understand their needs and get useful product insights?
I don’t fully trust myself on this, so I reached out to my friend Enzo Avigo, who is the founder and CEO of June. June is a fantastic product (no affiliation!) that plays in an extremely competitive space: analytics. Incumbents are listed on the NASDAQ, raised hundreds of millions, and have thousands of employees, while June is just a small team that raised an equally small seed round.
Yet June found early product market fit in a way that almost feels magical, and Enzo attributes that to one skill: talking well with customers.
So I brought him in to write this piece together 👇
More than 60 years ago, Peter Drucker penned a maxim in Managing for Results that I think about often: “The customer rarely buys what the business thinks it sells him.”
BlackBerry sold phones — but customers bought communication and connection on the go.
Blockbuster sold video rentals — but customers bought convenient home entertainment.
As soon as someone offered better mobile communication and more convenient entertainment, customers switched away en masse.
Deciphering what customers truly want is as much of a struggle for startups as for mega-corps. That’s because, as Drucker said, “There is only one person who really knows: the customer.”
“Only by asking the customer, by watching him, by trying to understand his behavior can one find out who he is, what he does, how he buys, how he uses what he buys, what he expects, what he values, and so on,” he continued. These are perennial, essential data points, things that would help you sell more of what the customer wants to buy. The only way to uncover them is to ask directly.
So here is what we will cover today:
🌐 Why customer interviews matter — and how the internet can both exacerbate and mitigate the disconnect.
📜 Not using slides or scripts — and letting the customer drive the conversation.
🧘 Cultivating your tone — to be calm and comforting.
❤️ Practicing empathy — through techniques like mirroring and labeling.
🔍 Asking laser-focused questions — to get truly actionable insights.
🌊 Using the four forces — that drive behavior change, and resistance.
Let’s dive in!
🌐 Why customer interviews matter
Customer interviews aren’t scalable.
They require effortful listening, questioning, probing, and time. Quite a lot of time.
This was an easier investment to justify, pre-LLMs, when interviews, surveys, and focus groups were the only way to get qualitative data. Today, companies strip-mine interaction data 24/7 and assume that’s enough to skip more opaque, laborious customer interviews.
A founder might see one user sign up from a blog about one topic and another user sign up from a PPC ad on a different topic and think “Aha! This tells me where each came from and what they’re looking for, therefore I know who they are.” These are colossal leaps in logic. Every user contains a multitude and every market is littered with unknown unknowns.
In 2002, Stewart Butterfield and Caterina Fake launched a game that was a financial failure. Customers weren’t spending money on it. They were, however, buying—or at least using—the game’s photo-sharing feature, built as a side project, which included the ability to embed the images on a web page.
“It was a convergence of all of this personal publishing stuff, as well as social networking and the rise of camera phones,” Fake told Jessica Livingston in Founders at Work. While they were busy building something to serve one purpose, their users found a wholly different use for it. The game was shuttered within three years of beginning work, but Flickr–their image-sharing “side project”–was so successful that Yahoo! acquired it for $25 million.
Focusing on what customers were actually using let Butterfield and Fake turn failure into success.
One of the easiest ways to maximize your exposure to customers, to see their wants and needs, hopes and dreams up close, is to involve more people in the process.
Usually, that’s some combination of the founder and customer-facing roles like sales, support, and PMs. I recommend taking it a step further and adding product engineers into the mix as devs who talk directly to users about what’s working and what’s not — but only if they have the necessary skills to get the most out of those conversations.
But what skills?
Talking to customers is a skill with a high ceiling. The best interviewers juggle improvisation, negotiation, reading between the lines, interpreting body language, expressing empathy, and a dozen other soft skills minute by minute.
It’s taken me years of deliberate practice and reflection to get to a point where I feel confident enough to share what has been the most useful during my interviews with users.
So here is my playbook:
1) 📜 Never use slides or scripts
The whole point of talking directly to customers is to shed light on things you don’t know.
Think of it like searching for treasure without a map. The more you let the customer steer the conversation, adapting and course-correcting on the fly, the more valuable your interviews will be.
I appreciate planning ahead and being prepared. But these conversations never go as expected. And even if they did, a list of pre-determined questions would box the customer into your expectations and views of the product and the problems it solves. Asking users to comment on things you’re already meditating on won’t reveal any new or interesting insights.
2) 🧘 Cultivate a calm and comforting tone
The second factor you should work on is your attitude.
We have evolved to recognize and respond to body language. Customers won’t relax and open up to someone who’s visibly tense and audibly stilted, so you’ll have to find ways to shed those habits.
I suggest starting with small, tangible changes. Some of my favorites are: