When Did You Last Talk to Your Customers?

I'll ask you a question, and I want you to be honest: when was the last time you talked to a customer?

Not a sales call where you were listening for deal signals. Not a support escalation. Not an NPS survey where you read comments.

An actual conversation. You and a customer. Talking about their work, their problems, and what's getting in their way.

If the answer is "more than two weeks ago," you're making product decisions based on assumptions. And assumptions are the most expensive input in product development.

Why Product Teams Stop Talking to Customers

It's rarely intentional. Nobody decides to stop. It just happens:

• Sprints fill up. There's always more to build. Customer conversations feel like a luxury when you're behind on commitments. So they get pushed. Then pushed again. Then dropped.
• Teams delegate it. "That's what UX research is for." "Sales talks to customers all the time." True — and none of them replace product having direct contact with real users.
• It feels unscalable. "I can't talk to all our customers." True. But five conversations per month will teach you more than any dashboard, survey, or competitive analysis combined.

The result is teams building products based on internal opinions about external realities. That's customer abdication in reverse — instead of doing whatever the customer says, you're doing whatever you think the customer wants. Both are dangerous.

What Happens When Teams Stop

Three things, in this order:

• Features drift from reality. The team builds what makes sense internally. Features work in demos and QA. But they don't map to how customers actually use the product. The gap widens with every sprint.
• The loudest voices win. Without customer evidence, internal opinions become the decision-making currency. The HiPPO (highest-paid person's opinion) drives the roadmap. The most persistent stakeholder gets their feature built. The team loses the ability to say "actually, customers need something different" because they can't prove it.
• Customer empathy atrophies. The hardest to see and most damaging. Customers become personas, data points, segments. They become abstractions. And you can't build great products for abstractions.

The Five-Conversations-a-Month Practice

You don't need a formal research program. You need a habit.

Five customer conversations per month. Not surveys. Not focus groups. Conversations. One-on-ones. 30 minutes each. Three properties:

• Unstructured enough to discover. Don't bring a 20-question script. Bring one open-ended question: "What's the hardest part of your work right now?" Then listen. The customer will tell you things no survey would capture.
• Structured enough to synthesize. After each conversation, write down three things: What surprised you? What confirmed what you already believed? What should you explore further?
• Regular enough to notice patterns. One conversation is an anecdote. Five is the beginning of a signal. Twenty is a pattern you can act on. The discipline is in the regularity, not the volume.

Five conversations a month is two hours total. That's less than most teams spend in a single roadmap planning meeting. The ROI is incomparable.

How to Make Conversations Strategic

The risk is that conversations become reactive — you hear problems and start building solutions. That's customer abdication. The fix is connecting conversations to strategy:

• Know your Eigenquestion before you call. You're not trying to learn everything. You're trying to answer a specific strategic question. Your five conversations should all circle the same question from different angles.
• Triangulate, don't react. A single customer saying "I need X" isn't a signal. Three customers describing the same underlying problem is. Look for the problem behind the request.
• Share raw notes. Don't filter conversations through a report. Share actual quotes, actual stories, actual frustrations. Let your team hear customer voices, not your interpretation.

Start This Week

Open your calendar. Block 30 minutes. Send one email: "I'd love to spend 30 minutes understanding what's working for you and what's not. No sales pitch — just me trying to understand your world better."

Most customers say yes. Most are flattered someone from product wants to listen. And most will tell you something that changes how you think about your next sprint.

If you're not doing this, your strategy is built on assumptions instead of evidence. And assumptions are the most expensive foundation you can build on.

Need help turning customer conversations into strategy?

In my Product Story workshop, B2B SaaS product teams build a narrative framework that connects customer insights to strategic decisions. We clarify what Product does, how to communicate it, and how to use customer evidence to make better decisions faster.

Book a Clarity Call — 30 minutes, no pitch. Just clarity on how to connect customer insights to your product strategy.

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