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The Two Magic Questions of Customer Interviewing

The Two Magic Questions of Customer Interviewing

August 08, 2025

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At a Glance

Effective customer interviewing requires specific questions focused on recent events
Follow-up questions put to customers without judgment will help you understand exactly what pain points they’re facing and how best to solve problems
Specific recent events broken down step-by-step will reveal insights, contexts, and workarounds that broad questioning misses
Use responses to customer interviews to identify patterns and create actionable next steps

Hey folks,

We've all been there—sitting across from a customer, armed with a list of questions crafted just right, to unlock all the insights we need. Yet, midway through the conversation, you start to feel that the responses you’re getting don’t actually tell you much.

"Users want better search functionality." "The dashboard needs more customization options." "Can you add more integrations? Sound familiar? These responses aren't wrong, but they are surface-level. They don’t offer the details companies need to change course, hit OKRs, and see real results.

After years of watching teams build features based on empty and unhelpful feedback, often yielding adoption rates that disappoint and stagnating customer satisfaction, I realized most of us are asking the wrong question. Or, even worse, we’re asking questions that are almost effective…but because of the way they’re presented, we’re setting the respondent up to give superficial answers.

This week's deep-dive tackles one of the most fundamental skills in our toolkit: customer interviewing. Instead of giving you a list of "good interview questions," I want to share two question patterns that consistently reveal the difference between what customers think they want and what they actually need.

Using these methods, you can uncover the real problems hiding beneath common customer requests. Communication is key—and once you start using these question patterns, you'll wonder how you ever built products without them.

Ready to transform how you listen to your customers?

Jeff

PS - We’ve got a lot of great classes coming up at Sense & Respond Learning. Check out the list below.

The Two Magic Questions of Customer Interviewing

Customer interviews can offer a treasure map for product development teams —but most customer interviews fail before they even begin. Generic questions like “What features would you like to see?” almost guarantee surface-level feedback…all while the real needs and problems of your customers remain buried.

After conducting hundreds of customer interviews, I've discovered two simple question patterns that can transform your research. These tools help you dig beneath customer feedback to find real problems worth solving.

The First Magic Question: "Tell me about the last time..."

Instead of asking customers what they typically want or generally think, ask them to walk you through a specific recent experience.

Bad question: "How do you normally manage your team's workload?"

Magic question: "Tell me about the last time you had to reassign work because someone on your team was overwhelmed."

The difference between the responses the first question prompts, as compared to the second, is staggering. The first question invites generalization and idealization. The second allows customers to recall an actual event with all its messy—and revealing—details.

When describing a specific event, customers can’t help but include context, emotions, and workarounds. Where a hypothetical question glosses over the different steps of a process, a “tell me about the last time…” lets you know exactly which tools customers used, what constraints they faced, and how they managed to find a solution.

How to apply it: Start with your assumption about customer behavior, then flip it into a "last time" question:

Assumption: Customers struggle with data analysis
Magic question: "Tell me about the last time you needed to create a report, but couldn't find the data you needed."

The Second Magic Question: "What did you do next?"

Once a customer starts talking about a specific incident, this follow-up question reveals the chain of actions and workarounds customers use when solutions don't exist or don't work.

Let's see it in action:

You: "Tell me about the last time you had to find information for a client presentation."

Customer: "Last Tuesday. I needed competitor pricing data. I started in our CRM, but the data was six months old."

You: "What did you do next?"

Customer: "I called Sarah in sales—she usually has all the intel. But that day, she was stuck in meetings for hours and hours.”

You: "What did you do next?"

Customer: "I spent two hours Googling competitors, copying prices into a spreadsheet. Then I had to verify everything with my manager."

You: "What did you do next?"

Customer: "I missed the first draft deadline, so I had to email the client asking for an extension. Pretty embarrassing."

Each "what did you do next?" reveals another layer: the original solution failed, the backup plan failed, the workaround was time-consuming, quality concerns emerged, and real consequences occurred. This sequence reveals a systemic problem that goes far beyond "we need better competitor data."

A Complete Example

Here's how both questions work together in an expense management interview:

Interviewer: "Tell me about the last time you had to submit an expense report."

Customer: "Last week. I got back from a work trip to Denver with a messy collection of receipts—some in my bag, some on my phone."