How Retrospective Case Analysis Can Transform the Way You Ask Questions

Over the last few weeks, I've had the privilege of interviewing candidates for key roles. Each conversation is a small window into how people approach problems, make choices, and learn from experience. It's made me think about how similar interviewing is to conducting customer research. Both are about curiosity and discernment: listening for what's said, and what isn't.

It's also reminded me of the power of behavioral questions. Even though some people roll their eyes at the thought of "Tell me about a time when..." questions, I rely on them. They reveal so much more than any "In general, I…" response ever could. What's surprising, though, is how often both sides of the conversation — interviewer and candidate — need nudging to use them well.

It's worth noting that not everyone thrives in this format. For some neurodivergent candidates, the "Tell me about a time…" structure can be harder to navigate. Behavioral science and neurodiversity research both show that some people access memories in fragments, not neat narratives. Under interview pressure, that can make strong candidates sound hesitant or disorganized.

That's where the interviewer's craft matters most. You can help people succeed by clarifying what you're looking for ("Walk me through a specific moment"), giving them a second to think, or prompting with gentle follow-ups like, "What happened next?" or "How did that start?" When you do that, you're not just being accommodating, you're practicing good research technique.

I often find myself saying, "I'm genuinely interested in hearing about a specific time this happenend, not what you'd do in theory." Once people understand what I'm looking for, their stories shift and sometimes, change completely. That's what happens when you move from polished generalities to real, grounded experience. Years ago, when I used to train corporate audiences on design thinking, I saw this pattern over and over. One thing I focused on was teaching people how to ask better questions: the kind that uncover what people really do, not what they think they do.

My favorite exercise went like this: I'd pair people up and say, "Imagine your job is to design a website that helps people plan vacations. Your goal is to learn how your partner does this."

I'd set them loose for a few minutes and wander around the room, listening. And not once, in any session I ever led, did a pair start in an ideal way. Without fail, every group opened with some version of, "So, how do you plan vacations?"

From an interviewer's point of view, that's a dead end. People can’t accurately describe what they "usually" do; they give you an idealized version, or what they wish they did, or what they think you want to hear. Behavioral science backs this up: humans are notoriously poor at recalling habits or predicting actions in the abstract. We tell tidy stories, not real ones.

After a few minutes, I'd pause the exercise. Everyone would smile, convinced they'd done a great job. Then I'd introduce a powerful technique I learned early in my career called Retrospective Case Analysis. It's simple and it changes everything. (No really. Try it.) Instead of asking how someone typically does something, you ask them to walk you through the last time they did it.

"Tell me about the last time you took a vacation. How did you get started planning?"

The difference is immediate. Conversations become more concrete. You hear specifics: "I was traveling with my kids, so I wanted to find a hotel with a pool. Do you know how hard it is to find pool pictures on hotel websites?" or "Honestly, my spouse plans everything." Suddenly, you're hearing reality, even the occasional surprise that you were talking to the wrong person altogether!

Once you've unpacked a single instance, you can step back and ask, "Was that typical for you?" If yes, great. If not, ask for another story. It's a simple, structured way to move from anecdote to insight.

Over the years, I've found this approach works far beyond user research:

When interviewing candidates:

• Tell me about a time you had to convince your team to go in a different direction.

• Tell me about a time you created something truly innovative.

When talking with customers:

• What were you trying to do the last time you used this product?

• Tell me about what was happening right before you ran into that error.

When connecting with colleagues:

• When was the last time you felt genuinely inspired at work?

• Tell me about the best concert you ever went to.

Each of these questions anchors people in a real experience, not an idealized one. That's when you get to the actual meat of a conversation.

So, the next time you want to understand someone, skip the "In general, I…" and ask about the last time.

Now you go: Tell me about a time you read a blog post that really stuck with you. 😉