Conducting User Interviews

The Power of Listening

🔄 Quick Recall: In the previous lesson, we designed surveys that yield measurable data. Surveys tell you what and how many. Interviews reveal the why—the motivations, frustrations, and stories behind the numbers.

A single great interview can change your entire understanding of a customer segment. It’s the difference between knowing “30% of users churn in month three” and understanding “users churn because the onboarding doesn’t show them the feature that would make them stay.”

By the end of this lesson, you’ll be able to:

Create an interview guide that uncovers genuine insights
Ask follow-up questions that dig past surface answers
Use AI to prepare for interviews and analyze transcripts

The Interview Mindset

Before we discuss technique, let’s establish the right mindset. Interviews aren’t:

Surveys read aloud. If you’re just reading questions and writing answers, send a survey instead.

Opportunities to pitch. The moment you start selling or defending your product, you’ve lost the interviewee’s honest feedback.

Validation exercises. If you’re only looking for people to confirm your beliefs, you’re wasting everyone’s time.

Great interviews are guided conversations where you genuinely want to understand someone else’s world. Your job is to be curious, not to be right.

✅ Quick Check: Have you ever been in a “feedback session” where it was clear the person asking wasn’t actually interested in your honest opinion? How did that feel?

Writing an Interview Guide

An interview guide is your conversation roadmap. It ensures you cover important topics while staying flexible enough to follow interesting tangents.

The Structure

1. Warm-up (2-3 minutes) Build rapport and set expectations.

“Thanks for joining me today. I’m trying to understand how people [relevant activity]. There are no right or wrong answers—I’m genuinely interested in your experience. This should take about 30 minutes.”

2. Context questions (5 minutes) Understand their background and relationship with your topic.

“Tell me about your role and what a typical day looks like.” “How long have you been using [product/doing activity]?”

3. Core questions (15-20 minutes) Your main research questions, phrased as open-ended prompts.

“Walk me through the last time you [relevant behavior].” “Tell me about a time when [situation] was particularly frustrating.” “What was going through your mind when you decided to [action]?”

4. Dream questions (5 minutes) Explore unmet needs and wishes.

“If you could wave a magic wand and change one thing about [topic], what would it be?” “What would the ideal version of [product/experience] look like?”

5. Wrap-up (2 minutes)

“Is there anything important we haven’t discussed that you’d like to share?” “Can you recommend anyone else I should talk to about this?”

How AI Helps

“I’m interviewing customers who recently cancelled their subscription to our project management tool. Create a 30-minute interview guide with: warm-up, 3 context questions, 5 core questions about their cancellation decision, 2 dream questions, and a wrap-up. Make all questions open-ended and non-leading.”

The Art of Follow-Up Questions

The best insights come not from your scripted questions but from what you ask next. Master these follow-up techniques:

Technique 1: The Five Whys

Keep asking “why” (or “tell me more about that”) to drill beneath surface answers.

Participant: “I stopped using the app because it was too complicated.” You: “Can you tell me more about what felt complicated?” Participant: “There were too many features I didn’t need.” You: “Why was that a problem for you?” Participant: “I couldn’t find the one thing I actually needed—the reporting feature.” You: “Why was reporting so important to you?” Participant: “My boss asks for weekly reports, and I was hoping your tool would automate that.”

Now you know the real issue: discoverability of a specific feature, not overall complexity.

Technique 2: Specific Examples

When someone makes a general statement, ask for a specific instance.

Participant: “The customer support is bad.” You: “Can you tell me about the last time you contacted support? Walk me through what happened.”

Specifics reveal much more than generalizations.

Technique 3: Comfortable Silence

After someone answers, wait 3-5 seconds before your next question. People often add their most insightful thoughts in the silence, feeling compelled to elaborate.

Interview Don’ts

Don’t	Why	Instead
“Don’t you think X is better?”	Leading—implies the “right” answer	“How do you compare X and Y?”
“Would you pay $20/month for this?”	Hypothetical—people can’t predict future behavior	“Tell me about the last time you paid for a tool like this”
“That’s a great point!”	Positive reinforcement biases future answers	“Interesting—tell me more about that”
Interrupt or finish sentences	Cuts off natural responses	Wait for full answers, then follow up
Take notes on a laptop (typing)	Can feel like a deposition	Record (with permission) or use a note-taker

Analyzing Interview Data

After conducting 5-15 interviews, you’ll have hours of conversation. Here’s how to turn that into actionable insights:

Step 1: Transcribe

Use recording + AI transcription. Don’t rely on memory.

Step 2: Code Themes

Read through transcripts and tag recurring themes: frustration with pricing, confusion during onboarding, delight with a specific feature.

Step 3: Synthesize with AI

“Here are transcripts from 8 customer interviews about why they cancelled: [paste excerpts or summaries]. Identify the top 5 recurring themes, rank them by frequency, and for each theme provide a representative quote and a recommended business action.”

Step 4: Create an Insights Report

“Based on these interview themes: [paste themes], create a one-page insights report with: key findings (3-5 bullets), supporting evidence (quotes), and recommended next steps (actions for the team).”

Try It Yourself

Prepare for a customer interview with AI:

“I want to interview customers of my [product/service type] to understand [research question]. Create a complete 30-minute interview guide and prepare me with: likely responses to expect, follow-up questions for each, and red flags that I might be leading the witness.”

Key Takeaways

Interviews reveal the “why” behind behavior—motivations, frustrations, and unmet needs
An interview guide provides structure with flexibility—cover key topics while following interesting tangents
Follow-up questions (five whys, specific examples, silence) uncover the deepest insights
Avoid leading questions, hypotheticals, and positive reinforcement that bias responses
AI helps prepare interview guides and analyze transcripts for themes and patterns

Up Next

In Lesson 5: Building Customer Personas, we’ll take the raw data from your surveys and interviews and transform it into vivid, actionable customer profiles that make decision-making easier for everyone on your team.