"Can you jump on a call to get customer feedback?"
You schedule 10 customer interviews. You ask: "What do you like about our product? What would you improve?"
Customers say: "It's great! Maybe add [random feature]."
You thank them, hang up, and realize you learned nothing you didn't already know.
Most customer interviews fail because they ask direct questions that generate superficial answers. Customers tell you what they think you want to hear, not the truth.
Good customer interviews don't ask "what do you think?" They uncover how customers actually make decisions, what problems they're really trying to solve, and why they chose you over alternatives.
After conducting 200+ customer interviews across product research, win/loss analysis, and case study development, here's the framework that actually yields insights.
The Five Types of Customer Interviews
Different goals require different interview structures:
Type 1: Jobs-to-be-Done Interviews
Purpose: Understand what customers are trying to accomplish and why
When to use: New product development, repositioning, category creation
Output: Deep understanding of customer motivations and decision criteria
Best for: Product strategy and positioning
Type 2: Win/Loss Interviews
Purpose: Understand why customers chose you (or chose competitors)
When to use: After deal closes or is lost (within 2 weeks)
Output: Competitive insights, objection patterns, sales process gaps
Best for: Sales enablement and competitive positioning
Type 3: Product Feedback Interviews
Purpose: Gather specific feature requests and usability feedback
When to use: Active product development cycle
Output: Feature priorities and UX improvements
Best for: Product roadmap prioritization
Type 4: Case Study Interviews
Purpose: Document customer success stories with metrics
When to use: Customer has achieved significant results (3+ months post-launch)
Output: Customer testimonials and case studies for sales/marketing
Best for: Sales enablement and demand generation
Type 5: Churn Interviews
Purpose: Understand why customers left
When to use: Immediately after cancellation
Output: Product gaps, onboarding failures, competitive threats
Best for: Retention strategy and product improvements
This guide focuses on Types 1 and 2 (JTBD and Win/Loss) since they inform strategic positioning and GTM.
The JTBD Interview Framework
Jobs-to-be-Done interviews uncover the real problem customers are solving.
The Interview Structure (60 minutes)
Part 1: The Timeline (20 min)
Don't ask "what problems were you trying to solve?" Ask them to walk through their timeline:
Questions:
- "Walk me through what was happening when you first started looking for a solution like ours."
- "What was the first moment you realized you had this problem?"
- "What changed that made you start looking for a solution now vs. 6 months ago?"
- "Who else was involved in recognizing this was a problem worth solving?"
What you're listening for:
- Triggering event (what created urgency)
- Pain intensity (how big was the problem)
- Stakeholders involved (who cared about solving this)
Part 2: The Alternatives Considered (20 min)
Don't ask "why did you choose us?" Ask about their evaluation process:
Questions:
- "Before finding us, what were you doing to solve this problem?"
- "What other solutions did you evaluate?"
- "Walk me through how you evaluated different options. What did you compare?"
- "What almost made you choose [alternative]?"
- "What concerns did you have about choosing us?"
What you're listening for:
- Real alternatives (including "do nothing" and DIY)
- Decision criteria (what actually mattered)
- Concerns and objections (what almost stopped them)
Part 3: The Decision (15 min)
Don't ask "what do you like about us?" Ask about the moment they decided:
Questions:
- "What was the moment you decided 'this is the one'?"
- "What specific thing convinced you we were the right choice?"
- "Who had to sign off on this decision? What convinced them?"
- "Looking back, what would have made the decision easier?"
What you're listening for:
- Differentiation (what actually mattered, not what you think matters)
- Buying committee dynamics (who had veto power)
- Decision friction (what slowed them down)
Part 4: The Outcome (5 min)
Questions:
- "What's changed since you started using our product?"
- "How would you describe what we do to a colleague?"
- "If we disappeared tomorrow, what would you miss most?"
What you're listening for:
- Actual value delivered (vs. promised value)
- How they talk about you (real messaging vs. your messaging)
The Win/Loss Interview Framework
Win/loss interviews are different: you're uncovering competitive dynamics and sales process effectiveness.
For WINS: Why they chose you
Interview within 1 week of close (while decision is fresh)
Part 1: The Evaluation (15 min)
Questions:
- "Walk me through your evaluation process from start to finish."
- "Who were the other vendors you seriously considered?"
- "What were your top 3 decision criteria?"
- "At what point did we become the frontrunner?"
What you're listening for:
- Who you beat and why
- What criteria mattered most
- Sales process effectiveness
Part 2: The Differentiation (15 min)
Questions:
- "What made us different from [Competitor X]?"
- "Was there anything about [Competitor] that almost made you choose them instead?"
- "What specific capabilities or features were must-haves?"
- "What concerns did you have about us? How did we address them?"
What you're listening for:
- Real differentiation (not what you think it is)
- Competitor strengths you need to address
- Objections and how sales handled them
Part 3: The Sales Experience (15 min)
Questions:
- "How was the experience working with our sales team?"
- "Was there anything in the sales process that frustrated you or slowed you down?"
- "What could we have done to make the decision easier?"
What you're listening for:
- Sales process friction
- Missing content or tools
- Demo effectiveness
Part 4: The Value Proposition (15 min)
Questions:
- "How would you describe what we do to a colleague?"
- "What outcome are you expecting from using our product?"
- "What would make you consider this a successful purchase 6 months from now?"
What you're listening for:
- How they talk about you (test your messaging)
- Expected outcomes (set success criteria)
- ROI expectations
For LOSSES: Why they chose someone else
Interview within 2 weeks of loss (while you're still top of mind)
This is harder because they chose someone else. Be gracious and genuinely curious.
Part 1: The Decision (10 min)
Questions:
- "Thanks for taking the time. We're always trying to improve. Can you share which direction you decided to go?"
- "What were the main factors in that decision?"
- "Was there a specific moment when [winner] became the frontrunner?"
What you're listening for:
- Who won and why
- Key decision factors
Part 2: Where You Fell Short (20 min)
Questions:
- "What did [winner] have that we were missing?"
- "Was there a specific feature or capability that was a dealbreaker?"
- "Were there any concerns about our product or company that we didn't address well enough?"
- "How did you feel about our sales process and team?"
What you're listening for:
- Product gaps (real or perceived)
- Positioning weaknesses
- Sales execution issues
Part 3: What Could Have Changed Their Mind (10 min)
Questions:
- "If you could change one thing about our product or approach, what would have made the difference?"
- "Was there anything we could have done in the sales process to change the outcome?"
- "Is there a scenario where you'd reconsider us in the future?"
What you're listening for:
- Real gaps vs. perception gaps
- Sales enablement opportunities
- Future re-engagement potential
The Interview Techniques That Work
Technique 1: Ask "Why" 3 Times
Customer says: "We chose you because you're more user-friendly."
Don't stop there. Dig deeper:
You: "What do you mean by 'user-friendly'?"
Customer: "Our team could figure it out without training."
You: "Why was that important?"
Customer: "Our last tool required a 2-month implementation. We don't have time for that."
You: "Why is time such a constraint right now?"
Customer: "We have 6 product launches in Q3. We needed something that works immediately."
Now you have the real insight: It's not "user-friendly" in general—it's "fast time-to-value for teams with launch volume."
Technique 2: Ask for Stories, Not Opinions
Bad question: "What do you think about our onboarding process?"
Good question: "Walk me through the first time you logged in. What happened?"
Why it works: Stories reveal truth. Opinions reveal what people think you want to hear.
Technique 3: Ask About Specific Moments
Bad question: "What was your evaluation process like?"
Good question: "Tell me about the moment you realized you needed to start looking for a solution."
Why it works: Specific moments are memorable. General processes are fuzzy.
Technique 4: Probe Objections Gently
Customer mentions concern but moves on quickly:
You: "You mentioned earlier you had some concerns about our enterprise features. Can you tell me more about that?"
Why it works: Objections reveal gaps. Don't skip over them.
Technique 5: Silence Is Powerful
After asking a question, shut up and wait. Don't fill the silence.
Customer finishes answer. You wait 3 seconds.
Customer often adds: "Actually, there was one other thing..."
That "one other thing" is usually the most important insight.
How to Document and Analyze Interviews
During the interview:
- Record (with permission) or take detailed notes
- Note direct quotes for positioning/messaging
- Mark surprising insights with INSIGHT
Within 24 hours:
- Transcribe key sections (or use AI transcription)
- Write 1-page summary:
- Key decision factors
- Direct quotes (verbatim)
- Surprising insights
- Action items
After 10+ interviews:
- Aggregate themes across interviews
- Identify patterns:
- Most common decision criteria
- Most mentioned competitors
- Most frequent objections
- Most resonant value props (in their words)
Output: One-page insights summary:
- Top 3 decision factors
- Top 3 differentiation points (in customer language)
- Top 3 objections to address
- Verbatim quotes for messaging
Common Interview Mistakes
Mistake 1: Leading questions
"You chose us because of our superior analytics, right?"
Fix: "What made you choose us?" (open-ended)
Mistake 2: Asking for opinions, not stories
"What do you think of our product?"
Fix: "Walk me through how you use our product in a typical week."
Mistake 3: Not probing deeper
Customer gives surface answer, you move on.
Fix: Ask "why" 2-3 times to get to root motivation.
Mistake 4: Talking too much
You spend 30 minutes explaining your product, 10 minutes listening.
Fix: 80% listening, 20% asking questions.
Mistake 5: Not documenting insights
You conduct interviews but don't synthesize findings.
Fix: After every 5 interviews, create summary of themes.
The Uncomfortable Truth
Most companies don't interview customers because they're afraid of what they'll hear.
"What if they say our product isn't good?" "What if they chose us for the wrong reasons?" "What if our positioning is completely off?"
The reality: You'd rather know the truth so you can fix it.
The best PMMs obsess over customer interviews because:
- They reveal why customers actually buy (vs. why you think they buy)
- They uncover the language customers use (better than your messaging)
- They expose competitive threats and product gaps early
- They validate (or invalidate) your positioning
Interview 20 customers. You'll learn more than 6 months of internal meetings.
Stop guessing what customers think. Ask them. Then actually listen.