You call a prospect who chose a competitor. "Thanks for considering us. Can I ask why you went with [Competitor X]?" They respond: "It was a tough call. You were great, but they were just a slightly better fit." You thank them and hang up.
You learned nothing. The feedback was polite deflection, not truth. The real reasons—your demo confused them, your pricing seemed predatory, your salesperson was pushy—went unspoken. You can't improve based on politeness.
After conducting hundreds of loss interviews and training dozens of product marketers on interview techniques, I've learned the pattern: getting honest feedback isn't about asking better questions. It's about creating psychological safety and using specific techniques that bypass social conditioning to be nice.
Here's how to get truth from lost deals.
Why People Deflect Instead of Being Honest
Reason 1: They don't want to hurt your feelings
Most people default to kindness. Saying "Your product seemed confusing and your sales rep was condescending" feels mean, even if true.
Reason 2: They don't want to seem difficult
"We went with the cheaper option" feels embarrassingly unsophisticated. "They were better fit" sounds more strategic.
Reason 3: They don't want to justify their decision
If they tell you specific reasons, you might argue or ask them to reconsider. Vague answers end the conversation faster.
Reason 4: They haven't fully articulated the real reasons to themselves
Decisions are emotional then rationalized. They chose based on gut feel or politics but constructed logical-sounding reasons afterward.
Your job is to make honesty easier than deflection.
The Setup That Enables Honesty
Before asking anything, set the frame:
"I really appreciate you taking time. Quick context on why I'm reaching out: I'm not in sales, I'm in product marketing. My job is to help our company understand what's actually happening in the market so we can improve. This isn't about trying to change your mind or save the deal—that ship has sailed and I respect your decision.
What's helpful for us is understanding the real reasons behind your choice, even if they're uncomfortable to share. Honest critical feedback helps way more than polite feedback. You won't hurt my feelings—this makes our product better for future customers.
Does that make sense? Cool, so with that context..."
This framing does four things:
- Separates you from sales (reduces fear of being re-pitched)
- Gives explicit permission to be critical (reduces social pressure)
- Explains how feedback will be used (gives them reason to invest time in honest answer)
- Acknowledges discomfort (makes it safe to say hard things)
Most people become noticeably more honest after this framing.
The Question Techniques That Reveal Truth
Technique 1: The assumption flip
Instead of: "Was our pricing competitive?"
Ask: "Our pricing obviously played some role in your decision. Walk me through how you thought about the price difference between us and [competitor]."
The assumption that pricing mattered makes it easier to discuss. They don't have to introduce uncomfortable topic—you introduced it for them.
More examples:
"Every product has weaknesses. What were ours that came up during your evaluation?"
"Sales processes are never perfect. What could our sales team have done differently that might have helped?"
Technique 2: The comparison question
Instead of: "Why did you choose [Competitor]?"
Ask: "When you put us side-by-side with [Competitor], what were the two or three things that made them the winner?"
Side-by-side comparison forces specific contrast instead of vague "better fit."
Follow-up: "And in that comparison, where were we actually stronger? I assume we weren't worse at everything."
This acknowledges reality that all vendors have trade-offs, making it psychologically easier to cite your weaknesses.
Technique 3: The "almost didn't" question
"What almost made you choose us instead?" or "What almost made you not choose [Competitor]?"
This reveals what was close, what mattered on the margins, and where the decision could have swung differently.
Example responses:
"We almost went with you because your UI is way cleaner, but ultimately we needed the Salesforce integration they have."
Now you know: UI was strength, integration gap was decisive weakness.
Technique 4: The third-party question
"What did people on your team say about us in internal discussions? I'm curious what concerns came up."
Attributing feedback to unnamed team members creates distance. It's easier to say "Some people thought..." than "I thought..."
Example responses:
"A couple people on the team felt your demo was really technical and hard to follow."
They're not saying they thought this. They're reporting what others said. The feedback is same but feels less confrontational.
Technique 5: The ranking question
"If you were ranking the factors that drove your decision from most important to least important, what would the top three be?"
Ranking forces prioritization. You learn what actually mattered vs. what was secondary.
Follow-up: "And where did [factor you care about] rank on that list?"
If they ranked your differentiator 7th, you learn your positioning isn't landing.
Technique 6: The awkward silence
After they give polite/vague answer, stay quiet for 3-5 seconds.
Most people are uncomfortable with silence and will fill it with additional detail that's often more honest than first response.
Example:
Them: "They just seemed like better fit overall."
You: [silence]
Them: "I mean, honestly, a big part of it was that our VP had used their product at her previous company and trusted it. We would have needed you to really wow us to overcome that, and the demo was... fine, but not amazing."
The silence prompted the real answer: internal champion for competitor, plus your demo didn't compensate.
How to Handle Common Deflection Patterns
Deflection 1: "It was really close, could have gone either way"
Your response: "That's helpful to know. Since it was close, what was the one thing that tipped it in their favor? Like if you had to point to the single deciding factor."
Forces them to identify what actually broke the tie.
Deflection 2: "We went with incumbent/status quo for now"
Your response: "Got it. What would need to be different for you to choose a new vendor over sticking with current setup? Like what's the bar a new solution would need to clear?"
Reveals what would overcome inertia, which tells you what's missing from your value prop.
Deflection 3: "Your pricing was too high"
Your response: "Makes sense. Help me understand that—was it that the absolute price was over budget, or was it that price relative to perceived value didn't make sense? Because those are different problems for us to solve."
Separates "actually too expensive" from "didn't see enough value to justify price."
Deflection 4: "We needed features you don't have"
Your response: "Totally fair. Which features specifically? And of those, which were absolute must-haves vs. nice-to-haves?"
Distinguishes showstopper gaps from wish-list items.
Deflection 5: "The team just felt more comfortable with [competitor]"
Your response: "Comfort is important. What specifically made them feel more comfortable? Was it brand recognition, the sales experience, the product itself, something else?"
"Comfortable" is vague. Push for concrete factors that created comfort.
The Question Sequence for Full Picture
Phase 1: The trigger (2 minutes)
"Before we talk about the decision, help me understand what kicked off this evaluation in the first place. What happened that made you think 'we need to look at solutions for this'?"
Context on why they bought reveals priorities.
Phase 2: The consideration set (3 minutes)
"When you started looking, how did you build your short list? Where did our name come from vs. competitors?"
Shows where you have brand strength/weakness.
Phase 3: The evaluation (8 minutes)
"Walk me through the evaluation. How did you narrow from initial list to finalists, and what was the process?"
"Which vendors made it to final round besides us and [winner]? Anyone you expected to consider but didn't?"
"When you put us side-by-side with [winner], what were the 2-3 things that made them come out ahead?"
"Where were we actually stronger? I assume we weren't worse at everything."
"What almost made you choose differently?"
This sequence moves from broad (the process) to specific (the deciding factors).
Phase 4: The outcome (5 minutes)
"Now that you've made the decision and started implementing [assuming they have], how's it going?"
If honeymoon phase has worn off, you might hear: "Honestly, implementation has been rough. If I'd known it would take this long..."
That reveals opportunity for repositioning around implementation speed.
"Is there anything we could have done differently that might have changed your decision?"
Direct question about what would have swung deal.
Phase 5: The learning (2 minutes)
"Last question: If a peer at another company asked you about evaluating [category] solutions, what advice would you give them?"
Their advice reveals what they wish they'd known or prioritized differently.
Reading Between the Lines
What they say: "They had feature X"
What they mean: Feature X was dealbreaker. If you don't have it, you can't win similar deals.
What they say: "They were more expensive but we felt it was worth it"
What they mean: You have value perception problem, not price problem.
What they say: "Their sales process was smoother"
What they mean: Your sales team did something that hurt the deal.
What they say: "We went with incumbent"
What they mean: You didn't make switching worth the risk and effort.
What they say: "They just seemed like better fit culturally"
What they mean: Either they liked competitor's team better, or this is deflection hiding real reason they don't want to state.
Listen for what's unsaid as much as what's said.
How to Record Without Killing Honesty
Option 1: Ask permission explicitly
"Would you mind if I record this so I don't miss anything in my notes? It won't be shared outside our product team."
Most people say yes. Some say no. If they say no, respect it and take good notes.
Option 2: Don't record, just take detailed notes
Write key quotes verbatim during call. Immediately after call, spend 10 minutes filling in details while fresh.
Option 3: Use transcription tool like Fireflies but disclose it
"I use a transcription tool so I can focus on our conversation instead of taking notes. Just FYI it's recording. Is that okay?"
Transparency maintains trust.
The Post-Interview Analysis
After call, rate their candor level:
High candor: Gave specific critiques, used concrete examples, didn't sugar-coat
Medium candor: Shared some specific feedback but also some deflection
Low candor: Mostly polite/vague responses
High-candor interviews are most valuable. Medium-candor interviews require reading between lines. Low-candor interviews tell you they weren't comfortable being honest (which itself is signal about relationship or how call was framed).
Common Mistakes That Shut Down Honesty
Mistake 1: Defending or explaining
Them: "Your product seemed too complex"
You: "Well actually, we have a simple mode that..."
They stop sharing. Don't defend. Say "That's helpful feedback" and move to next question.
Mistake 2: Asking leading questions
"You didn't think our price was too high, did you?"
Leads them to answer you want, not truth.
Mistake 3: Acting hurt or disappointed
Emotional reactions make them regret being honest. Stay neutral and appreciative regardless of feedback.
Mistake 4: Following up to "correct" their misconceptions
Them: "You didn't have feature Y"
You [after call]: emails "Actually we do have feature Y, let me show you..."
Now they won't be honest in future because they know you'll use feedback to re-pitch.
The Honesty Continuum
Level 1 honesty (polite deflection):
"They were just better fit overall."
Level 2 honesty (surface reasons):
"They had features we needed."
Level 3 honesty (specific critiques):
"Their Salesforce integration is native while yours requires Zapier. That was a dealbreaker."
Level 4 honesty (uncomfortable truths):
"Honestly, our CTO had used their product before and wasn't willing to look seriously at alternatives. The evaluation was kind of going through motions."
Your interview techniques should push from Level 1 toward Level 3-4. That's where strategic insights live.
Getting honest feedback from lost deals isn't about clever tricks. It's about making honesty psychologically safe, socially acceptable, and tactically easy. Frame the conversation correctly, ask questions that bypass deflection, stay genuinely curious and non-defensive, and most people will tell you truth. That truth—even when it stings—is what makes your company better at winning future deals.