How to Conduct Win-Loss Interviews: A Step-By-Step Guide

Running effective win-loss interviews is an art.

Without the right approach, you risk burning through resources and breaking buyer goodwill, all in the name of surface-level feedback.

In this guide, you’ll learn:

• How to use Klue’s D.E.P.T.H. framework to conduct high-quality interviews
• How to pick the right candidate for the job
• 11 more practical tips for nailing your next interview

Let’s dive in.

📌 Looking for a complete overview? Check out our ultimate guide to win-loss. 

First Step: Automate the Busy Work

Conducting great win-loss interviews starts with reducing the manual work that surrounds them.

Think about it:

Every hour spent transcribing conversations, tagging insights, and analyzing patterns is an hour that could be spent having deeper conversations with more buyers.

That’s where automation can help. Tools like Klue Win-Loss automatically handle interview transcription and identify win/loss reasons, turning hours of manual work into minutes.

No automation tool? We still recommend optimizing your process:

• Create interview templates in Google Docs
• Use free transcription tools like Otter.ai
• Build a simple spreadsheet to track themes across conversations
• Record Zoom calls and share key segments with stakeholders

The goal here is to free up time so you can put more energy into (and produce more of) your most high-impact activity – buyer conversations.

Now that we’ve addressed the admin work, let’s focus on how to run high-quality interviews with the D.E.P.T.H. framework.

The D.E.P.T.H. Framework for Win-Loss Interviews

“A successful win-loss interview ends with insights your stakeholders didn’t previously know.”

That’s Andre Csapo, our Research Director at Klue, cutting to the heart of what makes a win-loss interview worth everyone’s time.

But how do you achieve this consistently? That’s where Klue’s D.E.P.T.H. framework comes in. Follow these five principles to get the most from buyer interviews:

• Details: Dig for details on key concern areas 
• Engaged: Be engaged and empathetic
• Personal: Integrate your buyer’s personality 
• Trust: Establish trust as an impartial third-party 
• High Impact: Focus on what matters most

Let’s break down each one. 

D: Dig for Details on Key Concern Areas

Every new interviewer faces the same challenge:

You ask a tough question. You get a half-hearted answer. Something in your gut tells you to just move on. 

After all, nobody wants to seem pushy or make the buyer feel uncomfortable. But let’s be honest: those easy, top-level answers are no better than your CRM drop-down codes.

Here’s how you dig deeper:

Use the “5 Whys?” Framework

This is your simplest tool for pushing past one-dimensional answers. When your buyer begins discussing a key factor related to their decision:

• Ask “Why?” to that initial statement
• Take their answer and ask “Why?” again
• Repeat this process up to five times

Here’s what it looks like in practice:

• If a buyer says “Your pricing was too high”
  • Ask “What made it feel too expensive?”
• If they say “The per-seat model”
  • Ask “What challenges did that create?”
• If they say “Hard to predict total costs”
  • “How did that impact your evaluation?”
• If they say “Our CFO needs fixed budgets”
  • “What would have made forecasting easier?”
• If they say “A tiered model with predictable costs,” ask
  • “What tiers would have worked?”
• Finally, they say: Fixed pricing for 0-50, 50-200, and 200+ users

Viola! You’ve moved from “too expensive” to a truly actionable insight: your pricing structure needs to be more predictable for enterprise finance teams.

Get Them Telling Stories

Their words hit harder than your summaries.

A quote like “We needed a PhD to use your dashboard” tells you exactly what’s wrong – and it’ll wake up every exec in your next win-loss review meeting.

To pull these out of your buyer, use natural follow-ups:

• “Then what happened?”
• “How did that play out?”
• “Take me back to when you first ran into this”

These prompts get buyers out of “interview mode” and into sharing real experiences.

Focus on Actionable Details

Your job isn’t just to collect feedback – it’s to gather insights your team can actually use.

Here’s what that means:

• If they struggled with security settings, that could be your product team’s next focus area
• If they misunderstood your pricing model, that’s a messaging fix
• If they got confused during demos, that’s a sales enablement opportunity

In short, when you’ve dug up a juicy detail, tie it to something specific you can improve. 

📌Want more question ideas? Our guide to 31 best win-loss questions can help spark deeper conversations.

E: Be Engaged and Empathetic

When a buyer agrees to do a win-loss interview, they’re volunteering their time to revisit a decision process that may have been stressful or frustrating. 

Your job? Create an environment where they feel comfortable telling you exactly what went wrong.

Here’s how to show you’re fully invested in their story:

Listen Actively

• Offer verbal cues like “I see” or “Got it”
• If you’re on video, maintain eye contact and give small nods
• Let them finish their thoughts, even if you think you know where they’re going

Show You Understand

• When they mention challenges, acknowledge them: “That does sound frustrating”
• Follow up naturally: “How did your team handle that situation?”
• Stay curious about their experience without jumping to fixes

Never Get Defensive

• When they criticize your product, don’t explain or justify
• Instead, probe deeper: “Which aspects felt most problematic?”
• Remember: your goal is to understand, not to change their mind

Match Their Energy

• If they’re passionate about a particular issue, lean into that topic
• If they’re more reserved, dial it back
• Let their communication style guide yours

Example of Empathy in Action

Buyer: “Your sales team kept pushing us to sign before we were ready. It left a bad taste.”

You: “I appreciate you sharing that. Which moments felt particularly pushy? Was it more the calls, emails, or something else?”

Notice the tone here. You’re not apologizing for your company but showing you want to understand their experience. This is empathy in action. 

P: Integrate the Buyer’s Personality

There’s no single script for win-loss interviews. A technical admin deep in API docs needs a very different conversation than a VP focused on ROI. Your job is to adapt while still getting the insights you need.

Adjusting to the Interviewee’s Role

For Technical Roles

• Get granular about features, integrations, and user experience
• When they mention specific modules, dig into the “why”
• Let them geek out on tech specs and documentation
• Listen for implementation headaches

Business/Executive Roles

• Focus on ROI, strategic alignment, and competitive differentiators
• VPs and Directors care about team efficiency and resource allocation
• Department heads worry about adoption and workflow impact
• Pay attention to mentions of competitors

Mid-Level Managers

• They bridge the gap between executives and end-users
• Ask about process bottlenecks
• Dig into team adoption challenges
• Look for cross-department friction points

Let The Conversation Flow

Yes, you need to cover certain topics. But the best insights often come from letting buyers go off-script.

Here’s what that might look like when chatting with an enterprise-level technical admin:

You: “What stood out most during your security evaluation?

• “Well, the SOC 2 compliance was table stakes, but what really caught our attention was your competitor’s implementation process”

You: “Tell me more about their implementation approach”

• “They actually flew out an expert to walk us through everything. Spent three days with our security team.”

You: “How did that influence your decision”

• “It showed they understood enterprise security isn’t just about features, it’s about getting the configuration right. This made us feel safe to go with them.”

In this case, by letting the conversation flow, you’ve uncovered something valuable – it wasn’t the security features themselves that lost you the deal (though, this might listed in your CRM). Rather, it was your competitor’s high-touch implementation support.

T: Establish Trust as an Impartial Third-Party

Trust-building starts the moment you invite a buyer to the interview. The more comfortable and respected they feel throughout the process, the more they’ll open up about sensitive topics like lost deals, product frustrations, or internal decision dynamics.

Here’s how to earn that trust:

Make It Clear Your Not Selling

• Open with: “This is not a sales call or win-back attempt. We’re here purely to learn and improve.”
• Explain exactly how you’ll use their feedback to drive internal improvements
• Keep the focus on learning, not reversing their decision

Handle Recording Right

• Ask before you start: “Mind if I record this for my notes?”
• Be clear about who will have access to the recording
• Offer to proceed without recording if they prefer

Make Confidentiality Crystal Clear

• Let them know that their name can remain private when insights are shared internally
• Assure them specific quotes won’t be used in marketing or sales materials
• Remind them they can speak freely about sensitive topics

Warm Up Before Diving Deep

• Spend a minute on relevant company news or achievements
• Show you’ve researched their role and challenges
• Let the conversation flow naturally into the interview questions

Example: Trust in Action

Don’t Say: “So our competitor got the deal. Between us, their security certifications are still pending – was price the main factor?”

Do Say: “I know security compliance was critical for your team. Could you help me understand how you evaluated different vendors’ security capabilities?”

Notice the difference? The first tries to undermine their decision and fish for price objections. The second opens the door for honest feedback about their security evaluation process

💡 Tip from Andre Csapo, Klue Win-Loss Research Director: “I always check their LinkedIn before we talk – where they’re from, their background, companies they follow. Finding that small connection point at the start gets them relaxed and talking.”

H: Focus on High-Impact Objectives

At the end of the day, win-loss interviews are only as good as the actions they generate. Interesting stories are great, but they need to translate to real improvements in your product, sales process, and competitive strategy.

Here’s how to make that happen:

Revisit Learning Objectives Before Each Call

Every interview should align with your win-loss learning objectives. 

If a primary objective is to investigate pricing concerns, focus your questions on the buying process:

• How do they evaluate ROI?
• What does their budget process look like?
• Which pricing models work best for their team?

The key is going in with questions that map directly to what you need to learn.

📌 For a deeper dive on setting learning objectives, check out our guide on how to get started with win-loss.

Look for Patterns That Drive Action

Not every insight will be a game-changer. The real value comes from patterns that emerge across multiple interviews – those “I’ve heard this before” moments that signal bigger issues or opportunities.

Here’s what to watch for:

• A competitor consistently winning in specific verticals
• Multiple buyers speaking positively or negatively about the same feature
• Your solution being perceived as “too enterprise” or “too small”
• Repeated mentions of a competitor’s new capability

When you hear something three times, it’s probably time to act. These recurring themes need to be highlighted in your win-loss reports and discussed with stakeholders ASAP. 

Selecting and Training Your Win-Loss Interviewer

Good questions matter. But the person asking them matters more. You need someone who can make buyers comfortable enough to share real feedback.

Here’s what to consider when choosing your interviewer:

They Stay Neutral

• Avoid using the original salesperson (even for wins)
• Choose someone who understands your product but isn’t emotionally invested
• When it doubt, go with Product Marketing – they’re curious and see the big picture
  • In fact, our 2025 Win-Loss Trend Report revealed that 41% of win-loss programs are already owned by PMMs, making it a safe bet.

They Match the Buyer’s Seniority

• VP-level buyers expect to talk to senior interviewers
• Technical users prefer talking to someone who speaks their language
• Mid-level managers want to talk with someone who understands team dynamics

They’re Poised Under Pressure

• They’ll hear tough feedback like “Your product caused multiple escalations”
• Wrong response: “We’ve never heard that before!”
• Right approach: “That’s concerning – could you share more about those incidents?”

Remember: The best interviewers blend structure with genuine curiosity. They know when to follow the framework and when to dig deeper on emerging insights.

11 More Win-Loss Interview Tips 

Beyond D.E.P.T.H., here are practical tips from Klue’s win-loss team to maximize every conversation:

Tie Questions to Objectives

• If a question doesn’t align with a learning objective, cut it. 
• The buyer’s time is limited – every question should serve a strategic purpose.

Have 20-30 Questions Ready

• But expect to only use 10-15 in a 30-minute interview. 
• Having extra ensures you can pivot when interesting threads emerge. 

Plan 30 Minutes, Schedule an Hour

• Aim for a half-hour conversation, but block out an hour on your calendar.
• This is a buffer in case the buyer is willing to go deeper.

Find a Distraction-Free Space

• Background noise or cluttered environments kill focus. 
• Turn off notifications, close extra tabs, silence your phone

Use Video Whenever Possible

• Seeing facial expressions and body language enhances empathy and trust. 
• Always request a video interview

Record & Transcribe

• Ask permission to record so you can focus on listening
• Review transcripts later for quotes and nuances you missed
• Upload your interviews into Klue and let our AI automatically generate win or loss reasons

Follow the 90/10 Rule

• Buyers should speak 90% of the time. 
• Keep your prompts succinct, then let them run with it. 

Avoid Leading Questions

• Wrong: “Wouldn’t you say our competitor’s solution is more expensive?”
• Right: “How did you compare our pricing with other vendors?”

Ask One Concept at a Time

• Don’t combine questions: “Was our interface user-friendly, and did sales address your concerns?”
• Split them up to avoid incomplete or rushed answers. 

Throw a Hail Mary Question

• End every interview with an open-ended question: “What’s one piece of advice would you give our company?”
• This will often reveal insights your structured questions missed 

LinkedIn

Send a Prompt Follow-Up

• If you offer an incentive (like a gift card or donation to charity), email them right away.
• Thank them again and note that they can reach out if they remember additional details.

There You Have It!

Great win-loss interviews get to the heart of buyer decisions. They uncover the real reasons you win and lose deals, so you can stop relying on shaky CRM drop-down options.

But getting these insights requires three things to work in perfect harmony:

• A structured approach (D.E.P.T.H.) that keeps conversations focused
• The right interviewer who can build trust and probe intelligently
• Practical techniques that turn good conversations into great ones

Most importantly, you need to act on what you learn. So get started!

Oh – and if you’re ready to learn more about win-loss? Check out our guides on:

• Sourcing win-loss interviews
• Analyzing win-loss data
• Scaling win-loss data collection

And don’t forget to download our win-loss executive summary template 👇