If you’ve set up a Win/Loss program, the next big hurdle is obvious: how do you actually conduct the interviews and surveys so buyers provide you with useful information?
It’s not enough to ask, “Why did you choose us/not choose us?” and call it a day. Buyers will give you quick, surface-level answers, such as “pricing” or “features.” If you stop there, you’ve basically learned nothing.
The art is in asking open-ended questions, listening, and then following up to peel back the layers. The best interviews often feel less like research and more like the buyer telling you their buying story from start to finish.
Who to prioritize for interviews
Not every buyer will talk. And that’s okay. Focus on:
- Those who already agreed to a conversation – don’t chase ghosts.
- Recent wins and losses – freshness matters; people tend to forget quickly.
- Strategic deals – the ones where insights can change roadmap, pricing, or GTM priorities.
If you’re resource-constrained, a handful of well-chosen interviews beats trying to cover every single deal.
Golden rules for interviews
- Start with open-ended questions – Avoid yes/no questions. Ask things like “Walk me through how your team evaluated options.”
- Let them tell a story – Buyers often reveal more when they narrate their process instead of answering checkboxes.
- Follow up with “why” and “can you tell me more?” – Surface answers rarely reflect the full decision-making.
- Don’t defend, don’t sell – This isn’t a second chance to win them back. Your only job is to listen.
- Record and transcribe (with permission) – You’ll miss details if you rely only on notes.
Sample Win/Loss Interview Flow
Here is a sample flow for the interview with some questions. Remember, we may not have time to address all questions, and that’s okay, too. The key to a successful Win-Loss interview is to ensure the interviewee is telling their story without any barriers.
1. Context Setting
- “Thanks for taking the time. We’re not here to resell you, just to learn how your decision came together.”
- “Can you tell me a bit about what problem you were trying to solve when you started looking?”
This sets the tone: it’s about their journey, not your product.
2. Buying process & evaluation
- “Walk me through your evaluation process — who was involved, and what steps did you take?”
- “How did you build your shortlist of vendors?”
- Follow-up: “Why was that step important? What criteria mattered most?”
This reveals decision drivers and how much weight different factors carried.
3. Perceptions of your company
- “When you first came across us, what was your initial impression?”
- “As you engaged with our team, what stood out — good or bad?”
- How did you learn more about our company and offerings?
- Follow-up: “Can you share an example?”
This helps you see how your brand, sales process, and messaging landed.
4. Competitor comparison
- “Which other vendors did you seriously consider?”
- “How did we compare to them on the factors that mattered most?”
- Follow-up: “Was there anything you felt they did better? Anything we did better?”
Here’s where you often uncover competitive intelligence gold.
5. The decision itself
- “What tipped the scales in the final decision?”
- “If you had to pick the top two or three reasons, what were they?”
This is the heart of the matter. Always follow up with
6. Reflection
- “Looking back now, how do you feel about the decision?”
- “Is there anything we could have done differently to change the outcome?”
- “What advice would you give us to improve?”
This is where buyers often share the most actionable suggestions.
This part is also a bit tricky since the prospect has already become a customer and they may be in the process of onboarding, which may attract its own challenges — are we meeting their expectations, did we oversell, did they underestimate the efforts, etc.
Interviewing Lost Accounts: Tricky, But Worth It
Talking to accounts you won is relatively easy. They’re happy, they just picked you, and they’ll often give you positive reinforcement. But the real gold often lies in the interviews with lost accounts — the ones who evaluated you and chose someone else (or chose nothing at all).
That’s where you find out what you didn’t see in the deal.
Why lost accounts matter
- They tell you what didn’t work in your product, pitch, or process.
- They’ll often mention things your sales team has never heard.
- They show you how competitors are winning against you, in the buyer’s own words.
Yes, these conversations may stink. But they’re the most actionable.
**How to **
get them to talk
Lost buyers aren’t always eager to jump on a call. A few tactics help:
- Timing is key – Ask within 2–3 weeks of the decision, while it’s still fresh. Too soon and it feels raw; too late and they’ve moved on.
- Neutral positioning – Frame it as research, not a sales follow-up. “We’re not trying to resell you, we just want to learn and improve.”
- Third-party interviewers – Lost accounts often open up more to a neutral consultant than to the vendor they just rejected.
- Offer value or goodwill – Keep it short (20–30 minutes max) and consider a small incentive or donation.
In Part 4, we’ll look at how Win/Loss programs evolve as companies mature — what it looks like at a startup vs a scale-up vs a global enterprise.