Win-loss interview

Ask a sales team why a deal was lost and the answer is usually price. Ask why one was won and it's the demo. Buyers often remember it differently. This template walks a recent buyer through their decision in order: what started the search, who made the shortlist, what got cut, and the one thing that settled it.

Best for: Sales, product marketing and product teams who close enough deals each quarter to see a pattern.

Use this template free

1 of 8

What was going on that made you start looking for a solution in the first place?

Made with Enform

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The questions

1What was going on that made you start looking for a solution in the first place?Long textThe event that started the search. It tells you what problem got the budget approved.
2Who else did you seriously evaluate before deciding?Long textNames the rivals you really compete with, which may not be the ones your team tracks.
3Walk me through how you narrowed it down. What got cut, and why?Long textAsking them to retell the steps brings out the deal breakers that never make it into the CRM.
4What was the single factor that decided it in the end?Long textAsks for one answer, not a tidy list. The one they pick is often not the one you expect.
5How did you make the final call?Single selectChose us / Chose a competitor / Built it ourselves / Did nothing. Split every other answer by this.
6Where in the process did you feel most confident, and where most uncertain?Long textShows the moments in your sales process that built trust and the ones that lost it.
7Knowing what you know now, would you make the same decision?Single selectDefinitely / Probably / Probably not. Doubt after a win is an early warning that the account may not stay.
8What's one thing we could have done that would have changed your decision?Long text

Sample replies, counted

These replies are made up to show the method.

Asked: What was the single factor that decided it in the end?

Their rep got our security questionnaire back in two days. Yours took two weeks and by then we'd moved on.Slow security review
SSO. we needed it on the base planMissing a must-have
The price, honestly. $18 a seat against $12 was hard to explain upstairs.Price gap
IT wouldn't sign off until we had a SOC 2 report and you didn't have one yetSlow security review
We could import our old data in an afternoon with them. With you it looked like a project.Migration looked hard
procurement stalled on the vendor form for ages and the other tool was already approvedSlow security review
No audit log, which our compliance team needs.Missing a must-have
my old boss used them at her last companyOther

8 replies, one label each
Label	Replies
Slow security review	3
Missing a must-have	2
Price gap	1
Migration looked hard	1
Other	1

Only one of eight lost on price. Three stalled in security or procurement review, so a ready security pack and a named contact for questionnaires will likely save more deals than a discount.

How to run it well

Reach out soon after the decision, while the buyer still remembers the details and hasn't tidied them into a neat story.
Talk to lost deals as well as won ones. Wins tell you what to repeat, losses tell you what to fix.
Have someone other than the deal's rep run it. Buyers go easy on a seller they liked.
Always ask who else they looked at. The rival they name is sometimes one nobody on your team was watching.
Tag every reply by outcome and deal size, then read the deciding-factor answers side by side. Repeated reasons there are worth more than any internal debate about positioning.

When not to use this: If the person already bought and later cancelled, this is the wrong script. Use a customer churn survey to learn why they left.

FAQ

Why talk to lost deals as well as won ones?

Wins tend to confirm what you already believe. Losses show the gaps: the missing feature, the moment trust slipped, the rival you underrated. You need both, but the losses usually change more.

How many win-loss interviews should I run?

Keep going until the deciding factors start to repeat, and track won and lost deals separately. Running a few every month works better than one big batch, because you notice when the reasons start to change.

Can win-loss work as a form instead of a live call?

Yes. A written form takes the rep out of the room and reaches more deals, and some buyers are more candid in writing. Branching in Enform asks the follow-up that fits each answer, so replies stay specific.

Where the method comes from

Win-Loss Analysis: What It Is and How It Works, Mazemaze.co
Jobs to Be Done Theory, Christensen Institutechristenseninstitute.org
Open-Ended vs. Closed Questions in User Research, Nielsen Norman Group (2024)nngroup.com