Win-loss analysis for small teams: questions and template
Run win-loss analysis without a research team: who to ask, eight questions, a one-page record and a tally that shows why you lose deals.
By DanPublished 3 min read
Ask a salesperson why a deal was lost and the answer is "price". Ask the buyer and you hear something else. They didn't understand the onboarding, or a colleague had used the other product before, or your demo skipped the one feature they cared about.
Win-loss analysis is the habit of asking the buyer. Large companies hire a research firm for it. A team of five can do it with a calendar link, eight questions and a spreadsheet. This guide shows how.
Who to ask, and when
Ask people who compared you with at least one other product and then decided. Include the deals you won. Winners tell you what to keep saying, and they are easier to reach.
Send the request within two weeks of the decision. After a month people remember the outcome and forget the reasons. A short email works:
You recently chose between us and another product. Could I ask you eight questions about how you decided? It takes 15 minutes, and it isn't a sales call.
Have someone other than the salesperson run the call. Buyers soften their answers for the person they turned down.
Eight questions
Ask them in this order. The early ones are easy and get people talking.
- What made you start looking for a product like this?
- Which products did you compare?
- Who else took part in the decision?
- What did the product have to do for you to say yes?
- What did you like most about the one you chose?
- What nearly stopped you from choosing it?
- How did price and contract terms affect the decision?
- What could the other side have done to change your mind?
When someone answers "price", ask one more question. "Too expensive compared with what?" turns a one-word answer into something you can use.
Record each interview on one page
Write the record the same day, in the same fields every time. Quote the buyer's own words where you can. Here is one filled in for a made-up deal.
- Outcome
- Lost. 12 seats, annual contract.
- Compared with
- Acme CRM and one spreadsheet-based process.
- Trigger
- A new sales lead joined and wanted pipeline reports by region.
- Main reason
- “Their mobile app meant our drivers' managers could update deals on the road.”
- Second reason
- Acme CRM was €4 cheaper per seat after its September price cut.
- What nearly changed it
- Our reporting. “Yours was better. If you had an app we would have signed.”
- Reason code
- Missing feature (mobile app)
- Follow-up
- Tell them when the mobile app ships. Add to the roadmap tally.
Give every deal one reason code
The record is for reading. The reason code is for counting. Pick one main reason per deal from a short fixed list:
- Missing feature
- Price or contract terms
- Easier to set up or use
- Trust (reviews, references, company size)
- Timing or no decision
- Sales process (slow replies, weak demo)
Keep the list under eight codes. With more than that, every deal gets its own code and nothing adds up.
Count after ten interviews
One interview is a story. Ten are a pattern. Tally the reason codes for lost deals once you have ten, and again every quarter. This example uses twelve made-up losses.
- Missing feature5
- Easier to set up or use3
- Price or contract terms2
- Sales process1
- Timing or no decision1
Illustrative numbers. Your own tally will look different.
In this tally, price is the main reason in two deals out of twelve. A missing feature decides five. A team that had only asked its salespeople would have spent the quarter discussing discounts.
Turn the tally into three changes
A tally that nobody acts on is a hobby. After each count, write down one change for each of these:
- Product. The missing feature that cost the most deals goes to whoever owns the roadmap, with the quotes attached.
- Sales. The objection buyers raised most gets a written answer in your battlecard.
- Website. The thing winners liked most moves higher on your home page, in their words.
Add what the competitor changed
Buyers describe the competitor as it was on the day they compared. That picture goes out of date. In the record above, the second reason was a price cut from September. A team that had seen the cut the week it happened could have prepared an answer before the deal was decided.
Plainrival doesn't run win-loss interviews. It covers the other half. It checks your competitors' public pages once a day and sends a weekly brief of what changed, so you can match a reason from an interview to the date the competitor made its move.
Weekly brief
Week 40 · 4 items · 23 changes filtered out
- Moved SSO into every paid planPricing page · acme.exampleImportance 922 h
- Launched AI inbox triage in betaChangelog · cedar.exampleImportance 841 d
- New page: “Lumen Billing vs your product”Sitemap · lumen.exampleImportance 782 d
- Starter plan up from €29 to €35 a monthPricing page · orbit.exampleImportance 664 d
Questions
Questions about win-loss analysis
How many win-loss interviews do I need?
Ten gives you a first pattern. Below that, treat every finding as a question to test in the next interviews.
Should I interview won deals too?
Yes. Winners tell you which claims worked, and those are the claims to repeat on your website and in sales calls.
What if buyers don't reply?
Ask within two weeks of the decision, promise 15 minutes and say it isn't a sales call. If they still don't reply, send the eight questions as a short form and accept shorter answers.