Sales · 15 min

Learn why you won or lost a deal, then use it on the next one

Copilot Chat

Short answer: After a deal closes either way, ask Copilot Chat for a short, neutral survey or interview guide for the customer. When you have answers, paste them with your own deal notes and ask for the real reasons, grouped and quoted. Pick one thing to change on your next deal.

Last checked against Microsoft docs: Oct 21, 2026

On a lot of teams, losses get talked about in the hallway and nowhere else. A real win/loss review turns one deal into a lesson for every deal after it. The rep who brings the team clear reasons, not excuses, is the rep people listen to.

A common situation (composite)

We lost a deal we were sure about.
Everyone has a theory.
Nobody asked the customer.

What you get

Data: the deal outcome, your notes, and the customer's answers.
Does: drafts the survey, then groups the reasons with quotes.
Output: a short survey and a one-page lessons summary.
How often: after every deal you win or lose that mattered.

Before you start

Needs: Microsoft 365 Copilot Chat. Not sure what you have? Start here.
Microsoft's label for this scenario: Microsoft 365 Copilot.
Where: Copilot Chat, plus Microsoft Forms or email for the survey.
Access: Copilot only uses content you already have permission to open. Use only information your company allows in Copilot.

The steps

Run the first prompt to draft five to seven neutral questions.
Send them through Forms or a short call with the buyer.
Paste their answers and your deal notes into Copilot Chat.
Run the follow-up to get the reasons and one change.
Share the summary with your team, without blaming anyone.

Copy this prompt

Draft a short win/loss survey for a customer who just [chose us / chose someone else] for [what we sell].
- 6 questions, neutral wording, no leading questions
- One rating question on how easy we were to buy from
- One open question at the end
- Under 5 minutes to answer

Then write a two-line email asking them to fill it in, thanking them for their time either way.

(Prompt from stuckwithcopilot.com/guides/win-loss-review/)

Make it better

Run this next, in the same chat.

Here are the customer's answers and my deal notes: [paste].

List the real reasons we [won / lost], grouped (price, product fit, relationship, timing, process, competitor). Quote the customer for each. Mark anything from my notes only as OUR VIEW. Then give me one thing to do differently on my next deal like this.

(Prompt from stuckwithcopilot.com/guides/win-loss-review/)

Data tip: use this with your work Copilot, and leave out passwords, payment details and anything your company marks restricted.

What a good result looks like

Reasons come with customer quotes, your own opinions are labeled as such, and you end with one specific change.

If a feature is missing

If the customer won't answer, run the follow-up on your notes alone and label every reason OUR VIEW.

Make it smarter

Keep a short "What it got wrong" note. Paste it above the prompt next time, like "Don't invent dates".

Not sure what to ask? Copy the quick note for your Copilot admin.

Questions people ask

Learn why you won or lost a deal, then use it on the next one?

After a deal closes either way, ask Copilot Chat for a short, neutral survey or interview guide for the customer. When you have answers, paste them with your own deal notes and ask for the real reasons, grouped and quoted. Pick one thing to change on your next deal.

What do I need for this?

Microsoft 365 Copilot Chat. If the customer won't answer, run the follow-up on your notes alone and label every reason OUR VIEW.

Will customers really answer?

Many will if it's short and you ask right after the decision. Lost deals answer more often than you'd expect, especially if you thank them either way.

Should I do this for wins too?

Yes. Knowing why you won tells you what to repeat.

How do I share a loss without looking bad?

Lead with what you learned and what you'll change. Owning a loss clearly builds more trust than hiding it.

Next step

Try it once, then make it yours.

Run the prompt on one real task this week. Then pick your next workflow.

See the workflow library ↗

Cite or share this guide

Learn why you won or lost a deal, then use it on the next one. Stuck with Copilot. https://stuckwithcopilot.com/guides/win-loss-review/ Last checked Oct 21, 2026.

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Where this comes from

Inspired by Microsoft's Copilot scenarios. See the original at Microsoft Copilot adoption (Microsoft 365 Copilot Prompt Pack for Sales). The prompts and steps here are rewritten and expanded by Stuck with Copilot. This site is not affiliated with Microsoft.

Official references

Get started with Microsoft Copilot Chat

Last checked against Microsoft docs: Oct 21, 2026.