You'll learn how to: Analyse a closed deal (win or loss) without the noise. Surface what actually drove the outcome and the patterns worth repeating or fixing.
Time: 25 minutes per session, end-to-end.
Prereqs: You have a recently closed deal (won or lost). Coaching enabled on your plan.
When to use
- Within one week of losing a deal. Capture what happened while it's fresh.
- After a surprising win. Understand what worked so you can repeat it.
- Quarterly pattern review. Run this on your biggest wins and losses to spot trends.
- Before your next similar deal. Use insights from the last one to sharpen your approach.
The session takes 25 minutes and produces a learning: what worked, what didn't, and what to do next time.
Steps
- At the bottom-left of the sidebar, toggle to Strategy mode.
- Click Coaching.
- The Coaching hub shows canvases grouped by category.
- Click Win/Loss Post-Mortem (under Deals & Proposals).
- A setup screen appears. You're prompted to:
- Pick one or more closed deals to analyse (pick one if you're new to this, multiple if doing a pattern review).
- Choose whether you're reviewing a win or a loss.
- Click Start.
- The coach opens with a brief: what this session is for and what data it sees.
- The structured session begins. Typical flow:
- The AI summarises the deal: buyer, size, timeline, decision makers involved.
- For wins, it highlights what went right: your approach, their need fit, the momentum you built.
- For losses, it surfaces the actual decision point: who said no and why, what objection stuck.
- It asks you 2-3 focused questions: what surprised you about the outcome, what would you do differently, what one thing made the difference.
- It generates a post-mortem report: decision drivers, your strengths in the deal, gaps or missteps, and one pattern to repeat or avoid next time.
- Save or export the review. Suggested actions:
- Share learnings with your manager or team.
- Use the pattern insight to change your approach on similar deals.
- If it's a loss, optionally schedule a customer call to get their side of the story.
What's in a typical review
- Deal snapshot (buyer, size, timeline, who said yes or no).
- Decision drivers. What actually made the difference. The moment or conversation where the outcome became clear.
- Your strengths in the deal. What you did well, where you showed up strongly.
- Gaps or missteps. Where you could have moved faster, where you missed a signal.
- One pattern to repeat or avoid. The single insight worth taking to the next similar deal.
- Next-deal checklist. Three things to do differently or the same.
After the session
Apply the learning to your next similar deal. Log the pattern insight somewhere you'll remember it (your personal playbook, deal board notes, or team playbook if you have one).
If something goes wrong
- Symptom: "Win/Loss Post-Mortem canvas isn't in the Coaching hub." → Fix: Your plan doesn't include Coaching. Check avatar > Settings > Account.
- Symptom: "Setup screen can't find the deal." → Fix: You haven't logged the deal as closed in Nynch. Mark it won or lost in your opportunity board, then retry.
- Symptom: "The analysis feels surface-level or generic." → Fix: Two likely causes:
- Your deal notes lack detail about why the outcome happened. Add context about the decision point, the buyer's objections, or what changed, then re-run.
- You skipped the coach's follow-up questions. Restart and answer them fully.
- Symptom: "Session ended without a clear pattern or insight." → Fix: The coach needs you to engage with its discovery questions. If you rushed through, restart and take your time.
- Symptom: "I want to analyse multiple deals at once." → Fix: In the setup screen, select more than one closed deal. The coach will look for patterns across them.
Related
AI coaching canvases | Run a Pipeline Review coaching session | Run a Proposal Teardown coaching session | Run a Meeting Prep coaching session.