── SKILL
deal-debrief✓ APPROVED

Pull the lesson from a closed deal before it fades.

Reconstructs the timeline, separates what moved it from noise, names the near-death moment, and lands one repeatable lesson.

Inside: The timeline, cause vs noise, and one portable lesson.

01 / HOW TO USE

Install it in one line, or paste it in.

1
In Claude Code (one command)
Copy the install line, paste it into your terminal, and restart Claude Code. The skill installs itself to ~/.claude/skills/ and runs automatically when it is relevant.
2
In Claude, ChatGPT, or a Project (no terminal)
Open the file, then upload it to your chat or paste its contents in. A skill is just a markdown file of instructions, so any capable AI can follow it.
New to skills? A skill is a plain-text file that teaches your AI a workflow. Point any capable assistant at it and it follows the steps, on your data.
02 / MAKE IT YOURS

Connect your context. Set it to your motion.

CONNECT YOUR CONTEXT · AND WHY IT HELPS
a CRM

it reads the stage history, close date, amount, and the activity trail automatically, so the timeline is real, not remembered.

a meeting or email tool

pulls what was actually said at the turning points, so the debrief is grounded in the record, not the story you tell yourself.

a product-analytics tool

on trials, shows whether usage matched the story the deal told.

SET IT TO YOUR MOTION

This was built for a B2B SaaS org running a staged pipeline. Set these to your stack:

The point is one lesson you will actually reuse, not a form nobody reads. Set the capture target to where your team will actually see it.

Set thisWhat it isDefault / Example
STAGE historyhow you see the deal's pathOpportunity stage historyclose date
OUTCOME fieldwon, lost, or no-decisionStageNameClosed Won / Closed Lost
LOSS_REASON fieldwhy it closed the way it didLoss ReasonCompetitor field
ACTIVITY sourceswhere the touch trail livesTaskEventmeeting or email tool
CAPTURE targetwhere the lesson is writtenyour notesa shared doca deal wiki
LESSON_SCOPEhow broadly a lesson should applythis repthis segmentthe whole team
03 / THE FULL SKILL

Everything the skill does, in full.

── WHAT THIS DOES

Takes one closed deal, won or lost, and pulls the lesson out of it before it fades. It rebuilds the timeline from first touch to close, separates what actually moved the deal from what only felt important, names the moment it nearly died, and lands on a single repeatable lesson worth carrying to the next deal. Then it captures that lesson in a form the team can reuse, so the same mistake is not paid for twice.

── THE METHOD
  1. 1
    Reconstruct the timeline (what happened, in order)

    Lay the deal out from first touch to close: the stages, the dates, the key conversations, the moments something changed. Use the record where you have it. A debrief built on memory alone remembers the story, not the deal.

  2. 2
    What actually moved it (separate cause from noise)

    Name the two or three things that genuinely moved the deal toward its outcome. Strip out what felt important at the time but changed nothing. A win from a warm intro is a different lesson than a win from a great demo. Be honest about which it was.

  3. 3
    What nearly killed it (the near-death moment)

    Every deal has a moment it almost went the other way. Name it. What caused it, what recovered it or failed to, and whether you saw it coming. This is usually where the real lesson lives.

  4. 4
    The one repeatable lesson (single, portable)

    Land on exactly one lesson that would change how the next deal is run. Not five. One, stated so plainly that another rep could apply it without you in the room. If you cannot say it in a sentence, it is not the lesson yet.

  5. 5
    Capture it (so it is not relearned)

    Write the lesson where the team will actually find it, tagged to the situation it applies to. A lesson that lives only in one rep's head gets paid for again by the next rep. Capture turns one deal's cost into everyone's edge.

── QUALITY GATES
  • The timeline is built from the record where it is available, and clearly marked where it rests on memory.
  • What moved the deal is separated from what only felt important, honestly, even when the honest answer is luck.
  • The debrief lands on exactly one repeatable lesson, stated portably, not a list of five.
  • Loss reasons name what actually happened, never a tidy category that hides it.
  • Any date or amount carried from the deal is shown as given or sourced, never invented.
── OUTPUT (EXAMPLE)
EXAMPLE OUTPUT
DEAL DEBRIEF · Acme Corp · CLOSED WON · $60K (illustrative)

Timeline
  Day 0    Inbound from a webinar
  Day 12   Demo to VP Ops (the eventual champion)
  Day 34   Stalled in legal for 3 weeks
  Day 61   Signed after an exec-to-exec call

What actually moved it
  1. The champion sold it internally while we were out of the room.
  2. The exec call broke the legal stall. The demo did not close it.

What nearly killed it
  The legal stall. We had no second thread and no exec sponsor until
  day 55. We got lucky the champion held on.

The one repeatable lesson
  Line up the exec sponsor before legal, not after the stall. Waiting
  cost us three weeks and nearly the deal.

Captured to: team deal wiki, tagged "mid-market, legal stall"
── EXAMPLE CHAT
EXAMPLE CHAT
You
Debrief the Acme deal. We just closed it and I want to know what actually worked before I forget.
CLAUDE
Rebuilt the timeline from the CRM stage history and your recap. DEAL DEBRIEF · Acme Corp · CLOSED WON · $60K (illustrative) What actually moved it: the champion sold it internally while we were out of the room; the exec call broke a 3-week legal stall. What nearly killed it: the legal stall. No second thread until day 55. The one repeatable lesson: line up the exec sponsor before legal, not after the stall.
You
Capture that so the team actually sees it.
CLAUDE
Wrote it to the deal wiki, tagged "mid-market, legal stall," so the next rep hitting a legal stall finds this before repeating it. One sharpener: connect the meeting tool so next debrief pulls the actual exec-call quote instead of your recollection of what got said.
04 / GO FURTHER

Where an operator takes this next.

The read is step one. Here is where an operator takes it once the manual version proves out.

One deal's cost, captured once, becomes the whole team's edge.

01
Trigger a debrief on every closed deal automatically

Wire a scheduled Claude task to fire whenever an opportunity flips to Closed Won or Closed Lost in Salesforce.

02
Surface past lessons before the next deal starts

Connect the deal wiki to your CRM so a rep entering a similar deal sees prior lessons tagged to that situation.

03
Pull the turning-point quotes automatically

Connect Gong so the near-death moment gets the actual transcript excerpt instead of a paraphrase.

05 / PART OF A BIGGER PLAY

One skill is the on-ramp.

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