Sales Rep pack
Claude Skill
Loss Debrief
Honest analysis of why a deal died — what really happened vs the convenient story.
What it does
After a deal closes-lost, this skill walks you through an honest debrief: what the prospect actually said, what you actually did, the moment the deal really died (not the moment they sent the no), and what to change for next time. Designed to surface the lesson, not protect your ego.
When to use
- ✓After a closed-lost deal you wanted to win
- ✓Before submitting a closed-lost note in CRM
- ✓When you're stuck in a pattern of similar losses
When not to use
- ✗Deals lost for clear non-controllable reasons (budget freeze, acquisition, etc.) — there's no lesson there
- ✗Right after the loss when you're still emotional — wait 24 hours
Install
Download the .zip, then unzip into your Claude skills folder.
mkdir -p ~/.claude/skills
unzip ~/Downloads/loss-debrief.zip -d ~/.claude/skills/
# Restart Claude Code session.
# Skill is now available — Claude will use it when relevant.SKILL.md
SKILL.md
---
name: loss-debrief
description: Honest analysis of a closed-lost sales deal — what really happened vs the convenient story.
---
# Loss Debrief
When the user describes a deal that just closed-lost, walk through an honest debrief.
## Required input
- Deal context (company, size, who you engaged)
- Timeline summary (key moments)
- What they said when they passed
- What the user thinks went wrong
- What they wish they'd done differently
## Process
Don't accept the surface answer. Most reps tell themselves the convenient story. Push past it.
### 1. The convenient story vs the real story
User will give you their version of why it died. Common convenient stories:
- "They had no budget" (often = couldn't justify our priority)
- "Went with [competitor]" (often = our positioning was weak)
- "Wrong timing" (often = no champion or no pain)
- "Decision was political" (often = stakeholder coverage gap)
Ask the question that would surface the real story.
### 2. The moment it actually died
The prospect's "no" is the END of the loss, not the moment. The deal usually dies earlier — when discovery missed something, when the wrong stakeholder said something, when a key feature wasn't shown, etc.
Identify the specific moment. Reference the timeline.
### 3. What was controllable
Some losses are not on you. But most have a controllable component. Be honest about which:
- **Discovery gap**: missed key pain, key stakeholder, key constraint
- **Champion gap**: never built one, lost the one you had
- **Positioning gap**: didn't differentiate, generic value prop
- **Timing gap**: too early, too late, wrong fiscal window
- **Process gap**: skipped a step, rushed a stage
### 4. What you'd do differently
Not generic ("be more proactive"). Specific:
- "I'd ask [specific question] in discovery"
- "I'd insist on [specific stakeholder] being in the room before going to demo"
- "I'd disqualify if [specific signal] showed up early"
### 5. The pattern check
Is this loss part of a pattern? If user has lost 3+ deals for similar reasons, the lesson isn't tactical — it's strategic. Name it.
## Output
A debrief that answers:
- **Real reason it died** (not the convenient one)
- **The earliest moment it could have been saved**
- **The 1 thing to change** for the next similar deal
- **Pattern alert** if this is the 3rd+ similar loss
## Constraints
- Don't soft-pedal. The point is to learn, which requires honesty.
- Push back if the user blames the prospect for things they could have controlled.
- If the loss truly is non-controllable (e.g., acquisition, budget freeze), say so and stop. Not every loss has a lesson.
Example prompts
Once installed, try these prompts in Claude:
- Help me debrief the Acme loss. Here's what happened: [paste deal history, what they said, what you did]. What did I miss?
Related prompts
Don't want to install a skill? These prompts in /prompts cover similar ground for one-shot use: