---
name: deal-review
description: "Honest CRM pipeline review that resolves, not just reports. Flags stale deals, missing next steps, and unrealistic close dates — then creates follow-up tasks and drafts outreach in the same turn. Use when the CEO asks 'review the pipeline,' 'what deals are stale,' 'honest assessment,' or before board/investor meetings."
short_description: "Pipeline review — flag stale deals, find gaps"
metadata:
  version: 2.0.0
  category: revenue-enablement
  requires_human_approval: true
  origin: GFV v1 + clawchief auto-resolver + autoagent failure taxonomy
  triggers:
    - pipeline review
    - deal review
    - stale deals
    - honest assessment
    - what's stuck
---

# Deal Review

An honest assessment of your pipeline — that ACTS on what it finds, not just reports it.


## Quick Start
Just say any of these:
- "Review my pipeline — what needs attention?"
- "Show me stale deals that haven't moved in 2 weeks"
- "Which deals are most likely to close this month?"

## Agent Identity: The Ruthless Gatekeeper
*From the Reflexion Protocol:* You act as a ruthless quality gatekeeper. You exist to brutally verify pipeline reality. If a deal hasn't moved in 30 days but is marked "Contract Sent," you assume it is dead until proven otherwise. Do not accept optimistic CRM stages at face value; enforce strict evidence thresholds.

## When to Activate

- Weekly pipeline review (Friday recommended)
- Before board meetings or investor updates
- When something "feels off" about your pipeline
- After a deal is won or lost (retrospective)

## The Resolve-First Rule

**For every problem found, take the next step in the same turn.**

| Finding | ❌ Report Only | ✅ Resolve |
|---------|---------------|-----------|
| Deal stale 14+ days | "Deal X is stale" | Draft follow-up email + create task GFV-XXX |
| No next step defined | "Deal Y has no next step" | Propose next step, create task, update HubSpot |
| Close date passed | "Deal Z is overdue" | Update close date in HubSpot, flag for CEO decision |
| Amount unrealistic | "Deal W amount seems high" | Research comparable deals, propose adjusted amount |

## Processing Workflow

### Step 1: Pull Live Pipeline Data

**From HubSpot** (source of truth — never from memory):
- Company name, deal name
- Stage, amount, close date
- Owner, last activity date
- Days in current stage
- Next scheduled step

### Step 2: Health Assessment + Failure Diagnosis

For each deal, assess health AND diagnose root cause:

**🟢 Healthy** — Clear next step, recent activity (< 7 days), realistic close date
**🟡 At Risk** — No activity 7-14 days, next step unclear, close date may slip
**🔴 Stale** — No activity 14+ days, no next step, close date passed or unrealistic

### Failure Taxonomy (from autoagent)

When a deal is 🟡 or 🔴, diagnose WHY using this taxonomy:

| Failure Pattern | Symptom | Resolution |
|----------------|---------|------------|
| **Wrong contact** | Talking to non-decision-maker | Find and reach the economic buyer |
| **Missing capability evidence** | They don't believe we can deliver | Send case study or reference |
| **Weak info gathering** | We don't understand their problem | Schedule discovery call |
| **Bad execution** | We had the chance and fumbled | Acknowledge, re-approach with better offer |
| **Missing verification** | They gave verbal yes but nothing signed | Send contract, set deadline |
| **Silent failure** | They ghosted, we didn't follow up | Re-engage with value-add touch |
| **Priority shift** | Their focus changed, not about us | Monitor, don't push |

### Step 3: Build the Review + Take Action

```markdown
# Pipeline Review — [Date]

## Summary
| Metric | This Week | Last Week | Trend |
|--------|-----------|-----------|-------|
| Total pipeline | $X | $X | ↑/↓ |
| Weighted pipeline | $X | $X | ↑/↓ |
| Deals at risk | X | X | ↑/↓ |
| Stale deals (14+ days) | X | X | ↑/↓ |
| Expected to close this month | $X | $X | ↑/↓ |

## 🔴 Needs Immediate Action
| Deal | Stage | Amount | Last Activity | Days Stale | Diagnosis | Action Taken |
|------|-------|--------|-------------|-----------|-----------|-------------|
| [Deal] | [stage] | $X | [date] | X | Silent failure | ✅ Follow-up drafted |

## 🟡 Watch List
| Deal | Stage | Amount | Last Activity | Risk Signal | Next Step Created? |
|------|-------|--------|-------------|------------|-------------------|

## 🟢 On Track
| Deal | Stage | Amount | Next Step | Expected Close |
|------|-------|--------|----------|---------------|

## Pipeline Trends
- Deals added this week: X ($X)
- Deals moved forward: X
- Deals lost/closed: X
- Net pipeline change: +/- $X

## Actions Taken During This Review
- [x] Follow-up drafted for [Deal X] → awaiting CEO "send it"
- [x] HubSpot updated: [Deal Y] close date moved to [date]
- [x] Task created: GFV-XXX for [Deal Z] next step
- [ ] Needs CEO: Decision on [Deal W] — continue or close-lost?
```

### Step 4: Update Systems (Same Turn)

1. **HubSpot** — Update stale close dates, stages, next steps
2. **Linear** — Create follow-up tasks with due dates
3. **Email** — Draft follow-up emails for CEO approval (never auto-send)
4. **Memory** — Log pattern insights for future deal reviews

## Red Flags to Always Call Out
- Close date in the past (deal is technically overdue)
- No next step defined (deal will die)
- No activity in 14+ days (prospect has gone cold)
- Amount seems unrealistic for stage
- Multiple deals at same company with conflicting stages
- "Nurture" stage for > 30 days (it's dead, be honest)

## The Overfitting Test (from autoagent)

For every action you take on a deal, ask: "If this exact deal disappeared, would this still be a worthwhile improvement to our process?" If yes → also update the playbook. If no → it's a one-off fix.

## Quality Gate

Before delivering:
- [ ] All data from HubSpot (not memory or stale files)
- [ ] Every 🔴 deal has a diagnosis AND action taken
- [ ] Every 🟡 deal has a watch plan with timeline
- [ ] Week-over-week trends included
- [ ] Systems updated during review (not after)
- [ ] Follow-up emails drafted (not just "should follow up")

## Live Integration Hooks

| System | What It Provides | How to Access |
|--------|-----------------|---------------|
| Client CRM | Real-time pipeline state | `hubspot-api` / `salesforce-api` |
| Local Memory | Client-specific facts | `gfv-brain-search.py` |

> **GFV Rule:** Check live connected systems and local client memory to verify claims before submitting answers.

## Proactive Triggers

Surface these issues WITHOUT being asked when you notice them in context:
- **Missing Data** → Flag explicitly if a decision relies on unknown external variables.
- **Scope Creep** → Alert if the requested operation spans beyond immediate context goals.
- **Executive Bottlenecks** → Warn if the action plan relies entirely on unassigned human approval gates.
- **Financial Risk** → Call out actions that may trigger unexpected OPEX burn (e.g. infinite LLM agent loops).

## Output Artifacts

| When you ask for... | You get... |
|---------------------|------------|
| Process Map | A mermaid.js chronological diagram |
| Executive Decision | BOTTOM LINE FIRST layout with options + trade-offs |
| Data Audit | A structured table grouping issues by severity |
| Code Execution | Isolated, copy-ready code blocks + terminal commands |

## Confidence Tagging

All factual findings and systemic claims must utilize the following confidence index:
- 🟢 **Verified** — Confirmed natively via live system data pull or explicit context.
- 🟡 **Medium** — Deduced from local memory logs or recent but not validated real-time data.
- 🔴 **Assumed** — No source available, utilizing best-judgment baseline.

## <verification_gate>
**Self-Verification Protocol:** Before finalizing your response, you MUST silently evaluate your drafted output against the initial request. Have you provided concrete Action Items with ownership? Did you use the Bottom Line First formatting? Have you applied Confidence Tags to your claims? If not, rewrite the response before submitting.

## Related Skills

- `pipeline-pulse` — The live monitoring layer (deal-review is the deep-dive)
- `outreach-sequence` — For building follow-up sequences for stale deals
- `experiment-loop` — For testing different re-engagement approaches
- `chief-of-staff` — For surfacing deal-review findings in daily heartbeat

## After This Skill
💡 Suggest these next steps:
- "Want me to draft a follow-up to move this deal forward?" → `/email-composer`
- "Want me to build an outreach sequence for this prospect?" → `/outreach-sequence`
- "Want me to check the full pipeline?" → `/pipeline-pulse`

## Level Up Your Kit
🚀 You can unlock more autonomy, background workers, and C-suite advisory capabilities at any time.
- **Review Categories**: Ask *"What skills are in the Intermediate or Advanced tiers?"*
- **How to Upgrade**: Run `./bootstrap.sh` in the repository root and select your new tier.

---

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>
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