fengyiqicoder HubSpot Pipeline Cleanup
Overview
A messy CRM pipeline destroys forecast accuracy, demoralizes reps ("everything looks stuck"), and hides real opportunities. This skill walks the user through a systematic pipeline audit that identifies which deals to close, push, or escalate — based on objective rules, not gut feel.
Core principle: A deal that hasn't moved stages in 2x the average sales cycle for that stage is either dead or being neglected. Treat it as dead until proven otherwise.
The 4-quadrant deal classification
For every open deal, classify into one quadrant:
| Recent activity (≤14d) | No recent activity (>14d) | |
|---|---|---|
| In stage <2x avg time | 🟢 Healthy — leave alone | 🟡 Nudge — needs activity |
| In stage ≥2x avg time | 🟠 Stuck — coach the rep | 🔴 Dead — close-lost it |
Definitions:
- "Recent activity" = email logged, call logged, meeting completed, or stage change
- "Avg time in stage" = your historical average for that pipeline stage. If unknown, default: Qualification 14d, Demo 21d, Proposal 14d, Negotiation 21d
Workflow
Step 1: Ask the user for context
1. Which pipeline are we cleaning? (Sales / Customer Success / Partnerships / Other)
2. What's your typical sales cycle (in days)?
3. Any deals you already know are dead?
4. Date of last formal pipeline review?
If user says "I don't know my sales cycle" → use defaults from references/sales-velocity-benchmarks.md.
Step 2: Pull the deal list
Ask user to export from HubSpot:
- All open deals
- Columns: Deal Name, Stage, Amount, Close Date, Last Modified Date, Last Contacted Date, Owner, Stage Entry Date
Save as CSV. If user pastes the list, parse it directly.
Step 3: Classify each deal
For each deal, compute:
days_in_current_stage = today - stage_entry_date
days_since_activity = today - last_contacted_date
stage_health = days_in_current_stage / avg_time_for_stage
if stage_health < 2 and days_since_activity ≤ 14: HEALTHY
if stage_health < 2 and days_since_activity > 14: NUDGE
if stage_health ≥ 2 and days_since_activity ≤ 14: STUCK
if stage_health ≥ 2 and days_since_activity > 14: DEAD
Step 4: Surface the cleanup actions
For each category, recommend specific actions:
🟢 HEALTHY — No action. List them only.
🟡 NUDGE — One-liner per deal: "Email [Contact] re: [last context]". Group by owner.
🟠 STUCK — These need a coach-the-rep conversation. Surface the pattern:
- "3 deals stuck in 'Proposal' for owner X" → maybe rep struggles closing
- "5 deals stuck in 'Demo' across pipeline" → maybe demo doesn't convert; root-cause it
🔴 DEAD — Recommend close-lost with reason. Ask user to confirm before bulk-closing.
Step 5: Forecast clean-up impact
After classification, show:
Pipeline before cleanup: $X across N deals
After removing DEAD: $Y across M deals (more accurate forecast)
Recovered hours: estimated X hours/month rep time wasted on dead deals
The "close-lost reason" trap
HubSpot's default close-lost reasons are too generic ("No decision", "Went with competitor"). They tell you nothing.
Push for specifics:
- ❌ "Lost to competitor" → ✅ "Lost to [Competitor] — they had [specific feature/price]"
- ❌ "Budget" → ✅ "Budget — wanted to stay <$X, our floor was $Y"
- ❌ "Timing" → ✅ "Timing — wanted to wait for [event/quarter]"
See references/close-lost-taxonomy.md for the actionable taxonomy.
Quarterly cleanup ritual
This skill should run every quarter at minimum. Suggest the user calendar:
- Week 1 of quarter: cleanup (this skill)
- Week 2: rep 1:1s on stuck deals
- Week 12: forecast finalization (informed by clean pipeline)
Red flags
- >40% of pipeline is "DEAD" → systemic issue: leads-quality, qualification process, or rep behavior
- Average deal age > 2x sales cycle → forecast is fiction; pipeline coverage ratio meaningless
- One owner has 3x the dead-deal rate → coaching opportunity, not a "lazy rep" judgment
- Recent activity = "task created" only → activity theater, not real engagement
- Deals reopening multiple times → poor qualification at top of funnel
Quick reference
| Symptom | Likely cause | First action |
|---|---|---|
| Forecast keeps slipping | Stale deals inflating coverage | Run this cleanup |
| Reps say "pipeline is full" but no closes | Quality vs. quantity issue | Filter by deal age |
| Same deal name appears 3x | Duplicate / re-entry | HubSpot dedupe tool |
| All deals close-date = end of quarter | Wishful thinking | Force per-deal date based on actual stage |
| Win rate dropping | Stuck deals diluting wins | Cleanup + qualification refresh |
What NOT to do
- Don't mass-close-lost without rep review — you might kill a real deal
- Don't change ownership during cleanup — does more harm than good mid-quarter
- Don't add new mandatory fields during cleanup — pile-on; do it next quarter
- Don't use AI to write the rep coaching message — the rep needs to own the relationship