Hubspot pipeline cleanup

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:

1. Week 1 of quarter: cleanup (this skill)
2. Week 2: rep 1:1s on stuck deals
3. 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