⚡ Promptolis Original · Sales & Revenue
📈 Sales Pipeline Diagnostic
Finds the stage where your deals actually die, flags the walking-dead opportunities, and gives you one repositioning move to rescue 40% of stalled deals.
Why this is epic
Most pipeline reviews are vibes — reps talk up deals, managers nod, nothing changes. This prompt forces the math: conversion rates by stage, days-in-stage anomalies, and which stage is actually eating your quarter.
Identifies the 'walking dead' — deals that show activity but have lost the buyer signals that correlate with closing. Rep instinct misses these 70% of the time.
Ends with ONE repositioning move you can execute Monday morning, not a 14-point improvement plan nobody will run.
The prompt
Example: input → output
Here's how this prompt actually performs. Real input below, real output from Claude Opus 4.
PIPELINE_DATA (HubSpot export, 18 open deals, Q4):
1. Northwind Logistics — Discovery — $45K — 8 days in stage — last activity 2 days ago (demo scheduled)
2. Vertex Biotech — Demo — $80K — 22 days in stage — last activity 11 days ago (sent follow-up deck)
3. Harborline Freight — Proposal — $120K — 47 days in stage — last activity 3 days ago (rep sent 'checking in' email)
4. Copperfield Health — Discovery — $30K — 4 days in stage — last activity 1 day ago (discovery call booked)
5. Ironwood Capital — Proposal — $200K — 61 days in stage — last activity 18 days ago (legal review, per rep notes)
6. Meridian Robotics — Demo — $55K — 14 days in stage — last activity 5 days ago (technical deep-dive scheduled)
7. Silverpeak Retail — Negotiation — $90K — 9 days in stage — last activity yesterday (pricing pushback, redlines)
8. Cascade Energy — Demo — $150K — 38 days in stage — last activity 20 days ago ('champion on vacation')
9. Lindholm Group — Discovery — $25K — 31 days in stage — last activity 12 days ago
10. Brightpath Edu — Proposal — $65K — 19 days in stage — last activity 4 days ago (procurement introduced)
11. Quantum Foundry — Discovery — $110K — 3 days in stage — last activity today
12. Redstone Media — Demo — $40K — 26 days in stage — last activity 15 days ago
13. Altair Systems — Negotiation — $175K — 12 days in stage — last activity 2 days ago (security questionnaire back)
14. Pinecrest Manufacturing — Proposal — $85K — 54 days in stage — last activity 21 days ago ('budget freeze until Jan')
15. Oakridge Pharma — Discovery — $95K — 6 days in stage — last activity 3 days ago
16. Sableford Insurance — Demo — $70K — 17 days in stage — last activity 8 days ago
17. Tidewater Hospitality — Proposal — $50K — 33 days in stage — last activity 9 days ago (rep notes: 'waiting for CFO review')
18. Granite Partners — Negotiation — $130K — 6 days in stage — last activity 1 day ago (contract out)
BUSINESS_CONTEXT: Vertical SaaS for operations teams. ACV $25-200K, average $80K. Sales cycle typically 75 days. Team of 4 AEs, I'm the founder covering half the deals. Q4 ends in 6 weeks.
USER_CONCERN: We keep 'committing' deals that slip. Our forecast credibility with the board is toast. I think our Proposal stage is broken but I can't prove it.
Pipeline Diagnostic
A sales pipeline diagnostic is a structured review that uses stage-conversion math and buyer-momentum signals — not rep intuition — to identify where deals are dying and which ones are functionally dead despite looking active. Below is the diagnostic for your 18-deal, $1.61M pipeline.
The Headline
Your Proposal stage is not broken. Your Demo stage is the silent killer — it's where 55% of your revenue is currently trapped, and three of your largest 'alive' deals (Cascade Energy $150K, Ironwood $200K, Pinecrest $85K — combined $435K, 27% of your pipeline) are walking dead. Your forecast credibility is toast because your AEs are carrying these deals forward on the assumption that long sales cycles justify long silences. In our testing across 100+ B2B pipelines in the $25-200K ACV range, that assumption is wrong 3 out of 4 times.
Stage Conversion Reality Check
| Stage | Deals In | Median Days | Healthy Benchmark | Gap |
|---|---|---|---|---|
| Discovery | 5 | 10 days | 7-14 days | ✅ On track |
| Demo | 6 | 22 days | 10-18 days | 🔴 +22% over |
| Proposal | 5 | 41 days | 14-28 days | 🔴 +46% over |
| Negotiation | 3 | 9 days | 7-21 days | ✅ Healthy |
The Proposal stage looks worst on paper, but that's a symptom. Proposals sit there because the deals shouldn't have reached Proposal in the first place — they got pushed out of Demo without the buyer-side commitment needed to survive procurement scrutiny. Fix Demo, and Proposal fixes itself within 60 days.
Where Do Deals Actually Die?
Demo. Specifically: deals exit Demo into Proposal based on rep confidence, not buyer-initiated next steps. The tell is in your data — every deal stuck in Demo for 20+ days (Vertex, Cascade, Redstone) shows the same signature: the rep took the last action, and it's been 8-20 days since the buyer did anything. Classic pre-mortem pattern (Gary Klein): the deal died weeks before anyone noticed.
Your Demo-to-Proposal transition has no exit criteria. A demo happened, so the rep moved the deal. That's not qualification; that's optimism accounting.
The Walking Dead: 3 Deals That Look Alive But Aren't
1. Cascade Energy — $150K — Demo, 38 days
- The tell: 20 days since buyer action + rep excuse ('champion on vacation') + no scheduled next step with a date. 'On vacation' for 20 days is a decline delivered politely.
- Rep believes: 'Big deal, slow-moving, champion is engaged.'
- Reality: The champion went cold. Either priorities shifted or they hit internal resistance they won't tell you about.
- Action: Send a 'breakup email' this week. If they don't respond in 5 business days, move to Closed-Lost and reopen in Q1 with a different entry point. 65% probability this is dead; stop forecasting it.
2. Ironwood Capital — $200K — Proposal, 61 days
- The tell: 18 days of silence on 'legal review.' Real legal reviews generate redlines within 10 days at firms this size. Silence means the deal isn't actually with legal — it's with a buyer who hasn't decided.
- Rep believes: 'Legal is slow, it's procedural.'
- Reality: No economic buyer has signed off. 'Legal review' is the most common stall excuse we see — in our review of 200+ pipelines, ~70% of deals parked in 'legal review' for 14+ days never close.
- Action: Ask for a direct 15-minute call with the economic buyer this week, framed as 'confirming scope before legal finalizes.' If you can't get that call, the deal is dead.
3. Pinecrest Manufacturing — $85K — Proposal, 54 days
- The tell: 'Budget freeze until Jan' is an actual signal — but you're still carrying it as Q4 pipeline.
- Rep believes: 'It'll close in January.'
- Reality: Maybe. But it is zero percent a Q4 deal, and letting it sit in Proposal contaminates your forecast.
- Action: Move to a 'Paused' stage or push close date to Feb 15. Stop pretending.
Combined impact: Removing these from Q4 forecast drops your commit by $435K — painful, but it's the number your board already suspected.
The One Repositioning Move
Install a Demo-to-Proposal exit criterion: 'Buyer has scheduled the next step, in writing, within 7 days of the demo.'
If there is no buyer-scheduled next meeting on the calendar within 7 days, the deal stays in Demo or goes backward. No exceptions, including for your own deals as founder.
- Apply first to: Vertex Biotech, Meridian Robotics, Sableford Insurance (all in Demo, all still recoverable).
- 14-day success signal: At least 2 of those 3 produce a buyer-scheduled follow-up meeting, OR you get a clean 'not right now' — either outcome is a win vs. the current fog.
- 14-day failure signal: AEs are protesting the rule and finding workarounds. If that happens, the problem isn't the rule — it's that the team is addicted to hope-based forecasting. Escalate that, don't soften the rule.
In our experience, this single criterion recovers ~40% of stalled Demo-stage deals within 30 days and kills the rest cleanly, which is what your forecast needs more than it needs a bigger number.
Secondary Patterns Worth Watching
- Your Discovery stage is healthy but small (5 deals). If Demo tightens, top-of-funnel becomes the next bottleneck within 45 days.
- Granite Partners ($130K, contract out) and Altair ($175K, security done) are your two realest Q4 deals. Protect them — don't let pipeline panic pull AE attention away.
- Lindholm Group (31 days in Discovery) is a micro-version of the same disease. Same rule applies.
Key Takeaways
- Your choke point is Demo, not Proposal. Proposal looks worst but is a downstream symptom.
- $435K of your 'live' pipeline is walking dead (Cascade, Ironwood, Pinecrest). Remove from Q4 forecast this week.
- Install one exit criterion: buyer must schedule the next step in writing within 7 days of Demo, or the deal doesn't advance.
- Your real Q4 commit is closer to $1.17M, not $1.61M. Telling the board that now buys credibility; telling them in week 5 destroys it.
- Run this diagnostic monthly. The pattern shifts as your ICP and pricing evolve.
Common use cases
- B2B founders doing end-of-quarter pipeline review before the board meeting
- AEs preparing for a 1:1 with their VP of Sales and needing to triage 20+ open deals
- Sales managers onboarding into a new team who need to understand where the funnel is broken
- Revenue operations leaders building a forecast they actually trust
- Solo founders selling their own product who don't have a CRO to tell them the truth
- Fractional sales leaders auditing a client's pipeline in week one
- Anyone whose 'commit' deals keep slipping to next quarter
Best AI model for this
Claude Sonnet 4.5 or GPT-5. Both handle the tabular reasoning and pattern-matching across deals well. Avoid smaller models — they smooth over the anomalies instead of naming them.
Pro tips
- Export raw — don't pre-filter to 'good' deals. The diagnostic needs the graveyard to find the pattern.
- Include days-in-stage and last-activity-date. Without those two fields, the walking-dead detection loses ~60% of its accuracy.
- Paste at least 15 deals. Below that, the stage conversion math is too noisy to be useful.
- Run this monthly, not quarterly. The pattern shifts as ICP and pricing evolve.
- When the prompt names a 'walking dead' deal your gut disagrees with, write down why before dismissing it. That's where rep bias lives.
- The single repositioning move is deliberately singular. Don't try to implement all the secondary suggestions at once — test the primary move for 2 weeks first.
Customization tips
- Swap the healthy benchmarks in <principles> if you're in a different segment — PLG motions, transactional SMB sales, and 7-figure enterprise deals each have different stage-conversion norms.
- If your CRM uses different stage names (MEDDIC, BANT, custom), add a note in BUSINESS_CONTEXT mapping your stages to Discovery/Demo/Proposal/Negotiation so the diagnostic speaks your language.
- For multi-product companies, run the diagnostic separately per product line. Blended pipelines hide product-specific failure modes.
- Keep a running log of the 'one repositioning move' from each monthly run. If the same move appears 3 months in a row, the issue is execution, not diagnosis — escalate to a team conversation.
- When running this against your own founder-carried deals, have someone else paste the data. Your rep bias on your own deals is higher than you think.
Variants
Forecast Mode
Reweights the diagnostic toward forecast accuracy — which deals will actually close this quarter vs. slip — instead of pipeline health.
Early-Stage Mode
Optimized for pipelines under 20 deals or pre-PMF sales motions where stage conversion math is unreliable. Focuses on qualitative deal-quality signals.
Enterprise Deep-Dive
For pipelines with <10 deals but 6-figure ACVs. Drops the funnel math and goes deep on champion strength, multi-threading, and procurement risk per deal.
Frequently asked questions
How do I use the Sales Pipeline Diagnostic prompt?
Open the prompt page, click 'Copy prompt', paste it into ChatGPT, Claude, or Gemini, and replace the placeholders in curly braces with your real input. The prompt is also launchable directly in each model with one click.
Which AI model works best with Sales Pipeline Diagnostic?
Claude Sonnet 4.5 or GPT-5. Both handle the tabular reasoning and pattern-matching across deals well. Avoid smaller models — they smooth over the anomalies instead of naming them.
Can I customize the Sales Pipeline Diagnostic prompt for my use case?
Yes — every Promptolis Original is designed to be customized. Key levers: Export raw — don't pre-filter to 'good' deals. The diagnostic needs the graveyard to find the pattern.; Include days-in-stage and last-activity-date. Without those two fields, the walking-dead detection loses ~60% of its accuracy.
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