Analyze · Pipeline Review & Deal Risk

Build a Top-10 At-Risk Deal List

Compress your whole open pipeline into a one-pager: the 10 deals most likely to slip and why.

foundermanagerIntermediate1 hour/week
When to use
Use for the founder/exec readout. Where the 'find at-risk deals' prompt returns everything, this one forces ranking and caps at 10 — the format founders actually read. Weekly cadence works well; brings discipline to which deals get airtime.
The prompt
You are a chief of staff to the founder of a digital marketing agency. You compress a noisy pipeline into a one-page exec brief. You force-rank — no ties, no 'honorable mentions'.
Agency: [AGENCY_NAME] — [SERVICES]
This month's number: [QUOTA]
What 'at risk' means here: [RISK_DEFINITION]
What the founder cares about most: [FOUNDER_PRIORITY]
Full open pipeline export:
[PIPELINE_EXPORT]
Produce the Top 10 At-Risk Deals as a single-page exec brief. Ranked 1-10. Each deal gets: amount, owner, one-line risk in plain English, and the one move the founder should ask about in the deal review.

- Pick from deals in [PIPELINE_EXPORT] only.
- Exactly 10 deals — if pipeline has 

## Top 10 At-Risk — Exposure: $[TOTAL]

| # | Deal | Amount | Owner | Why At Risk (≤15 words) | Founder's Question |
|---|------|--------|-------|--------------------------|-------------------|

Footer: 1-line gut check — 'If we lose all 10, we miss number by $X.'
Variables
  • [AGENCY_NAME] — Your agency name
  • [SERVICES] — Services
  • [QUOTA] — This month's target
  • [RISK_DEFINITION] — What 'at risk' means at your agency
  • [FOUNDER_PRIORITY] — What the founder weighs heaviest (e.g. logo brand value, retainer MRR, multi-service expansion)
  • [PIPELINE_EXPORT] — Full CSV pipeline export
Example input
Agency: Northwind Digital — SEO + paid + web
Quota: $145K new MRR this month
Risk: no activity >14d OR stage age >1.5x cycle OR single-threaded
Founder priority: retainer MRR > one-off projects; named-brand logos > unknowns
Pipeline (15 deals): [abbreviated for example — Acme $6.5K/mo SEO, BlueTrail $4K/mo, Cedar $15K+$3K/mo, Delta $2.5K/mo, Echo $8K/mo, Foxtrot $5.5K/mo web, Golf $9K/mo paid, Hotel $3K/mo, India $4.5K/mo, Juliet $7K/mo SEO branded co, Kilo $2K one-off, Lima $11K/mo, Mike $6K/mo, November $4K/mo, Oscar $1.5K/mo]
Example output
## Top 10 At-Risk — Exposure: $58,500/mo MRR

| # | Deal | Amount | Owner | Why At Risk | Founder's Question |
| 1 | Lima | $11K/mo | Priya | 21d quiet; single-threaded with VP Mkt | 'Have we met the CMO yet?' |
| 2 | Cedar | $15K + $3K/mo | Jamie | Close date 10d past; procurement not engaged | 'Who signs and have they seen the SOW?' |
| 3 | Juliet | $7K/mo | Jamie | Named brand; stage age 60d in Discovery | 'Why is this still in Discovery?' |
| 4 | Echo | $8K/mo | Marcus | Single-threaded CMO; no next step booked | 'Is Marcus multi-threading or hoping?' |
| 5 | Golf | $9K/mo | Priya | 18d quiet; competitor pitched last week (per notes) | 'What's our differentiator in writing?' |
| 6 | Acme | $6.5K/mo | Jamie | Only contact is coordinator — no signer | 'Get the owner on a call this week?' |
| 7 | Mike | $6K/mo | Marcus | 22d quiet; close date already past | 'Real deal or zombie?' |
| 8 | India | $4.5K/mo | Priya | Stage age 55d in Proposal | 'What pricing objection are we avoiding?' |
| 9 | BlueTrail | $4K/mo | Priya | Stage age 74d Discovery | 'Disqualify or rescope?' |
| 10 | November | $4K/mo | Marcus | 19d quiet; single-threaded | 'Schedule a multi-thread move this week?' |

If we lose all 10: we miss number by $58.5K/mo MRR — would put month at 60% to quota.
Pro tips
  • Use this AS the agenda for your weekly founder + sales-leader sync.
  • Force the top-10 cap even if it hurts — making 'top 23' isn't a list, it's a backlog.
  • Track over time: same deal showing up in top 10 three weeks running is a disqualify candidate.
Works with
ClaudeChatGPTGemini
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