Pipeline Health Analyzer

Identify pipeline risks, predict deal outcomes, and prescribe specific actions to accelerate stalled opportunities.

Contents

• references/output-template.md - Full report skeleton to populate.
• references/stage-analysis.md - Per-stage deep-dive patterns (Discovery, Demo, Proposal) and why deals stall.
• references/forecasting.md - Forecast tables, probability calibration, AI re-scoring, scenario planning.
• references/email-templates.md - Re-engagement email templates for stalled and dark deals.
• references/examples.md - Trigger phrases, a worked example request, and best practices.

Workflow

1. Obtain the pipeline data. Request a CSV export with deal name, stage, value, rep, deal age, days in current stage, last activity date, close date, and probability if not provided.
2. Compute pipeline-by-stage metrics: deal count, total value, average deal size, average days in stage, and stage-to-stage conversion rates. Compare each against historical benchmarks.
3. Score each deal across six health dimensions: stage velocity, engagement level, qualification depth, stakeholder coverage, competitive position, and 30-day momentum.
4. Identify stalled and at-risk deals. Flag deals exceeding benchmark time in stage, with no recent activity, with slipped close dates, or with single-threaded contacts.
5. For each critical deal, determine the root cause and prescribe prioritized actions (immediate, this-week, backstop). Pull re-engagement copy from references/email-templates.md.
6. Build the forecast: categorize deals (Commit/Best Case/Pipeline/Upside), calculate weighted and risk-adjusted value, check probability calibration against actual close rates, and re-score outliers. Follow references/forecasting.md.
7. Model best-case, expected, and worst-case scenarios against quota, with a mitigation plan for the downside.
8. Produce strategic recommendations across immediate, short-term, and long-term horizons.
9. Assemble the report using references/output-template.md. Use plain status words (Healthy / At Risk / Critical) and trend words (Up / Flat / Down); never use emoji.
10. Close with the report card, next-review date, and week-over-week KPIs to track.

Operating Principles

• Run weekly, not monthly; pipeline health degrades fast.
• Base assessments on activity metrics, not rep intuition.
• Disqualify dead deals early; a flowing pipeline is healthy.
• Always end with concrete next steps, not just analysis.
• Coach with the insights; do not weaponize them against reps.

See references/examples.md for trigger phrases, a worked example, and the full best-practices list.