The autopsy that finds deal rot before the review

You are a Revenue Operations specialist. Review the following deal data from Salesforce and assess risk for each opportunity:
For each deal, evaluate:
● Days since last activity
● Stage vs close date alignment (is the timeline realistic?)
● Missing next steps or champion contact
● Any mismatch between deal size and engagement level
Output a risk rating (High / Medium / Low) for each deal with a one-line reason and a recommended action.
[PASTE DEAL DATA HERE]

I want to inspect my own deal hard and find what's wrong with it before my manager does in a deal review — or before it slips. Be the skeptical inspector I need, not a cheerleader.

The deal:
- The opportunity: [ACCOUNT, SIZE, PRODUCT, STAGE, EXPECTED CLOSE]
- What I know about the buying side: [CHAMPION, ECONOMIC BUYER, OTHER STAKEHOLDERS, THEIR PROCESS]
- The compelling event / why now: [WHAT'S DRIVING URGENCY — or my honest admission there isn't one]
- Where I think it stands: [MY READ]
- What I'm relying on: [THE ASSUMPTIONS HOLDING THIS DEAL TOGETHER]

Inspect it ruthlessly:

The risk scan — go through the deal's vital signs and flag what's weak or missing: do I have a real economic buyer or just a champion? Is the champion actually powerful or just friendly? Is there a genuine compelling event or am I hoping? Do I understand their buying/approval process or am I guessing? Is the deal single-threaded? Have I confirmed budget? Name every gap.

The wishful-thinking check — where am I believing what I want to believe? Call out the optimistic assumptions I'm treating as facts (they said they're interested ≠ they'll buy; my champion likes me ≠ they can get this approved). Be blunt.

The single points of failure — the one thing that, if it goes wrong, kills this deal, and how exposed I am to it (one champion, one stakeholder, an unconfirmed budget).

The stage-reality check — is this deal actually at the stage I have it at, or am I sandbagging the truth to keep it in my forecast?

The hardest questions — the 3-4 questions my manager (or a tough buyer) will ask that I can't currently answer well. These are my real gaps.

The action list — for each gap, the specific thing to do to close it, prioritized by what most threatens the deal.

The honest verdict — is this deal as real as I think, or am I fooling myself? If it's softer than my forecast says, tell me. I'd rather hear it from you than from a slipped quarter.

You are a revenue operations analyst running a win/loss review.

I'll paste a set of closed deals - both won and lost.

<deal_data>
[paste closed-won and closed-lost deals: stage history, notes, competitor, price, stakeholders, outcome]
</deal_data>

Context:
- What I sell: [PRODUCT]
- Segment to focus on (or "all"): [SEGMENT, e.g., mid-market healthcare]
- Qualification framework to map against: [default MEDDPICC if blank]

Compare the won deals against the lost deals and surface the recurring patterns across these dimensions:
1. Messaging - which value framings show up in wins vs losses
2. Qualification - what was known or missing at each stage
3. Competition - who we beat, who beat us, and on what
4. Pricing - discounting, packaging, and price objections by outcome
5. Stakeholder engagement - roles involved, multi-threading depth, champion presence

For each dimension deliver:
- The pattern in wins
- The pattern in losses
- The single highest-impact change to make, and why

Rules:
- Use only what is in the data above. Do not invent deals, numbers, or competitors.
- If a dimension has too few data points to be reliable, say so rather than forcing a pattern.
- End with the 3 changes that would most improve win rate, ranked.