Deal Risk Scoring

Evaluate individual deal health through multi-signal analysis to prioritize coaching, intervention, and resource allocation.

When to Use This Skill

• Weekly deal reviews and pipeline scrubs

• Before QBRs to identify problem deals

• When deals stall or push close dates

• Prioritizing manager coaching time

• Allocating SE/executive resources

Methodology Foundation

Based on Gong's Deal Intelligence research and Winning by Design's Revenue Architecture, analyzing:

• Engagement velocity (email, meeting frequency)

• Stakeholder breadth (multi-threading)

• Competitive signals

• Timeline alignment

• Champion strength

What Claude Does vs What You Decide

Claude Does You Decide

Scores deals on risk factors Which deals to save vs. let go

Identifies missing elements Resource allocation priorities

Suggests intervention actions Executive sponsor assignments

Tracks velocity trends Final stage/probability updates

Flags competitive threats Win strategy adjustments

What This Skill Does

• Multi-signal analysis - Engagement, stakeholders, timeline, competition

• Risk scoring - Green/Yellow/Red health status with reasons

• Gap identification - Missing stakeholders, stalled stages, unclear next steps

• Action recommendations - Specific interventions to reduce risk

• Trend tracking - Velocity changes over time

How to Use

Assess the risk for this deal:

Deal: [Company Name] Value: $X Stage: [Current Stage] Close Date: [Target Date] Days in Stage: X

Recent Activity:

• [List emails, meetings, calls with dates]

Stakeholders:

• [Name, Title, Role in deal, Engagement level]

Competition: [Known competitors] Champion: [Name and strength assessment]

Instructions

Step 1: Engagement Velocity Score (0-25 points)

Criteria Points

Meeting in last 7 days +10

Email response in last 3 days +5

Multiple contacts engaged +5

Prospect initiating contact +5

No activity 14+ days -15

Step 2: Stakeholder Coverage Score (0-25 points)

Criteria Points

Economic Buyer identified +10

Champion confirmed +10

Technical evaluator engaged +5

Only 1 contact -10

No C-level access -5

Step 3: Process Alignment Score (0-25 points)

Criteria Points

Clear next step scheduled +10

Mutual action plan agreed +10

Decision timeline confirmed +5

Close date pushed 2+ times -15

No defined process -10

Step 4: Competitive Position Score (0-25 points)

Criteria Points

No competition +15

Differentiation clear +10

Incumbent advantage -10

Price pressure -5

Unknown competitive status -5

Step 5: Calculate Total Risk Score

Score Health Action

75-100 🟢 Green Monitor, standard process

50-74 🟡 Yellow Intervention needed

25-49 🟠 Orange Escalate, major action

0-24 🔴 Red Rescue or disqualify

Examples

Example 1: At-Risk Enterprise Deal

Input:

Deal: TechCorp Global Value: $250K ARR Stage: 3 - Proposal Close Date: Feb 28 (pushed from Jan 31) Days in Stage: 28

Recent Activity:

• Jan 15: Proposal sent to John (Dir of Ops)
• Jan 22: Follow-up email (no response)
• Jan 29: Called, voicemail
• Feb 5: Email asking for update (no response)

Stakeholders:

• John Smith, Director of Ops, Champion (was engaged)
• No other contacts

Competition: Competitor X mentioned in discovery Champion: John - went silent

Output:

Deal Risk Assessment: TechCorp Global

Overall Score: 28/100 🔴 RED - HIGH RISK

Score Breakdown

Critical Risks

1. 🔴 Champion Gone Dark - John hasn't responded in 14 days

   • Possible: Left company, lost internal support, chose competitor

2. 🔴 Single-Threaded - No other relationships

   • If John is out, deal is dead

3. 🟠 No Economic Buyer - Never met decision maker

   • John may not have authority to close

Recommended Actions

This Week:

1. Research John on LinkedIn - still at company?
2. Find another contact via LinkedIn/referral
3. Send "breakup email" to force response
4. Check if Competitor X is in active eval

If No Response by Friday:

• Move to Stage 2 or Closed-Lost
• Free up forecast slot

Red Flags to Watch

• If proposal was forwarded to competitor
• If budget was reallocated
• If project was deprioritized

Save Probability: 25%

Without new contact access, this deal is likely lost.

Example 2: Healthy Deal Review

Input:

Deal: GrowthCo Inc Value: $85K ARR Stage: 4 - Negotiation Close Date: Feb 15 Days in Stage: 7

Recent Activity:

• Feb 1: Demo to full team (8 attendees)
• Feb 3: Pricing discussion with CFO
• Feb 5: Legal reviewing MSA
• Feb 7: Call scheduled for Feb 10

Stakeholders:

• Maria Lopez, VP Sales (Champion, highly engaged)
• Tom Chen, CFO (Economic Buyer, positive)
• Legal team (reviewing contract)
• 8 end users attended demo

Competition: None identified Champion: Maria - actively selling internally

Output:

Deal Risk Assessment: GrowthCo Inc

Overall Score: 88/100 🟢 GREEN - HEALTHY

Score Breakdown

Strengths

1. ✅ Multi-threaded - Champion, EB, and end users engaged
2. ✅ Process momentum - Legal reviewing = serious intent
3. ✅ Executive access - CFO in pricing discussions
4. ✅ Champion active - Maria driving internally

Minor Risks

1. 🟡 Legal review - Could surface unexpected blockers

   • Mitigation: Pre-review common redlines

2. 🟡 No competition confirmed - May be unknown

   • Mitigation: Ask directly in next call

Recommended Actions

Feb 10 Call Prep:

1. Prepare redline responses for common legal issues
2. Confirm decision process post-legal
3. Ask: "Is anyone else in consideration?"
4. Get verbal commit from Maria

Close Probability: 85%

Deal is on track. Focus on removing legal friction.

Skill Boundaries

What This Skill Does Well

• Objective risk scoring from available data

• Identifying gaps in deal coverage

• Prioritizing which deals need attention

• Suggesting specific interventions

What This Skill Cannot Do

• Know information not provided (internal politics)

• Predict competitor moves

• Replace relationship judgment

• Guarantee score accuracy with incomplete data

When to Escalate to Human

• Strategic accounts requiring executive judgment

• Deals involving partnerships or M&A

• Unusual contract structures

• Competitive intelligence gathering

Iteration Guide

Follow-up Prompts

• "What's the single most important action for this deal?"

• "Compare risk scores for my top 5 deals."

• "What questions should I ask in the next meeting?"

• "Draft a re-engagement email for the silent champion."

Refinement Cycle

• Initial assessment → Identify top risks

• Take action → Update activity log

• Re-score → Track improvement

• Weekly review → Trend analysis

Checklists & Templates

Deal Health Checklist

• Champion identified and engaged this week

• Economic Buyer met at least once

• Next step scheduled within 7 days

• Competition status known

• Close date validated by prospect

Risk Score Template

Deal: [Name] | Score: X/100 [Status Emoji]

Quick Stats

• Value: $X | Stage: X | Days: X | Close: [Date]

Scores

Top 3 Actions

References

• Gong Deal Intelligence Research

• Winning by Design Revenue Architecture

• MEDDPICC Qualification Framework

• Force Management Command of the Message

Related Skills

• pipeline-forecasting

• Aggregate deal health into forecast

• lead-qualification-meddic

• Deep qualification framework

• account-health

• Post-sale relationship scoring

Skill Metadata

• Domain: RevOps

• Complexity: Intermediate

• Mode: centaur

• Time to Value: 10 minutes per deal

• Prerequisites: Deal details, activity history, stakeholder map