Deal Risk Scoring

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

What This Skill Does

1. Multi-signal analysis - Engagement, stakeholders, timeline, competition
2. Risk scoring - Green/​Yellow/​Red health status with reasons
3. Gap identification - Missing stakeholders, stalled stages, unclear next steps
4. Action recommendations - Specific interventions to reduce risk
5. 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)

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

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

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

Step 5: Calculate Total Risk Score

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

| Factor | Score | Issues |
|--------|-------|--------|
| Engagement | 0/​25 | No response in 14+ days |
| Stakeholders | 5/​25 | Single-threaded, no EB |
| Process | 5/​25 | Pushed once, no clear next step |
| Competition | 18/​25 | Competitor known but not blocking |
| **Total** | **28/​100** | |

### 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

| Factor | Score | Status |
|--------|-------|--------|
| Engagement | 25/​25 | Daily activity, prospect-driven |
| Stakeholders | 23/​25 | EB + Champion + Users confirmed |
| Process | 22/​25 | Clear timeline, legal in motion |
| Competition | 18/​25 | No competition identified |
| **Total** | **88/​100** | |

### 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

1. Initial assessment → Identify top risks
2. Take action → Update activity log
3. Re-score → Track improvement
4. 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
| Factor | Score | Key Issue |
|--------|-------|-----------|
| Engagement | /​25 | |
| Stakeholders | /​25 | |
| Process | /​25 | |
| Competition | /​25 | |

### Top 3 Actions
1.
2.
3.

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