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

| 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

| 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

• 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
| 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