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Deal Risk Assessment

Identify and mitigate deal risks

by PromptingLLM•v1•2/7/2026
Closing
You are a sales manager who helps reps forecast accurately and spot at-risk deals early.
 
 I have a deal in my pipeline that I want to assess objectively for risk.
 
 DEAL DETAILS:
 - Opportunity: [Company, deal size]
 - Stage: [Current stage]
 - Timeline: [Expected close date]
 - Champion: [Name, title, engagement level]
 - Competition: [Known competitors]
 - Deal history: [Key milestones, what's happened]
 
 MY GUT FEELING:
 [What makes you confident or concerned]
 
 Run a comprehensive deal risk assessment:
 
 1. RED FLAGS CHECKLIST
  Score each (0=no risk, 10=critical risk):
  
  RELATIONSHIP RISKS:
  - [ ] Only talking to one person
  - [ ] Haven't met economic buyer
  - [ ] Champion has low influence
  - [ ] Weak executive sponsorship
  - [ ] Relationship feels transactional
  
  PROCESS RISKS:
  - [ ] Buying process unclear
  - [ ] Timeline keeps slipping
  - [ ] Can't get next meeting scheduled
  - [ ] They won't commit to next steps
  - [ ] Multiple approvers not engaged
  
  VALUE RISKS:
  - [ ] ROI case is weak
  - [ ] No clear pain identified
  - [ ] Solution isn't a priority
  - [ ] Budget isn't confirmed
  - [ ] They're exploring, not buying
  
  COMPETITIVE RISKS:
  - [ ] Don't know who else they're evaluating
  - [ ] They mention 'cheaper' options
  - [ ] Comparison criteria unclear
  - [ ] Status quo is comfortable
  
  TOTAL RISK SCORE: [Calculate]
 
 2. DEAL HEALTH DIAGNOSIS
  Based on score:
  - Healthy (0-15): On track
  - At Risk (16-30): Needs attention
  - Critical (31+): May not close
  
  Your deal: [Diagnosis and reasoning]
 
 3. MISSING INFORMATION
  What don't you know that you should?
  - Questions to ask
  - Information to uncover
  - People to talk to
 
 4. MITIGATION PLAN
  For each red flag:
  - What to do about it
  - By when
  - How to measure if it's resolved
 
 5. FORECAST RECOMMENDATION
  Should this be:
  - Commit (90%+ confidence)
  - Best Case (70-90%)
  - Pipeline (50-70%)
  - Upside (<50%)
  
  Recommendation: [With reasoning]
 
 6. MANAGER CONVERSATION PREP
  What to discuss with your manager:
  - Help you need
  - Resources to request
  - Strategic guidance needed
 
 Provide as a deal review document.
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