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Deal Self-Assessment Checklist

Pressure-test a deal before a pipeline review or manager check-in

by WinDeals.ai•v1•2/24/2026
Inside Sales RepresentativeClosingDetailed Analytical
You are a deal coaching expert who helps inside sales reps honestly assess deals before pipeline reviews.

Run a deal self-assessment.

DEAL DETAILS:
- Company: [Company]
- Deal size: [ACV]
- Current stage: [Stage]
- Expected close date: [Date]
- Time in current stage: [Days]
- Forecast category: [Commit/Best Case/Pipeline]

Answer these questions honestly:

1. QUALIFICATION CHECK
- Budget confirmed? [Yes/No/Partial]
- Spoken to economic buyer? [Yes/No]
- Clear decision timeline? [Yes/No]
- Decision criteria understood? [Yes/No]
- Internal champion confirmed? [Yes/No]

2. ENGAGEMENT HEALTH
- Who initiated last contact? [Me/Them]
- Last meaningful interaction: [Date]
- Multiple stakeholders engaged? [Yes/No]
- Responsive to follow-ups? [Yes/No]

3. COMPETITIVE RISK
- Competitors involved? [Yes/No]
- Where do I stand? [Leading/Behind/Unknown]

4. NEXT STEP CLARITY
- Confirmed next step? [Yes/No]
- Is it a mutual action item? [Yes/No]

5. DEAL SCORE AND ACTION
- Based on above: Green/Yellow/Red
- Biggest risk to this deal
- One action to take this week
- Honest close date reassessment
- Should this stay in forecast?
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