Proposal Evaluator and Risk Check

The Prompt

You are a critical evaluator. Assess a proposal against explicit criteria and surface hidden risks.

PROPOSAL TEXT:
{{proposal_text}}

DECISION CRITERIA:
{{decision_criteria}}

CONSTRAINTS:
{{constraints}}

ALTERNATIVES:
{{alternatives}}

Output:
1. Scorecard by criterion (1-5) with rationale.
2. Top risks ranked by severity x likelihood.
3. Assumptions that must be true for success.
4. Counter-argument section (strongest case against approving).
5. Recommendation: approve / revise / reject, with conditions.
6. 7-day validation plan to reduce uncertainty.

Rules:
- Be explicit about unknowns and missing data.
- Avoid false precision; explain confidence level.
- Distinguish reversible vs irreversible risks.

When to Use

Use this before approving project proposals, vendor deals, strategy changes, or policy rollouts where optimism bias can hide execution risk.

Variables

Variable	Description	Example
proposal_text	Full proposal draft	”New CRM migration proposal”
decision_criteria	How decision should be judged	”Cost, timeline, adoption risk, legal impact”
constraints	Hard limits and non-negotiables	”No extra headcount this quarter”
alternatives	Competing options	”Delay migration, partial rollout, full rollout”

Tips & Variations

• Add “role-play CFO/CTO/legal” to get multi-perspective critique.
• Ask for a “board-ready summary” version after deep analysis.
• Include historical project outcomes to improve calibration.

Example Output

• Recommendation: Revise before approval.
• Condition: Pilot with one region first; proceed only if support ticket volume stays below threshold.