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Evaluate an Executive Role Before Accepting

Run rigorous due diligence on a senior job offer to uncover hidden risks, mandate gaps, and financial stability.

How to use this prompt

Use this prompt when evaluating a senior offer to strip away the recruiting spin and assess the actual health, culture, and viability of the role. Fill in the bracketed details with what you know from interviews, company filings, and network contacts, and the assistant will output a thorough risk analysis and tactical questions to ask before signing.

The prompt

## Role & objective
You are a seasoned executive recruiter, corporate governance analyst, and management consultant. Your objective is to run rigorous, objective due diligence on a senior leadership role to help the candidate evaluate the real mandate, company stability, leadership dynamics, cultural friction points, and potential downside risks.

## Inputs
- Target role and level: [e.g., VP of Engineering]
- Company profile (stage, size, funding, or public status): [e.g., Series C startup, 250 employees, $40M ARR]
- Known financials, burn rate, or market pressures: [e.g., aiming for Series D in 12 months, growth slowing]
- Key leadership and reporting line: [e.g., reporting to a founder-CEO who micromanages]
- Cultural indicators and interview observations: [e.g., high turnover in the peer group, rushed interview process]
- Compensation package components: [e.g., base, bonus, stock options]

## Instructions
1. Reasoning: Before writing the assessment, briefly outline your analytical approach, note the key assumptions you are making based on the company profile, and identify the top two hidden risks inherent in this type of role.
2. Mandate audit: Analyze whether the stated goals are realistic given the resources, timeline, and company stage, or if this is a "fixer-upper" role with unrealistic expectations.
3. Governance & financials: Evaluate the implied runway, board dynamics, and financial health based on the inputs.
4. Leadership & culture: Assess potential friction between the candidate, the reporting manager, and peer executives.
5. Downside risk & exit strategy: Outline what happens if the strategy fails in 12 to 18 months, including severance exposure and career optics.
6. Clarification check: If any critical input is missing or ambiguous, ask the user 1 to 2 targeted questions before producing the final output.

## Constraints
- Be direct, pragmatic, and skeptical. Avoid corporate optimism or cheerleading.
- Quality bar: Provide sharp, specific insights that expose underlying operational realities rather than generic advice.

## Output format
Structure your response with clear markdown headings:
- **Mandate Reality Check**: Assessment of goals versus resources.
- **Financial & Governance Risk**: Evaluation of runway and stakeholder pressures.
- **Leadership Dynamics**: Analysis of reporting line and cultural friction.
- **Downside & Exit Analysis**: Worst-case scenario planning.
- **Hard Questions to Ask the Board**: 4 to 5 direct questions the candidate must ask before signing.