Here's how you might analyze your decision to leave your current director-level job for a C-level role at a startup using the 6 Thinking Hats method:

1. White Hat (Facts and Information):

- Current Role: Stability, familiarity with company culture, secure benefits, and a clear career path.

- New Role: High potential for growth, likely increase in responsibilities, and a chance to shape company culture and strategy from the top.

- Risks: Startups often face financial instability and high pressure; potential for the company to fail.

2. Red Hat (Emotions and Feelings):

- Current Role: Excitement and enthusiasm about the opportunity to lead a company and potentially disrupt the industry.

- New Role: Fear of the unknown and potential failure of the new venture.

- Risks: Pride in being considered for a C-level position.

3. Black Hat (Judgment and Caution):

- Current Role: The startup may lack the resources and structure of a large established company, leading to increased stress and uncertainty.

- New Role: Potential loss of long-term benefits and securities, such as retirement plans and health insurance.

- Risks: The risk of the startup failing could harm your career trajectory and financial stability.

4. Yellow Hat (Optimism and Benefits):

- Current Role: A successful stint at a startup could significantly enhance your resume, showcasing your versatility and ability to scale businesses.

- New Role: Potential for substantial financial rewards if the startup succeeds, including stock options and bonuses.

- Risks: Being at a C-level position could offer a more significant impact and more substantial personal and professional growth opportunities.

5. Green Hat (Creativity and Alternatives):

- Current Role: Consider negotiating a contract with the startup that includes equity and severance protections.

- New Role: Explore the possibility of part-time consultancy with your current employer to maintain some security.

- Risks: Use your network to gather more insights into the startup’s financial health and growth potential.

6. Blue Hat (Process Control):

- Current Role: Set a timeline for making your decision, with milestones for achieving clarity on key uncertainties about the startup.

- New Role: Arrange meetings with key stakeholders in both the current and potential new company to gather insights and advice.

- Risks: Evaluate the decision periodically after joining the startup, with predefined criteria for success to reassess and adjust your career path as needed.

Using the Six Thinking Hats allows you to look at your potential career move from all angles, helping to ensure that your decision is well-rounded and considers multiple perspectives.

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