Identify your Target Boss, Company, and Compensation

After you’re clear on your personal motivations, it’s time to move on to your ideal boss, company and offer package.

Your ideal boss

• What title do they have? CEO, CMO, CTO, CLO, GM, president, etc.

• What is their Zone of Genius?

• What do they want to be doing more of and less of?

• Have they had a Chief of Staff before?

• Are they a first time top executive or a seasoned leader?

• Are you expected to be on call 24/7 or can you have a life?

• Is your tour of duty timeboxed or open ended?

• How open are they to mentoring and developing you in your career?

• What are your exit opportunities?

Your ideal company

• What kind of company culture do you want to work in?

• What size company do you want to work at?

• What industry or sector do you want to work in?

• Are you virtual, hybrid or remote?

• What stage company do you want to work for?

• How well capitalized is the company?

• How risky is the business?

• How much turnover does the company have?

• What position are they in their market?

Your ideal offer

• How much do you want to get paid?

• What matters more, cash or equity?

• When do you want to start?

Make sure to add “and why?” to the end of each question to get to crystal clear conviction. This will help you identify target opportunities and speak much more confidently in interviews.

Ready to join our Cedar Talent Network of aspiring and current Chiefs of Staff? Submit your application and get started here.