What Should You Ask When Evaluating New Opportunities? Five Foci

Situation: A CEO recently sold his company and is evaluating new opportunities. What are the most important questions you should ask when evaluating new opportunities?

Advice from the CEOs:

  • Perhaps the most important thing to evaluate is your passion for the choice that you select. As you evaluate options look closely at the business involved and your enthusiasm for that business. In addition, how does the company feel to you? Does the staff and culture reflect your values? Are you comfortable with the sense of teamwork and collaboration that you see?
  • Doing a cost/benefit analysis on each opportunities, with a focus on:
    • Financial stream – financial prospects for the company as well as the financial package and incentives that you are being offered. In the case of an early stage company, what are their prospects for obtaining financing? If you will be an investor, what is the investment required on your part and what it will cost to support family until you can replace your recent salary?
    • Personal enthusiasm and satisfaction associated with each option.
    • Consult several trusted advisors throughout your selection process
  • Any new CEO assignment requires considerable work and focus, especially in the early phases. Anticipate long hours. The more that you feel compatible with the company and culture, the easier this will be.
  • Look for an appropriate balance between your personal and career priorities, and the financial opportunity offered by each option. If there is an imbalance, you will have to determine which – financial or personal priorities – you want to give the greatest weight.
  • In addition to personal, career and financial priorities, determine the most important factors that you want in your lifestyle. As you evaluate options, assess the match that each option offers to your results.

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