9 Questions to Ask When Making a Difficult Strategic Decision

  1. Why now?
  2. Is this a reversible or an irreversible decision?
  3. If irreversible, what makes it so? Can I break it down into multiple smaller decisions, some of which may be reversible?
  4. What factors won’t change in 10 years? How much of our plan is optimizing for durable traits versus betting on new trends and traits that will change?
  5. How do we know we are succeeding in our goal?
  6. What are the top controllable factors that impact the outcome of this decision? Have I focused on them appropriately?
  7. What are the top uncontrollable factors? How am I mitigating their risk?
  8. What is the worst-case scenario? What concrete steps can we take to ensure that the worst-case scenario does not happen? What steps can we take to rebuild, should we hit the worst-case scenario?
  9. What decision would the CEO of the company most likely make if they were in my shoes?
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