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10 Questions Top Advisors Ask Every Business Owner They Meet

10 Questions Top Advisors Ask Every Business Owner They Meet

  1. How do you see your involvement in your business changing or evolving in the future?
  2. What’s your next great adventure after you leave your business?
  3. What obstacles are you seeing that could derail your business or personal goals in the coming years?
  4. What role does your business need to play in helping you achieve financial freedom?
  5. What is your plan for your ownership interest in your business: do you plan to pass ownership along, or arrange for a sale someday?
  6. What method or methods have you used to assess the value of your business, and how confident are you in that process?
  7. Given your (buyer or successor) plans, have you thought about who the best leader for your business might be?
  8. Tell me about what will happen with your customers, your vendors, your employees, and your competitors if something happens to you.
  9. What planning suggestions have other business advisors given you to prepare for the future ownership of your business?
  10. What do you see as your greatest challenge when you think about planning for the future?


  • What other questions should I be asking?
  • How can I help you and your business be more successful?

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