Why Don’t Most Business Owners Plan Their Sale?

About the Episode

The majority of business owners don’t plan their exit. Not planning your exit can leave money on the table and decrease the chances of a successful sale. Why don’t most owners plan their exit? What should you take into consideration when planning an exit from your business? What are the common pitfalls of business owners looking to sell? How long does it take to adequately prepare your business for sale? We answer all these questions and more during this in-depth interview with Wendy Dickinson, a business coach specializing in helping mid-market business owners with exit planning. Wendy has a background as a therapist, so we also discuss the intersection between life and business and how entrepreneurs can bridge this gap to ensure their exit meets both goals. We also discuss the psychology of transitions, how you can leave money on the table, and the basics of corporate governance for family businesses.

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In this Episode

5:05 What is exit planning?
6:25 What percentage of business owners have an exit plan in place?
7:00 Why do so few business owners plan their exit?
9:40 How long does it take to prepare an exit strategy?
10:55 When is the right time to start thinking about an exit strategy?
14:00 Why is it important to plan your exit?
17:20 Why do most business owners tend to DIY their exit planning?
18:35 What does the exit planning process look like?
24:00 What are the basic components of an exit strategy?
32:45 What unique concerns do family businesses need to address when planning their exit?
41:20 What is 360-degree feedback?
46:00 What tools do you commonly use to help owners plan their exit?
47:45 What’s your advice to an entrepreneur considering launching a new product or service before selling their business?
49:30 How do you address the intersection between life and business?
53:00 What are the different tools to use for family governance?
55:45 How has your background as a therapist impacted how you help owners navigate the process?
59:30 How common is it for business owners to sell their business because they think it will make them happier?


  • It’s critical that your team of advisors (attorney, accountant, etc.) have M&A experience.
  • It doesn’t take long to prepare an exit strategy, but it does take a long time to execute the steps outlined in your exit strategy.
  • Executing one major objective per month over a period of five years allows you to execute 60 major objectives toward a successful exit.
  • For many entrepreneurs, the purchase price isn’t always the deciding factor when selling a business.
  • Most business owners do not have an accurate assessment of what their business is actually worth.
  • Speed is critical to a successful sale – planning your exit speeds up the process and minimizes the chances of problems occurring during the sale process.
  • Most small business owners don’t have an advisory board. An advisory board is different than a board of directors.
  • We, as humans, tend to avoid difficult decisions and conversations.

Learn More About This Episode

Resources Mentioned in This Episode

Meet Our Guest

Wendy Dickins

Wendy Dickins

Founder of Ascend Coaching Solutions LLC

Wendy Dickinson is the founder of Ascend Coaching Solutions LLC, a coaching firm that specializes in working with business leaders and executives who plan to expand their leadership capacity as the company grows. They offer a therapeutic approach to business coaching, and meet clients at the intersection of business and life.

As an expert in organizational culture within government and business settings, Wendy offers talent optimization tools, along with value-added, consciously profitable strategies to potential investors, future prospects, and strategic partners. Techniques include increasing an organization’s changeability, psychological safety, and resilience.

Wendy has co-founded three companies, one of which sold to a Fortune 1000. Raised with small business in her blood, founder Wendy is from a family of entrepreneurs who created jobs for themselves, not assets in a portfolio. Growing up, she saw the impact of creating a job rather than an asset from a privately held business.

Wendy holds a Master’s in Counselor Education from the University of Virginia, a Bachelor’s degree from the University of Mary Washington, and certification from the International Coach Federation. Wendy brings her experiences as an individual and group therapist to every coaching relationship. She is passionate about seeing business people who have spent their lives building their businesses reap the rewards of their efforts.

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