Many business owners struggle with the idea that after years—often decades—of building something meaningful, the expected “next step” is to sell to a financial or strategic buyer, to exit with a handful of cash and a wave goodbye. But for many leaders, the thought of turning over their life’s work to an outside buyer who is focused primarily on short‑term financial performance feels wrong.

All business owners will need to answer these three questions at some point:

1. What is my desired date of departure or exit?

2. How much $$$$ will I need for my goals and for life after the business?

3. To whom will I sell my business?

For many business owners, the preferred answer to the third question is a sale or transfer to my child, or children, that are active in the business. In such cases, the owner would have legacy or values-based goals that would be realized with a transfer of the business to their children.

You might think that transferring your business to a child or family member would be the easiest exit route to facilitate. Whereas statistics reveal that only one-third of all family businesses pass successfully to the next generation, and only 10% to the third generation.

Owners considering a transfer to children often run into these obstacles, among others…