The Conversations that Make or Break Succession

The biggest risks in a business transition often show up long before the paperwork is signed. After years of working in the business day in and day out, business owners can fill in the blanks with assumptions that never get tested.

By truly understanding what their successor thinks about the business, business owners can help eliminate assumptions that can throw a major wrench into the succession process. Read on to learn how to navigate conversations with your successor to have the best transition possible.

Why Early Conversations are Crucial

Judi Cunningham is a Certified Exit Planning Advisor (CEPA®) who specializes in assisting business owners with internal transitions. Before any documents regarding the sale of the business are drawn up, Judi, founder of Trella, says that business owners need to have honest conversations with their successor.

“The beginning of this process is one of the most important times, because it sets the stage and sets the tone for the whole exit process.”

A major decision, such as transitioning a business internally, needs time to breathe. By urging their clients to connect with the successor, business owners and the next generation of ownership are less likely to look back with regret at the end of the process.

Assumptions that Kill the Succession Process

Just as important as having early conversations with your successor is having the right conversations. Judi suggests being up front with whoever is involved in the succession process and asking blunt questions.

“Ask them what they want. Do you have any interest in any of this? Do you see yourself ever being involved? Do you care about the business? What do you think about me selling the business, et cetera?” she says.

The longer that assumptions about the business are left to sit, the more likely they are to harden into a perceived reality. By asking these questions and asking them early, business owners and their advisors can avoid having to make difficult adjustments later on in the succession process when things are more set in stone.

Every Transition is a Family Transition

CEPAs should encourage their business-owner clients to ask these questions, even in exits that don’t involve an internal transition. In the 2026 edition of the Annual Exit magazine, Judi explains that “every single transition is a family transition.”

While some business owners might not put a lot of weight on their legacy after an exit, most want their families to be set for the future. It’s for that reason that Judi insists that every transition is a family one. If family isn’t consulted during the exit planning process, fractures that weren’t obvious before can begin to show after an exit.

The best succession plans are built on honest conversations, not assumptions. When a business owner keeps everyone involved in the business early and often, they create a smooth transition for both the business and the family.

About the Certified Exit Planning Advisor Credential

A Certified Exit Planning Advisor (CEPA®) is a professional credential for advisors who wish to engage with business owner clients through the exit planning process using the Value Acceleration Methodology™. Through the CEPA credential, advisors can provide new offerings for clients and stand out from their non-CEPA peers, all while gaining access to education, resources, and a vast network of like-minded professionals.

Related Resources

• How CEPAs can Guide Succession Planning
• Exit Planning vs. Succession Planning
• The Cha-Cha of Succession