Q: My two siblings and I all work for our father in our family’s business. Lately my dad has been talking more about retirement and stepping back. The problem is, he built this business from the ground up and has always been heavily involved with the day to day decisions. He won’t seem to let go of the reins. How are we supposed to ever take over if he micromanages us until the 11th hour? Plus I fear he is going to give the top leadership position to my brother, because he’s older, even though I believe I would do a better job. How do I bring up these concerns to him?

A: In successful small to midsize businesses day will eventually come when the owner must begin the process of handing over the reins to someone else if the business is to survive without them. Often this can be difficult when the habit of making all key decisions is well established by the owner. According to exit planning expert Pat Ennis, ideally a business owner should begin the transition process years in advance; creating scalable systems and turning over responsibilities to the next generation of leadership. This is particularly true in family businesses where adult children are likely to be taking over those responsibilities. When there’s more than one candidate, the question of who will take that top leadership role can be dicey. Initiating a bottom up conversation about these sensitive topics requires diplomacy, curiosity, humility, and empathy from everyone involved. Many people in your family likely have strong opinions about these issues, so protecting your family relationships during these negotiations can be challenging. Sometimes having an outside professional to help you can be incredibly helpful. If you feel you’re at an impasse, our compromise coach Cherie Morris, JD suggests you consider asking your father about inviting an experienced neutral person to help you all talk through these issues.


Pat Ennis is the founder and president of Ennis Legacy Partners.  He and his partner Corby Megorden’s mission is to help business owners enjoy life in the business and plan for life after the business.  Kentlands Psychotherapy’s owners have worked with this team and found their assistance to be invaluable.

Cherie Morris is the co-owner os Recompose.Us .  Her mission, along with her partner Elizabeth Carr, is to help people resolve conflicts while preserving and repairing their relationship.


In the video below, the four of have a lively conversation on the issues using the HBO series Succession as an example of what NOT to do. Enjoy