Nobody talks about this part. There is plenty of content about how to plan a succession, who should succeed you, what the documents should say. But the situation I want to address today is the one that does not get written about: you have already named a successor, done the paperwork, started handing things off, and somewhere in the last six months you have had the quiet realization that something is not right.
This happens more than most business owners would admit. And I say that with zero judgment because I have watched it happen to smart, careful people who did everything the right way and still ended up here. The reason it happens is not usually that they chose the wrong person in some obvious way. It is that the skills that made someone an excellent number two do not always translate seamlessly to running the show. Being a great operator under someone’s direction and being the person who has to make the calls and carry the weight of final decisions are genuinely different things.
The Earlier You Have the Honest Conversation, the More Options You Have
If you find yourself in this situation, the most important thing I can tell you is that time matters. The longer you wait to acknowledge that something is not working, the more you constrain your options. Early in a succession that is going sideways, you still have room to restructure roles without anyone losing face, to bring in outside perspective, to have a direct conversation that might redirect things in a way that works for everyone. Wait too long, and the damage starts to compound. Client relationships get affected. Team morale shifts. And now you are not just fixing a succession problem, you are also fixing everything that went wrong while the succession problem was being avoided.
Having that honest conversation is hard. Especially when the person you are having it with is someone you genuinely care about and have invested in. But staying the course out of loyalty or because you feel responsible for the situation is how you end up in the worst outcome: having to take the business back after significant damage has already been done.
The Plan B You Should Have Had Before You Started
The best succession plans I have seen are not the ones that went perfectly. They are the ones that had a plan B built in before anyone needed it. What happens if the succession is not working at the 12-month mark? Who makes that call, and how is it made? What is the structure that allows you to course-correct without it becoming a crisis? Those questions feel uncomfortable to ask at the beginning, when you are optimistic about the person you have chosen and the plan you have built. But they are the questions that separate a succession plan that holds up from one that falls apart under pressure. Been there. Done that. Build the plan B before you need it.
