- Date: August 14, 2026
Emotional challenges of transitioning out of your business
- 6 min read

Business owners often tell us that every time they think about transitioning out of their companies, they get stuck. To evaluate the severity of their “transition paralysis,” we ask: Does your business transition keep you up at night? The typical answer is something like “It’s hard to sleep when I don’t know which step to take first. There are so many moving parts, so many people involved, and so much at stake.” And our typical answer is, “You’re right.” It’s not easy to leave your company in the hands of

It’s my life’s work to help business owners create transitions out of their companies that meet their most important goals, keep their relationships intact and position their companies to succeed under new leadership. That’s a tall order, and no transition is as perfect as owners envision because, more often than not, one of their goals (or more) conflicts with others. Then what? Let’s look at a father-daughter family succession case study. From Simple to Complex: A Father-Daughter Family Succession Case Study Owner Greg and his daughter Lisa (not their real

I’ve written in this blog about communication during business transitions. Productive dialogue between owners and successors, owners and spouses and owners and key stakeholders isn’t easy but it’s a requirement for successful transitions. In this post, I will describe how you can use your succession plan to keep your promises. Effective Communication From long experience, I’ve developed four guidelines for owners who want to communicate effectively during and throughout the succession planning process. Prepare for conversations. Know what information you want to gain from the conversation and what information you

In The Dance of Business Successor Development, we described the three phases of teaching and mentoring successors. In Phase 1, owners lead, and successors follow. In Phase 2, owners and successors alternate the lead, and in Phase 3, successors lead, and owners follow. The trickiest part of the dance is Phase 2 because when successors begin to assume greater levels of responsibility, they make mistakes and owners must let them. It’s awkward, and miscommunication and misunderstandings are almost inevitable. That’s why we developed three rules of engagement for successor development

When was the last time you thought about how you do what you do to make your company successful? If you are like most owners, the answer is “I don’t think about how I do what I do. I just do it.” Part of succession planning, however, involves teaching a successor to do what you do. We call this phase of succession planning “The Dance of Business Successor Development.” The Dance of Business Successor Development Before the dance begins, you create a curriculum meaning you break down what appear to

Have you ever imagined that the transition out of your business could be the capstone of your career as a successful owner? Or do you think of the succession planning process only as contingency planning for your retirement? For a moment, consider the possibility that business succession planning can lay the groundwork for your next adventure and ongoing success of your business and all those who depend on it. First, the transition of a business is not just a one-time event. It is a journey that involves owners, their families, successors, and companies. Second, the business succession

Successful business owners are typically visionaries. They have the ability to look ahead, anticipate both threats and opportunities and take action accordingly. Just as typically, the eventuality they will one day leave their companies can be a blind spot. Even owners who recognize they will put their companies in the hands of successors “someday” often don’t know how to approach the topic with others without making everyone uncomfortable — or worse. If you are one of these owners, here are six tips we share when we coach owners through introducing

Succession planning, business transition planning, business succession planning and exit planning: These are just a few of the terms that business owners see in messages, posts, and newsletters from their CPAs, attorneys, investment advisors, life insurance agents, business consultants, business brokers, and even their bankers. Unlike business succession consultants, many of these professionals have added exit or succession planning to their core practices. Regardless of what they call themselves, all mean well: They want to contribute their expertise to help business owners transfer their companies to family members, employees or

I’ve written before about why it’s never too early to start business succession planning. Yet, even when owners recognize the benefits of planning for the transition of their companies well in advance of any transfer, some continue to put it off. Why? In my work with business owners, my team and I identified four assumptions that they commonly make about the succession planning process. 1. Expect perfection When owners begin to get a clear picture of everything that’s involved in a successful business transition, many get stuck. For good reason!