Passing the Baton before You Retire
Passing the Baton before You Retire

Passing the Baton before You Retire





Passing the Baton before You Retire

A Q&A with entrepreneur and Trust Company of Illinois founder on how he prepared for his next lap.

Relinquishing the business that has defined you is no walk in the park. For many entrepreneurs, it’s more like a walk through a wilderness. Amazon is populated with books on succession planning. And yet successful transitions are rare in smaller organizations. The timing of the entrepreneur often doesn’t match up with the needs of the business.

Many entrepreneurs can’t let go.  Others stay on too long.

In January, Greg Osko, founder of the Trust Company of Illinois and TC Wealth Partners, retired. The transition was planned well in advance of his retirement. Greg and his wife now live near a beautiful Tennessee lake, where spring comes a lot earlier than it does in the Chicago area. In this interview, Greg Osko reflects on the process of passing the baton—so both entrepreneur and company are poised for the next lap.


You retired at 70 – a little later than typical retirement.

Greg Osko: With the change of leadership to Bill Giffin, the new CEO, our company went through a disruptive time. There was a change of personnel and long-term goals. This type of transitioning takes time. Seventy-five percent (75%) of our clients switched to another TC Wealth Partners advisor over a five-year period and we’ve retained almost all of our clients. I wanted to make sure the company had the right person in leadership and that the company was stable before I retired.

I planned to be out of day-to-day leadership at 65 and active service at 70. And that’s what happened.


How did you navigate the changes during the five years?

Increasingly, I had fewer clients and responsibilities. I sat on the board and leadership team but wasn’t running anything or engaged in any kind of long-term projects—because I wasn’t going to be around long term.

It was a good transition from being fully engaged to not being engaged at all. Bill (Giffin) and I are low-drama guys, and we got along well. While the transition was not without its bumps, our relationship was always strong and warm.

The last year I had one foot in the door and one foot out the door.


What’s that like?

I would say there is more good than bad. You’re not going from full-bore to sudden shut-down—in which you have a completely different life. From that standpoint, a wind-down is good and beneficial.

In my case, it was kind of a glorious period. I was still around, and I could still contribute, but I didn’t have the pressure of being the leader anymore, which is what I didn’t want. That requires a lot of energy. It requires someone who is Bill’s age, not mine.

Progressively, I learned I didn’t want the responsibility anymore. At one point, obviously, I thrived on all that. But at the same time, I could see that the truism is true: speed of the leader is the speed of the team. When you’re 65, you just can’t operate at the same speed level that you can at 45.


So why keep one foot in the door?

I felt I had a responsibility to our clients and shareholders.

A lot of business owners and entrepreneurs don’t think through and execute a transition like this. They just sell their business. While that can be an expedient, financially rewarding way to end things, it doesn’t necessarily serve the clients best. A lot of times the sale of the business results in turmoil; this can negatively impact clients.

We had an objective of being a multi-generational, independent business. Consequently, we planned for succession for a long time. Some businesses struggle with issues that we didn’t face. For example, some entrepreneurs might want their son or daughter to lead the business but realize for a variety of reasons that he or she isn’t capable of the task or doesn’t want any part of it. That’s not easy.

One of the big problems, though, is simply a lack of succession planning.


What’s the risk with delaying or avoiding succession planning?

Aside from not serving clients and shareholders, the business loses value. The leader/owner is a big part of the value of the business. And if he or she is not coming along—or leading a succession plan—then the business loses its value.


What would be your advice to entrepreneurs struggling to let go?

They should hire a business transition consultant, with expertise in family and relational dynamics, especially if they have no plans to sell. If you are planning on continuity, you need a game plan. But that first requires the owner to recognize the problems and demonstrate a willingness to address them. Part of the challenge is often the owner is in denial. It’s simply too painful to address.

In addition, for many entrepreneurs, their business is a huge part of their identity. There is nothing to look forward to in retirement. If a business owner does get an offer, I often say, “Take it.” The temptation is to think, “I’ll get another offer down the road.” My advice is to strike while the iron is hot.


Can you identify with the struggle to let go?

Absolutely. But because I’ve lived through some of these problems—and advised clients struggling with these issues—I may be a bit more aware. I think I finally reached a place where I no longer needed work to validate my ego. That might sound simplistic, but I am at peace with what I am doing in retirement because I believe that I’m simply following God’s directive for my life.

I have felt that for a long time.


Tags:  Business Transitions, Entrepreneur, Founder, Leadership, Leaving an Organization you Founded, Leaving Behind a Thriving Business, Life after Retirement, Mid-size Business Leadership, Passing the Baton, Planning for Retirement, Retirement, Retirement Planning, Small Business Leadership, Succession, Succession Planning, Transitions

Note:  The content of this article is for guidance and information purposes only and is not intended to be construed as advice. Information provided is not intended to provide investment, tax, or legal advice.