Part I
Wrapping up VMA’s Business Planning Retreats for the year gave me a front-row seat to nearly 150 business owners laying out their plans for 2026. Their optimism was contagious, and the clarity of their goals reminded me why this program matters so much.
Each retreat included round-table discussions on key business topics. Instead of turning these sessions into mini-lectures, we asked participants to talk about the issues that keep them up at night. The topic I chose to lead centered around a shift many owners experience as their business matures: moving from a “can-do-it” mindset—one that defines most small business founders—to becoming a conduit for others.
I’ve seen this shift occur once an owner is no longer battling to make payroll every week or wondering whether the business will survive another quarter. Success brings its own questions. People start reassessing the sacrifices they’ve made along the way, and some even begin to reconsider their definition of success altogether.
My groups included not only owners but also senior managers representing companies of all sizes, stages, and generations. Over five sessions, I had roughly 75 to 100 participants.
Here are the six questions I posed:
- How do you define the word elder?
- How has your definition of success changed as you’ve gotten older?
- What tasks or decisions were the hardest for you to let go of, and why?
- How do you balance the urge to jump in and “just do it” with the responsibility to delegate and lead?
- How do you want the next generation to view you and the role you’ve played?
- What legacy do you want your leadership to leave?
To set the tone, I began with the first question, curious to see how often the word older would surface. While a few mentioned age, most spoke instead about wisdom, mentorship, guidance, and stewardship. More than one participant described working for someone younger who, nonetheless, carried the presence and insight of an elder.
Certain themes echoed throughout the conversations: integrity, experience, humility, role modeling, and leadership.
What struck me most was how many participants—regardless of age—recognized that their position in the company already made them an “elder” in the eyes of others. People were looking to them not only for answers but for example.
That realization seemed to shift the room, from can-do-it achievers to leaders willing to become conduits for the generations following behind them. Next week, I’ll explore the discussions my groups had around questions two and three. In the meantime, you might find it interesting to ask those questions of yourself and then see how your answers line up with the group’s.
Hear more on this topic in Chuck’s latest interview on Straight Talk! with Jeff Cross
