Part IV
I concluded each of my breakout sessions with the same question: What legacy do you want your leadership to leave?
I was struck by the consistency of the responses, especially considering the age gaps and variety of titles, genders, and familial relationships of the participants.
When these leaders talked about the legacy they hoped to leave, they didn’t point first to balance sheets or headlines. They talked about who they are, not what they’ve done.
They wanted to be remembered as resources, not crutches; steady mentors who helped others learn to run the business with confidence. The goal was for their ambition to be measured by character—not KPIs—including wisdom, approachability, clarity, and a steadiness that outlasted any quarterly metric.
These leaders hoped their impact would extend beyond their own tenure, creating something durable enough to serve the next generation, whether that’s generational wealth, a stronger community, or a culture that makes people better for having been part of it. Integrity, ethical service, and follow-through are non-negotiables, as are respect, trust, and honesty. They value learning, hard conversations, and the courage to do what’s right even when it’s inconvenient.
Legacies are built in small, daily interactions: caring for customers, supporting their teams, and taking responsibility for more than their job descriptions demand. They want to be the kind of people others seek out for wisdom or advice—not because of their title, but because of their character. A reliable advisor. A mentor. A good father or friend. Someone who leads with love, builds deeper relationships, and shows up authentically.
Ultimately, they understand that the more experience they gain, the more they recognize how much they still have to learn. That humility fuels a growth mindset anchored by accountability. It keeps them curious, grounded, and committed to serving others rather than being served.
If their legacy is anything, they hope it’s this: a life that lifted others, a business that outlasted them, and a reputation defined by the kind of person others were proud to follow.
In conclusion, it would have been easy to assume that the thirty- and forty-year-old owners in the groups were singularly focused on the typical challenges of early-stage companies. But as I listened, I realized that wasn’t the case. Instead, they shared the same concerns as everyone else.
In the end, while many expressed the usual frustrations of running a business: cash flow, hiring, customer and employee retention, competition, and so forth, they understood that leading a legacy business isn’t about stepping away from the work; it’s about stepping aside so others can step forward.
A leader’s legacy isn’t measured by how many problems they solve, but by the culture they shape and the people who grow because of their consistency, integrity, and wisdom—especially during the tough times. Real impact doesn’t come from doing more, but from empowering others to do what they once held tightly.
The through-line in all the breakout sessions was that regardless of the age of the business or the age of the business leader, they all recognized that their job of being a leader was about character, not just accomplishments. That success isn’t defined by how many trophies you raise, but by how many people you lift up.
Hear more on this topic in Chuck’s latest interview on Straight Talk! with Jeff Cross
