Part III
During my breakout sessions at Violand’s Business Planning Retreats, the next question I asked was similar to the previous one: How do you balance the urge to jump in and “just do it” with the responsibility to delegate and lead?
Many participants appeared to struggle with clarifying their thoughts. That’s because this isn’t a tactical decision, it’s an identity shift.
Most owners had built their businesses by being the fixer, the expert, the one who could always “just do it.” That role often became familiar, even comforting. But as the business grew, the very habits that once fueled success could end up keeping them stuck in the weeds. I wrote about this in another Monday Morning Note (November 24, 2025: When Freedom Becomes a Cage).
The discussion groups recognized that real leadership requires moving from doing the work to becoming the conduit through which others learn, grow, and eventually surpass them. They also understood that this shift isn’t mechanical, it’s emotional. It demands discomfort, trust, and the willingness to let go of the identity that once defined their value.
Some participants observed that letting go often stalls the company—not because owners are unwilling, but because the next chapter isn’t clear. This is one of the things attendees were working to clarify at the retreats. When leaders don’t know who they’re becoming, it’s hard to let go of who they’ve been.
For many, significance has been tied to being needed, so stepping back felt risky. And even when they were ready, the reality often hit: they couldn’t delegate to people who hadn’t been prepared to take the reins. Their leadership pipeline hadn’t been built, or daily pressures had kept them from developing the next wave of leaders. In the end, it isn’t the act of letting go that proves most difficult, it’s finding people they can trust, who are capable of handling what they are given.
The next question was: How do you want the next generation to view you and the role you’ve played?
Because some participants in these breakouts were managers rather than owners, they brought additional perspectives to the conversation. Many realized they were responding not only to how they wanted to be perceived but also reckoning with how they may actually be perceived currently.
The leaders people want to follow are those who show up not just with authority, but with genuine care. They serve as trusted advisors—steady, honest, and fair—offering perspective without becoming a crutch. Several spoke of wanting to be mentors and teachers who empower others to run the business, helping them stretch their sense of what they’re capable of and positioning them to eventually outperform their boss.
Some talked about investing in people as individuals first, employees second. These leaders provide stability and support, showing up as a calming, “Superman-in-your-corner” presence when challenges arise.
At their best, most participants hope to be viewed as servant leaders who coach, encourage, and contribute to the community around them. They aspired to be knowledgeable and valuable, yet hold that knowledge loosely, sharing it in ways that help others grow rather than depend on them.
They spoke of caring deeply, listening well, and creating environments where people felt safe enough to pursue their ambitions. A few even described wanting to be “dream makers”—leaders who take satisfaction in helping others achieve goals that may have once felt out of reach.
Through this combination of humility, strength, and intentional guidance, these leaders hoped to inspire future leaders and foster a culture where people can thrive.
Hear more on this topic in Chuck’s latest interview on Straight Talk! with Jeff Cross
