WHEN SUCCESS CREATES A NEW DILEMMA, PART I
Not long ago, I had conversations with two small business owners that reminded me of a seven-part Monday Morning Notes series I wrote back in 2016. In that series, I argued that the role of a small business CEO can be distilled into three core responsibilities: charting the course, building the team, and tracking performance. (If you’d like a copy of this series in a white paper format, I’d be happy to send you one.) While the specific activities may change as a company grows, these three responsibilities remain constant.
The owners I spoke with had built thriving companies. One was leading a second-generation business, while the other had started his company fourteen years earlier. Both enjoyed strong profitability, steady cash flow, and stable workforces. Importantly, each had a capable management team running the day-to-day operations. Neither had any desire to sell, especially since their children were already involved and being groomed for leadership and, ultimately, succession.
Despite their success, both found themselves in a familiar quandary: What does a business owner do after essentially working themselves out of the job they’ve known and loved?
The Paradox of Success
It may sound counterintuitive, but this stage can be one of the most challenging times for a business owner and the company they’re running. The owner has worked hard to build a successful business, navigating years of struggle, economic turbulence, and shifting market demands. Deciding whether to transition out of the business or stay and enjoy the fruits of their labor can be surprisingly challenging.
Staying too involved risks unraveling what they’ve built. When an owner re-inserts themselves into work that managers were hired and are being paid to handle, it often creates confusion among employees and resentment among managers.
On the other hand, checking out—whether physically, mentally, or emotionally—can be equally damaging. It may leave employees feeling abandoned or uncertain about the company’s direction.
So, what’s the right balance?
Shifting from Operator to Mentor
For many owners, purpose has long been tied to being the chief problem-solver—the person everyone goes to with the toughest challenges. That role often provides both meaning and ego satisfaction. But when the business reaches a level of maturity, the owner’s role must evolve.
The key is to transition from an operator’s mindset to a mentor’s mindset. This shift ties directly into two of the CEO’s enduring responsibilities: building the team and tracking performance.
In Part II of this series, I’ll explore a handful of questions that can bring clarity to a CEO’s evolving role and help prepare them for this challenging yet rewarding chapter in the life of their business.
