From Hiring Executives to Engaging Advisors
Why the most meaningful growth happens when leaders step back
Running a business inevitably creates pressure to solve problems quickly. As complexity increases, many founders and owners respond by hiring more executives, people tasked with managing day-to-day operations, optimizing functions, and keeping the machine running.
That instinct is understandable. But in many cases, it treats the symptoms rather than the cause.
Over time, I’ve observed that the more consequential shift is not adding another operator inside the business, but engaging someone who works on the business—helping the leader step back, clarify what actually matters, and make better decisions when the stakes are high.
That role is the business advisor.
Working On the Business Versus In It
Executives are essential. They execute, manage, and operationalize decisions within the
organization. Advisors serve a different function entirely.
An advisor operates outside the daily cadence of the business. Their value lies in perspective, helping leaders examine assumptions, recognize patterns, and navigate tradeoffs that are often invisible from inside the system.
This distinction matters most during moments of transition: growth, stagnation, restructuring, or strategic uncertainty. When decisions carry long-term consequences, clarity becomes more valuable than speed.
A Familiar Example: Apple and Mike Markkula
One of the clearest illustrations of this dynamic comes from Apple’s early years. Steve Jobs did not simply surround himself with operators; he sought guidance from Mike Markkula, who became an investor, mentor, and strategic advisor.
Markkula helped shape Apple’s marketing philosophy and long-term vision, work that went far beyond operational execution. His influence wasn’t about managing tasks; it was about shaping how the company thought about itself and its future.
That distinction played a meaningful role in Apple’s trajectory.
Advisors as Catalysts for Innovation
Advisors bring an external vantage point that allows them to challenge assumptions without being constrained by internal politics or historical momentum. They ask questions that rarely surface in operational meetings:
- What problem are we actually solving?
- What assumptions are we protecting?
- What no longer fits the stage of the business?
Howard Schultz has spoken openly about the influence of advisors and mentors throughout Starbucks’ evolution. The decision to transform Starbucks from a coffee bean retailer into a global coffeehouse experience wasn’t an operational optimization, it was a strategic reframing shaped by outside perspective.
That reframing changed everything.
Leadership, Judgment, and Decision Quality
At its core, advisory work is about improving the quality of leadership judgment.
Jeff Bezos has often described how advisors played a critical role in Amazon’s early years, helping him think through decisions that couldn’t be reduced to metrics alone. As Amazon scaled, those conversations helped shape a long-term orientation that resisted short-term pressure.
Good advisors don’t make decisions for leaders. They help leaders make better decisions themselves.
A Note from the Literature
Michael Gerber captured this distinction succinctly in The E-Myth Revisited when he wrote:
“The entrepreneurial model has less to do with what’s done in a business and more with how it’s done.”
Jim Collins echoed a complementary idea in Good to Great, emphasizing that vision alone is insufficient without disciplined thinking and the right people around the leader.
Both underscore the same principle: enduring success is rarely accidental, it is shaped by how leaders think, not just what they do.
Stepping Back to Move Forward
Hiring executives to manage complexity is often necessary. But when businesses plateau, struggle, or face pivotal decisions, the limiting factor is rarely execution alone.
More often, it is clarity.
The leaders who navigate these moments well tend to have someone outside the business helping them slow down, examine their thinking, and choose deliberately. That perspective, quiet, disciplined, and independent, is what allows organizations to evolve rather than simply react.
In my experience, that is where the most meaningful growth begins.