“He's been here since he graduated. He helped us build this thing. I just don’t understand how we got here.”
That’s what the CEO said—quietly, after a long meeting.
The executive in question wasn’t just a hire. He was a foundational member of the team. Loyal. Hardworking. Deeply invested. For years, he showed up, figured it out, and made himself indispensable.
But over the last 18 months, something shifted.
His initiative waned. Deadlines slipped. And, frankly, the role outpaced him. Instead of rising to meet it, he resisted it.
But, the CEO wasn’t angry. He was heartbroken.
Because it wasn’t just about performance. It was about letting go of someone who had been part of the climb.
And as painful as it was, he realized:
Not everyone who got you here is equipped to take you where you’re going next.
Why Leadership Must Evolve as Businesses Grow
As a business moves from startup to scale-up to steady-state, the leadership it needs changes drastically. Skills, mindset, and operating tempo must evolve in lockstep with complexity and growth.
Often, however, leaders who once thrived begin to stall—creating a drag on performance, morale, and margin.
Pro Tip: The most dangerous misalignments aren’t between departments—they’re between a company’s direction and its leadership team.
Phase One: Startup Leadership – Hustle Over Hierarchy
In the early days, leadership is defined by grit and adaptability. Teams are lean. Decisions are fast. Leaders rise because they step up, not because they’re formally prepared.
What works:
-
Generalist problem-solvers
-
Rapid execution
-
Deep loyalty
-
High flexibility
What breaks:
-
Lack of scalable systems
-
Minimal delegation
-
Inconsistent accountability
Pro Tip: Early success doesn’t always translate to long-term leadership potential. Loyalty and longevity must be supported by capacity and growth.
Phase Two: Scale-Up Leadership – Structure and Strategic Execution
Once a company exceeds certain revenue and employee thresholds, the chaos model fails. Infrastructure, planning, and performance management become non-negotiable.
What’s needed:
-
Cross-functional coordination
-
Strategic delegation
-
Financial visibility
-
Repeatable systems and workflows
What shows up if fit is lacking:
-
Resistance to structure
-
Inability to lead through others
-
Siloed decision-making
-
Poor cross-department execution
Pro Tip: When the business outpaces a leader, the symptoms are rarely loud. They show up quietly—in missed deadlines, tension, and operational friction.
Phase Three: Steady-State Leadership – Optimization, Maturity, and Risk Management
In steady-state, leadership must shift again—from building to optimizing. From speed to sustainability. The company’s value lies in predictability, profitability, and strategic vision.
Key traits of effective steady-state leaders:
-
Operational discipline
-
Scenario planning
-
Focus on margins, cash flow, and ROI
-
Long-term team development
What becomes problematic:
-
Legacy leaders who resist change
-
“Founder’s friends” who lack scalability
-
Leaders who miss the transition from urgency to stewardship
Pro Tip: Don’t let high tenure mask low fit. Steady-state requires different muscles—and not everyone wants to build them.
When Legacy Becomes Liability
The moment a role outgrows the person in it, the business begins to slow down. Many CEOs hesitate to make a change because of history, loyalty, or guilt.
But time and again, companies pay the price for waiting too long.
Common warning signs:
-
Missed targets without accountability
-
Shifting blame or deflecting data
-
Avoidance of new systems or reporting
-
Culture strain from passive resistance
Pro Tip: The kindest leadership decisions are often the clearest ones. Delaying what’s necessary only creates confusion and harm—for the team and for the individual.
How to Evaluate Leadership Alignment as You Scale
Here’s a simple framework for evaluating whether current leaders can scale with the business:
-
Define the next 12–24 months.
What does the company need to accomplish, and what leadership traits will support that? -
Identify the capabilities required.
Think in terms of complexity, visibility, communication, and strategic oversight. -
Evaluate each leader objectively.
Use scorecards, outside advisors, or structured reviews to remove bias. -
Take decisive action when needed.
Exit with respect. Protect the business.
Pro Tip: Consider bringing in a strategic advisor to facilitate this process without internal bias or emotional blind spots.
Final Thought: Respect the Climb—But Protect the Summit
Letting go of a long-standing leader doesn’t erase their contribution. It honors it—by ensuring the business continues to grow beyond where they left off.
Growth requires clarity. Clarity requires courage.
Evolving leadership isn’t a betrayal of the past—it’s a commitment to the future.
Need Support Evaluating Your Leadership Team?
The William Stanley CFO Group helps growth-stage businesses evolve their leadership structure, financial performance, and strategic clarity. With deep experience from startup to scale and beyond, our team equips organizations with the tools—and people—they need to go further.
