No One Taught Me How to Delegate and It Nearly Broke Me
I used to think delegation was a luxury.
Something you did once your systems were perfect, your team was seasoned, and your workload was manageable. Until then? You rolled up your sleeves, stayed late, and carried the weight yourself. That’s what responsible leaders did—or so I believed.
That mindset nearly burned me out.
When I became head of a 360-student K–8 school with limited resources, I walked into an environment defined by scarcity. No admissions director. No marketing team. No instructional specialists. An overextended administrative team. A board that expected rapid academic improvement after years of stagnation.
And me—trying to hold it all together.
Like many leaders, I responded by doing more. More hours. More decisions. More responsibility absorbed into my own plate. I told myself I was being committed. In reality, I was becoming a bottleneck.
I still remember the moment when that reality hit me squarely. One of my administrators came into my office, exhausted and visibly upset. She said quietly, “No one’s going to say this to you, but you’re pushing people too hard.”
She wasn’t accusing me of being uncaring. She was telling me the truth: my leadership style—rooted in control and urgency—was unsustainable. For me. For the team. For the school.
That was the moment I realized something important: delegation isn’t about offloading work—it’s about redesigning leadership.
The Shift That Changed Everything
One of the first people who helped me see this differently was Laurie, our office administrator.
Laurie was exceptional. Organized. Warm. Trusted by parents and staff alike. She handled secretarial duties flawlessly—and quietly took on admissions-related work whenever we needed help. Over time, it became obvious that we were underutilizing her strengths.
Instead of keeping her boxed into a role she had outgrown, I made a decision that felt risky at the time: I created a new position—Admissions Director—and promoted her into it, adding responsibility for PR and multimedia as well.
The result?
Laurie thrived. She brought energy, creativity, and ownership to areas where the school had long struggled. The school benefited immediately. And years later, she still reaches out to thank me—not for reducing my workload, but for believing in her.
That experience reshaped how I understood delegation. I wasn’t “losing control.” I was multiplying leadership capacity.
Why Leaders Resist Delegation (Even When They Know Better)
Across industries, leaders resist delegation for remarkably similar reasons:
“It’s faster if I do it myself.”
“If I’m accountable, I need to stay involved.”
“I don’t want to burden my team.”
“What if it’s not done right?”
These concerns feel rational in the short term—but they carry long-term costs. Leaders become exhausted. Teams become disengaged. Growth stalls because everything funnels through one person.
Delegation isn’t a personality trait. It’s a learned leadership discipline—and one most of us were never taught.
What Delegation Really Is (And Isn’t)
Delegation is not dumping tasks.
It’s not abdicating responsibility.
And it’s definitely not micromanaging from afar.
True delegation is the intentional transfer of authority, not just activity. It requires clarity, trust, and patience—and it develops people in the process.
When done well, delegation creates:
Stronger decision-making
Increased engagement and ownership
A leadership pipeline instead of a leadership dependency
Reduced burnout without sacrificing accountability
Or said more simply: the organization functions even when the leader steps away.
Lessons Any Leader Can Apply—Starting Now
Whether you lead a school, a nonprofit, a startup, or a corporate team, the principles are the same:
Identify what only you can do—and stop there. If someone else can do it 70% as well today and better tomorrow, it’s a delegation opportunity.
Delegate for development, not convenience. The goal isn’t speed. It’s growth.
Match responsibility to readiness. New leaders need direction before autonomy. Delegation is a process, not a switch.
Stay accountable without staying in control. Monitor outcomes, not methods.
Let go of being indispensable. Leaders who are irreplaceable become organizational risks.
Why I Wrote Becoming the Delegating School Boss
After years of coaching leaders—and watching the same patterns repeat—I realized how few people had been shown how to delegate well. We talk about leadership constantly, yet avoid one of its most essential skills.
This book is my attempt to change that.
Becoming the Delegating School Boss isn’t about doing less. It’s about leading better. It’s about building teams that don’t collapse when the leader is absent—and leaders who don’t collapse under the weight of doing everything themselves.
If delegation has ever felt risky, irresponsible, or unclear to you—you’re not alone. And you don’t have to figure it out the hard way.
Because real leadership isn’t about how much you can carry.
It’s about how much capacity you can build in others.