Leadership That Multiplies
Leadership Question
How should leaders measure their success?
"Leadership reaches its highest expression when the people you develop begin changing lives you will never meet."
— Dr. Dwan Anthony Jordon
When people ask me about the accomplishments I am most proud of, they often expect me to mention schools that improved academically, accreditation milestones, strategic initiatives, or organizational transformation. Those achievements certainly matter. They represent the responsibility leaders have to deliver results for the communities they serve.
But when I reflect on nearly three decades of leadership, those are not the accomplishments that come to mind first.
I think about people.
I think about the leaders who now serve children, families, educators, and communities because someone once believed in them.
For me, leadership has never been measured solely by what I accomplish during my time in an organization. It is measured by what continues because I was there.
Leadership is not additive.
Leadership is multiplicative.
The true legacy of a leader is not found in the number of people who followed them. It is found in the number of leaders they helped develop who continue expanding opportunity long after they are gone.
That philosophy did not emerge by accident.
It was given to me.
Throughout my career, I was fortunate to work for leaders who invested in me beyond the position I held at the time. Gail Golden never saw me simply as an assistant principal. Michelle Rhee challenged me to think beyond immediate success and toward organizational sustainability. At Friendship Public Charter Schools, I was given opportunities to study systems, governance, and organizational design rather than remaining confined to a single school building. At Cesar Chavez Public Charter Schools, I witnessed leadership that viewed community transformation—not organizational recognition—as the ultimate measure of success.
Each of those leaders shared one characteristic.
None of them prepared me only for the job I had.
They prepared me for the responsibilities they believed I would one day carry.
That changed the way I lead.
One leader immediately comes to mind.
She joined our school as an instructional coach directly from the classroom. From the very beginning, I saw something difficult to quantify but impossible to ignore. She possessed exceptional intelligence, relentless drive, deep compassion for children, and an insatiable curiosity about leadership. She was not satisfied with knowing what decisions were made. She wanted to understand why they were made.
Rather than shielding her from the complexities of school leadership, I invited her into them.
We discussed difficult personnel decisions, organizational culture, instructional leadership, operations, budgeting, and the countless competing priorities that leaders navigate each day. I wanted her to understand that leading an urban school required far more than instructional expertise. It required the ability to think systemically while never losing sight of individual children.
After one successful year, she approached me about becoming an assistant principal.
She expected me to say yes.
Instead, I told her she needed another year.
She wasn't ready.
That conversation could have damaged our relationship. Instead, it strengthened it.
She trusted my judgment because she knew my decision was not about limiting her opportunity. It was about protecting her future. I wanted her first experience as an assistant principal to be one where she could flourish rather than simply survive.
A year later, she stepped into leadership fully prepared.
Today, she serves as a Regional Director for Teach For America, developing educators whose collective work impacts thousands of students across multiple communities.
Watching her leadership unfold has become one of the greatest rewards of my career.
Not because I created her success.
Because her leadership now reaches children I will never meet.
That is multiplication.
At John Philip Sousa Middle School, leadership development was never accidental.
It was part of our organizational design.
I believed every teacher should understand how schools operate beyond their classroom.
Every instructional coach should understand how principals make decisions.
Every assistant principal should begin thinking like a principal.
Leadership information was never reserved for a select few.
I never believed in gatekeeping knowledge.
People cannot grow into responsibilities they are never allowed to see.
Transparency became a form of leadership development.
Looking back today, I smile when I think about where so many members of that team are now.
Former teachers have become chief executive officers of charter school networks.
A new assistant principal has become a veteran head of an independent school.
A special education teacher is now one of the longest-serving principals in Washington, D.C.
A mathematics teacher who joined us through Teach For America advanced into senior school leadership at one of the region's highest-performing charter organizations.
Another assistant principal now leads a technology preparatory school.
The list continues to grow.
People occasionally ask whether that was intentional.
The answer is simple.
Absolutely.
I never hired people to stay in the same position forever.
When someone joins my team, I immediately begin thinking about the leader they can become.
My responsibility is not simply to supervise their work.
It is to prepare them for opportunities they cannot yet see for themselves.
That means sharing information rather than protecting it.
It means explaining not only what decisions are made, but why they are made.
It means modeling excellence while creating the psychological safety necessary for people to learn, make mistakes, ask difficult questions, and continue growing.
Their success has never threatened mine.
Their success is part of mine.
One experience reminds me why that philosophy matters.
I once hired a dean who had been an exceptional classroom teacher. Students respected him. Colleagues admired him. Several trusted educators encouraged me to give him an opportunity in leadership.
I saw tremendous potential.
I also understood the enormous difference between leading children and leading adults.
Leadership has a way of revealing strengths—and weaknesses—that remain hidden until responsibility arrives.
I knew he would either become an extraordinary leader or struggle significantly.
There would be very little middle ground.
I chose to trust what I saw in him.
He exceeded every expectation.
Years later, he was recruited into a senior leadership role by one of the highest-performing charter school organizations in another state.
Sometimes leadership requires believing in people before certainty exists.
Someone once did that for me.
Now it is my responsibility to do the same for others.
As I have reflected on my own career, I have come to believe that organizations become healthier when leadership is viewed as something to be multiplied rather than protected.
Great leaders do not build dependence.
They build capacity.
They do not create followers who need them forever.
They develop leaders who eventually surpass them.
That is not a loss.
It is the greatest evidence that leadership has fulfilled its purpose.
Because leadership is never ultimately about the leader.
It is about the lives that continue changing because one leader chose to invest in another.
Reflection
Leadership begins with believing in people.
But belief alone is not enough.
Belief must become investment.
Investment must become growth.
Growth must become multiplication.
Only then does leadership extend beyond one person and begin shaping institutions, communities, and generations.
That leads to the next question.
If leadership is about multiplying people, who does leadership ultimately belong to?
The answer is stewardship.
This article is adapted from my developing leadership philosophy, where I explore how belief, stewardship, systems, and policy work together to build institutions that expand opportunity.
