What I'd Do Differently If I Started Over in Leadership?!
If I had the opportunity to start over in leadership, I would not begin by learning how to do more.
I would begin by getting clearer about how I wanted to lead.
Like many new leaders, I entered leadership ready to work. I cared deeply about people, felt responsible for results, and wanted to prove that I could handle the role. I learned how to solve problems quickly, respond to competing priorities, support my team, and keep moving when the pressure was high.
Those strengths served me, but some of them also became traps.
Because I was capable, I carried too much.
Because I cared, I sometimes delayed difficult conversations.
Because the work felt urgent, I did not always protect the time and energy required to think strategically.
And because I wanted to be a good leader, I sometimes focused more on proving myself than defining the experience I wanted my leadership to create.
There are many things I am proud of from my years in school and charter network leadership.
There are also lessons I wish I had learned sooner.
That is why Season 2 of Leadership in Real Life is centered on one theme: What I’d Do Differently If I Started Over in Leadership.
Reflection is not regret
Looking back does not mean dismissing the leader you were.
Earlier versions of us were leading with the knowledge, experience, support, and capacity we had at the time.
Reflection allows us to honor that reality while still being honest about what we would change.
The goal is not to relive every mistake. The goal is to extract the lesson.
Effective leaders ask themselves:
What did this experience teach me?
What patterns helped my team and which ones limited us?
Where did my intent match my impact?
Where was there a gap between what I believed and what people experienced?
What do I want to practice differently now?
That kind of reflection is not weakness. It is a leadership discipline.
Good intentions are not the same as effective leadership
Most leaders do not wake up intending to confuse, overwhelm, or disengage their teams.
They want to communicate clearly. They want to build trust. They want people to feel supported.
They want strong performance and sustainable results.
But intention alone does not create impact.
When a leader cares about people but avoids necessary accountability, expectations become inconsistent. When a leader values excellence but communicates only through urgency, the team may experience pressure without clarity. When a leader wants ownership but continues solving every problem, people learn to wait for the leader instead of exercising judgment. When a leader gives everything to the role without protecting their own capacity, exhaustion begins shaping decisions, communication, and relationships.
This is what I call a Leadership Effectiveness Gap: the distance between the leader you intend to be and the leadership your people actually experience.
Closing that gap requires more than motivation. It requires self-awareness, practical skills, aligned systems, honest feedback, and the ability to balance empathy with accountability.
The first thing I would change
If I were beginning again, the first thing I would do is create a Self-Leadership Plan.
Leaders are routinely expected to create strategic plans, team-development plans, performance plans, and organizational priorities. Yet few leaders are encouraged to develop a plan for sustaining the person responsible for carrying all of them.
Without that plan, leadership can take everything you are willing to give it.
It can consume your calendar, attention, evenings, weekends, and mental space. Constant availability can begin to feel like commitment. Exhaustion can look like evidence that you are working hard enough. Carrying everything can be mistaken for being indispensable.
But the goal of leadership is not to become the person without whom nothing can function.
The goal is to create the clarity, trust, capacity, and systems that allow people and performance to thrive even when you are not in the room.
A Self-Leadership Plan begins with six questions:
What protects my energy?
What boundaries do I need?
How will I make space to reflect?
What are my actual priorities?
Who is part of my support system?
What am I carrying that effective leadership requires me to put down?
Self-leadership is not separate from leadership effectiveness. The condition of the leader affects the quality of the leadership.
Your capacity influences how you communicate, listen, make decisions, coach, respond to conflict, and hold people accountable. You are one of the people your leadership is responsible for sustaining.
What we will explore in Season 2
Season 2 is not a collection of abstract leadership advice. It is a practical and honest examination of the lessons I would apply sooner if I were starting again.
We will explore what it means to:
Build a self-leadership plan before building another leadership plan
Define your leadership identity before trying to prove your competence
Address hard conversations before avoidance makes them harder
Communicate in ways that create genuine clarity
Coach and develop people instead of carrying their responsibilities
Balance empathy and accountability
Pay attention to how your leadership is experienced not only what you intended
These conversations are especially important for new and emerging leaders, but they are not only for them.
Sometimes experienced leaders also need to start over, not by abandoning everything they know, but by releasing the habits, assumptions, and patterns that no longer serve the people or outcomes they are responsible for leading.
You do not need to begin again to lead differently
You cannot return to your first day of leadership with everything you know now.
But you can decide what the next version of your leadership will look like.
You can have the conversation you have been postponing. You can clarify the expectation your team has been trying to interpret. You can stop carrying work that someone else needs to learn to own. You can create boundaries that protect your capacity. You can ask for feedback about how your leadership is experienced.
And you can close the gap between your intentions and your impact, one intentional practice at a time.
Season 2 of Leadership in Real Life: What I’d Do Differently If I Started Over in Leadership premieres Monday, September 21, on YouTube at Balanced Leadership w/ H-Monét.
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