A Superintendent’s Advice for Becoming an Administrator

I was recently invited to speak to aspiring superintendents about my journey to superintendency. I’m frequently asked about the path toward administration, so I wanted to share advice I would give anyone pursuing superintendency or educational leadership.  

Below, you’ll find my key advice for how to achieve leadership goals and thrive once you land your desired role.

Know who you are, and embrace it

As leaders, we’re often encouraged to be our authentic selves—but doing so requires courage and introspection. A successful leader is self-aware of their strengths, values, triggers, and goals. 

It’s difficult to create a compelling vision for an organization without a clear understanding of who you are and how your identity influences how you lead. If you haven’t done self-inquiry, begin by asking yourself these questions:

• What motivates you to lead? 
• What are your core beliefs about how effective schools are run? 
• How has your upbringing influenced your beliefs about school, people, and leadership?  
• Who are your mentors? Why did you choose them?  
• What sacrifices are you willing/unwilling to make for your desired position?
• How do you define success? What would success look like for you in this role? 
• How do you manage conflict and high levels of stress? 
• What would make you walk away from a job?  

District leadership can stretch you in ways you never thought possible. It’s imperative that you have a strong sense of self and the confidence to sustain you through a storm.

Stay Connected to your coaches and mentors

Friends aren’t the same as mentors and coaches. Sometimes they’re a great sounding board, but that’s not a substitute for coaching support. 

You’ll need mentors, coaches, and accountability partners if you really want to get to the next level in your leadership. Who tells you the truth, even if it hurts? The higher you go in leadership, the less likely it is for people (e.g., your subordinates) to tell you the truth, at least to your face. You have to seek out truth-tellers who push you toward greatness.  

Mentors can help you reflect on your journey and decision-making. A coach helps you discover your next steps and clarify your vision. They shouldn’t offer advice; rather, they should listen more than talk, ask clarifying questions, and help ensure that your actions are congruent with your stated goals.  

If you don’t have a leadership coach, ask colleagues for referrals. Many superintendent-preparation programs offer coaching. For example, the Institute for Education Innovation has an aspiring-superintendents program. The School Superintendents Association has several, such as the Urban Superintendents Academy, the Aspiring Superintendents Academy for Latino and Latina Leaders, and the Women of Color Education Collaborative, which offer free support.

Lean into what scares you

When I took my first role outside of the New York City Department of Education, I realized I was out of my comfort zone in a few key areas. One major challenge for me was budgeting, mainly because school and central budgets in a large city district are constructed by a central office, not by a small group of district leaders who have to work with a board of education to get a budget approved by voters.  

It took me time to wrap my head around the process, and for a while it was my Achilles’ heel. As I interviewed for superintendent positions, I did well until I had to respond to finance questions. But as soon as I learned to face my fear and immerse myself in the process, I got different results.  

You can’t avoid the things you aren’t good at—and there will always be things you aren’t good at. Be relentless about applying yourself to learning them. Sit in on your district’s budget meetings; since most board meetings are posted on YouTube, watch budget presentations from other districts; shadow your assistant superintendent for finance; choose professional development in areas that are outside of your expertise, such as a law and policy conference to get updates on labor contracts and school legal cases. Once you recognize your limits and set a goal to go beyond them, there’s nothing you can’t accomplish.

Call out when you need help 

You will fail, so expect it. When those moments come, don’t be so down on yourself that you don’t reach out for help. I was once told it’s not the mistake that defines you but what you do next that does.  

Make sure you reach out to your small circle of trusted advisers for support and advice when you need it most. I’m a member of a few national superintendent collegial circles, and one of the things I value most about them is knowing there are colleagues I can call on. Stay in community. You don’t have to go it alone.

Curate new professional relationships

Some people subscribe to the saying “No new friends.” When it comes to your professional network, I couldn’t disagree more. I’ve been enriched by remaining open to new professional networks. Not only have I benefited from them, but my district has as well. Some of the most important lessons I’ve learned haven’t come from “experts” but from colleagues as we learned side by side. 

Don’t be the leader who doesn’t invest in your own learning. Don’t get caught in the trap of thinking that you are too busy to go to conferences or professional gatherings. There’s always more work to do, but you have to “lead from the balcony,” as Stephen Covey says, and look down to see the bigger picture.  

Be in spaces with people who challenge and inspire you. Choose your professional development wisely, but don’t deny yourself the right to learn.

Take care of yourself

The term self-care is overused and minimized by some to mean shopping and massages. I advocate for a more expansive view that includes nurturing our spiritual selves, making time for relationships, and tapping into passions. We have to be just as intentional about family and friendship circles as we are about work.

You’re entitled to live a full life. As you embark on your leadership path, be sure you make space and a plan for joy.