When Warren Morgan took over as CEO of Cleveland schools in the summer of 2023, he felt ready to manage the urban district and serve its 36,000 students.
He assumed the lead role following stints working in the Illinois senate and as a White House fellow during the administrations of both Barack Obama and Donald Trump. He’s also been a teacher and a high school principal in Chicago. He arrived in Cleveland after working as the chief academic officer for the Indianapolis school district.
But despite his resumé, Morgan said nothing fully prepared him for the complex and all-consuming job of leading a school district.
Like others, he had an incomplete understanding of the nuances of the job before he stepped into the role. The superintendent’s job is often perceived as one of managing a district’s day-to-day operations. The reality, he said, is that he spends much of his time forging strong community relationships, advocating for students and staff, and, at times, leading the district through political change and conflict.
His experience is backed by research. In August, the Holdsworth Center released a report detailing many of the same misperceptions about the job of a superintendent or school district CEO, and cautioned that the incomplete picture of the role could contribute to turnover in districts’ top seats.
Rather than managing internal departments, the job largely entails working with people outside the district—community members, parents, advocates, politicians, and others—to forge important partnerships, said Morgan.
That echoes a key finding from a survey of superintendents released earlier this year by the RAND Corp. and the Center on Reinventing Public Education. Superintendents of large districts reported that external and internal communications, including communications with school board members, took up the largest chunk of their time. They also reported that political issues were a top stressor.
Superintendents of smaller districts, by contrast, reported that budget management, district operations, and facility maintenance were among the tasks that consumed the most time.
Education Week spoke with Morgan in November about his experience as a new district leader and the lessons he learned through his first year on the job in Cleveland.
This interview had been edited for length and clarity.
How did you end up as the CEO in Cleveland?
People ask all the time if this is a role that I thought I was going to do. Of course there are things that put me in a position to do the job—I have my doctorate and I’m certified to be a superintendent, and I’ve done a superintendent prep program. So, I had thought about it in some capacity, but it wasn’t a thing where I had set out and said, “This is the role I’m going to do.” Even up to a year before going into this role, I wouldn’t have thought it’d be where I ended up.
In my last role [in Indianapolis], I loved the superintendent and felt comfortable, but I was doing all of these different programs, including a superintendent prep program through Yale.
I had a conversation with Eric Gordon [the immediate past superintendent of the Cleveland district who served in the post for 12 years] when he decided to resign and he said I should consider it. I wasn’t sure, but he was doubling down and said, “This is something you can do” and, “I believe in you.”
I share that to say it means a lot because the roles are tough, and when there’s someone saying, “I believe you can do this,” that was my encouragement to apply.
So I did, and ultimately I emerged as a finalist for both Cleveland and New Haven [Connecticut] schools at the same time. I like to say fate chose where I’m at.
Is being CEO like what you expected? If not, in what ways is it different?
No matter how close I was to the superintendent, even as I was No. 2 in that system, it cannot prepare you for when you’re actually sitting in the seat.
When you are in a superintendent’s cabinet, your proximity to the CEO or superintendent or the board enables you to understand how to run the district.
I don’t mean this arrogantly, but the running of the system—like how to have a strategy and vision, or a 90-day plan—that part was simple. That was the stuff programs and fellowships can prepare you for.
What has helped me is having coaches who have done the job because it can be a very lonely job.
What I was not prepared for was the stakeholder engagement. Not from a typical sense of doing political mapping—because you learn that in classes—but the deep relationship-building, the understanding of decisionmaking, and how the decisions you make internally for staff or the decisions you make externally, they all have consequences, and sometimes they have a ripple effect, that are nuanced.
I also think the work is challenging, and you will hear bad things about yourself. It’s the first time where you literally hear the worst about yourself sometimes, and it’s not even things that are true. There’s no classroom, no role, that can prepare you for that but sitting through it.
If nothing can prepare you, what helped you through the initial year as CEO?
What has helped me is having coaches who have done the job because it can be a very lonely job.
There’s no one you can be completely vulnerable with, even your family, because they could be a listening ear, but they don’t know what you’re going through day in and day out.
So having coaches who have actually done the role and who you can be completely vulnerable with and have them be completely vulnerable with you is so important.
They can say, “Get out of your feelings and get back in there and do it,” which can be a game changer. I always recommend people to have a coach and have other trusted colleagues that you can bounce things off of because there’s no textbook on how to do this.
What kinds of things could superintendent prep programs better address to prepare future leaders for the job?
There’s some work and research coming together around the political framework of the superintendency, and how the superintendent now has to be very sophisticated and politically nimble. I think that will be really helpful.
When you think about school board dynamics and changes in board leadership, state leadership, city leadership—we’re about to have a new president—those are things you have to be able to work with.
You have to respect the people in those roles and the policies that come in and make it make sense for your system and the context of your community. Those are things that I think that the research is becoming a little bit more sophisticated in to prepare people for it.
I also recently got a chance to preview some upcoming research about the politics of identity. That’s one thing I’m continuing to unpack as a young leader of color. Sometimes people can’t put their finger on why people may question them and not others. Sometimes it’s just based on who you are, and you can’t make excuses about that. You don’t want to be frustrated about it, but you have to know it. The awareness of who you are, the context you’re in, and the scrutiny you’re going to face helps you navigate it. It doesn’t make it easier, and it doesn’t go away, but it prepares you.
What lessons did you learn in your first year that have made you better in the second?
What I learned really quickly is that listening and learning is not a moment. It’s a way of leading.
Especially here in Cleveland, with such an engaged community, so many people are passionate about education, and what that tells me is I need to continue to listen, have my ear to the ground, and implement the ideas and feedback that come out of that.
The other part is just around humility. There’s always more to do, but it’s really important that no matter what challenges you face, you take it, you lead through it, and you get back up and going because your community is looking to you for strength.
Another lesson I learned are just the things I need to help ground me: my faith, my family, my coaches. Those are things that help ground me and keep me motivated.
In a conversation with one of my mentors a while back, they told me something that I really took to heart, which is that the school district and schools are not ours from an ownership standpoint.
When you think about school board dynamics and changes in board leadership, state leadership, city leadership—we're about to have a new president—those are things you have to be able to work with.
I’m the CEO of this district. I’m here. I’m a steward of it. I care. I’m passionate about this community. But it’s not mine and I don’t own anything.
When you hear that at first, it sounds kind of harsh. But what is relieving about it is when you’re hearing from the community and with the community, the community guides you to lead.
They’re looking to you to lead, but they’re not looking to you to determine everything, because it’s not mine, it’s shared, collectively together.
As America prepares for Donald Trump to be sworn in as president for a second term, what do you think is most important for district leaders to remember in times of political change?
Election week brought a lot of mixed emotions. We passed our levy that was on the ballot but, for me, personally, some of the other elections were hard. But I know based on the results of the [presidential] election, this shows that the country itself is very passionate.
I don’t want to take a position that everyone is feeling the same way about some of the other elections as I am. But what it tells me, even with all the feelings that people have, this is a time to lead. Kids are looking for leadership.
There are political implications on the national level, but the work we’re focused on is the work we can do in our communities. ... They need us to lead, especially in a time where there may be so much uncertainty.
I was at a high school earlier today and they were talking about culture and climate issues in their school. They were talking about why they can’t do extra field trips, because they don’t have funding in their schools for it.
All of those are things that we can do something about. And, yes, there are political implications on the national level, but the work we’re focused on is the work we can do in our communities. They need me. They need us. And they need us to lead, especially in a time where there may be so much uncertainty. I feel a sense of sense of responsibility to step up in this moment.
All of us are leaders in our own right, so however you’re feeling about this election, whether you’re excited about it or whether you’re not, it’s a time to lead. We need to lead, for the sake of the students.
What’s your biggest piece of advice for aspiring district leaders?
Know deeply who you are and why you’re leading. I think if it starts in that place of knowing deeply who you are, what your assignment is, and what you’re charged to do, the rest of it will fall into place.
