Neil Gupta, a longtime ASCD member and former member of the ASCD Board of Directors, is starting a new position this fall as the superintendent of the Oakwood School District in Ohio. Gupta began his career in education as a math teacher and worked his way up through a variety of school and district leadership positions, including director of teaching and learning and director of secondary education. An associate with Creative Leadership Solutions, Gupta is also a widely known presenter and social media commentator on education leadership issues. We recently asked him about the challenges facing new school leaders today and what types of support they need.
You’re starting a new position as a district superintendent this fall. How have you prepared yourself mentally for this job?
For me, part of the mental preparation has just been years of already thinking about the superintendent position—of aiming for that higher level as part of how I want to serve students and educators. But in general, as leaders, we have to make sure the job is the right fit and the time is right for our families. We’ve got to have those clear conversations as a family about what the impact of the job will be. And once that is accepted and embraced—once we have that support—the mental part becomes a lot easier.
I also think that as leaders we tend to get into trouble when we feel like we have to come in and quickly solve a lot of things that may either be problems or perceived problems, rather than coming in and just really investing time in listening and asking a lot of questions to first understand the background, the true needs, and impactful solutions. And so really my preparation, once I accepted the position, was spending a lot of time just talking with people in the district, trying not to come in with preconceived notions but instead with questions and then listening.
There were a lot of people who asked me early on what was my vision for the district and what were my plans going to be? And you know, you have to be careful with that. I think that’s where not only stress comes in at the very beginning, but that’s where problems come in later—if you’re trying to push things in from previous experiences or previous districts and trying to make changes that may not fit or fit well. A big part of preparation for a leadership position is being open to learning about the context of your new district or school.
What are your biggest concerns coming in as a new district leader?
I tend to think about things in three buckets. The first bucket is student achievement and growth. This means looking at the continuum of how we want students to grow in their learning, from preschool to not just high school graduation but beyond. I’m also very concerned about achievement gaps. We know that, post-pandemic, there are gaps we need to close. We need to make sure we’re looking at the data for all subgroups, not just patting ourselves on the back because 90 percent or 95 percent of our kids are passing or doing well, but looking at who are those 5 percent who aren’t and what can we do to better support them. We talk about how minutes count with our kids, and we want to make sure that we’re maximizing the minutes with all our students.
The second bucket is safe school environments. That’s what keeps me up at night. I obviously want school to be challenging academically for our students—I was a math teacher, after all—but first and foremost, we want to make sure they feel safe, physically safe, in our schools. That means doing the right audits and making sure we have the right plans in place.
But safe school environments are not just about the physical aspect: It’s that social-emotional piece as well. Do our kids feel mentally safe? Do they feel socially safe to be in the classroom? Do they feel like they’ve got friendships and positive relationships? Do they have a trusted adult who they are able to talk to at school? We’ve got to make sure we’re creating and teaching those metacognition skills that enable kids to articulate what’s working for them and what’s not and what makes them feel safe and what makes them feel confident to share.
The third bucket is efficient and effective operations. This refers to finances and facilities. We are public stewards of tax dollars and we’ve got to make sure we’re being efficient with that money, that we’re spending it effectively. So we have to ask tough questions about how to streamline programs and how to make sure that we’re vetting things properly. This especially applies to professional learning, which is where I’ve often seen things fail. Sometimes we blame the resource or instructional program, but the real problem was poor implementation—that we didn’t have the right training or follow up with the staff. So we’ve got to talk about those systems.
The facilities part goes back to the safety and well-being issue. We have to ensure we have clean air and natural light and other design accommodations in our buildings so that kids are able to flourish in those spaces.
What knowledge or training gaps do new building administrators, such as principals or assistant principals, tend to come in with, in your experience?
I think the biggest mistake new school leaders make—which comes from faulty understandings of leadership—is trying to bring in too many initiatives at once and responding to too many issues at once. This often creates a lack of clarity, and ultimately initiative fatigue starts to set in. This is so common in schools that it’s basically a running joke among veteran teachers—you know, they don’t concern themselves too much with new initiatives, because those initiatives will just be replaced with something else, often something completely different. So my advice—really where my leadership journey has taken me—is to choose a few initiatives and go deep with them and stick with them.
My advice—really where my leadership journey has taken me—is to choose a few initiatives and go deep with them and stick with them.
Obviously, there are going to be other things you have to respond to. But you have to be in a place where you think about that “end user.” You’ve got to think about the parents, the students, and the teachers. How can you make change manageable and meaningful for them. You can’t be worried about showing the community or your staff how many new things you can put in place—like “Look at these 50,000 new things we’re doing!”
My hope is that people will say about me, “Neil keeps talking about these same three or four things.” If people are rolling their eyes because I keep talking about the same priorities, that’s actually a good thing. Because that means we’re getting toward saturation, and people are starting to finish one another’s sentences because they’re so familiar with what you’re trying to do. That’s when you know it’s happening. By contrast, when we’re in a place of constant change, it just conveys that nothing is that important.
What plans or projects are you putting in place for building leaders in your district, particularly new leaders?
I think that, again, this comes back to the idea of listening and learning. During my transition, I invested time in meeting with each leader separately to begin building relationships and learning about their background, their family, their hopes and dreams, and what they are most proud of at their school or level. Investing time like that has already paid dividends in starting to build trust. The next step is building our team’s development and collaboration. We just had a leadership retreat where we conducted team-building activities and continued to refine our mutual goals for the year. I plan to meet with each leader once a month separately to continue checking in, building relationships, and seeing how I can support them in their personal and professional growth as well as address any needs they have. We have one new leader this year, and I know this kind of relational support will be a great support to her.
What kind of support was most important to you when you first became an administrator?
I’m going to say mentors, plural. You may have a mentor assigned to you in your district and that’s fine. And you need to listen to them; I’m not trying to diminish that. But that better not be all you have. I can probably name 50 people that are mentoring me right now. You need people who have different lenses and specialties—someone who has a lot of experience in technology, someone who’s a veteran superintendent, someone who knows about school finance. And these have to be people who are trusted sources—people who are going to listen to you in confidence but also give you critical feedback and tell you when you’re wrong and need to change direction. You don’t need someone who’s just going to echo what you want to hear. That’s not going to help you. So you’ve got to be in a place where you’re cultivating a very strong and diverse network of mentors.
You’ve written on your blog that for school leaders, “success is not about creating a plan for implementation, it’s about creating a plan for sustainability.” What do you mean by that?
Basically, I mean that everything can’t be predicated around you. You’re eventually going to leave that leadership position one way or another. You’re going to change jobs or move or retire. So you have to think long-term—past your own ego investment. How many initiatives have we seen die because somebody moves on and all of a sudden the ownership is gone? And in that case, did true leadership really happen? Did any real true change take place? It’s not about just getting something off the ground. It’s more about what happens when you step back from an initiative for whatever reason. Does it stay standing? Are there people who are going to lift it and keep it moving?
So when you think of your goals as a leader, instead of the idea of just getting things up and running, your whole action plan changes because you start to realize you have to get more people involved. You have to build in more systems.
Education leadership is a field that has a notoriously high burnout and turnover rate. To what do you attribute your growth in the field?
ASCD is all about the whole child. For those of us in education leadership, we have to think about the whole adult, the whole leader, however you want to say it. First, you have to face the hard facts and realize that burnout can happen to you if you’re not careful. You’re not Teflon, you don’t have superpowers. You’ve got to be careful of the kind of inner thoughts that predict, It’s not gonna happen to me. You’ve got to take steps to care for yourself and create good boundaries. It’s good if you have someone to help you with this. My wife, for example, knows when I’m starting to get stressed out and getting into that fatigue stage. So every now and then I’ll get a text from her saying it’s five o’clock and it’s time to come home for our walk.
ASCD is all about the whole child. For those of us in education leadership, we have to think about the whole adult, the whole leader.
Take care of yourself physically—that has to be front and center. But the other thing—and I’ll say this over and over—is you have to make sure you’re connected to others. You know, if all I did was keep it bottled in when I’m feeling stressed, that’s not healthy. But if I feel like I can only go to my family members, that’s not always healthy, either. My family should know sometimes when things are happening, but you can’t keep bringing things home every day. And sometimes you might be able to talk about it with your staff, but sometimes that might not be the case. So I always say, find that best friend in another state, find that best friend that’s not even connected to your district. My best friends in the field are people I met through social media, and I’ve known a couple of these guys for 10 years. And we text all the time and I know their hearts, I know their character, I know their value systems. They can empathize with what I’m going through and help me work through things. Those kinds of connections are invaluable.
That’s wonderful. So as we’ve been talking about, this is obviously a challenging and fraught time in education with concerns about learning gaps, staffing, and cultural divisions. Do you have any specific advice for individuals who are just starting out as school leaders at this time?
There are a lot of major challenges right now, and it can be easy to get frustrated or distracted from what’s important. So my main piece of advice is: stay connected with the kids. That can help you maintain your “why” in terms of why you do this work. It’s very easy to start making decisions based on what different sets of adults might be thinking or the politics around an issue. But you have to put yourself in a place where you’re connecting with the kids and you’re continually asking what’s best for them.
This is not to mention that these connections are a tremendous source of energy and revitalization. When I find myself stressed or disillusioned, I ask myself whether I’m connecting enough with the students. Then I’ll find ways to do that—even if it’s just going to a school sporting event or play or visiting classrooms. That can really bring you back. I’ve found that students can also be a wonderful source of feedback on things we are trying to do. They can provide a lot of clarity on why things are working or not working. Having lunch with students is always an eye-opening experience on many fronts.
Finally, keep an eye on your core values and your beliefs. You’re not going to make everybody happy. But we signed up for public education, which is an exciting place of trying to do what’s best for kids.
Editor’s note: This interview has been edited for space.
