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How One Principal Stays Connected by Teaching

For Jennifer Connolly, principal of the 370-student Preston High School in the Bronx, being an instructional leader means actually getting back into the classroom.

Connolly and her two assistant principals teach at least one block-scheduled class [meeting every other day] each semester, both to ease staff scheduling and stay connected to students and teachers. Connolly spoke with Education Week about how she returned to the classroom, and how her dual roles have strengthened each other.

This interview has been edited for length and clarity.

How did you make the decision to return to teaching as a principal?

We don’t really have anybody else in our district [who is a teaching principal] that we have to follow. I became principal two years ago, and I made the decision that every administrator—myself and the two assistant principals—was going to teach a class, for a couple of reasons. One, we were all teachers and we love it. But the other reason is that teaching during COVID, when we were hybrid, when your administration really couldn’t comprehend how that felt, there was a big disconnect and people were very unhappy. So I wanted to make sure we understood what teachers and students were going through.

You taught for 18 years before you joined the principalship. How has teaching changed in the time you’ve been doing that?

I taught history and for my last three or four years of being a classroom teacher, I was teaching Intro to Law, Economics, and Government, and a course I created on race, class, gender, and United States history. For the past two years [as a principal], it’s been our Intro to Law class, which is a senior elective, because I’m also an attorney. That’s not going to run next year, so I’m going to teach a section of economics and government that’s required for every senior in New York state to take.

There’ve been huge changes. Some of it is in content, right?

Like, I teach a law class; up until 2022, we taught Roe v. Wade as kind of the end of the fight for reproductive rights; not the whole end, because you still taught [Planned Parenthood v.] Casey and Whole Women’s Health [v. Hellerstedt rulings]. But then there’s the Dobbs [v. Jackson Women’s Health Organization] decision in 2022, and all of a sudden you have to really change your curriculum. … There’ve been these huge events that have changed the content of what I taught, but also how you teach is different.

[For] the course I created on race, class, and gender, I did not want to give that course up because I loved it. But if [as a student] you’re studying U.S. history and society today and you’re looking at these topics, you really have to question authority. And as a teacher, I felt comfortable having [students] do that, but I knew as the principal, they would not be comfortable in my presence questioning some of these institutions.

Is there something you wouldn’t have known about as a principal if you weren’t still teaching?

I think part of it is the need for civil dialogue. I had a student who didn’t do any of our homework for the last quarter—and I think it takes a lot of guts to have the principal as a teacher and not do your homework! I reached out to her and her parents and she did it, but she did it after grades were submitted. Then she emailed me and was like, “I can’t believe you made me do all this homework. I didn’t get any credit for it. You never gave me a due date.” I was like, “No, no, no. You missed all the due dates.”

I think being in that situation, having to have that conversation myself as a teacher, lets me know what teachers are dealing with. If you’re just in your office, you’re not as aware of what the teacher-student dynamic is like.

With the upcoming election, we’re doing a lot of thinking about programming for our students, but also for our faculty, to help them help students have a civil dialogue. I think it’s lacking in society in general, for people to be able to hear from each other and discuss it without making things personal and actually listening to listen, not to respond. So we’re going to do some work on that. And that’s definitely something I’ve noticed being in classrooms, that we need to do more work with students on how we engage with each other.

How do you balance the workloads of being a teacher and a principal?

Ha, not well. I get things done at work. It’s just my personal life that I don’t balance well. But it is harder to get things graded. I used to pride myself that if I collected homework on Monday, they had it back graded on Wednesday. And there are just times now with being the principal and a teacher, that’s not possible. You have to carve out time in your day to say, ‘OK, yeah, no, I really need to focus and make sure I’m ready for this class.’ But going into the classroom, all three of us [administrators] have said that’s a break for us. You step out of the office, and for 82 minutes, you get to leave the worries of administration behind and really focus on your students.

Is there any advice you have for a principal who would like to start teaching also?

I think that you have to give yourself some grace that you’re not going to be the same teacher you were when you were a full-time teacher. Choose classes where you can control [the structure] and it’s something you love, because if you’re going back, you want to enjoy that time while you’re in the classroom.

How can school leaders better mentor teachers to join the principalship?

You have to lead by example, right? I think you have to show teachers that you can make this transition from teaching to administration, but you can still continue to teach. I feel like there’s the perception—even, I had it as a teacher—that administration was kind of the dark side, and you didn’t want to go over to the dark side because they didn’t really care about actual teaching.

But no! You can still teach, you can be involved with the students [as a principal]. So I think you have to show that you are doing this job because you love it. It’s helping teachers where they need it, but recognizing teachers as professionals in all that they do, and then showing them that there’s really not as much of a divide between teachers and administrators as they think.

This was never on my career plan. I was never going to be a principal. I loved teaching. I was [the] history department chair; I was the head of our scholars program. I never really thought I would do this.

And then COVID happened, changes to the school happened, changes to the society happened. And I felt like we needed someone who I knew understood our kids, understood our school, knew our history. And so I threw my hat in the ring and here we are. So even for young teachers who are like, ‘I would never,’ I think, ‘You never know.’”

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