In this insightful interview with Jessica Cabeen, we are privileged to learn from an accomplished educator who has spent her career balancing leadership with empathy. Currently the Principal of Alternative Education Programs in Austin, Minnesota, Jessica has led in various roles, including principal of the Woodson Kindergarten Center and Ellis Middle School, and she is the 2021 ED Dive National Principal of the Year. An advocate for both innovative learning environments and educator self-care, she brings a wealth of experience in leadership, student engagement, and school culture.
Jessica is also a sought-after speaker, known for her authenticity and ability to turn complex educational strategies into practical solutions for administrators and teachers alike. She has authored and co-authored several books, including Principal in Balance: Leading at Work and Living a Life (2023), where she emphasizes the importance of achieving work-life balance in school leadership.
For principals and administrators, this interview provides essential insights into how to lead with intentionality, prioritize student connections, and foster a positive and inclusive school culture—topics that are critical in today’s evolving educational landscape.
This interview has been transcribed and edited for clarity.
The Importance of Student Connections in Leadership
In your article “A Warm Demander Approach to School Leadership,” you emphasize the importance of making time for student connections. How do you practically manage your daily responsibilities while ensuring that you consistently prioritize meaningful interactions with students?
Authenticity in Student Connections
Authentic quality versus quantity. What that means is how you engage with kids is authentically you.
For example, one of the things I love to do on Fridays, even here at the high school, is have a fun little “jammy pack,” which is like a little Bluetooth speaker that I wear, and I literally dance kids into the building every Friday.
Now I think there might be people that read that and are like, “I could never do that!” That would give them a panic attack to have to dance in front of their student body. So, making sure however you’re connecting with kids is relevant and relatable to you is primary because then you’re going to want to do it. You’re going to want to go out and dance on Fridays. Or I love to greet all the classrooms in the mornings.
Quality Over Quantity
When I was a kindergarten principal, and now here at the high school, I did one-on-one meetings with students and got to know them, especially our Tier 3 students in the MTSS model.
Again, the quality versus quantity. Saying, “Oh, I’m going to get into every classroom every day,” is probably unrealistic and unreasonable for all the other work you have to do.
Like I said, for me it’s Friday dance parties. Every day I try to get up and walk the halls at least a couple of times and then make those meaningful connections at least once a quarter with kids. I have my own expectations and a chart that I cross off: did I meet with this student? That accountability helps so I don’t miss anybody.
But if this is new work for you, just take it slow and pick 5 to 10 students that, in the next two weeks, you’re going to have a one-on-one conversation with. The value of those individual conversations really helps your overall leadership to understand what kids need. Oftentimes, we make a lot of decisions without asking kids what they think. Whether they’re 5, 14, or 19, they all have an opinion and appreciate having that voice. When we think about that Warm Demander approach again, it is about trying to build those authentic relationships to really understand the needs and wants of our students, so that we can articulate and implement them.
Creative Approaches to Student Engagement
You’ve implemented creative approaches like setting up your office in the halls and using tools like Along.org. What metrics or feedback loops do you rely on to assess and adjust these approaches? What advice would you give to other principals looking to adopt similar practices?
Connecting with Students Virtually
I think about going back to that Why.
Why are you doing what you’re doing?
Along.org really came from becoming a virtual school principal after being an in-person learner my whole life, and then a leader. How am I going to be able to connect with kids outside of content? How do I get to know who they are outside of the classroom?
When using Along.org, it has a monthly prompt I can send out and then have what we call asynchronous conversations. They would send a text response, and I could text back. I had a lot of great conversations with students that, when I had them in middle school, never talked aloud.
I would circle it back with staff to say, “Okay, here’s what the kids thought about the winter gathering or social meet up,” or “Here’s what kids are suggesting for other kids as to how to stay organized online.”
I would use that information to help us think about how to make adjustments in our practices that are relevant and meaningful for kids.
Office in the Hall: A Student-Centered Approach
For some of the seniors this year, I was their kindergarten principal, and I had them in middle school, so they know me. And yet today, when I just called the student down to do a selfie because she earned a credit towards graduation, she asked, “Am I in trouble?”
When kids get called to the office, there is this perception of “I did something wrong or bad.” Their anxiety is already elevated before they even walk in the door. That office in the hall is just a quick way to check in with kids without causing unnecessary anxiety.
The kids know on Thursdays from 1 pm – 3 pm, Mrs. Cabeen’s just up in the halls. She’s got her computer up if kids have questions about their grades, or accessing their content, and I’m finding out what they want to do after high school.
We’re just doing that in a more informal, relaxed environment versus coming to the office. Plus, I like the hallway check-ins because it minimizes the loss of instructional time.
We are a super big building here. For the students I serve around the third floor, if you think about them coming all the way down to first floor to meet with me then going back up, they could lose twenty minutes of instructional time versus just coming out of the hall, talking to me, and going back. That’s the metric too, as I wanted to have as little disruption to learning as possible. That means I need to move to meet the kids’ and teachers’ needs then.
That’s what I got to do.
Building Student Aspirations and Providing College Access
How do you create a positive and inclusive school culture that supports the academic and personal growth of diverse student populations, and what strategies do you use to identify individual needs and tailor learning experiences to help each student reach their full potential?
Elevating Student Aspirations with AP Courses
Somewhere between kindergarten, middle school, and high school, student aspirations and innovative things that they want to do diminish each year, especially for students from diverse backgrounds. I’m meeting students who are juniors and seniors, and they have no idea what they’re going to do after school because they don’t see those opportunities in themselves.
So, one of the things we did in our online school was to have every student take one Advanced Placement (AP) course. These are not students that are normally honors track, but maybe more in the academic middle.
How we frame that is we put together a video with the teacher and me, and we send it out to all the families and just say right away, “What does an AP class mean, and what could it do for your child?” Like, here are some of the things that it could do by taking the course, like increasing understanding of content and enhancing the ability to write and respond to questions.
They’re not required to take the AP test at the end of the year, but if they do, it could include college credit down the road. As soon as you’re in that AP course, you’re going to get mailings because people are going to be interested in you. Interestingly enough, when you look at our data prior to implementing the AP Human Geo class, our passing rate was right around 70% or 80%, and now we’re upwards of 90%. We haven’t changed our student population. We’ve just changed the mindset, and we enhanced the rigor. But it was all about letting kids know that we believe in them and that we would scaffold and support them to meet their needs.
Supporting College Access with Direct Admissions
Here in Minnesota, we have this awesome program called Direct Admissions. It’s a partnership with the Office of Higher Ed in Austin High School, Austin Online, and Austin Area Learning Center.
With Direct Admissions, our seniors have their GPAs and course offerings uploaded into a system. Then the Office of Higher Ed prints out a letter that says, “Based upon your GPA and the courses that you took, here are the X amount of 60 two-year trade school vocational or four-year private and public colleges you gained access to.”
They’ll also help with the application process. Last year was our first year doing it, and we actually had a Signing Day and brought over 300 high schoolers into our auditorium to let them open their envelopes.
Now, over 60% of our students are non-white. I think we have over upwards of 30 different languages represented in our high school, so lots of opportunities, but it was heartbreaking to hear how my students say, “Mrs. Cabeen, they think I can go to college. Mrs. Cabeen, look at the letter. They think I can go to college.”
And I was just heartbroken. What have I not done or what are we not doing that they believe they can’t go to college? It is one thing to have that piece of paper that says, “We’re going to admit you.” But what happened? Where’s the disconnect? So, there are some things that the high school is super proud of that they’re putting in place starting freshman year, so we can get that mindset shifted for all our students.
I’m really excited about this year’s Direct Admissions Day. More students are going to get these letters, and we’re going to have more students really see the potential for their abilities after high school.
Sustaining Positive Culture Through Staff Morale
A positive school culture often depends on strong staff morale, but schools frequently undergo changes that can disrupt this culture. How do you sustain this positive culture during times of transition or upheaval in your leadership role?
Remembering We Are People First
One of the things that’s been really helpful for me is always remembering we’re people before our positions. Every single one of us comes into school to become the title of teacher, paraeducator, or office administrator. But before we walk in the doors, we’re a parent, a wife or a husband, a mom or a dad, a grandchild, a dog mom. Whatever it is—we are so many things outside of our school role, and sometimes as leaders we get really busy, and we only focus on who we are in our day job, and we forget about who we are outside of work.
Building that understanding and willingness to get to know people outside of their positions really helps that culture and foundation about how much we want to be seen, heard, and valued. We say that a lot about our students, but we forget that that means the adults too.
As an adult, I want my superintendent to see, hear, and value me too. That means a lot to make time to do those things while being authentically you. Maybe you’re not the Baker, I’m sure not. I’m not the one who’s bringing treats every month, but I might be the one who writes that card of affirmation to start the school year on our school campus. We do a Staff Member of the Week, so each week we highlight a different staff member and send them a certificate.
Embracing Vulnerability and Owning Mistakes
Being vulnerable is another piece too. That positive school culture is, as a leader, being willing and able to admit when you make a mistake and own it. I know in one of my Edutopia articles, I talk about the infamous zipper schedule, where I built a schedule for a building of 800 middle schoolers and it went south quickly. I think on the third day of school, the kids weren’t getting lunch. It was a mess. The staff was great, but for the staff meeting, I had to go and say, “You guys, I screwed this up. This is not going to work. I’m going to have to fix it.”
I thought they’d all be mad, but afterward, a number of them came up and said, “Thanks. We knew it wasn’t working, but thanks for admitting it.”
Having the humility to say when you did something wrong and being willing to fix it actually gets you more street cred than trying to cover it up or pretend it does not exist.
Even today, my best example is when I made this wonderful poster board for ALC, and I spelled ‘learning’ wrong. Posted it on social media. I’m leaving it up. I’m going to own it.
We make mistakes, and we learn from them. I also think that just opens the door for people to get to know you and realize you’re a human too and be willing to dig in and work a little bit harder together.
Connect with Jessica Cabeen
If you found this interview as inspiring as we did and want to dive deeper into Jessica Cabeen’s approach to leadership, education, and personal well-being, be sure to follow her on social media. Stay updated with her latest insights, tips, and creative strategies to lead with intention while living a balanced life.
Follow her on X, Instagram, and Facebook.
You can also learn more by visiting her Linktree and her website, jessicacabeen.com.
