Tune in as host CT sits down with Dr. Stacy Winslow, Superintendent of Derry Township School District, on the power of focused, community-driven leadership in education. Dr. Winslow shares her path from teacher to superintendent, emphasizing the importance of aligning district priorities with community values and fostering student growth through social-emotional learning and equity. This episode offers insights for leaders interested in creating impactful, student-centered environments by combining tradition with purposeful innovation.

Key Takeaways:

Balancing Tradition with Innovation

Dr. Winslow highlights the importance of respecting community traditions while adapting to modern educational needs.

Clear, Student-Centered Priorities

By focusing on social-emotional learning, equity, and collaboration, the district ensures consistent growth and support for students.

Empowering Educators through PLCs

Professional Learning Communities foster collaboration among teachers, improving teaching strategies and student outcomes.

Community-Driven Leadership

The district’s commitment to Milton Hershey’s legacy fosters a strong community bond, supporting students and staff alike.

Authenticity in Leadership

Dr. Winslow’s journey underlines the power of genuine, student-focused leadership to drive positive change.

Chapters:

00:00 Introduction

02:30 School District Insights

06:03 PLC Implementation

10:55 Staff Development

15:37 Leadership Journey

19:56 New Teacher Support

24:25 Superintendent Insights

29:03 Career Pathways

32:53 Future Opportunities

39:53 Final Reflections

Connect with Dr. Jim: linkedin.com/in/drjimk

Connect with CT: linkedin.com/in/cheetung

Connect with Dr. Stacy Winslow: https://www.linkedin.com/in/stacy-winslow

Music Credit: Shake it Up - Fesliyanstudios.com - David Renda



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Stacy x CT

CT: And it's a great pleasure to have with me in the studio dr. Stacy Winslow. She's the superintendent of Derry Township School District in Hershey, Pennsylvania. Stacy, welcome to the show.

Stacy: Thank you so much, CT. Thanks for having me.

CT: So tell us a little bit more about Derry Township School District and the community that you're in.

Stacy: Sure. So we are in the Hershey community, which is a unique community. If you don't know the thing, myths and the legends around Milton Hershey and the chocolate factory. That is the community that I am. It's the sweetest place on earth. And our community lines and our school district lines are the same.

Stacy: We've had up to 3600 students in the district that gets pretty uncomfortable in our buildings. Right now we're pretty comfortable at 3100. We have a very high rate of graduation and students that go on to college. We have a high performing district. It is a really super special place. We have great students, great teachers, an incredibly supportive community that values progressive education, and we have a just a strong, we have a strong history and a strong academic standard as well as a strong focus on the [00:02:00] whole child.

CT: That's amazing. And I'm just going to be a little bit facetious, but I am curious about this. Do you guys get like Hershey's chocolate kisses and hugs for the students lunches?

Stacy: No, but there is an abundance of candy around here if you ever want some.

Stacy: I think one of the things that I'm most proud of just being at Derry Township School District. I've been here for 12 years now, and both as assistant superintendent, a super and a superintendent. One of the things that we have. Worked very hard to do is maintain a focus on three main district priorities So we're going on close to 15 [00:03:00] years now of having those three priorities as our focus and they've been in our comprehensive plan They're part of how we plan strategy and how we plan what we're doing for staff development And those three elements are social emotional learning equity and professional learning communities And so we don't, we take a lot of pride in not chasing the shiny thing, which is something that happens a lot in education.

Stacy: Both for academics and for behavior. As we know, behavior is a huge barrier for academics sometimes. And our whole goal is to educate kids. So we want to remove barriers that keep them from their education. We also believe very strongly that regardless of socioeconomic background, regardless of, what neighborhood you live in.

Stacy: If you want to take AP Calc before you graduate, we're going to make sure you get to take AP Calc before you graduate so that all students have those same opportunities. And then we are a huge learning community, like the whole district. emphasizes professional learning. We believe strongly in professional learning because the more that we know, the more that we can then pass on to our students.

CT: That's great to hear. One of the things that you mentioned around staff development and professional learning communities is something I want to dig into a little bit more because think as you said, if you're the adults in the district are constantly learning, constantly growing, not only are they role modeling that to the children, they're then able to pass those that knowledge over to the kids.

CT: And from all these conversations, one of the things that also stood out to me is sometimes as an educator and a teacher, it can be a little bit isolating. Within the classroom and these PLC is actually helped to break down those barriers to be able to share learning across and you need that agility almost as the needs become more complex as you mentioned.

Stacy: That's a great question. So our middle school was actually the building that dove into the PLC process first, and they had started it before I got here. I came in 2012 as the middle school principal, and I celebrated the fact that PLCs were already in place. As assistant superintendent, I've worked with the elementary team.

Stacy: administrative team and with the high school team to implement PLCs in their buildings as well. Because the middle school has been at it the longest, I'll use them as the example. So they're organized into teams and they have time built into their daily schedule for either a team meeting or a PLC meeting.

Stacy: They then take that information and create new lessons based on how well did the kids do. Thank you. With what they just taught they work together to make sure that they're sharing resources. Maybe last year, I had a student who has autism and displayed, particular learning proclivities that I developed some things with and with their case manager.

Stacy: So I had some help with that. But now I have those resources. And now this year, my colleague has a student who has very similar learning proclivities. So I can be like, Hey, this is what worked for me. And this is how we planned it. This is what we did. So I want to share those resources with you. The other piece that we look for here.

Stacy: And so constantly learning from one another as colleagues. So your kids did really great on it on this assessment and your kids are really demonstrating proficiency with this. Mine aren't. What are you doing that I can then do with my kids? The other piece that we see with it with the PLC groups in particular, because they're organized by subject area.

Stacy: Let's say it's a, an English language arts class, and we have a group of kids who are just, they're flying, they're ready to go, and we have a group of kids who are just they're doing what they need to do, and we've got a group of kids who really need some remediation in a particular area. The teachers will divide up by strength, and one will remediate all of the kids from all of the classrooms.

CT: Yeah, it certainly sounds like that. And, the methodology that you're describing sounds like it's pretty well established as well. What has been the, what's been the feedback from the teaching staff on this process?

Stacy: Again, because the middle school has been doing this for so long, it's. Really just what they know. It's how it works. At the elementary level, it took us several false starts to get it going. And one of the key elements with professional learning communities in those collaborative team times is making sure that it's part of the daily schedule.

Stacy: If someone took it from you I know it feels like at the beginning, it feels like more work. It feels like you're doing some learning outside of your comfort zone. It feels like you're maybe even being very vulnerable by sharing What your kids are not doing so great at, and having other people look at your classroom data.

Stacy: But once this, once you build that trust in those relationships, if someone tried to take this from you, and, remove it from your schedule, you'd be really mad. And we are now at that point with our elementary teams. Our high school teams were still, it's very difficult at the high school level with all of the moving parts of a schedule.

Stacy: We're getting closer, but we're not quite there yet.

CT: What you talk about sounds like a really interesting case study and change management where you're, and then it's very relevant for the leadership listeners. And on this podcast, because it's, it sounds like in some environments. There, there was an approach where you seeded it and it grew its own momentum and it blossomed.

CT: And then in middle school, it sounds like, it's like fish in water, right? You don't even notice it. This is just, it's exactly it is. And then within the high school, they're in the midst of that change management process where there are additional complexities that you're dealing with and pushing it through.

CT: Do you have like Champions within each of these grade levels that are driving this.

Stacy: They are positive and they are just, this is how you do it in math. This is how you do it in ELA. This is how you do it with discipline. Like they, and every time I've gone to one or every time I've heard one of their speakers, because we've had some of their speaking authors come to our district as well.

Stacy: have some extra training to then support their colleagues and to be the champion for what we're trying to move forward. And it also allows a safe space for the teachers. So if they're struggling and they need assistance and they feel comfortable being vulnerable with their instructional coach who doesn't evaluate them, it's, it just opens up a space for them to Be vulnerable in their own learning and to figure that piece out without having to feel like even though the administrators wouldn't be, poorly evaluating them because they need help.

Stacy: That's not what we do and we also recognize that's still a sense that like it's hard to it. Tell your principal, Hey, I need some help with this. It's not going well.

CT: Okay, do you find it challenging at all to have teachers and staff raise their hands to take on these appointments? Because there's secondary to their primary responsibilities.

Stacy: So we actually, at our middle school, we had our math instructional coach role was empty for, gosh, I think two years. Very important to us to fill it with the right person who really wants to take on that leadership role. But also it was a void that was very difficult to have as a void because as administration, we rely on those folks to be an intermediary and to be.

Stacy: And the other one is focusing on science and math and already seeing That kind of bounce back in oh, that's right. We like this. We like being challenged. We like coming out of our comfort zones a little bit. We like to know more about how we can support our kids and our teachers do truly like they want to do a great job and they truly love their kids and that's an awesome space to work

CT: How has that impacted you as a leader?

Stacy: I think one of the things that I truly believe and. Is part of leadership theory. It takes 3 to 5 years to get something going and it takes 7 to 10 years for it to be sustainable so that you can walk away and it would exist without you leading it.

Stacy: Is if there's a, if there's a kindergartner or first grader who's really struggling, I'm going to know who that kid is. I'm going to know that kid's name. I'm going to know the family's name. I'm going to know what interventions we're putting in place. I'm going to hear it on our radios. I'm going to I'm going to know and what I get to witness from this level is the interventions that we put in place Working over time and that can be a hard that can be a hard part for a classroom teacher to see because it might feel like I've done this over and over and over again and I am because that teacher is seeing that kid every single day and they get worn out.

Stacy: And it also helps me to be encouraging. To our staff and to those who are working with particular students and even to families when they are starting to get frustrated either because there's a child in their child's class who they feel is too disruptive or it's their own child who's causing the disruption and I can say, listen, I've watched this work like what we're doing works and it takes time.

Stacy: It, it might be 21 days, but it also might be 435 days. And you just keep going and you keep reinforcing and you keep setting out expectations. And but then over time, you see those interventions and all the work that people have done together in the teams to support a child. You see that child become successful.

Stacy: And that's a really cool perspective from the leadership chair.

CT: And that's particularly powerful as within education, because as an educational leader, you've seen this, you've been through it, and you've had that stability with your communities, with your kids, to be able to stare and impart this knowledge to the new generation. You think that it's.

CT: Do you see that happening a lot?

Stacy: Yeah, and that is another place where systems are so important. And I had that same experience as a new teacher. Like I came out of my student teaching. Thinking that I like I've got this is great. I love this. It's going to be wonderful And my very first teaching job was a long term sub job at a neighboring district for just a semester I walked in second semester and By the end like literally by the end of the semester, I couldn't breathe because I was having back spasms so bad I didn't know I did not know what I was doing.

Stacy: So I just was like, all right, I'll just get here really early. Cause nobody told me what time I'm actually supposed to get here. And I didn't know what time I was allowed to leave. So I just stayed until I started seeing cars leave the parking lot. So just a very unsupportive environment. And it wasn't at that point in time, it was very district.

Stacy: Oriented if you wanted to provide support for new teachers or not. Then I went to the district where I spent 20 years and they had a full two year induction program. They had a mentor program. They had administrators who would come around and observe you. And give you tips and help you. They had a department chair who would come in and observe you.

Stacy: No, I did not know that if somebody hadn't been in there to tell me, I would have probably spent 15 years teaching to the right side of the room. But just an incredible program. And then I was also at a middle school there where there were teams and those teams were very supportive as well.

Stacy: New teachers without those levels of support, they're probably still having the same experience that I had and probably even worse. And that, that level of support is huge. And what we know about new teachers is that if we can keep them for three years, we've probably got them for life.

CT: They get, get over that hump and start to see the impact of their work on the kids, I think the way that you've described it. It sounds like it hooked you from earlier in your career and it continues to inspire you to inspire others to get to that point as well.

Stacy: And I don't want other people to go through what I went through. Horrible. I almost quit teaching altogether because of

CT: can't believe that you didn't, not even knowing, no one even bothered to tell you what time to get to work or what time to leave.

Stacy: right?

CT: That is incredible.

Stacy: Yeah.

CT: Was there any hesitation? How did you think about this whole process?

Stacy: When you and I talked a little bit before, I was like, my, I never meant to be like, that wasn't really what I went into this for. I knew since I was a little girl that I wanted to be a teacher. And that was my path and I really thought that I would spend my whole life in the classroom because I love being around kids, I love teaching I love those lightbulb moments, I love the ridiculous and crazy things that kids come up with, and, the things they say, and the things that make you laugh, and the, I don't know, like every year, you're like I've never saw that before yeah.

Stacy: I don't know if she's even still alive. But she was wonderful. And by my third year of teaching, I could, she was giving me responsibilities and pushing me in a particular way. And I can remember looking at her and being like, Ruth, I don't want your job. I like what I'm doing. But at that district, I had a lot of really great opportunities to Grow my knowledge to be what I would call intellectually nosy.

CT: In 2001, that is incredible. Yeah.

Stacy: And I was like, I'm doing this thing. I'll do that. To I feel like I can take that on at the same time and it turned out that I just, I really liked helping my colleagues like it was fun and it was interesting. And I got to see how our department built budgets were built. I got to see, how, what's the ordering process look like?

Stacy: What are some of the things that people need that I can assist with? And I really enjoyed that. I liked being able to help my colleagues as well as then spend time with the kids. And then that job grew and evolved over the years. With new superintendents who came in and we had a superintendent who came in, who was very curriculum oriented and trained all of the department heads in like really solid curriculum work.

Stacy: So then it was okay. How are we gonna get social studies aligned? I was a social studies teacher. So how are we gonna get social studies aligned? K 12 and that was really exciting and challenging work. And ultimately I was doing that halftime and teaching halftime. And then I had another mentor, another assistant superintendent.

Stacy: Like it was, I just, I was really blessed. I had some just really phenomenal opportunities. And then a colleague was like, let's get our doctorates. I was like, all right, so I went home. We talked to my husband. I'm like, what do you think? He's you'll have it by the time you're 40 do it see how it goes.

Stacy: And that really let me then I really got to dive into my intellectual nosiness. Like really by then I was seeing a big, more of a big picture idea of how the district functions and how the different departments interact and how the school, I was going to a lot of school board meetings and presenting at the school board and working with school board members that were learning that governance piece.

Stacy: And that it got to a point after the recession in 2008, 2009, it really started hitting districts pretty hard in 2009, 2010 in our area. And at that point, my boss was like, we can't, you can't just do staff development. You're gonna have to do. And I was like all right, what do he's finish your principal cert or we're going to make you dean of students.

Stacy: And I was like, I don't want to be dean of students. Then all the kids will hate me for discipline and all the teachers will hate me for the staff development. It was terrible. And I was, I had not finished, I had done everything except the internship piece of it. I'd even passed the test and he was like, just do your internship, take the class and you'll be ready to go by fall.

Stacy: And honestly, CT, there was a Friday afternoon. I was working with my colleagues, Aaron and Laurie. We were in the. In the main office, everybody was gone. And I was like, I love it here so much. I'm going to retire from this job. This is what I'm going to do the rest of my life. I love it. And literally three days later, the assistant superintendent called and was like, so what do you think about applying for the assistant superintendent for curriculum job?

Stacy: And I did that for eight years and again, did not mean to become superintendent, like each of these steps. I didn't, it was like, I'm not going to do that. Um, and I will tell you, we had a board meeting here and as assistant to the superintendent, we had to attend board meetings and my assistants still have to attend.

Stacy: They're delighted by that. And but we had, yeah. We had an incident happen where we had a fight at the high school and the fight was. Was provoked by a white student. And a black student. Want to say finish the fight. And it was so ugly. It was really ugly because this kid was provoked and it was portrayed as someone who doesn't belong here shouldn't be here.

Stacy: If this is how our community is going to respond when things like this happen. And of course, it was only a segment of the community, but in that moment, it felt a little overwhelming. And then the next morning, I got up and I was like, you're not giving up. You're not walking away from this.

Stacy: Who are you kidding? Somebody needs to be here to do this work. There are definitely, That did not represent the whole community and clearly there are people who still need to hear the message and that was the day that I decided I would be superintendent and that I would be willing to move into this role

CT: Your journey really inspires me in a few different levels. One is, I think a hallmark of your journey is this ability and willingness to lean in and say yes to the experience. And you definitely credit a lot of opportunities that came your way, but. I think you deserve a lot of credit for leaning into those as well, because not everybody does.

CT: And I think the 2nd piece that came across very strongly is. At every stage of the journey, you found something that resonated with you. You found something that made you think, actually I'm happy where I am. And that is also critical because as leaders and, many of our listeners are aspiring leaders and they're always thinking about, I've been there in my mid twenties.

CT: So it's not just, it's not just about your own experience, your own journey, and you're constantly looking out like, what is it that I'm, what is it that I can contribute? What is it that I'm bringing to the table? And it's inspiring to hear that in leaders and inspiring to hear that from you.

CT: So thank you for sharing all of that. And, 1, final thing that we'll touch on is we spoke a bit. About how you think about other leaders and other teachers in, your district that you're reaching out to and and helping them along in their journeys.

CT: When you think about the amount of mentorship or the amount of support that you're giving to them, is there any kind of framework or approach that you use to guide you in thinking through building up leaders for the next generation?

Stacy: Letting them run with that strength to, to support others being available to, to answer questions and then also to look for some career pathways and that has, Um, I'll tell Sarah's story. When she first came to the district she was the secretary for the it department and it became evident really fast. And especially through our COVID experience that her talents. We're not being used to the [00:36:00] extent that they could be used.

Stacy: It's she's super talented person really smart. Definitely a go getter willing to jump in wherever needed. And. If we didn't find a way to, to grow her into something bigger, we would lose her. And so we were at a space where we were transitioning one person out of the communications role.

Stacy: And I knew I was going to need somebody in there. And I went downstairs to her office and I was like, so if this would become available, is this something you would be interested in? And she was like, yes, I would. And she has been phenomenal in this role. Just grown our district presence on social media created a bank of communications that are, we always have to rework them anyhow, but it's so nice to have something to start with.

Stacy: So we've been working on. How do we get me out there into the community to talk to people? It's just a phenomenal person in her role and everybody in the district relies on her. Teachers send her pictures and, administrators reach out for help with communications and directors do as well.

Stacy: She's revamped our whole entire website. She brought our food services website over onto the district website this year and it's accessible now. Like she's, working with our equity lens to make sure that people who are visually impaired or have any other kind of impairment or who speak a different language can still access the material on our website and none of that was happening before.

Stacy: If you're gonna, if you're gonna lead a district K 12, you really should have a picture K 12 in some way, shape or form. I know that was a huge benefit to me getting years of working with K 12 teachers. Elementary educators with their curriculum work. So moving them into assistant principal positions and then principal positions at the secondary level to give them that broad scope of experience.

CT: Yeah,

Stacy: And then when I talk in with people, I'm always like, where do you see yourself in three to five years? What do you want to do?

CT: so Stacy, I gotta say, even though you say there isn't much of a framework, I think what you've just described And having heard your own personal journey, it sounds like this is your DNA, what you've gone through as a leader, like looking actively looking at opportunities and leaning into them. You're now on the opposite end, creating these opportunities for people, and I'm willing to bet my last dollar that for someone to thrive in your team, they would need to have that openness to opportunity as well.

Stacy: The one thing that I always tell someone who's starting a leadership program is don't piecemeal it. Just get all of the certificates while you're doing it. Don't be like me, like that had to go back and be like, ah I'm never going to do that. So I'm not getting that one right now. I have to go back five years later and get it.

Stacy: Just get them all. You never know when you're going to use them. So I do tell people that all the time. But I think the other piece is be nosy, be intellectually nosy take risks, put yourself out there. If there's an opportunity that you're interested in or something that you're curious about, let people know that you're curious about it.

CT: Absolutely. And there's a whole thesis around living your life with this regret minimization these theory, right? And you have to take those opportunities when they're there. Well, thank you so much for inspiring me today, Stacy and I'm sure you've inspired many who are listening really appreciate you hanging out on the show.

CT: And for all of you listening, thank you for listening and I appreciate you hanging out with us over the course of this episode it's been a real pleasure hosting the Engaging Leadership Show once again. My name has been CT and I'm signing off.