Linking Leaders PodCASt
Linking Leaders PodCASt features candid conversations with top educational leaders who come together to share experiences and explore pathways to success. In each episode, we engage with dynamic leaders to uncover real-life stories, practical strategies and bold insights on timely and relevant topics. Listen up to link up and let us help you expand your network of innovation and support!
Linking Leaders PodCASt
Culture, Teamwork and Bon Jovi: Insights from An Award-Winning AP
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In this episode of the Linking Leaders PodCASt, Dr. Alicia Bowman sits down with Dr. Dana Mulligan, 2026 Connecticut High School Assistant Principal of the Year, to explore what it means to lead with heart, humility, and a "we're all in this together" mindset. From building a family-centered school culture through daily advisory to making tough decisions guided by “what would I want for my own child,” Mulligan shares practical insights from over two decades in the AP role. It’s a candid look at the small moments, shared leadership, and yes—those livin’-on-a-prayer days—that define impactful school leadership.
Hi, and welcome to the Linking Leaders Podcast. Linking Leaders Podcast features candid conversations with top educational leaders who come together to share experiences and explore pathways to success. In each episode, we engage with dynamic leaders to uncover real-life stories, practical strategies, and bold insights on timely and relevant topics. Listen up to Link Up and let us help you expand your network of innovation and support.
The Woodland Community And Culture
SPEAKER_01Hello, listeners. Welcome to the Linking Leaders Podcast. This is your host, Dr. Alicia Bowman, and today I'm thrilled to introduce and welcome my guest, the 2026 Connecticut Association of Schools High School Assistant Principal of the Year, Dr. Dana Mulligan. Now here's an impressive stat. Dr. Mulligan has been an assistant principal for over 22 years, 15 of those years dedicated to the community in which she resides, leading Woodland Regional High School, serving the towns of Prospect and Beacon Falls. I have no doubt that today's conversation will be filled with humble reflections and insights from her impressive career. Dana, thank you so much for joining me on the Linking Leaders podcast. Let's dive in. Thank you for having me. Thrilled to be here. Great. So to ground our listeners in your work and your world, can you start by painting a picture of the Woodland school community, who you serve, what matters most there, and what makes your context unique?
SPEAKER_02So as you mentioned, Woodland Regional High School serves the communities of Beacon Falls and Prospect. We did not have a high school for those two towns until 2001 when Woodland was built. The students who lived in those two towns prior to that went to either local high schools, Wolkett, Massick, some went to Holy Cross, Seymour. So I guess by high school standards, we're relatively new. We have a population of about 550 students. And I think that what makes Woodland unique is we really try to take a family approach to our school building. We look at it as it's two towns, but we're one region, we're one family. The school, when it was created, the kind of cornerstone of it is our advisory program, as well as what we call the Woodland Way. The Woodland Way is really a code for which we all are going to conduct ourselves, that we're going to be responsible. We are going to be dedicated to the fact that we will take care of each other, that we will have respect for one another and everyone's right to learn. So I think that it's one of those things where you could just kind of mention in the hallways, is that the Woodland way? And then a student knows that means they weren't doing the right thing if they were being questioned about it. And as you mentioned, also my context is also kind of unique in that I live in prospect. And so I serve the community in which I live. And, you know, that's sometimes a challenge, but it for the most part, it's been the most rewarding part of my job to be able to watch the students that I see out in the community flourish and grow to be successful alumni.
Why She Chose Assistant Principal Life
SPEAKER_01That's wonderful. So you've clearly found your stride in this role as AP. And I'd love to just rewind a bit. What drew you to the assistant principal role and what keeps you in it after all these years?
SPEAKER_02So I started as an assistant principal at Hamden High School. I was a teacher there and I had just finished my 092 program. And one of our assistant principals was leaving mid-year. So I was asked if I would assume the role for the remainder of the year. And I thought that was an excellent opportunity to see if that was truly what I wanted to do because I loved the classroom. And I thought for certain what was going to happen was I was going to go do that job for a few months and then head back into the classroom where I loved being with my students. But I found that I really enjoyed my time. You know, I got to work with students in a different capacity than I did in the classroom. I got to see them work with teachers, work with students, and more importantly, I got a better opportunity to work with families, which is something that I've really come to enjoy. I just kind of got the sense that I got to finish each week knowing that I made it some kind of small difference, even if it was just getting somebody back to class who was struggling, or whether it was, you know, helping some students to set some goals, to have a better week the following week. It kept me coming back to the role year after year, knowing that I could make a difference for people. And there's nothing better than watching a student receive their diploma after you've worked with them for four years. And you don't often get that capacity as a teacher because you have students who come in and out of your classroom. And so I just found that I love what I'm doing. I think, you know, sometimes you say, oh, well, have you explored other positions? Or I think I was born to be an assistant principal. I just love it.
Leading Like It Is Your Child
SPEAKER_01That's wonderful. So, Dana, as leaders, we're faced with numerous decisions throughout the day and often some really difficult ones. What was evident when I read through your application and your interview and just the site visit is how you are guided by this core principle of what would I want for my own children? And you use that when navigating difficult decisions. Can you share with listeners an example of how that principle shows up in your practice?
SPEAKER_02Yeah. So, you know, my own children attended Woodland. So I think, and my friends' children's attend have attended Woodland, but I think if everyone approached their position with what would you want for your own children, it really is a strong guiding principle in all that you do. You will look at curriculum differently. You will look at how you deal with families differently. You will look at how you discipline differently because you'll treat all of those scenarios with the mindset of not just wanting what's best for students, because I think that's why we all do this job, right? We all do this job because we want to do what's best for students. But when you look at it and say, how would I want my own family to be treated? It does definitely help you to take a different approach to things. So it's been a guiding principle for me, even from when my kids were young before they went through the high school with me, that I knew I was setting up programs and things that would eventually benefit them. And if you can have that kind of mindset, even if you don't have the opportunity to work in the same school with your children, I think that you're always going to make the right decision.
SPEAKER_01Yeah. I think, you know, when we do have to make difficult decisions or when we do have to make choices, or sometimes even when we have to say we're going to try something different for a child that maybe we've never done before. I think if we can go back to those core values and make it really clear to those that we serve that we're leading with that, you know, what would I want for my own child? It helps helps you to kind of sleep at night and to be able to say, okay, you know, I'm doing the best that I can for the community that I serve.
SPEAKER_02You know, I think part of that too is anybody who's a parent knows, you know, you're always questioning, did I make the right decision? Am I, am I guiding my child in the right direction? And so if you go into the role of an assistant principal, knowing that you might not always make the right decision. But if you have a certain level of humility when you approach things and are reflective in what you do, then you can look back on it and say, okay, I didn't do a great job with that, but the next time I can do better.
SPEAKER_01Absolutely. You know, that's a whole nother piece of leadership is that reflective component and being self-aware and being able to own, like we're not perfect. We do make mistakes and we're always trying to do our best, but knowing that and saying it and then trying to do better the next time. Yeah.
SPEAKER_02Exactly.
Share The Load And Build Trust
SPEAKER_01So yes, you've found your stride as the assistant principal, but needless to say, you juggle so much day to day, discipline, instruction, relationship, system. So, what's one leadership practice or like a leadership move that you rely on consistently in your role? And why does it work?
SPEAKER_02I think one of the things that I kind of embrace in my leadership role is sharing roles. So if you go back to times when you struggle, or if you look at when you have to make a tough decision, if you share that decision making with other people, you're going to benefit from the input that you're going to receive. You may not always agree with one another, but just the idea that you're going to be open to other people's ideas is a big part of how I approach my position. I'm fortunate to work with excellent teachers and excellent administrators. Honestly, I share this award with them because they're the reason why I'm able to be successful doing what I do. Riot McKenzie, who's the other assistant principal here at Woodland, Chris Daly, our athletic director, Kurt Ogren. I can't think of a better team to work with. And I'm fortunate to work with a very strong district office as well. So sharing roles is a big piece of my approach to really making the right decisions on people's behalf. I also think that I'm fortunate to work with people who don't have that mindset of like it's not my job. So I think it's always, and this is kind of how I was raised. And before I even started working, like if you want to be a good leader, you have to know what everybody's role is and be willing to do their job as well. So you have to be willing to know what the custodian does day in and day out, and be willing to help out with what they may need assistance with. You have to know what a para does and know what our BTs do and be willing to assist with that because that's kind of the mindset I think that you gain respect by doing that, but you also gain a better appreciation for the work that other people do.
SPEAKER_01Yeah, it sounds like what you're really referring to is perspective, like perspective by inviting people into the decision making or running things by people, right? We all have blind spots or or maybe a little too close to the situation or feel emotional. So having those people and then just recognizing perspective through the different roles that people have and that everybody's kind of coming from that place. But it definitely helps to paint the bigger picture when we have to make decisions and to manage kind of the day-to-day when everyone's willing to give.
SPEAKER_02And I think it's important too that you get to know the people that you work with. And that kind of comes with when you stay somewhere for a long period of time. You have no choice but then to know what's going on in their personal lives oftentimes. So, you know, I've been fortunate to work with a lot of the same staff for the time that I'm here because we don't have a high level of turnover. So we know each other's families, we know each other's ins and outs, we know when somebody's family is struggling personally and they just might need a spot to take a break. Or, you know, I'm gonna give you a little bit of break if your grades weren't in on time because I know your family's struggling. How can I help? So I think that there's something to be said for longevity in one position because even though sometimes some people will feel like, oh, well, then you get stagnant in it, but I also think at the same time you get to have a level of comfort with those people that you work with that helps to raise your game.
A Dream Course For Real World Skills
SPEAKER_01Absolutely. I mean, knowing your people deeply, right, is one of the best leadership strategies and certainly can be an advantage when you build that kind of that family feel. Yes. So let's just dream for a minute. If you had an innovation grant with no restrictions, what dream project would you launch for your hawks?
SPEAKER_02So, you know, I one of the parts about being an educator is oftentimes we have these conversations among ourselves as educators. But I think a big piece of kind of understanding what the needs are, especially for high school students, is to have conversations with people who aren't in education. And getting some feedback from them to like, what are you finding when you're hiring people right now, or even talking to those people like the next level in college? Like, what are you finding that our students need? And so my dream would be to run a course that addresses all of that feedback that I receive. My husband works in the business world and you know, they're always hiring people, and we have conversations like, you know, the these people that we hire, like these are the skills that we wish that they had and that sometimes that aren't as strong as maybe a generation or two prior had. So I would love to run a course at something like a student success seminar, kind of similar to your freshman year experience that they do at college. Yeah, it would be more so based on some of those soft skills that are needed. So, for example, like communication skills. And when I say communication skills, something as simple as talking with somebody on the phone or reaching out when you need to communicate with somebody about your needs. Conflict resolution is a huge one. How to do that effectively, because I think with our students now, a lot of their conflict resolution takes place by texting people or, you know, commenting inappropriately on social media posts, whereas there's a proper way to resolve your conflicts. You know, and I think that goes to the idea of digital citizenship as well. But even some of those my new things, just as like those simple executive functioning skills such as time management, independent living skills that students probably are lacking, workplace readiness. And that workplace readiness can be as simple as being ready to work as a high school student, not just workplace readiness for their career down the line. And I think a lot of that could be accomplished by giving students the opportunity to do internships. We have a great chip program that our students take part in junior and senior year, but that's a choice for our students to do an internship. But I would love to see more students almost have that required of them to spend some time in the workplace to understand how to function out in the real world. So I think my dream grant would be spending time getting students ready for those real world skills.
Daily Advisory That Bonds Students
SPEAKER_01I love it. So you spoke about this a little bit in your intro when you're talking about things that make your Woodland community special and unique. And one of those things is your advisory program. Can you tell us a little bit about that and kind of maybe what makes it so successful and how it's endured over these many years?
SPEAKER_02So when Dr. Frank, who was the first principal of Woodland, was creating division for Woodland Regional High School, he was insistent upon advisory meeting every single day, which back in 2001, that was not happening in places. I don't think it happens in a lot of places now. We meet every single day for at least 20 minutes, and the intent of the advisory program is so that every student has an adult. Every student has a go-to person in the building. And every staff member has an advisory. I have an advisory, Kurt Ogren, our principal, has an advisor. Every person. We get between 10 and 12 students from the first day freshman year, and they stay with us all the way until they graduate. And advisors are the person who hands each student in their advisory their diploma, which is a really special moment. So I always joke, it ends up being a dysfunctional family because we, you know, we start out, they don't all know each other. It's a little awkward freshman year, our freshman year activities are built on team building and service. So the students are getting to know each other and also providing service back to the community, either the school community or the community at large. But it really is a special, a special program in that I can say I still talk to my advisories that I had from the very first year that I was an advisor. People talk about they go to the weddings of their former advisor. So because you create this relationship and it goes back to that idea of having a family atmosphere. And like I joke, I say dysfunctional family because not everybody's always going to get along all the time. But it's a great way for students to learn to respect each other's differences, but also to be able to coexist and work with each other on a daily basis.
Why Collaboration Feels Hopeful
SPEAKER_01Yeah, that's really cool. So as we look forward, Dana, when you think about students and staff and systems of support, what feels most hopeful about the future of your school or just about the education profession in general?
SPEAKER_02So one of the things that I've noticed in, you know, starting my teaching career back in 1999. So I've been around education for a very long time. When I first started teaching, you you taught in your classroom and you were behind your door, and there wasn't a lot of collaboration with your colleagues. You know, it's started to grow over the years, but I think what I'm most hopeful for is I think people collaborate now more than ever. And I think that benefits everybody. There's so much to be learned from your colleagues. You know, we've kind of put an emphasis here in Region 16 on a lot of our professional development now is actually delivered by our staff members because there's a lot to learn from the people that you work with. It doesn't necessarily have to be people attending outside PD because there's so many people doing so many great things. And I think that with the evolution of being able to get information online and being able to attend webinars, somebody can learn something and take something away from that. And now, because I'm not behind my door doing it myself, I'm sharing that with my colleagues. I'm saying, look at this great thing that I found, or look at this great app that our students can use, or I learned this great method for differentiating in my classroom. I want to share it with my colleagues. So that makes me really hopeful because the more that we collaborate with one another, I think the better education is going to be year after year.
SPEAKER_01Absolutely. And not only for, you know, our students and the impact on them, but also professionally. It's more fun. There's more joy in the work when you're doing it with others and kind of that deprivatization of our practice, as you said, like back in the day, it wasn't really like that. But now it's like, yeah, come in. And it's just a regular way of doing business and learning from each other. I used to always use the phrase like, we're learning from the experts. And I would talk about teacher to teacher. We are the experts, you know, we're doing the work.
SPEAKER_02So yeah, that's it's part of our practice at Woodland. We do collegial walks. So, you know, we encourage our teachers to go into each other's classrooms and not just within your own department, but to go cross-curricular because there's always something to be learned. Maybe it's a classroom management technique, or maybe it's something in how you deliver your instruction. Or, you know, we have a lot of teachers who are doing an awesome job of integrating technology into the classroom. And so you could benefit from learning from your colleagues. So again, that idea of opening up your doors and letting others come in to learn from you just really benefits everybody. Absolutely.
SPEAKER_01All right, Dana, it's time for Ignite Round. So these are quick instinctive responses, just designed to give listeners a snapshot of your leadership style and your personality. So no overthinking, just first responses. Okay. You ready? I'm ready. All right, leadership and one emoji.
SPEAKER_02The laughing emoji, because I think you have to approach it with a sense of humor, otherwise, you're gonna have long days.
SPEAKER_01That's right. A phrase you say so often your staff could mimic you is we'll get through this.
SPEAKER_02You know, if it's something a difficult time, often we'll get through this. We'll do it together. You can't start your school day without Well, I'd say a cup of tea, but if you're like a cup of tea, I like to take a walk. I like to walk the halls a little bit, get the energy going in the morning. So I can't start the day without my cup of tea and a few laps around the hall.
SPEAKER_01Sounds great. The best advice you've ever received as a school leader. Teamwork first. A song that perfectly captures the AP role on some days.
SPEAKER_02Well, I'm gonna say Living on a Prayer by Bon Jovi. Give a little shout out to my Jersey upbringing, and I think there's some days that's definitely the appropriate song.
SPEAKER_01I love it. A leadership skill you're intentionally working on right now.
SPEAKER_02Probably just that going back to that idea of shared practice. I know that I said that it's something that I really embrace, but there's times where I think that I will take on the load just to get something done where you might have the, you know, it might be best to share that responsibility rather than just taking on that full responsibility yourself.
SPEAKER_01Mm-hmm. If you weren't an educator, you'd probably be a coach.
SPEAKER_02I was a coach when I was a teacher, and I've coached my children all growing up. And I honestly I think being a coach has benefited my leadership practice because I take a lot of the ideas behind how you work with athletes into my role as a leader in a school.
SPEAKER_01100%. So many parallels in those two roles. Yes. A book, a podcast, or resource that you would recommend to other leaders.
SPEAKER_02I think that if you're gonna read anything right now, I think you need to read about technology with students. So we've engaged in uh I'm reading the disengaged teen right now. And we're doing that as a book talk, actually. I have 40 staff members as part of that, but the book I read before that was The Anxious Generation. So I think right now to have a real understanding of where our students live versus where we grew up is an important thing to consider.
SPEAKER_01Absolutely. Your preferred way to recharge after a tough week.
SPEAKER_02So if I'm in the building and I need to be recharged, I head down to the life skills classroom. And hang out with the life skill students because they always brighten your day. Or I'll attend an athletic event because I love watching our students participate in athletics. But if I'm home, it's just time with family. I don't think that anything can recharge you better than spending time with your family because they're always the ones who are ground you and bring you back to your happy place.
SPEAKER_01Yes. And the last one one thing every assistant principal deserves more of.
SPEAKER_02Time. I think a lot of times it's time. We all carve out time in our day to get certain tasks accomplished, but the role of assistant principal never seems to work out that way. I'm just finding it fortunate that we haven't been interrupted yet as we're having this conversation. So just that time that you need during the day or even at the end of the day to just kind of have some silence and some moments to yourself to kind of collect and reset.
Pride Questions And What Leaders Share
SPEAKER_01Yes, absolutely. So before we wrap up, Dana, I want to end with a few reflective questions. What's something you're secretly proud of? It could be personal or professional, but rarely get asked about.
SPEAKER_02So we've talked about the fact that my children attended Woodland. And I think people always have asked them, what was it like having your mom as an assistant principal in the building where you work? But very few people have asked me what it was like to have my children in school. And so I'm pretty proud of the fact that we navigated that for a total of six years. I had a child in this school with me. And we navigated that, I think, pretty well. So I'm proud of their accomplishments, but I'm also proud of the relationship that we were able to have while they were students in the same school building.
SPEAKER_01That's really special. You're actually the second leader that I've talked to this week interviewing for our podcast who's had a similar experience with their children in their school. It's really special. Is there anything you'd like to ask me?
SPEAKER_02So I know that you have done many podcasts and spoken to many school leaders. And so what has been the, would you say is the common characteristic of the leaders that you've spoken to that if someone said, well, what do all these people have in common, what would you say?
SPEAKER_01I would say what comes through, and they may not say it exactly in these words, but just that core belief of leading with what's best for kids. So, like you said, you know, what would I want for my children? And other people might use different terms. But at the end of the day, as leaders, we make lots of decisions, whether we're interfacing with community members or families or students or teachers. And sometimes we have to make a decision that's not favorable or we know isn't going to be easy or is going to take resources from somewhere else. But I think going back to leading with that core value of what's best for kids allows leaders to do this job and do it feeling good about what they're doing, even when the decisions might be tricky or unfavorable or just really challenging because you're choosing something over another thing. So I would say I'm always speaking with the principals who have won some type of recognition, whether it's school of the year or principal of the year, and that core value always shines through.
SPEAKER_02Yeah, I would think that that would be the case because I think if you if you lead with that mentality, then you know, nine times out of ten, you're going to make the right decision.
SPEAKER_01Right. Right. And sometimes you're you're having a really hard conversation with somebody and you're not seeing eye to eye. But if you can get to that common place of like we want what's best for this kid or your child, it helps to navigate a bit. Yes. So and finally, Dana, where can listeners go to learn more about you and your work?
SPEAKER_02Well, I've always said that, you know, kind of that idea of the door is open. Where can they go? They can come here. They can come visit us at Woodland Regional My Beacon Falls. I we have lots of visiting teams that come, especially to learn about our advisory program. Our door is always open. I would love to meet with anybody that would love to come and check out Woodland Regional High School. We were the CASS High School of the Year, the inaugural CAS High School of the Year, because we do good things and we have good people here and we love to talk about Woodland. I love to talk about Woodland. So I would encourage anybody to come and just reach out, send an email, and be happy to have you as a visitor.
Open Door Invitation And Closing
SPEAKER_01Thank you. Dr. Dana Mulligan, thank you again for joining me and congratulations on being named the Connecticut Association of Schools High School Assistant Principal of the Year. Your leadership, your commitment to Team First, and the way you show up for students and staff truly reflect what this role can and should look like. To our listeners, this episode is a reminder that assistant principals are not just supporting schools, they are shaping culture, strengthening communities, and leading with heart every single day. If you enjoyed today's conversation, be sure to subscribe to the Linking Leaders podcast, share this episode with a colleague, and continue the conversation in your own leadership communities. Thank you for tuning in, and until next time, keep linking your leadership to who and what matters most.
SPEAKER_00Thanks so much for joining us for this episode of the Linking Leaders Podcast. This episode is brought to you by the Connecticut Association of Schools, serving schools and their leaders since 1935.