Summary: On this episode of the Engaging Leadership Show, host CheeTung (CT), co-founder of EngageRocket, converses with Tim Winter, Superintendent of South Kitsap School District. They discuss what it means to belong, believe, and become, focusing on building schools from the inside out with the best people. Tim shares insights on the unique qualities of South Kitsap, their commitment to enhancing math and literacy education, and initiatives like multi-tiered support systems and professional learning communities.

They delve into leadership challenges, the importance of relationships, and the core values of South Kitsap, known as the SK Way, which include love people, get better every day, know your purpose, think big, and have an attitude of gratitude. Tim also reflects on his personal leadership journey, emphasizing the role mentors and relationship-building play in effective leadership.

The episode highlights practical strategies for aspiring leaders and the significance of creating a sense of belonging within educational communities.

Key Takeaways:

• Creating a Sense of Belonging: The district prioritizes creating an inclusive environment where students, staff, and the community feel they belong, which is crucial to their success.
• Building Schools from the Inside Out: Leadership development is emphasized across all roles, from bus drivers to nutrition services, ensuring everyone sees themselves as an integral part of the district’s success.
• Leadership Philosophy: Tim Winter's approach centers around vulnerability, building trust, direct praise, and effective conflict resolution to foster strong relationships and accountability.
• Continuous Improvement: Importance of daily self-reflection and striving to get better every day, aligning with the district's 'SK way' five core values.
• Mentorship and Development: Personalized approach to developing leaders, focusing on authenticity and building individual potential rather than relying on standardized programs.

Resources:

The Culture Code by Daniel Coyle

The Advantage by Patrick Lencioni

Upstream by Dan Heath

Leadership and Self-deception by The Arbinger Institute

Dare to Lead by Brene Brown

Barking to the Choir by Gregory Boyle

Win Forever by Pete Carroll

Chapters:

00:00 Introduction: Belong, Believe, and Become

00:33 Meet Tim Winter: Superintendent of South Kitsap School District

01:24 Community and Resilience: The Heart of South Kitsap

02:01 Recent Achievements and Focus Areas

05:05 Building Schools from the Inside Out

07:49 The SK Way: Core Values and Leadership

11:19 Tim Winter's Leadership Journey

13:21 Operationalizing Leadership and Building Relationships

18:56 Mentorship and Growing Leaders

30:09 Final Thoughts and Advice for Aspiring Leaders

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

Connect with CT: linkedin.com/in/cheetung

Connect with Tim Winter>: https://www.linkedin.com/in/tim-winter-45b550124

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



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CT: EngageRocket is a leadership listening and insights tool to help school district leaders to improve teacher retention, engagement, and ultimately student achievement outcomes. And today in the studio, it's a great privilege for me to be speaking with Tim Winter, superintendent of South Kitsap School District.

CT: Tim, welcome to the show.

Tim Winter: Thank you, C. T. Happy to be here.

CT: So Tim, tell us a little bit more about South Kitsap School District and what makes it special.

Tim Winter: We're surrounded by water. Thank you we have we're close enough to the I 5 corridor to access to things we need to access, but far enough away that we still feel rural. That's our community. One of the things about this district, and you mentioned people, we have great people in our district, and I think that's such a critical piece to success in any organization, but it certainly has been critical in ours.

Tim Winter: We have a lot of people who have. Been in this community for a long time. A lot of people who've been in this district for a long time. And these people are really dedicated to their work. They're very resilient. I think during the pandemic, it showed how resilient we were. They really want to get better every single day and be the best they can be for our students and for our community.

Tim Winter: This is my sixth year in the school district. 11th year as a superintendent. So I came in from a smaller district and we've had a lot of things. There's a lot of tradition, a lot of pride in our community, a lot of things that have worked over the years. But I think we're in a place where we really need to maybe push a little bit on that sense of urgency.

Tim Winter: to make some good things happen for our students. And so we've really been dedicating some things math in particular. I think that's probably a nationwide thing. We're really focused on mathematics and teaching our students math. Literacy is also really important. We are engaging, re engaging in our professional learning community resources and practices.

Tim Winter: We've been probably for the last 10 or 15 years have really been into professional learning communities, but we haven't really brought those back as a reinvestment. So that's one of our focus areas. We have things we're calling the big three, and that's one of the big three this year is reinvesting in our PLC work.

CT: That's great. And, one of the things that comes up a lot school district tends to contribute quite a significant amount to the economy of the community. You build a lot of partnerships with, the transport with the lunches, people deliver the milk, stuff like that.

CT: And you drive a lot of jobs within that community. And so one of the unique things about leadership in the school district is that you have almost indirect community leadership. Do you feel that to be true in the six years that you've been in the role? And what kind of weight has it been bearing on you?

Tim Winter: One of the things unique about Port Orchard though, is we don't have a whole lot of business here. Like I mentioned, it still is pretty rural. Most of the business opportunities are surrounding us. And so that's been a little bit of a challenge and I can talk about that a little bit later too, but we haven't passed a bond in 35 years.

Tim Winter: But again, that goes back to that relationship and the power of relationships.

CT: What does that look like for you? How did you chance upon this approach.

Tim Winter: I, one of the things when I got here six years ago and I'd worked for 13 years in a neighboring community. And so I knew about South Kitsap, but when I was Preparing to come here. One of the things I heard over and over again was just how great the people are. And I think a lot of organizations say that but I have found it to be really true here.

Tim Winter: There, there are really amazing people in this district and in this community. One of the thing though, that, and I mentioned the bond, we have some old schools, and so one of the things that happens is people come to our community and they might drive by a school and make a judgment about what's happening in our schools based on what they see on the outside.

Tim Winter: That whole idea of collaboration. It's more than just How do we become the best teachers? But we collaborate with our bus drivers. We collaborate with our food nutrition services and our facilities team and our it team, because I think all of us play a role in the success of our district. And I really believe that leadership is not just the role of the superintendent or the principal, but every bus driver is a leader.

Tim Winter: Every. Person who works in food nutrition services is a leader. Every custodian is a leader. And so we try to develop that within our district too, that we all we all have skin in the game. We all play a pretty important role for our students and for our community. And we try to really bring that forward and lift people up.

CT: What are the other two?

Tim Winter: So the other two the MTSS multi tiered system of support. So that's with academics, with behavior and with attendance. And we're really trying to create levels of intervention for our students. But the other one really that we've been focused on for the last couple of years is this idea of belonging.

Tim Winter: And we hear a lot about diversity, equity, inclusion, accessibility, but really we're focused on this idea of. Of when everyone belongs, they have a much better chance of being successful. And it's difficult to do because I think one of the things that I appreciate sometimes when you call something out like belonging people will call you out if they don't feel it.

Tim Winter: And I would include our parents in our community. We're safe. It's an environment that's safe. We're comfortable being who we are. I think we have a much greater chance than of looking to the future to see what's possible. And that's really one one thing we're really trying to work in with our community is our community deserves great schools.

Tim Winter: And our students deserve great schools. And we want them to believe think big is one of the values that we have. We want them to be thinking about what are the great possibilities for their lives. And we just know through a belonging and having a spirit of belief, they can become anything they want to become.

CT: I think that really cuts to the heart of what makes a community tick, that sense of belonging, that sense of we're in this together. We got each other's back. How have you gone about defining that with your team?

Tim Winter: And I think sometimes that can be misunderstood as soft but I think we were just talking today about conflict. When you love people, you still engage with people when you have conflict, but you work for resolution treat people with respect, build trust okay. Dignity along the way. So that's something that's really important, especially right now, I think in our country there's some divide and we've got to try to come together regardless of what our beliefs are.

Tim Winter: We've got to come together to support the success of our community and in turn, the success of our district. So loving people we have a desire to get better every day. That's another thing that we push on another one of our values knowing our purpose. I mentioned think big. And then the last one is attitude of gratitude.

Tim Winter: And one of the things I've really tried to stress too, I may call it love people. Somebody else may say, build relationships. I may call it, think big. Somebody else may say. high expectations or thinking outside the box. But really, it's the actions that go with that are the most important part.

CT: I love those five values. I think they resonate a lot and they would fit very neatly in pretty much almost any organization that you're trying to build strong community in. How did you narrow it down to just these five values?

Tim Winter: I think that I don't know. It was an interesting process because really through a lot of just listening and talking to people I came to this district with some of those already intact and presented those and say, this is my philosophy as a leader. This is what I believe leads to great culture, which leads to great achievement.

Tim Winter: And so I think, again, that's important that our, if people are using our language. The South Kitsap language to, to hold us accountable. I don't think we can ask for much more than that, because that means people are understanding the direction we're trying to go.

CT: I want to pull on that thread that you mentioned that this kind of developed along with your own personal leadership journey. How did your leadership journey bring you to the point where you are today? What made you say? Say yes to that superintendent job.

CT: Given that so many around the country are saying no or bailing out,

Tim Winter: But, I think about Simon Sinek said in his podcast recently, I was listening, he said, the first criteria to being a leader is wanting to be one. And so I asked this question of our principals at the end of last year and said, Think about what your first memory of as a leader. And I go back to second grade, my first memory of leadership.

Tim Winter: I love being around kids. I love having that relationship and that impact resisted a little bit going into administration. But as I think happens to a lot of us, we have someone in our lives who gives us a nudge, maybe directly or indirectly. And we end up going down a path and I became a principal.

Tim Winter: And I really wanted to see would that success translate into the role of a superintendent? And I have found in my 10 plus years now that I believe it really does. And maybe it's not the norm but I like to think it's the way that we should be doing things is being open and vulnerable.

Tim Winter: Having courage to connect with people and build relationship.

CT: How do you operationalize this? Because I think the need to build relationships is recognized within leaders. But the way that each leader goes about doing so can differ quite dramatically from person to person. What is your personal style for building these relationships?

Tim Winter: I mentioned vulnerability. I think that's when we have to show our true selves. We have to be comfortable enough with ourselves to show who we can say, Hey, I made a mistake or I'm sorry, or, Hey, that's a good idea. Let me ponder that. So that's one way. I also think I am a big believer in names.

Tim Winter: We spend a lot of time in our world talking, but how much time do we really spend listening? And I try to get around the district office here on a daily basis and checking with people and talk with them, but also try to get out into the district and have conversations. And I would say that would be the number one frustration of my job is.

Tim Winter: It's way way less opportunity for connection and contact. I've really got to go out of my way to make it happen. But I think that's something that I've been trying to continue to develop in my leadership is that I want to get out and be with people in meaningful situations not in any artificial environment, but something that's really meaningful that I just believe if people know who I am they're gonna understand the decisions I make.

Tim Winter: And I think it's important for me to know who they are as well.

CT: This was early in your career, and what was the transition like for you?

Tim Winter: It was pretty natural. I think that even as a teacher there was, I look back and can see some leadership that was happening. Certainly my experience as a coach, I coached high school basketball for 16 years. And so there's a lot of leadership that goes with that. So I think again, back going back to my parents and the way that I was brought up and the conversations we were having around the dinner table.

Tim Winter: My dad is one of the most influential people in my life just because he showed me what it means to, to work hard have integrity, connect with people. The importance of that purpose driven life and moving forward towards a vision. And I would say it was a natural progression, but anytime you move into something like that, you do have to adjust your mindset adjust your heart sometimes, and that can be a challenge too.

CT: Okay. And what were some of the things that you had to learn on the job when you first took on that leadership position? Because leading a sports team can be in some ways similar to leading a group of educators, but in other ways, it could be quite different.

CT: So what are some of the things that you had to pick up?

Tim Winter: So one of the things that I had been a teacher at the high school where I was an administrator, I'd been there for four years as a teacher. And so I had a lot of relationships with colleagues at teacher to teacher relationship friendships. And then I became an administrator and that relationship naturally changes strictly by title and job role.

Tim Winter: But that's the challenge. And going back to your earlier question is how do we build that relationship again?

Tim Winter: I think it's really important that I show who I am and people understand the purpose of my leadership in my life.

Tim Winter: And I think that, that's a challenge. So there's times I go to the grocery store and I'm either recognized as a superintendent or I'm maybe recognized as a neighbor. We have neighborhood gatherings and I get to be me and there's certain places where I know I get to be me and other places where I know that I'm the superintendent of South Kitsap and that's okay, that's part of.

Tim Winter: Part of the job but I think it's it's a challenge certainly. And knowing which hat to put on and when you can let your hair down, so to speak. But that's an important thing to understand too, even with people that you work with. Sometimes we all have these close relationships and there are people that we need around us.

Tim Winter: We use the phrase shoulder to shoulder here that we're, it's not, I've got your back. I'm going to be standing shoulder to shoulder with you to support you. But sometimes those shoulder partners are your confidants too. And you can go behind closed doors and you can have really honest conversations.

Tim Winter: And I really value that.

CT: To get you to this point I'm sure that you've worked with many other great leaders in the past. What would you be able to describe, say the best leader you've ever worked with and what, She or he was like,

Tim Winter: Yeah. So I mentioned my dad earlier and taught me things at a young age and helped me develop some of those leadership skills, even when I didn't even. Think I was developing leadership skills, but I look back and I can see a lot of those things he did for me as my dad that, that helped me along the way.

Tim Winter: Had a mentor named Grant, who actually was the interim principal at the school where I worked. And we've formed a relationship that has been 20 years really now of mentorship. And he really taught me this idea of relationship and how important it is and to bring energy to the job every day.

Tim Winter: You don't have to be somebody else, just be who you are internally as a leader and let that part come out and bring that energy every day. And then I had a coach in college that was the first male, other than a family member who looked me in the eye and told me he loved me. And that was interesting and unique for me.

Tim Winter: But it really was It meant a lot. It was inspirational throughout my career and I've had the chance to call him and tell him, you really made a difference for me because you were the first person who showed me how important that was. And it has had an impact on my vision for my life and my purpose and what I'm doing.

Tim Winter: Yeah, I think I've been really fortunate to have a lot of people who have believed in me over the years and have lifted me up and shown me either indirectly or directly, hey Tim, this is who you can be. And it goes back to that belong, believe, become. I have felt really lucky in my life to belong in a lot of situations I've been in, which has led to, Me believing that I can achieve just about anything I want to want to achieve.

Tim Winter: And again, I think it takes people. That's why the power of relationships is so important to me and the importance of people is that by raising the level of our belief in others, we can really do great things. And that happens through recognition. It happens to celebration. It happens through knowing people, vulnerability, trust, all those things.

CT: And then ultimately becoming, do you feel like that had, you've just taken that along with you in your entire journey and now you're sowing these seeds across the district

Tim Winter: Yeah, I think there's been numerous examples throughout my lifetime throughout my career where just believing in somebody and showing them that you believe in them. And like you mentioned, looking someone in the eye and just telling them how you feel have really made a difference for other people.

Tim Winter: And those relationships last, which I think are even more valuable as they go through the years and you get to connect. As a matter of fact, I got a text from somebody today that that just was reminding me of the relationship that we had. And it's really it is uplifting. I think sometimes it's easy.

Tim Winter: They're in the coaching world, the teaching world, teacher's pet, the favorites. It's really easy to have people who, Would be classified as favorites because they do what you ask them to do. But there's a lot of people who really want to be connected to us that maybe we don't recognize.

Tim Winter: They may just be introverted. They may not quite know how to go about it, but those are the people that I think we really got to pay attention to and focus on because people want to connect. I really believe that people want to be connected to other people. And especially in a leadership situation, I think people that we lead want to feel connected to the leader.

Tim Winter: But in a way that's real and authentic, not in a way that's artificial or staged or manufactured in some way.

CT: and speaking of building and lifting other people up. How have you use what you know as a coach and as a leader over the course of your career? entire leadership journey to grow the leaders around you. And I wouldn't be surprised if you mentioned that it first starts with the sense of belonging and the belief in them.

Tim Winter: So again, I think it goes back to the self awareness, situational awareness. You have to read the room. You have to know what's going on around you. One of the, when I was coaching, I had the phrase, watch the person in front of you. They'll tell you what to do. And I think it relates to leadership to watch the people in front of you.

Tim Winter: They'll tell you which way you should go. I do a lot of lot of people write notes and cards and I do that periodically, but mostly what I do is I go write to people and try to recognize them verbally in person. I had a a colleague, administrative colleague of mine who came from a different district and I sat down with him after the first couple of weeks he was here and I gave him some specific positive praise on something.

Tim Winter: Have some critical conversations with them. And that's something that we're trying to build within our leaders, too, is that don't be, don't shy away from feedback, but don't shy away from conflict, too. And conflict doesn't mean argument or a fight. It means we disagree. Let's see what we can do together to come up with a resolution.

Tim Winter: And preferably not that. I win or somebody else wins, but we both win. We come together. And so I think my approach has been, like I mentioned, getting to know who people are, not just from a work standpoint, but from a personal standpoint, really trying to recognize and celebrate who they are and how they lead.

Tim Winter: And then not being afraid to say, Hey, here's some suggestions moving forward. I think when we have things like the SKA and those five core values, and we call out what our expectations are as leaders, it makes it that much easier because we know what is expected of us. And our school board does a great job of that with me too.

CT: Wow how do you keep track of all of these things? Do you keep them in your head or do you have a notebook somewhere that you.

Tim Winter: I use my calendar. I have a great executive assistant. She is phenomenal. She helps keep me on track. And, I talk about people who are She is definitely one of those. And I can sit down with her and we can talk through things and she'll remind me, Hey this is what happened. Or remember you're going to do this, but I also find that people once they get in the habit that this is how we're going to operate, they're on the lookout for things.

Tim Winter: So again, they're watching what's happening in front of them. So many times I get people who will send me a note and say, Hey so and so did this. You might want to check in with them and just tell them that you're aware of what's happening. So I think being in a team is really important and having people who are willing to work together is really valuable.

Tim Winter: And that's a great question. I think I have always shied away from what I would call a canned program. I read a lot of books. I listened to a lot of podcasts even when I'm watching movies or I'm always relating it back to, okay how would this relate to the work I do? I really like to go from I'll just say from the heart for lack of a better term that I know what my purpose is as a leader and what I would like to see in other leaders, and it may not be what everybody wants, but when we talk about how do we grow our leaders, it goes back to our five values of the SQA.

Tim Winter: And I think that's part of it is just that, that again, I'll go back to the vulnerability and the courage to have tough conversation with people and say, Hey, this is something that would help you. Down the road to be a more effective leader, whether it's a better communicator or have better systems or better be a better leader of learning.

CT: Got it. So most of this seems to come from you yourself as a person. So as we speak even though you say you're an introvert, it feels like you're more, I don't know how well versed you are with strengths language, but you're like a relater, right? You build these one on one relationships with people and You instinctively individualize your approach for each one and you help them become not so much more of you, but more of who they are as leaders.

CT: And that comes naturally to you. And then you sound like you, you don't really need to rely on any kind of systematic programs or anything that and this may be more authentic that way.

Tim Winter: That's one of my approach. is trying to be connecting outside of my comfort zone. I do need that quiet time and quiet space to recharge at the end of the day. But I get to do that through exercise or through reading or just being quiet and being still. But yeah, I just, I, again, I think that the power of relationships is so important.

Tim Winter: And that word love, there's a commercial that I've seen on TV a number of times. And the question is what's hard to say. And somebody said it's really hard to say I love you. I don't think it's that hard. I think that's one of the key components to our lives with human beings is we should love all people.

CT: Yeah. And I think that. If that approach like approaching people fundamentally with that idea of starting point of love, starting point of respect for their dignity you really can't go wrong. In, in being able to build those relationships. So thank you for sharing that. If you had one, one tip for any educator who's aspiring to leadership that doesn't know how to get started, like what would you tell them to think about?

Tim Winter: The first thing I would say is just reflect on, I think all of us have led at some point in our lives. Like I mentioned I go back to second grade where I had a little speaking part in a class production. At the time I wasn't thinking that was leadership. Now, 50 years later, I think.

Tim Winter: I think that's one of the mistakes we make. Sometimes we think leadership is about a title. Or a role. And it's not it's just about inspiring and motivating, connecting people together. And so I think that would be the one thing I would say is look for those times in your life where you've already been there and hopefully that will build some belief and confidence to move forward.

CT: That's really helpful advice. Thank you so much for sharing all of your experiences with us, Tim, on, on this show. And thank you for being so open and honest about how you go about leading your district.

Tim Winter: Yeah, absolutely. Thank you. I appreciate the opportunity to share.

See you again soon.