Summary:

Dr. Jim and Steve Wilder, Superintendent of Sycamore School District, discuss the power of reflection over action in leadership. Steve shares his transition from science teacher to superintendent, emphasizing the importance of building trust, coaching leaders, and fostering a reflective culture. They explore the challenges of leadership in education, strategies for impactful decision-making, and the value of patience and open communication. Tune in to learn how leaders can create long-term impact by taking their time and encouraging thoughtful reflection within their teams.

Key Takeaways:

• Leadership Development: Effective leadership involves mentoring and coaching, encouraging leaders to grow and reflect.
• Visible Leadership: Maintaining visibility and engagement with students and staff is crucial for any educational leader.
• Building Relationships: In a new leadership role, taking time to build trust and relationships is more valuable than immediate task completion.
• Patience in Decision-Making: Being patient and reflective leads to better decision-making and stronger leadership culture.

Chapters:

00:00

Leadership Lessons from a Superintendent's Journey

07:53

Evolving Leadership: From Task Orientation to Growing Leaders

11:00

Building Trust and Patience in Leadership Transition

20:33

Balancing Mandatory Coaching Sessions with Informal Engagement

24:14

Building Leadership Capacity Through Reflection and Long-Term Impact

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

Connect with CT: linkedin.com/in/cheetung

Connect with Steve Wilder: linkedin.com/in/steve-wilder-3a1009206

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



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And in today's conversation, we're going to. to focus on how over indexing on the first hundred days can lead you down the wrong path in the K through 12 space. What if instead of a bias for action, you built a bias for reflection? Would creating a culture of reflection drive results better than creating a bias for action?

His area of focus as a leader include coaching and mentoring, technology, communication, and facilities. On the personal side, Steve and his wife, Michelle, have been married for 24 years and they have four kids, Sam, Maren, Maggie, and Sean. Steve, welcome to the show.

[00:01:27] Dr. Jim: I'm pretty pumped about this discussion because I think you're going to be one of the first conversations that we've had where we deconstruct what you learned on the second go around of being a superintendent. So it's going to be an interesting conversation because I'm sure you walked into your first role thinking a certain number of things and that's probably been modified a little bit, . Before we dive into the big part of the conversation, one of the things that's going to be helpful is for you to walk us through a little bit about your background and story, and particularly some of the details about the district [00:02:00] that you're in currently.

And then it started to appeal to me. Did that for five years and resisted my principles. Encouragement to go get my admin degree for a couple of years but finally gave in, she saw some leadership qualities in me that I didn't quite see, but it's worked out really well. So I was a principal in a middle school for about four years assistant principal in a high school for four years and then took on my first superintendency in, in Knoxville about 14 years ago, every step along the way, I've been passionate about supporting students. And like you read and talked about earlier, giving them the tools to chase their dreams. It was hard for me to let go of that, not being in the classroom, but I think the draw was as a, as an administrator, as a leader, I have the opportunity to influence more students other than the ones that are just in my classroom.

[00:03:10] Dr. Jim: Appreciate you sharing that background. I think one of the things that I'd like to get a little bit more detail around is, you started out as a teacher and you resisted. You said that you resisted your principles advice to pursue a leadership track. What was behind that resistance?

That's exactly what I had. And my first job was the opportunity to build those relationships with students and their families in the community. And you see that direct impact, the impact on students the way they react to you the way they listen to you and I think a lot of educators have seen throughout their career.

In fact, I'm still in touch with a lot of my former students from 20 years ago on, on social media, keep up with them and that's what it was all about and I was, I think a big part of me resisting administration and leadership was letting go of that and a fear of not being able to have that influence on students lives.

If I stepped out of the classroom and while it's not as direct as it used to be the ironic thing is that I've had a chance to influence a lot more students indirectly throughout my career than I probably would have if I had stayed in the classroom.

So how are you satisfying that desire? When you're so far removed at the superintendent chair, what are some of the ways that you still satisfy? That need for impact in your current role.

They get to know me a little bit. But being in the classrooms, it's still really what it's all about. What's going on in the classrooms. What are students doing? How are our staff interacting with them and supporting them and just seeing the awesome things that happen there. But I think the other joy [00:06:00] that I get now is not just visiting schools and being around students and staff.

Especially the last couple of years, a lot of joys come from interacting with our leadership team. And not just directing them or facilitating conversations and making decisions together. It's truly watching them grow as leaders, coaching them through difficult conversations, mentoring them through difficult moments, sometimes encouraging them to grow by, seeking other opportunities.

And then having the fortune to welcome them back after they've grown and come back to our district. Again, it's the direct impact, it's the influence, it's seeing a positive outcome and being part of that's, that still brings me joy to this day.

This isn't your first rodeo as a superintendent. And when I opened the show, I mentioned that oftentimes if you're oriented towards bias for action, it can lead to a lot of good things, but it can also lead to a lot of bad things. How has that related to your experience as a first time [00:07:00] superintendent and now a second time superintendent?

What are the needs of the district? And maybe what are some problem areas that we need to address right away? Developing those plans and then achieving those plans, marking them off our list, checking those boxes and. You're successful and that you're getting things done, you're producing things or you're marking things off your list, but I think you missed the opportunity to have a greater impact.

And we talked about that earlier, the impact on students and staff and the leadership team and the great opportunity when I came here to sycamore was. Really stepping back and thinking about how I wanted to approach the second go around as a superintendent and the leader in the district, can I be doing more, I still want to accomplish things.

We were really pretty task oriented, but almost right from the beginning was looking for opportunities to help our leaders grow. I also realized that I was a little older than I thought it was compared to some of the other leaders in the district and maybe had some life lessons to, to share with them.

I'm not looking to develop leaders to be the exact same person that I am. Everybody's got their own leadership style. So one of the things I do is to just try to draw that out of our leaders. Help them to grow, help them to seize opportunities, help walk them through difficult conversations and difficult moments that they have with students, staff, or their families, I didn't have that before.

And that was a great opportunity. When I came here to Sycamore, I I saw that I could not only accomplish tasks. But delegate a little bit more. There's a little bit larger leadership team here than there was in my last district, show them that I could trust them to delegate things to them, know that I, that they would get done.

But again, also help them develop as leaders, challenge them a little bit, help them to see things differently. And just yesterday I was talking with one of our assistant superintendents about maybe a change that we needed to make in one of our departments. Um, but I talked about an opportunity to grow the leader in that department by challenging them a little bit, but then also just having conversations with them, getting them to reflect on.

[00:10:11] Dr. Jim: I really appreciate that perspective, Steve.

It's a really good line of sight into some of the things that you were thinking about, but you said something in your answer that Caught my interest. And that was sometimes when you're so task oriented, you miss the opportunity to make a greater impact. And the reason why it caught my attention is that I talked to superintendents all the time and they talk about the importance of the first 100 days and how that can lend itself to that task orientation that you were talking about.

Where you're always picking off the low hanging fruit. I'd like you to step back. Into that comment that you made the opportunity missed the opportunity to make a greater impact. How can you marry those two things getting line of sight on the biggest impact possible while still keeping true to that.

[00:11:00] Steve Wilder: Yeah, I think when you step into a new job, there are probably some things that you need to accomplish right away. And some of it's demonstrating to the board or your community that you can do those things. But they don't, my experience is that they don't usually have to be done immediately.

And identifying those things, working with your team to identify those things, involving them in the conversation, getting their perspective on those things, developing a plan of attack to address those things together and really just taking a little bit more time to have a little bit more conversation about it.

And what I like to do is be less directive in conversations. I tend to sit back and usually answer last unless I have to but really just ask questions that cause the leaders to, around me to, to reflect. If you were in my shoes what would you do? If you think about our community and the expectations what do you think is the the path that we need to go?

[00:12:03] Dr. Jim: so I can appreciate that perspective. And your comment about building discipline around answering last is usually pretty helpful. Flip that perspective to somebody that's reporting into you. So you're the new guy that comes into the organization.

And a lot of times the new guy is there because the old guy or gal didn't do a good job. So here I am as somebody reporting into you wondering, Oh, How much runway do I have before this guy rolls me out of the organization now that's a private sector lens that I'm applying to this, but you have that sentiment that's there and then here you are coming in saying, Hey, I'm going to try to answer last when you have a room full of people that are probably like, what is this guy about?

Who's on the chopping block? What do I need to do to protect myself? So when you're dealing with that as the new person in the seat, what were the things that you did to break down that resistance so that you're creating the space where you can answer?

I've gotten really good at wait time, they teach us that and our teacher prep programs, give it some wait time. But I've been pretty fortunate that sooner or later, there's somebody who was willing to take that 1st step and, just put something out on the table. And I learned from a great mentor of mine years ago.

When you're dealing with tasks and you're planning and, always approach that as there's no idea in the kill zone, really give, um, meaning to anything that's out there at the end of the day you find the response or the solution that you think is going to work best, but really valuing what people bring out and I felt the more I did that.

Those first couple of meetings, there was a lot of that kind of holding back, but I would say within the first three or four meetings that we had we really started to come together. People started to trust that I was going to listen. I was going to make the final decision. That was part of my job, but I was going to listen to anything that got brought up, any idea that was thrown out on the table.

Sometimes, being vulnerable myself, telling the group, Hey, I don't know what the answer is here, help me out, what do you think? But the more I gave them time and demonstrated that I valued their input, the more comfortable they became. Amen. We've had some pretty difficult conversations and haven't always agreed, but there's, it's always been done from a place of respecting each other's opinion and respecting each other's role.

Building operational capability. And I hate operations. So if that was true about your experience coming into Sycamore, what were the things that you did deliberately slow so you could advance building a true coaching and supportive culture that feeds into that need for reflection before you move into taking action on something.

Tell us a little bit about that.

But I think the other piece of that is. When you recognize that you've got some time being patient, and that was a very deliberate effort as a superintendent, I'm constantly planning out and some things need to be done in a month, some in [00:16:00] six months, some a year, some three or five, 10 years down the road.

So always having an idea of where we're going and the things that we're working on, what's the timeline for those addressing the things quickly that needed to have to be addressed quickly, but you can take time being very deliberate about that. And really controlling how I approach the rest of the group, making sure that both my words, my non verbals were really inviting that I wasn't a power hungry, it's got to be done my way, kind of leader.

It really was a lot of taking time. Giving people a chance to respond, to grow to take a leap of faith, if, gosh, if I talk is he really going to respect that? They could see that in their peers, but they didn't always demonstrate that. And there's still some times that I have to ask people directly, Hey, Thomas, what do you think or Sarah, what do you think?

But making sure that I'm respecting that taking time where we can and involving as many members of the group as I can.

Where you end up getting into everybody's kitchen and that can be the case, especially if you're an early stage leader. Tell us about some of the things that you did from a coaching perspective that set up guardrails so that you're not actually directing people what to do. You're actually being an effective coach.

I needed to push myself a little bit. So I got involved in some opportunities through our state superintendent organization here in Illinois, IESA, and. One of two of those opportunities were really focused on coaching your team, coaching yourself a little bit, being open to coaching yourself, but then learning how to coach, others.

And I thought I was being patient. I learned how to be even more patient as I went through some coaching for leaders training. Not being directive is really, it's a really important part of that process. Every once in a while, there are times where I have to be directive again, that's part of my job, book stops, at my desk, so to speak.

Conversation, we talk about personal things. We talk about professional things. It's non evaluative. It is absolutely just an completely transparent, open conversation. I don't dictate what we talk about. The leader that I'm working with kind of picks the topics and what's going on in their career or at home as they're willing to talk about it, but it's not being directive at all.

It's really, even when I know, when I think I know the right answer or the direction they should go. It's asking question after asking question, getting them to reflect. Because my experience of what I've learned is that deep down, most of us know the direction that we need to go.

Sometimes we were living in denial a little bit. Sometimes it just takes a little bit of conversation or reflection to bring that out. But one of the other deliberate things I've done is meet with our leaders one on one and just. Ask a lot of questions and not be directive at all.

So define that out a little bit for us.

And so there is a bit of a requirement. What I've learned this year is when leaders don't sign up, I don't chase them down. I don't hound them, if they're not comfortable that may be a signal that they're not comfortable with that. But I put it out there. I want them to know that's something that I'm willing to do something that I want them to do and to push them to, to get them to grow a little bit.

It has been really beneficial for our team.

And the reason why I caught the, it caught my attention is this. If people on your leadership team, or even your broader team are noisy, good or bad, that's good. That's a good thing for you as a leader. What you need to start worrying about is when it's silence. So if you're not going to chase people that don't meet this requirement, I take that as silence.

So what are the things that you're doing to make sure that people are actually reengaged in meeting with you? Because I'm not necessarily sure if I would take that path of not chasing people. Clarify that for us.

Maybe it's not that one on one that, that really That gets them that really grabs them. So one of the things I do on, in addition to that is when I'm out visiting buildings, periodically, I'll pop in and talk to the principal or here in our administration offices, I'll pop down and talk to our assistant superintendents or some of the directors, so I'll pop in and have a conversation.

And every once in a while walk in and shut the door and just ask how things are going. That's different from what I practice is a coaching session. It's just it's completely loosely structured. It's just a conversation. I don't ask them what's on their mind. I don't ask them what they're working on.

Nobody's really resisted that. I, I think for the most part it's appreciated because sometimes they don't sign up for those coaching sessions because they've just got a lot going on and that slips through the cracks. That happens to me, happens to all of us, but I don't want them to be silent and I don't want them to think that I've forgotten about them.

So a big part, it's still really important to me going back to those relationships is making sure that when there is a void that we reconnect in that they know, Hey, I'm still here for you. If you're not, if the coaching session's not your thing. I'm not going to beat you over the head with it, but I'm going to still stay in touch with you and give you opportunities to talk with me and check in and see how you're doing.

But one, I want to tie this back to something that you mentioned earlier on when you were talking about taking on this role at Sycamore, one of the things that you noticed early on is, you want to build more Capacity and [00:24:00] capability across the entire organization from a leadership perspective.

As you've been putting these things into place, what have you noticed now that you're, a couple, two, three years into the role? What have you noticed in terms of how that's showing up across the organization?

But what I've also seen and heard is that they've taken some of those things that, that I've practiced with them, asking a lot of questions, prompting a lot of reflection. They take those back to their buildings, they take those back and those are part of conversations that they have with their staff.

I've had some of them tell me, instead of just jumping in and telling a staff member, how to deal with a specific situation, they're more likely to stop, take their time and kind of ask the staff more questions. Why did that happen? Why do you think that happened? How could you address that?

But if our leaders are functioning at their best, then our students and our staff and our families are going to get the best possible experience day in and day out. Again, that's why I do it. Those are the things that I've seen as a result, I think, of the work that that we've done together.

So this is a weird conversation for me to have. But when you think about. Building the capacity for that reflective type [00:26:00] culture for that superintendent or that leader that's listening to this conversation. What are the key pillars of executing that? That you feel is important for them to keep in mind as they try to do this in their own environments.

And if you want to have a larger impact, it's more than just the the action piece. Absolutely important. I don't don't want to decrease that, too much. Still have to get things done. But if you want to have the long term impact of growing your leaders, improving your school district and the impact that it has in our community, always be thinking about that and how you can have short term actions, how you can do things, day in and day out that will have [00:27:00] long term lasting impacts in the school district and really.

We know that leaders don't always stay in the job that they're in, right? They move, they have other opportunities, the, for a variety of reasons, leaders move. The other thing that kind of drives me is that if I have that kind of impact on our leaders here, it's not just in Sycamore, I hope it's just here in Sycamore, cause this is a great community that I'm here for a reason.

But when they leave and they go to other districts or they talk to other colleagues, they share some of those things. You also know that the impact is bigger than just here in Sycamore. It kind of filters out beyond that. Think of that. I would tell young or early leaders in their career, take your time, think through things, reflect yourself, but always be thinking about what's the long term impact that you want to have on your school district and your community.

And how do you need, what do you need to do every day in and day out to get there?

[00:27:51] Steve Wilder: So email is always really good. People are always welcome to call me. It's a little harder to get in touch with me. If you call me, but you can call, look us up on, on the our website, which is [00:28:00] www. syc427. org, but I'm on social media too. So you can find me on LinkedIn.

You can find me on Facebook, Tik TOK you name it. I would always love to talk shop and talk about the things that we're doing. I'm glad to share lessons, but always glad to hear from other people too, and what they're doing, try to incorporate that into what we do too.

And I think one of the things that I would add when I think about this conversation is that if leaders want to build a culture of reflection, they first need to be really comfortable with those uncomfortable silences and what happens with new leaders when they step into any new role or even experienced leaders when they step into any new role, they feel like they have a responsibility.

So people aren't going to be able to reflect on what's going on in their own heads. If they're always listening to you as the leader, offer your two cents. So learn how to shut the hell up and you'll be better off. That's a, that's my two cents, not your two cents. But anyways, I appreciate you you hanging out with us and sharing your input for those of you who've been listening to this conversation.