Thriving Leadership in Challenging Times with Dr. Jill M Siler (Ep 37)

March 08, 2022/ By

Dr. Jill M Siler has been serving as the Superintendent of Gunter ISD since 2012 and has been in education for nearly 25 years. Jill has a passion for helping others reach their goals and has been a frequent speaker at TASA’s First-Time Superintendent Academy, TCWSE and is currently serving as the lead facilitator for TASA’s Aspiring Superintendent Academy. Jill’s first book, Thrive Through the Five, was released in September and focuses on how to thrive through the most challenging seasons. Follow Dr. Siler on Twitter at @jillmsiler and visit her website at

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Dr. Nathan Lang-Raad: Hey there. Nathan here. Welcome to the podcast. I had a wonderful conversation with Dr. Jill Siler. She is the new author of Thrive Through the Five. Dr. Jill Siler has been serving as the superintendent of Gunter ISD since 2012 and has been in education for nearly 25 years. Jill has a passion for helping others reach their goals and has been a frequent speaker at TASA's First-Time Superintendent Academy, TCWSE. And is currently serving as the lead facilitator for TASA's Aspiring Superintendent Academy. Jill's first book, Thrive Through the Five, was released in September and focuses on how to thrive through the most challenging seasons. I hope you enjoy the episode. Jill, thanks so much for being on the show.

Dr. Jill M Siler: Thanks for having me. It's so great to be here.

Dr. Nathan Lang-Raad: Oh my goodness. I was so excited whenever you had said yes to being on the show. You just released a book and it was hitting the bestseller list, Amazon number one, and I'm so excited to read it. It's called Thrive Through the Five, a really catchy and fun name, [crosstalk 00:01:22] and published through DBC. And so I love to just start by asking you why you wrote the book, and then of course, I'm interested to hear as our listeners what these five things are that you write about.

Dr. Jill M Siler: Yeah. So I love my job. I serve as a superintendent for a small school district in Texas, and I absolutely love what I do. I love everything about it. Love being able to set the vision and create this culture and be a positive role model. I love being a small part of making things great for kids. So I love my job. And I tell people all the time, "I love my job 95% of the time." And people are like, "That's incredible. Who loves their job that much?" But there's this 5% that is so incredibly difficult. Indescribable, really. Certainly in the realm of leadership.

Dr. Jill M Siler: But I would argue really in anyone's work that they do, there's this 5% that is really, really challenging. And for so long my mode of operation was just survival. Like, "How do we survive those moments?" And then I finally just hit a place where I was like, "We owe it to ourselves and everyone around us to do more than just survive. We need to learn how to thrive through those moments." And that's why I wrote the book. How do you thrive through the most challenging seasons of life? Now, the funny part to that is I wrote it the year before COVID, and of course, it released in the middle of this global pandemic when I would argue that many people are experiencing a percentage that is much greater than 5%, including myself.

Dr. Nathan Lang-Raad: Yeah. Well, interestingly, I'm sure it will be so applicable during COVID. I mean, all those principles will definitely be able to transfer over to the current context. I'm interested in digging into this 5%. What are some of these challenges that you talk about in your book, as far as educators are concerned? What are some of these things that we have to really not only, like you said, survive through but thrive through?

Dr. Jill M Siler: Yeah. I think you know the list when you look at it from a leadership perspective and teacher perspective. Anyone really in the work that they do, that 5% are things like the tragedy that impacts your school community, the aftermath when anyone in your building makes a poor choice, young or not as young, the aftermath when we make a poor choice as teachers in our classrooms or leaders on our campus or in the district. It's the negative social media posts, it's not having enough funding, it's the challenging parents or community members. It's all of those things above and beyond just the great stuff that we get to do as educators that make things challenging. So you take that context and then you throw it in the midst of a global pandemic when everything has been turned upside down, and we really have found ourselves in some significantly challenging times.

Dr. Nathan Lang-Raad: We really have. And your role as a superintendent has been very unique in this because as a superintendent, the needs of the community, the needs of your students and teachers... I mean, there are so many different hats you wear and roles that you work through. I'm interested to hear what has been your primary focus and how has that effected your daily actions? Because like you said, we're in the middle of the pandemic right now. There's a lot of traumatic experiences, a lot of stress. So I'm curious about what are some of those things that you're focusing on, and how has that affected your response?

Dr. Jill M Siler: Yeah. So I think one of the challenges for being a leader is to be really in tune with your people and with your organization and what they need and not necessarily what you want them to have. Joe Sanfelippo, a great superintendent in Fall Creek, Wisconsin just put out his One Minute to Work video. And what he talked about was exactly that. They held this professional development day, and instead of pushing out any new initiative, what he really did was give his people time. And so as I have approached this crisis, it has really been looking at that, right?

Dr. Jill M Siler: There's a lot of things that we wanted to move forward in, and we eventually will, but leadership is about prioritization of what is needed at that very moment. And what is needed from me in my leadership role is to make sure that we have seamless processes around COVID, how we're going to make sure that we keep our kids and our adults safe, how we're going to deal with quarantine situations. Pretty much everything we've had to do we've had to pick up and look at how do we do this from start to finish in this new environment. How do we do libraries? How do we do music and singing and band? How do we do athletics and extracurricular activities? How do we do lunch and arrival and dismissal? We've had to change all of that. And so my role has been really to support my team that's been thinking through and brainstorming through those activities and then finding out how can I support them now where things are really challenging, especially in the classroom.

Dr. Jill M Siler: We went from a situation where we are at because our case count has been pretty low. We have been mostly in-person for our teaching. And so our teachers are having to do the in-person learning, but they're also having to do support full-time remote learning. And we really got a handle on that after a couple of weeks, until our case count for COVID started to rise a little bit and the number of kids that were going out on quarantine or short-term leave was rising. And so now our teachers are trying to do all of this, and it becomes really challenging. So my job as a leader is to support them where they're at and take obstacles out of their way and figure out how we can do this best for our kids.

Dr. Nathan Lang-Raad: That's a lot. And it's amazing, again, just hearing the day in the life of Jill, what that looks like-

Dr. Jill M Siler: I forgot to mention selling football tickets. That's a big [crosstalk 00:07:04].

Dr. Nathan Lang-Raad: Right.

Dr. Jill M Siler: [crosstalk 00:07:07] limit capacity.

Dr. Nathan Lang-Raad: Right. I want to say, well, you're in Texas and football is a big part of the school culture there and everyday culture really. I lived there. I definitely know that. It's so interesting. I don't think anyone ever intended on teachers having to do teaching remote learning and in-person learning at the same time. It seems unconscionable that that happens. But I know that our teacher... And just because they are our heroes, just because our teachers are so dedicated and talented, it doesn't mean that we can say, "You know what? You're so good. We're just going to put all these responsibilities on you and make it work."

Dr. Nathan Lang-Raad: And obviously you're not doing that. You're being very supportive. I'm wondering, what are those supports that teachers are asking for right now in your district or districts that you've heard around maybe here or in different contexts? But what are they asking for, teachers asking for right now? And how do you feel you're able to effectively support them at the highest level?

Dr. Jill M Siler: Yes. On one hand, right? I've been a firm believer. And I even blogged about this earlier in the year that the same things that make us an incredible teacher face-to-face are the same things that make us an incredible teacher remotely in terms of our passion, our ability to connect kids, our ability to create community. Those things are directly transferrable. But let's be clear that teaching in person and teaching online are two completely different things. And I think a lot of non-educators look at what's happening in our K-12 systems and say, "Well, why is this such a challenge?" Well, you can't take what you do in person and just hope that it's going to magically transfer to remote. It's a very different... You have to use different tools. And so in the spring we did incredible work as we transitioned our system. We knew pretty early. Just saw the writing on the wall that we might not reopen.

Dr. Jill M Siler: And our teachers, we created an online platform and... Just a one point of contact for our kids. Had great engaging learning. Our teachers had to learn a lot in that short period of time, but they really did an incredible job. And I was so proud and I thought that that was fantastic until I contemplated the notion that a good portion of our students were going to come back in-person. And we're a district whose size is such that we don't have standalone staff to do both separately. All of our people are going to have to do all of it. And so that really became a decision point for us. "Well, if we continue the way we were doing it in the spring, which was fantastic, but a full-time job and ask our teachers to do it the same way this fall, it was going to be untenable."

Dr. Jill M Siler: And so we had to make some really hard decisions on how we were going to support our students and our teachers in that process and then we did so. But that has been the challenge. What our teachers need more than anything, certainly, is support and professional development. Always adding tools to the toolbox, our teachers do a great job with that. But what they mostly need is time. And so as we have been looking through... Even now, we're in October and I'm bringing to our board next week a proposal to change our calendar. To give a half day a week for the rest of the school year for our teachers for planning.

Dr. Jill M Siler: That's unprecedented. Who changes the calendar in the middle of the school year? But when you get to the place where you realize this isn't working... It's not because my teachers aren't doing a great job. They're doing a great job, but what we're asking them to do is too much. And so how do we support them in that? And this is the only way I know how at this point. So that's what we're moving forward with.

Dr. Nathan Lang-Raad: It is so important, Jill, as a leader and as the highest leader in a school system that teachers hear that, that they hear the empathy that you have. Because again, you've been a teacher, you've been an educator, so you understand and know what they're going through. But it's really important because especially after being in a leadership position for a while, that you continue to empathize and say, "I understand that it is a challenging time and I want to do everything I can to support you." And I think you are definitely meeting their needs by giving them more time. I remember asking a retiring teacher once, "After 30 years, what has been the most... Thinking back at professional development, what was the best PD that you've ever received?" And he said, "Actually the best PD we ever received was time, a time to collaborate with our colleagues."

Dr. Jill M Siler: Right.

Dr. Nathan Lang-Raad: Which is amazing because we always go to conferences and we go to these even amazing PDs that we plan in in-district and out of district, but what's most compelling and what's most productive for a teacher is just given time to collaborate with colleagues. And I think that's so important. I'm so happy to hear that that's something you're going to do for teachers. And I'm curious too, do you think also not only giving time, but collaborating with teachers and the principals and leaders in your district to think through what the time is going to look like, or do you give them a lot of autonomy to let them decide? Because we know that they are professionals and we know that they want to be able to use the time in ways that are meaningful to them. So I'm curious to hear about what kinds of experiences they will be planning with this extra time if it all goes well.

Dr. Jill M Siler: Right. And that's important. It's not approved yet, and we're just [crosstalk 00:12:48]-

Dr. Nathan Lang-Raad: Yes. Right.

Dr. Jill M Siler: ... process. But I think it's important to approach it as an or instead of a... It's important to approach as an and instead of an or, right?

Dr. Nathan Lang-Raad: Yeah. Yeah.

Dr. Jill M Siler: And so both giving autonomy over time and giving some small pieces of professional development and support where needed. And so even in this process, as we've been thinking through it, the very first thing we did was send out a survey to our teachers and say... Because I feel I have a good pulse on what they're thinking and feeling and what their pain points are, but you always want to make sure that you're in touch. And so asking those questions in this particular way that we're serving our full-time remote learners, how much work is it? How little work is it? And asking that for feedback. What changes could we make?

Dr. Jill M Siler: And thinking about how we're serving our short-term quarantine students, how much work? How little work? How could we be doing this differently? And then asking about the calendar process and asking those questions, what would you want to use this time for? How can we support you in this? I think one thing that changed for me was my thinking around professional development this past spring. I really hadn't thought about it like we need to do a PD day or a PD time. And what we found in that survival mode is we were in the process of completely transitioning our systems into online was that it wasn't about that.

Dr. Jill M Siler: It was about giving the small pieces in bite-size palatable chunks and layering them on top of one another until we build proficiency. And so with that, I no longer approach things like, "Oh, we need to have this day. No, let me put out a four-minute screencast on whatever it is, whatever skill we feel like we need that could build the toolbox and send it out on that day." And so I think it's important that we find that fine line between support and professional development. And I think that the context sometimes impacts that tremendously. This is not the time to move forward with a whole slate of new initiatives. This is the time to give more autonomy and time and structure collaboration for our teachers because they're in the midst of this crisis.

Dr. Nathan Lang-Raad: Agreed. And this is so powerful, Jill. I also hear you using tools and modeling the kinds of experiences that you want your teachers to facilitate for your students. So we keep saying, "Hey, let's be innovative in a way that we are reaching students. Let's use the most effective EdTech tools." But then if we are asking to do in-person traditional faculty meeting, that's not really showing that we understand how the thinking and learning happens. And so the fact that when you can, doing a four-minute screencast or a video, or some way where you're using some asynchronous opportunity to engage leaders, I think it's really important, especially from the very highest level of leadership that you are modeling that for the district. Because obviously we are all learning right alongside each other.

Dr. Jill M Siler: Absolutely.

Dr. Nathan Lang-Raad: I'm also wondering too... I don't want to diminish the challenges that we are going through right now because the challenges are many, but I know as educators, we always look for the opportunity and we always look for this ability to turn the challenging situations to more meaningful opportunistic times. I'm wondering, going through what we did with closures in the spring and then of course with the challenges of doing remote and in-person right now, would you see there any things that you have decided as a leader, or just you can even say in education if it's not necessarily in your district, but where you would say, "You know what? We were able to do this during remote learning and I don't want to go back to this?" Can you fill in those blanks? Is there anything that comes out that you think this is a new way we're going to do things from now on?

Dr. Jill M Siler: Yeah. They say that crisis doesn't define leadership, it reveals leadership. And I think that that is true for everything that's happened in every role. This has really revealed the core of who we are and the work that we are about. And I saw incredible things happen in the spring and have continued this fall. I would never have wished this on anyone. That has to be said first and foremost.

Dr. Nathan Lang-Raad: Right. Absolutely.

Dr. Jill M Siler: But I will say that the growth that has happened with my teaching staff in terms of... We had pockets of just greatness in terms of tech savviness. But we had recently in the past couple of years gone through very significant financial challenges. And so we're not even a one-to-one district. Our use of technology is shared ChromeCarts, may happen, may not, very spotty internet at home. All of those pieces were in place. So that was our starting line. And so to turn that into this robust, vibrant online learning was a challenge and our teachers did it.

Dr. Jill M Siler: So it was incredible to watch them overcome failure, fear, all of those sorts of things to get to a place where they were serving kids and serving them well. So that's first and foremost. Is that just this has revealed again, how incredible our teachers are, how resilient our teachers are. I'd also say from a leadership standpoint, this has really forced our hand in addressing some equity issues that have been longstanding. And I'm talking specifically about device access and internet access at home, right?

Dr. Nathan Lang-Raad: Right.

Dr. Jill M Siler: We can handle those needs at school, but this is about at home. This is more than a question of we want to do this or we don't want to do this. We have always wanted to do this. But when a district steps up to do a one-to-one initiative, you're also putting yourselves in a financial position where it then becomes you're at risk, right? And to think that this global pandemic is not going to have economic fallout at the end, we would be remiss not to recognize that.

Dr. Jill M Siler: And so our board of trustees was placed in this position of do you step out on this limb and take care of these equity issues because we have to have it in order to survive our current existence, which is on any given day, our kids may be home or they may be at school and they won't even know until the night before or the morning [inaudible 00:00:19:11]. And so our board took that huge step of faith to go ahead and move one-to-one to make sure that every student who needed internet access would have it to a huge financial cost and a cost that's not necessarily being reimbursed.

Dr. Jill M Siler: I know that there's lots of talk about all of this funding that is going towards pandemic. We have not seen that in the local district where it's really standalone funding for these things. And so that's been a huge challenge that we've overcome that in the long run will serve us so incredibly well, but is also risky financially. And so that's one of those things we just have to measure of. The cost versus the cost on the other hand. So I'm really excited that we've done that and it's going to pay off hugely for us, but it has been a challenge.

Dr. Nathan Lang-Raad: Well, additionally, Jill, we talk a lot about social emotional learning. I'm so happy to hear that the local school district there has said, "Yes, we see the digital divide. We see the equity gap and we want to do everything in our power to solve that." I think it's really important to say, explicitly say, "We see it, this exist. We have to fix it or do everything in our power to fix it." And so I applaud you and leadership for doing that. I also makes me think too about social emotional learning. And we talk about all the time how important it is that we have SEL embedded. And before the pandemic as teachers, we could embed the SEL competencies in the classroom.

Dr. Nathan Lang-Raad: We had a lot more control over the kinds of learning environments that our students were a part of, because again, they were coming to school. Many kids don't have that luxury now because they may have to learn in a parking lot, or they have to go to their parents workplace, or they have to go to a fast food restaurant and use their WiFi. I mean, all they have is just one device in the family to use. And those social emotional needs are not being addressed until we can address the equity gap. I'm curious to hear your thoughts about that.

Dr. Jill M Siler: Yeah. I think I was at the beginning of this interview talking through what is the 5%? And the last thing that I have on my list is the weight, the weight of all of these livelihoods resting in your hands. That's part of the 5%. And part of the most challenging piece of leading during this time is the weight of these decisions, right? Physical health is so important, but we also know the healthiest place to be is at home, right? But then on the other hand, we have this social and emotional health of our kids, academic gaps in our students. And we're trying to weigh these things of how do we create this learning environment that is safe, but also knowing that there's risks.

Dr. Jill M Siler: But just like you mentioned, that social and emotional piece has been critical in the fact that we do have the majority of our kids back face-to-face. We have already started to see significant change with their social and emotional wellness. And you do everything in your power to keep every person in your organization as safe physically as they can be, but also knowing that it's a risk too. But that social and emotional piece is so important.

Dr. Nathan Lang-Raad: It really is. And I think we've always known... Well, at least in the last few years as educators, we have worked to ensure the SEL is foundational, that it is front and center, but with the pandemic happening, it definitely refocused us to ensure that these needs have to be met. We have to understand what our kids are going through. And also the SEL needs of our teachers too. I'm curious, what are some of those self-care and SEL needs of teachers that you're kind of helping to address a year level?

Dr. Jill M Siler: Yeah. I think the most important thing is that they are heard, right? And so over the summer, and even in the spring, I mean, the surveys are constant, okay? But it's our way to check in and hear and get a pulse check in and see how are they doing and how can we support them. The biggest things that we can do from a social, emotional standpoint for our staff is to hear their needs are, and then try in any way possible to meet them. And so what we heard in these first few weeks is, "We need time." And that's what we've been trying to give them, is that time.

Dr. Jill M Siler: And so we're constantly encouraging teachers like, "Turn it off after 4:30 or whatever that time is it and walk away." But teachers are dedicated people and they do tend to try to do as much as I can for their students and in the process... As I started this year what I was just really thinking about is, "So what is this going to look like at the end of November? What is this going to look like at the end of April?" Because where we're at right now from a social and emotional health of my staff, it's not doable. We've got to make a change.

Dr. Nathan Lang-Raad: I think it's so important that we not only acknowledge where we are, but say, "As a leader I'm going to do everything in my power to make a difference." And that's what I'm hearing from you, Jill, and why I'm excited to read your book. And it's one thing to say, "Oh, we're in such a challenging time right now, we're in such a predicament, but I'm going to do everything in my power to change the course and to make sure our teachers are successful and effective. Most importantly, our students can be successful and learn at the highest levels." So I appreciate all the work that you are doing in this space to make that happen.

Dr. Jill M Siler: Thank you. I appreciate it.

Dr. Nathan Lang-Raad: Well, Jill, thank you so much for being on the show today. I can't wait to have this episode broadcasted. I know I'm going to go back and listen to it myself just to get... I have to write down some of your amazing truth bombs that you dropped during the episode. For our listeners who want to find you and to find out more about your book, where can they find you on social media and in your website?

Dr. Jill M Siler: Yes. I'm all over social media and I'm @jillm That's my website. And then on all the social media platforms as Jill M Siler.

Dr. Nathan Lang-Raad: Jill, thanks again for being here. It was such an honor and pleasure to speak with you.

Dr. Jill M Siler: Thanks. It has been great to talk with you today.

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