Dr. Jill M. Siler: Moving Beyond Survival Mode

A Conversation with Dr. Jill M. Siler

By Marie Kressin Last Updated: October 25, 2021

All the Hamilton fans out there will know exactly what Dr. Jill M. Siler means when she says she always wanted to be “in the room where it happens.” For those not yet on the Hamilton bandwagon, let’s just say Siler was not long into her education career before she knew she wanted to be the one making the hard decisions.

With 26 years in education, Siler takes her ability to impact students’ lives seriously, especially during hard times. In fact, after nearly 10 years as superintendent of Gunter ISD in Texas, Siler authored the book Thrive Through the Five: Practical Truths to Powerfully Lead Through Challenging Times. Now, as she transitions into her new role as the Deputy Executive Director of Professional Learning with the Texas Association of School Administrators (TASA), she is seeking to extend her influence as a leader even further.

Direct and driven in her leadership, Siler is passionately devoted to her work. And while it would be tempting to describe her as fearless, she would say good leadership is less about the absence of fear and more about the ability to act despite it. We had the opportunity to speak with Siler about her book, her experience navigating the superintendency as a mother, and how—with a little bravery and openness—leaders can not only survive hardship, but thrive in the midst of it.

What inspired you to write your book, and what led you to title it Thrive Through the Five?

The superintendency is, of course, a male-dominated role, and in Texas the average tenure for a superintendent is around four years. We serve somewhere for a little while; then we’re called to move on to the next district, which may be bigger or have different kinds of challenges. I didn’t feel compelled to leave, though. We love the Gunter ISD community, and we wanted to stay here. We wanted our kids to grow up in a school where they could know others and be known. But after six years in this role, I felt like I was being called to something more. I loved my district, and I loved the things we were doing, but I started questioning what was next for me.

Eventually, I realized I didn’t have to leave in order to lead the way I was being called to. I began wondering what it would look like to stay here and do the work that I love for this community, but also to expand my impact to other leaders across the state and, by extension, the 5.5 million students in Texas. Ultimately, those are the things that led me to write this book.

As far as the book’s title goes, I tell people all the time that I love my job—95% of it. I love that I get to set the tone. I love that my why is inherent. You get to see it in front of you each and every day: young people—and not so young people—growing and becoming better versions of themselves. But we don’t talk enough about the 5% that is really challenging, whether it’s a tragedy, the unavailability of funds, or negative viral social media posts. The weight of the job—that’s the 5%.

Of course, there are definitely seasons where that 95:5 ratio is true in concept, but not in reality. I turned in my manuscript in November 2019, before the pandemic hit. Now, after having led through COVID-19, I might retitle it Thrive Through the 55 or When the Five Becomes the 95. This has been a truly difficult time, but I think the basic question is more relevant than ever: How do you lead through challenging times?

In your book, you write about feeling unprepared for the superintendency. How did you evolve into the role?

One of my mentors who has impacted me greatly is a phenomenal woman named Dr. Jenny Preston, who served as superintendent in both Graham ISD and Allen ISD in Texas. When I first met with her, I just wanted to be an assistant superintendent; that was the next step on my path. But, after we got a chance to visit, she said, Jill, I’m telling you there’s a district out there in need of your leadership, and I hope you’re open to that call.

Shortly after, the Gunter ISD position opened, and I became the superintendent there. I think it’s true that you don’t know what you don’t know—and there were so many things that I didn’t know. I definitely was not ready. I could count the number of board meetings that I had been to from start to finish on one hand. I was sitting in my first meeting as superintendent thinking, Am I supposed to vote? Does a superintendent vote? Or just the board members? I should have known, but I just didn’t. There were so many things I wasn’t ready for.

There’s no way, though, to be fully prepared for the role until you step into it, and even then something’s always coming around the corner that you haven’t yet faced. But good leadership is good leadership. If we allow ourselves to step into what we’re being called to do, incredible things can happen.

What advice would you give to women in education looking for mentorship?

When it comes to finding a mentor, the goal is to become a better leader, teacher, and human being. That’s what mentorship is about. Sometimes, we take a passive role when it comes to mentorship, but we can’t do that. We can’t just wait for that one special person to appear and open up all the doors or help us find the right job. We have to ask.

Jenny Preston became my mentor because I sought her out. When I met her, she was leading AASA’s Aspiring Superintendents Academy for Educational Leaders. I decided I wanted to be like her when I grew up.

When the Academy ended, I went up to her and asked if she’d meet me for coffee. She was so gracious, and she said yes. She lived in Dallas, and I lived in Austin, so I drove hundreds of miles round-trip to have a cup of Starbucks with her. That’s the piece I want to get at: If we want mentors, we have to pursue them.

I’ll also say that mentorship is easy to find in the early stages of your leadership journey. When you’re a teacher and you want to become an instructional coach or an assistant principal, the opportunities for mentorship are abundant. As you go further into your journey, those people who were mentoring you become your colleagues and friends, so finding a mentor becomes more difficult. That makes it even more important to be aggressive about going after mentorship.

Over the course of my time as superintendent, a huge passion of mine has been investing in aspiring leaders, especially women. We have a tremendous leadership organization in Texas called TCWSE, the Texas Council of Women School Executives, and we’ve been able to do so much work with that group of women—empowering them to take the steps that they are equipped and called to take. Being mentored is fantastic, and mentoring others is such a great opportunity, but the beauty happens when both are occurring at the same time—when you are pouring into others and people are pouring into you.

How did your family’s relationship with your role as superintendent change over time?

Right now, my daughter is a junior in high school, and my son is in seventh grade. For the most part, this is the only life they’ve known. When I started, my daughter was going into second grade and my son was 3 years old. That was a challenge for me. You barely see women in the superintendency, especially when I started 10 years ago. You certainly didn’t see moms with young kids. When you don’t have that model, it makes you question whether you can do this work—or whether you should.

Of course, those are two entirely different conversations, each with their own set of emotions. When I started the superintendency, though, my kids were young, so they didn’t know anything except “Mom as superintendent.” In the beginning, there were plenty of things that I was able to move the needle on. They very much had this idea of me as a superhero: Mom is the superintendent, she’s the best, everyone loves Mom, and it’s fantastic. Not everyone loved Mom, but in their eyes everyone did.

Over the years, it has become more difficult, especially as my daughter has gone into high school. You cannot lead effectively without making very hard decisions, but that’s really challenging. There is fallout and there are consequences—and that comes back onto your family.

As I’ve transitioned out of the superintendency, both my family and friends have commented on my being “a different person.” The kind of life you have to live as a superintendent is different from the life of just a mom, just a parent. You have to live life from afar a little bit because the decisions you make have real implications and there can be hurt from that. So while I love this community and pouring into this community, there’s also that sense that I can’t truly be myself because the job is the job.

How can the superintendency be more accessible to moms?

Let’s take COVID-19 and the current political climate out of the equation. Even without all that, when it comes to leading as a mom, the job is challenging. I’ve held leadership positions all the way from assistant principal to superintendent, but none of them have been like the superintendency. Part of our work is creating boundaries—saying, I am going to turn my phone off—and part of it is reconceptualizing what balance looks like.

Say you have this image in your mind of a perfectly balanced day. You wake up in the morning; you have your personal time of study and devotion; you spend some time outdoors; you make breakfast; you walk the kids to school; you have a great day at work; you’re involved in the kids’ activities; you make dinner; you play board games; you read stories. None of that is realistic—but when our real lives don’t meet that impossible standard, we feel this guilt and shame. Balance is a constant struggle because real life is not balanced.

So what does my family’s real life look like, and how can we create boundaries to support that? How can my kids feel that I am with them? Back in my day, if my dad was at the office or if my mom was at work after hours, they were gone because they were physically gone. Then, when they got back, they were really home. Now, it’s totally different. It doesn’t matter where you are because your phone is attached to you 24/7.

The hardest part about being a superintendent, though, is not just the hours we keep or the work we do. It’s the weight we carry that stays with us all the time because, at the end of the day, the livelihoods of so many people rest in our hands.

We can have full lives with our whole selves and our families by creating boundaries and understanding that there are seasons. The first six months that you go into the superintendency are not reflective of the next six years, but the first six months have to be what they are.

When COVID happened and we began to shut down schools, you better believe my job did not look like it normally does. There are seasons in this work when the job does take the forefront. That’s the role of the leader. It’s sacrificial in nature—but for seasons. I make this joke that if you asked my kids what August, October, April, and May have in common, they will say,  For mom, August is busy, October is really busy, April is crazy busy, and May is just insane.

As a family, though, we also have this discussion about how November, December, June, and July are barren in comparison—and there is balance in that. Yes, I have this job that is 24/7 and 365 in nature, but I also have this incredible executive position that still gives me Thanksgiving, spring break, Christmas, and summer off—and there’s balance in that, too.

How does your family cope with the level of visibility that comes with the superintendency?

Superintendent after superintendent will tell you that having your family prepared for this role is so incredibly important, especially your spouse. If they aren’t all in, this job is a no-go.

In my very first year as a superintendent, I changed the dress code, and that decision was very controversial in the community. My husband was approached at a donut shop by some folks expressing how thankful they were for the change. He responded by saying he couldn’t believe some of the negative comments others had been making. Immediately, I knew that we were not prepared for this. Who knows who else was in that donut shop? We had not had the necessary conversations about what to say and when.

We’ve done a lot of work over the years since then regarding what we can talk about, what we can’t, and how we have to be careful with what we say to our kids. They tell us what they’re hearing at school, and, of course, I can’t confirm or deny anything—but we can have a conversation with them. We can say, Here’s what you need to really think about when you’re talking, and, by the way, please don’t talk about this. It’s just a matter of getting them to understand that there’s a bigger picture, that there are two sides to everything, and that what they’re hearing is not necessarily the whole truth. It’s really challenging, but open communication and being clear about your expectations are really helpful.

Reflecting back on your superintendency, what has been your proudest moment?

I went into the superintendency with these visions of going to Friday night football games with my family, thinking about strategic planning, and bringing our district to new places. But when I think back on my proudest moments, they’ve been the hardest ones. Even though those were the hardest decisions that I’ve ever had to make as a leader—or even as a human being—I was so thankful to be in that seat because I loved that community so much.

The last 18 months of my superintendency were so incredibly difficult, but I still count it a privilege to have been the person in that role. My proudest moments were the things that were difficult, but that we led through and led through well.

Why is it important for superintendents to be open about the 5% of the job they may not love?

Part of the growing process is this feeling of being inadequate; it’s this feeling of being overwhelmed. It’s thinking: I must not be fully equipped for this job. I must not be the person for this job because if I were, I wouldn’t have these feelings of inadequacy. But that’s leadership. It’s stepping in and taking action, even in the midst of fear.

In the first year of my superintendency, I walked into a financial crisis. I lost 20% of my staff that year. It was one of the most excruciating journeys to go through as a leader, especially as a first-time superintendent in this community that I loved, knowing that we ultimately weren’t going to  be whole as a staff. Now, I recognize that as tough as that journey was, as tough as that season was, I was a much better leader after the fact—because I had experienced that hardship.

Even now, we’re going through this pandemic thinking, How can this get any worse? How can we be more divisive than we are right now, with mask and anti-mask, vaccine and anti-vaccine, and all the other discussions creeping into our schools and communities? But as leaders, we will get to the other side of it and recognize the tremendous work that has been done. There is strength in recognizing that you not only made it through, but you thrived.

Book cover image of 'Thrive Through the Five" by Dr. Jill M Siler


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