The Demands on the First-Time Rural Superintendent

Case studies of four leaders of remote districts on their early-career challenges
By Cari L. Wrysinski-Guden/School Administrator, March 2016

Cari Wrysinski-Guden
My work as superintendent leading the 600-student school district in the village of Edgar in central Wisconsin doesn’t differ much from many other small, rural districts. I came to that conclusion after completing a doctoral dissertation about a year ago that studied the roles and challenges faced by first-year superintendents in rural communities.

My research focused on administrative demands, curricular development and instructional leadership and yielded evidence of specific leadership actions taken by superintendents during their entry periods in small, rural school districts. The four districts ranged in size from 420 to 600 students, and all are located in Wisconsin.

Given the lack of literature relevant to first-time rural superintendents, my study might serve as a bridge between the little research that does exist and the practitioner’s hands-on professional training needs. In addition, my study gave the participants an opportunity for their voices to be heard by those in the field of educational administration when much more attention is directed toward larger school districts.

The new, rural superintendents identified five important tasks that they performed in their first years. As their top priority, they pointed to this: “consult with, model and actively coach other professional staff in the district.”

In the four short narratives that follow, the participants individually relate some of their challenges as early-career superintendents in small, rural school communities. Because the subjects were granted anonymity, the superintendents have been given pseudonyms, but all other details about them and their scenarios are factually accurate.

Superintendent Pentermann
Wayne Pentermann was shocked by how much he did not know about the job when he started as superintendent of a rural district in west-central Wisconsin that drew 600 students from four villages and the surrounding area.
“Based on the experiences I had at the principalship, I thought I had a broad range of skills and understanding of the system, but I think that the delegation of time to yourself and where you put things really sort of stresses a person out,” Pentermann said.

The complexities of the organization fell to the superintendent to figure out. Without clear direction from the school board upon his hiring, he created his own transition plans, one for the first 45 days, the other for 90 days. The first plan called for him to meet a wide array of constituents to understand the school system. But starting work in July hampered that good intention.

“You want to meet with your principals and all of a sudden, you find out that they’re not year-round employees and they’re off on vacations and what-not, so you’re kind of there trying to absorb written material … going over policies and looking at past board minutes and just trying to absorb sort of a knowledge base of what that organization looks like and what are their challenges. … So it wasn’t what I expected. It was a little lonelier in that initial entry period,” Pentermann said.

He considered the transition plans significant documents, so he asked the board of education to use them as part of his evaluation. He had hoped these would give the board members, some of whom were new, a clearer picture of his day-to-day responsibilities as a rural superintendent, forestalling any misconceptions.

Pentermann found it necessary to differentiate his management system from that of his predecessor when dealing with staff members. This included spelling out early on how he wanted problems to be handled.

“You deal with your own problems. I’m not here to take on your problems,” he said he told them. “I’m happy to solve them, but you probably won’t like the way that I solve them, so it’s better off that you do.”

When Pentermann found his organizational skills put to the test in his first year, he was assigned a mentor, a nearby superintendent, by the region’s educational service agency. The two initially met once a month and spoke occasionally by phone.

When he thinks back about addressing challenges as a new rural superintendent, he considers personal integrity the most influential factor. “You have to kind of maintain your integrity when even people within the organization do things that are against your own belief system and you have to deal with that, especially when they’re your boss, in some cases,” Pentermann said. “I think trying to maintain a personal sense of integrity — trying to keep your energy up, especially now in the climate that we’re in.”

Superintendent Jerson
Soon after Justin Jerson was promoted from the high school principalship to the superintendency of a 420-student district in southeastern Wisconsin, he recognized the need to establish a close relationship with his board of education to understand their expectations.

Early on, he approached the board about his authority to replace an ineffective building principal at year’s end. The members granted that latitude. Jerson met with the principal to discuss the nonrenewal of his contract and the posting of the position. A week later, the board had changed its mind, met with the principal and issued a new two-year contact.

“I felt stabbed in the back,” Jerson said. “They made me look like a fool.”

In his capacity as the instructional leader, Jerson was determined to introduce the use of technology into classrooms — an area in which many school staff lacked experience and were resistant to change. “The building principals have no idea how a computer works, so they can’t talk … about what teachers should be doing in the classroom because they don’t know,” he said.

When Jerson met with teachers, he was disappointed about how little they knew of technology integration. Recognizing the school district needed to stay competitive with neighboring districts, he took a top-down approach where staff members were not given a choice to implement technology. He implemented a “Bring Your Own Device” initiative in grades 6-12, stating, “This is the way it’s going to be.”

Educating his rural board members had to be part of this process. “Many times [school board members] went to school and graduated from high school, so they’re an expert,” Jerson said. “I’ve tried, over the years, to inform them, but they’ve lived in the rural town for 60 years and they’ve been involved with the schools since age 5, as a student or a parent or now a board member for 20 years. How can an outsider to our district tell me differently?”

Superintendent Bishopson
The one thing that surprised Charles Bishopson the most during his first months as superintendent of a 600-student district in southwestern Wisconsin was the challenge of maintaining a calm environment. He described the staff as “very scared, nervous and unsure of their future.”

It wasn’t their unfamiliarity with Bishopson that spurred the fearful climate. He had been the elementary school principal for 4½ years before he was promoted to superintendent.

What had so dramatically altered the work climate was the state government’s strong arm in radically changing the rules of collective bargaining in public schools in short order. This completely transformed the role of management in employee relations in his first year, and Bishopson was left to grasp all of the legal and regulatory changes and to develop a new employee handbook.

“It’s so ridiculously complicated right now, and I think that was kind of born out of the speed with which the change took place,” Bishopson said. He felt that the rapid overhaul caused a great deal of confusion and angst among teachers.

A significant benefit toward his understanding and handling of administrative demands during this early chapter of his superintendency was his involvement in state and local professional associations. Yet as a small rural district superintendent, Bishopson sometimes felt his voice was not heard at meetings with colleagues.

“I can try to get my voice out there full well knowing that the rural school people probably need to get together and bring their issues up as a small group or as a group of small schools because it’s really not a small group, it’s a very large group if you bring them in — there’s strength in numbers.”

Subsequently, Bishopson joined a startup group, the Wisconsin Rural School Alliance, to raise the visibility of superintendents’ concerns over rural school issues. He considered this an important means for highlighting the differences between a rural school education and an urban school education.

Superintendent Houston
Richard Houston said he experienced a smooth transition into the superintendency of a 530-student district in central Wisconsin. He had been able to work closely with the superintendent in his previous district, also small and rural, where he was the high school principal. “I kind of knew what to expect,” he said.

Many of the job’s responsibilities were new, so Houston said he needed to “learn by doing” during his first year. One immediate challenge involved preparing for the district’s annual budget hearing and annual board meeting, both in August, just a month after his start.

He found it helpful to rely on routines to deal with the many managerial tasks that begged for his time. This became especially so at the end of his second year when he cut $800,000 from the operating budget, requiring him to assume a dual role as superintendent and high school principal. This change in duties sharply increased the number of staff evaluations the superintendent had to complete, among other school-based duties.

“I’ve had to streamline things and make sure that I rely on a calendar and the things that we’ve done in the past,” Houston said.

He said it was strategically advantageous to share instructional leadership responsibilities with all staff members, using a professional learning community model. By giving teachers a voice, Houston explained, they feel more connected and willing to make changes. He conceded the idea of letting go of key decision making was difficult for him.

Through the PLC model, Houston had to find ways to communicate his message of excellence, while giving staff members the autonomy to lead the change process. He discovered it was important to develop a strong knowledge base about implementing PLCs and how they worked before asking the school board for approval.

Houston adjusted the school calendar to give staff members time to meet twice a month in their professional learning communities. “They understand the expectation of excellence and what we want to do here, and they go and look at how we can accomplish that. So I think PLCs have caused me to back away from having to do that.”

Cari Wrysinski-Guden is the superintendent of the Edgar School District in Edgar, Wis. E-mail:

My Connection to This Study

When I reflect back on my first year as superintendent in Edgar, Wis., I can relate to the findings collected in my doctoral study about the leadership actions of newcomers in small, rural school communities. My own early experiences, overseeing a 600-student, K-12 system, most closely correlate with the challenges of the job described by superintendents Bishopson and Houston in my research.

I completed the study, which was titled “How New Rural Superintendents Address Administrative Demands, Curricular Development and Instructional Leadership: Facing Challenges and Improving Learning in Their First Year,” for my Ph.D. at the University of Wisconsin-Madison during my second year in the superintendency. I previously spent eight years as a high school principal in a school district more than twice the size.

Interestingly, one responsibility facing new, rural superintendents that surprisingly was not raised by the participants in my research is the substantial time and energy a superintendent must spend on promoting the school district. I realized early on the significance that student enrollment has in regards to leading a district effectively. In today’s education domain, student enrollment is no longer a constant. Owing to legislative actions at the state level enabling open enrollment, student enrollment in school districts has changed dramatically in Wisconsin.

During my first year as superintendent, I was part of several projects intended to promote our district among families outside the community. Marketing schools is just the beginning of what I believe will be the new norm for school districts, especially in rural and smaller school districts, all of whom are battling financial crises.

I believe my study provides support and valuable information that can be used by other new superintendents who are appointed to lead rural school systems. It can be accessed at