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In Conversation With

In Conversation With ... Jim Flynn

on preparing the state’s superintendents
Kentucky School Advocate
June 2019
In Conversation With … features an interview between a leader or figure involved in public education and a representative of the Kentucky School Advocate. 
Jim Flynn Jim Flynn will become executive director of the Kentucky Association of School Superintendents in July after spending the past 16 years as superintendent of Simpson County Schools. Here, the 30-year educator discusses how his past work in education will inform his leadership of KASS.

Q: After 16 years as superintendent of Simpson County Schools, why did you want to lead the Kentucky Association of School Superintendents (KASS)?

A: I want to help the next generation of superintendents do this work and continue the progress we’ve made over the last 30 years. And, I’d like to share what I’ve learned.

Q: You are a longtime member of KASS. Talk about that experience.

A: I’ve been a member 16 years, was on the board and served as president. As legislative committee chair, I helped lead our advocacy priorities in Frankfort. As a superintendent, you learn how important policymakers are to our work and how important it is to bridge the intersection of P-12 practitioners, the policymaking world and higher ed partners who prepare the next generation of educators. We need those partnerships to make smart policy decisions and communicate among those in the field doing the work, those who prepare educators and do the research and those who enact laws and regulations that influence our work.

Q: Do you have a plan to better connect these groups?

A: In my 30 years in education, I have developed many relationships, not only in school districts and schools but within the higher education community, the legislature and with other agencies, like KSBA. My plan is to leverage those partnerships and find areas that we have in common and make good things happen in areas of common interest across stakeholder groups.

As a first-term superintendent, you’re kind of drinking from a fire hose, trying to figure out how to do this job effectively. I want to help new superintendents see things sooner than later that will help them be effective advocates, not only in their local communities but at the state level. We need to get clear communication out, have strong talking points and have a strategy to advance legislative priorities with our partners and the legislators we’ll be working with, and certainly with the Kentucky Board of Education.
Q: What do you consider your greatest accomplishments in Simpson County?

A: We have an amazing team here and a great culture. I believe if we want to raise student achievement, it’s about the people.
Q: Did you put that team and culture together? 

A: Yes, the superintendent has a big stake in that. You set the tone and work with your board team and district and school leaders to set a clear course of how to make our vision, mission and goals happen, and you build a culture that’s going to help you achieve that. We have a student-centered, high-performance culture. I’m proud of the team we assembled, but I’m also proud of what our students have achieved. We were the first school district in Kentucky to require a college or career-ready credential for graduation. When we first embarked on that, some said, ‘Are you prepared for your dropout rate to skyrocket, graduation rates to plummet and bad outcomes to happen, because kids are not going to be able to do this.’ But we felt differently. We said if we raise the bar and put in the systems and processes students need, then they can and will do it. And sure enough, they did. 
Q: What advice have you shared with Tim Schlosser, who will become superintendent in Simpson County? 
A: Tim’s a wonderful leader who understands that people matter most in a school organization. That’s what I always tell new leaders, that it is about the people and relationships. I’ve seen a lot of superintendents come and go. When they leave under conditions that are less than desirable, it’s always a leadership issue. You’ve got to be a leader who focuses on people. That means building a strong relationship with your board where you focus on the most important things together. New superintendents often worry about technical issues like budgets. What I see is that people get so focused on the technical side they lose focus on the leadership and people side. 

Q: What are some of your plans for KASS as you step into the role this summer? 

A: We’ve got a big legislative session coming up next year and it’s a budget session. We will see again discussion and proposals around the pension issue. We’re certainly anticipating proposals around privatization. We’ve taken a strong stance in opposition of any privatization of public funds for education purposes and we’ll continue to oppose that. One issue is how to attract, retain and develop educators and school district leaders. What policy initiatives do we need to consider to ensure a strong teaching staff, school leaders and district leaders? 

Q: Superintendent tenures in Kentucky are on the decline. Do you have any thoughts on why this is occurring? 

A: If you look at enrollments in teacher education programs, we’ve seen declines. That’s a nationwide trend. In terms of superintendents, we have to help board teams understand that you see strong outcomes more consistently in districts with stable leadership. One reason I came to Simpson County is that they were looking for someone who would stay. I was interested in providing leadership over time and what you could do to change and build a culture that’s sustainable even after you leave. Our board team and community leaders will tell you it’s made a big difference for our school system to have stable leadership.

Q: Is additional training for superintendents part of your plans?

A: I want to discuss building an aspiring superintendents program with our board. 

Q: What about superintendents who are already on the job?

A: We’ve also discussed follow-up training for first-term superintendents that would include modules in key areas. For example, modules for finance, construction and facilities, board teams, community relations – areas that a first-term superintendent might need help with and want to build their skill set and knowledge base. Also, Tom recently implemented the superintendent leadership academy. We’ve been thinking about its next iteration. How do you develop the executive leadership capacity of second-term superintendents and beyond? I’ll be meeting with the board to lay out some proposals, get their feedback and approve a strategic plan. We want to personalize training for superintendents by thinking about what they need at various times in their career.

Q: Trying to accomplish so much with tight budgets puts superintendents under pressure. Does that keep people from aspiring to the role?

A: It is a job that’s not for the faint of heart. You need a high degree of courage and to know what you value and believe. What I found is that if you consistently make decisions that align to your and the organization’s vision, mission and goal, and the values and beliefs, that even when you disappoint people, they’ll be OK. 

Q: What’s your advice for how school board members and superintendents can work together best?

A: Every team’s foundation is built around trust, and trust comes through open, honest communication. Everyone has to be prepared for the difficulty that open, honest communication brings because it’s wrought with discourse, debate and sometimes arguments. We don’t surprise each other; we talk about things and at the end of the day we find areas that we can agree on and move forward. I keep a stuffed skunk on my conference table. It is a metaphor. You have to put the skunks on the table and talk about the smelly, uncomfortable stuff to find common commitment. There’s also a sign in our boardroom that reminds us that our decisions must improve student learning in some measurable way. Because if a decision doesn’t improve student learning, why do it?
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