Episode 2: A Conversation with Dr. Jason Andrews

Steve Barkley: Welcome to the Leaders Learning From Leaders podcast. Joining us today is Dr. Jason Andrews, the current superintendent of Windsor Central School district in New York State. Dr. Andrews was the New York State superintendent of the year in 2019 and he has served as the superintendent of Windsor central for the past 18 years. Welcome, Jason.

Dr. Andrews: Thank you very much.

Steve Barkley: As I did some preparation research for our conversation, I came across the information that you started your experience with school boards at a rather early stage. I’m wondering if you’d start us with that story.

Dr. Andrews: Yeah, sure. So now, and seems even more ridiculous at the time when I was still a senior in high school and I was very active in things. We had a longtime superintendent, a veteran. Let’s just say he was not particularly collaborative in his decision-making approach. Had burned some bridges over the years and there was a particular issue that really got the community up in arms and they had a big meeting and I was the senior class president and the student council president of the Honor Society president. I’m there in this packed auditorium, people with, quite literally, their pitchforks and torches. And they were there really to not just discuss this particular issue, but really every issue that had happened in his 13 years as the superintendent. And so I remember one particular student getting up and speaking and screaming a series of profanities at the superintendent and saying she was speaking on behalf of the students. And I thought, well, I guess I should say something. And so I got up and, at my age, I’m not sure if I was even 18 yet but I proceeded to chastise the entire audience that we didn’t see them at any of our activities, they didn’t come to our games, they didn’t come to our events but now they came there. And so in the Hollywood version of that story, they look at one another and they say, you know, that kid is right. That’s really profound. They reflect and they say– that’s not quite what happened though. So the crowd turned against me and yelled and screamed profanities at me. I still remember this moment, it could have been last night. So this went on for hours and this superintendent was just absolutely ridiculed in any way you can imagine. And really, he had created a lot of the issues. So now they are going to go into executive session, which ultimately they did and placed him on leave and eventually, there was a separation agreement, so on. But he pulled me aside in between this probably two to three hours of this public bashing and he said to me, he said now when you’re speaking in public and people aren’t responding, well, you just stay on message, don’t respond to them. I still think about that.

Steve Barkley: Wow.

Dr. Andrews: There he is, his career is really going up in flames and he takes time to give me a little mentoring session.

Steve Barkley: A little coaching. Yeah, terrific.

Dr. Andrews: And so he was placed on leave and as the class president, I went to the board and said, look, this is the only superintendent we’ve ever had. In just a couple of months, a few months, we will be having our graduation, the class would like him to present us with our diplomas. And, of course, the board said, absolutely not and he will not be presenting you with your diplomas. And so I decided I’d run for the school board and I ran for the board as a senior actually, against two of my friends’ parents, which was interesting and I was elected to the board while I was still in high school and then I spent the next almost eight years on the board, including–.

Steve Barkley: Wow.

Dr. Andrews: I think four years as the board president. So it was a great learning experience but it was not– I wish it had been more strategic and said, I really, someday, want to be a superintendent. It was none of those things. So I joke I went to SUNY Cortland as an undergrad with lots of education majors. I often joke to say that was really my pickup line. You’re an education major but if you’re looking for a job, I’m on the school board you know. So I don’t know that worked very well either but I did spend a lot of time and really had a great experience and learned a ton.

Steve Barkley: Awesome story to go from there, two years later being the superintendent.

Dr. Andrews: Yeah. I joke about but it’s really true because I went from the board right into administration. So for the entirety of my adult life, I have attended school board meetings once or twice a month. And so it’s really a sad description of my social life but I really have spent now over 30 years of school board meetings.

Steve Barkley: Would you tell us a little bit about the Windsor Central School district?

Dr. Andrews: Yeah, sure. So we are in upstate, New York. We border the city of Binghamton. We’re just east of Binghamton. We’re fairly large geographically. We encompass about 118 square miles. We have five schools, three elementary schools, one middle school, one high school. Approximately a little over 1,800 students is our current population. An interesting dynamic in that we are high poverty and we tend to be relatively high performing. That’s not always been the case but really is a great district and an incredibly talented staff, lots of great opportunities for kids so really a great place to be.

Steve Barkley: What would you point out as some of the key progress that the district has made in the more recent years?

Dr. Andrews: Yeah, sure. When we look at the journey that the district has been on now for some time, I started working here as a high school social studies teacher and Coach in 1997 and really what we were known for in those early days was boys athletics and it was a very strong athletic program for the boys premier sports but that’s really what we were known for. Not a lot of focus on academics and really since– when I started in January of 2006, we’ve really tried to transform the educational opportunities for kids. So some of the progress that we’ve made has been around some of those really measurable areas. We went from a 78% graduation rate in the early 2000 and 2005 to 95% graduation rate, four-year graduation rate. We tend to rank near the top in our region on state assessments and we used to be 13th out of the 15 in our region. But what we’ve really focused a lot on beyond the– we say that’s the proof of concept is those objective measures but when we look at a lot of the things, what we’ve really tried to do is focus on lots of opportunities for kids and in particular, a number of– we have eight pathways that we work toward with students from engineering and computer science and trades, agriculture, education, business, healthcare, etc., that it’s really aligned pre-K through 12 to get kids lots of different exposure. About 58% of our kids live in poverty so that college route isn’t the only way. So really, what we’re trying to do is help kids build a resume, make sure they’re college and career ready and when they graduate, whether they’re moving into a two-year program or a four-year program or right into the military or work, that they have a strong resume and can do well. And so it’s really, really neat to see how much we’ve grown in these areas.

Steve Barkley: In the accomplishment of the goals of the district, how do you go about sharing the goals with your staff and assisting them with staying focused on the goals?

Dr. Andrews: Yeah, sure. So it’s a great question and really, it’s always a work in progress. But when I started in 2006, we had one school and it was a high school and we’ve added four additional schools. So as the district has grown, that’s always been a real challenge is the scaling of the work. But what we do have is a pretty clear direction. We’re on an annual cycle for a lot of the things that we do. So for example, in May, we actually will engage over 90 staff and students in some goal-setting for the coming year. We do that with the board in August and we really develop some real clear indicators of what the year is going to look like. Now, I would say that you need to be a little careful about how you talk about goals because it doesn’t mean that you can’t do a lot of other things. We need to be clear about what the really high priority work is and we do some monitoring during the year to see how that’s coming along and make adjustments when needed. So for example, in November, the board and I are going to do a retreat, again, looking at the goals that we’ve set forth and the direction that we’re heading and looking at our indicators and looking at our progress and really what we’re trying to do is align the resources, both human and financial, and the focus of the district around the things that are most important. So when people say they don’t have time to do things, it really isn’t the case, it’s about where we’re putting our time and energy.

Steve Barkley: You talk about a goal cycle. Could you give us some more details on what that cycle looks like?

Dr. Andrews: Sure. So in May, we really begin the conversation with a lot of folks. And so I’ll have meetings, a lot of conversations. We involve all the staff in the conversation, all the teachers, our teacher assistants, our custodians, secretaries. Really, I think it’s so important to get the input of the people that are actually doing the work. A lot of these goals are non-negotiable, so to speak. We will not negotiate with people’s feedback about safety for children.

Steve Barkley: Yes.

Dr. Andrews: There are other areas that we say, well, we want your input and your feedback but at the end of the day, we need to align the work and we need to make sure that we’re putting our resources in the right place. So in May, we begin the process. It involves some surveys and things. So when we develop the goals in August, it’s based on a lot of feedback. And then, as I said, throughout the year, we actually have a leadership team, a 23-member leadership team that meets every other week and we actually go through and actually monitor the progress toward those goals. So it’s not– I think sometimes when you talk about goals, people say, well, that’s really a top-down approach, it’s not. It really is a lot of input from a lot of people, a lot of review, and then it’s a lot of checking to see how we’re doing. And so as we have that November retreat, what we’ll do is we’ll say, OK, we’ve made this progress toward our goals. Now we need to take a look at the next steps and what we have found is by keeping this cycle moving is that we’re able to see the progress, we’re able to measure the progress and as I mentioned earlier, it’s not that other things aren’t important, it’s just that we’re being really clear about where we’re going to put our time, energy, and our resources.

Steve Barkley: I’m wondering how your central office staff, those central office administrators, are held accountable for their progress toward district goals?

Dr. Andrews: Yeah, sure. That’s a great question and we use a lot of those same mechanisms. One of the things that I think is really critical when you’re working with your senior leadership team is to really have them invested in the work. And so when we look at each of our five schools, we have five principals, we have directors, and a lot of these individuals have been promoted from within the organization. But what we really try to do is to develop them as leaders. So for example, my assistant superintendent actually came from the business office. My director of student services started as a teacher assistant in the district and so on. And so one of the things that we really talk about is what are the indicators that they’re looking at? And really, what we’re trying to do is to make sure that we’re using a backward design process that what we’re really clear about what our indicators are and then we need to align our strategies. And so when we look at what our strategies are, then the next step becomes the action plans and so the action plans really drive the work. And so when we get to the leadership team meetings, we’re really checking in on the action plans. So it’s not, what’s happening, are things going well, are things not going well? It’s really looking at what are the key action steps and what is the progress.

Steve Barkley: You talked a little bit earlier about your use of committees and how you involve your staff in committees. Could you expand a little bit on that?

Dr. Andrews: Yeah, sure. So when I started in 2006, one of the things I really knew was important is to make sure that we’re getting the feedback from all the different stakeholder groups. One of the challenges, and as a high school principal, I used to say this is one of the worst things about school districts is we have 1,800 students, we have 500 staff, and we have all these parents but we’re all in our own little places.

Steve Barkley: Yeah.

Dr. Andrews: So what we do is we use lots of different mechanisms. So for example, we use a steering committee process, we use advisory committees, we have a lot of parent forums, a lot of student forums. So for example, last week, I spent about 90 minutes in a forum with our students at the high school. We did a forum with the staff, we did a forum with parents, a forum with community members. So what we really try to do is use a lot of different mechanisms. We do a lot of different surveys, I mentioned earlier that in May, we start with some surveys. So we do a lot of this throughout the year to try and get the input of all the stakeholders and try and get the feedback to make sure that we’re– because at the end of the day, I really believe that the key is to make sure that you’re aligned around the work. And so if we’re trying to move the work forward, we need to know what people are thinking. So if I think about our recent forums, we asked questions about safety for children. We asked questions about the quality of the work, we asked questions about our goals. We asked questions about our areas of growth. We asked questions about our areas of strength. And what’s interesting is a lot of times you get some great feedback and then sometimes you get feedback and you say, OK, that’s good but that’s not where we’re heading. So we need to take all that feedback and then we need to make sure that we’re putting our time and energy and our resources on the things that are really going to get us where we want to go.

Steve Barkley: I know you mentioned forums. You also mentioned surveys. Are there any other methods that you use to collect stakeholder input?

Dr. Andrews: Yeah, those are the primary ones but we also do a lot of focus groups. So for example, right now, we’re working on our budget process for next year and so we have some focus groups that are coming up in the next couple of weeks. We also– I’m a big believer in being in the community and being visible. So for example, one of the things I do is I go to all the PTA meetings and it’s really important for me to be at all those meetings, not just for me to be there but for people to hear the same message. And I think it’s really important for people to know that when I go to a PTA meeting, I’m not there to take over the meeting, I’m there to support the work of the PTA but also to share the information about what’s happening in the district. So when we’re talking about areas of growth or areas of strength or when we’re talking about things that are coming up, people are hearing the same message. So those are some of the other ways that we collect feedback.

Steve Barkley: You mentioned earlier that you have a leadership team and I’m wondering what role they play in the district’s decision-making process?

Dr. Andrews: Yeah, that’s a great question. So our leadership team is really critical to the work and one of the things that’s really important for me is to have alignment around our key strategies and our key indicators. So I mentioned earlier that we have five schools and we have directors and one of the things that I think is really important is that everybody understands what we’re trying to do. So for example, at the beginning of every year, we actually spend a lot of time looking at our goals, looking at our strategies and really talking about what our indicators are. And so our leadership team, for example, when we meet every other week, we’re actually looking at those indicators and we’re looking at the progress toward the goals. And then the other thing that we’re looking at is we’re looking at the strategies. So I’ll give you an example. One of the areas that we’re working on is an area of literacy. And so we’ve really done a lot of work to really identify what are the indicators of success going to be, what are the strategies we’re going to use to get there, what are the action plans, and how are we going to monitor the progress. So when the leadership team meets, it’s not about talking about all the different things that are happening in all the different schools, it’s really focused on what are the key indicators, what are the key strategies, and what’s the progress. And so we’ve actually built a monitoring system, a data system that we actually use to help us understand what the progress is.

Steve Barkley: What are some examples of the type of data that you collect and monitor?

Dr. Andrews: Yeah, great question. So I’ll give you some examples. So when we look at some of our student achievement data, we’re going to look at some of the standardized tests that we use. So for example, we use the state standardized tests and we use a number of other tests. We also look at things like the number of students that are participating in our advanced placement courses. We look at the number of students that are participating in our career and college ready courses. We look at the number of students that are getting industry credentials. We look at the number of students that are actually employed when they leave us. We also look at things like attendance data. We look at discipline data. We look at surveys from our students, from our parents, and from our staff. We also look at things like what are the types of professional development that our staff are participating in. We look at what are the types of resources that we’re allocating. We also look at things like our budget process. So we’re really looking at– and that’s really one of the benefits of the technology that we have today is we’re able to collect a lot of data and we’re able to analyze the data and we’re able to then use that data to make decisions.

Steve Barkley: How do you communicate the progress toward goals and district initiatives to your stakeholders?

Dr. Andrews: Yeah, that’s a great question. We actually use a lot of different mechanisms. One of the things that I think is really critical is to make sure that you’re communicating a lot. And so one of the things that we do is we use a lot of different social media platforms. So for example, we use Facebook, we use Twitter, we use Instagram, we use LinkedIn, we use YouTube. We use a lot of different mechanisms to actually communicate with our stakeholders. We also use our website. We also use our website to actually post information, post data, post surveys, post the results of surveys. So for example, if we’re doing a survey, we’ll actually– and we do a lot of surveys, we’ll actually post the results of the survey. We also use a lot of meetings. So for example, when I mentioned that I was at the PTA meeting, I was actually at a parent forum. We also do a lot of community forums. We also do a lot of staff meetings. So for example, we’ll do a leadership team meeting where we actually go through and actually go through all the indicators and we go through the progress. So those are some of the ways that we actually communicate with our stakeholders.

Steve Barkley: I know one of the challenges that leaders often face is resistance to change and I’m wondering if you’ve encountered any resistance to the district’s goals and initiatives and how you’ve addressed it?

Dr. Andrews: Yeah, great question. I think that any time you’re working in education, change is always difficult. I’ve been doing this work for 30 years and I’ve been an educator for 30 years and I can’t think of a time when we weren’t actually working on some sort of change. And so I think that there’s always going to be some resistance to change and I think one of the challenges is to really be clear about why you’re doing what you’re doing and what the purpose is. And so one of the things that we really try to do is to really talk about why we’re doing the work and really try to get people invested in the work. So for example, if we’re doing work around literacy, we’re not just doing the work because we think it’s important for the district, we’re doing the work because it’s important for the kids. And I think one of the things that we really try to do is to get people invested in the work. The other thing that we try to do is to make sure that we’re involving people in the work. So for example, if we’re doing a new initiative, we’re not just going to make a decision in a vacuum, we’re actually going to involve people in the decision-making process. So for example, when we were looking at our technology plan, we actually had a committee of students and parents and staff and administrators and we really made the decision as a group. And so I think that those are some of the ways that we really try to get people invested in the work and also make sure that they’re involved in the work.

Steve Barkley: You’ve mentioned the importance of involving stakeholders in the decision-making process and I’m wondering if you could give some advice to other leaders on how they can effectively involve their stakeholders in the decision-making process.

Dr. Andrews: Yeah, great question. I think that one of the things that’s really important is to make sure that you’re involving a lot of different voices. And so one of the things that we really try to do is to involve students, parents, staff, administrators, community members. And so for example, when we were doing our budget process, we actually had a budget committee that was made up of all those different stakeholders. And so I think one of the things that’s really critical is to make sure that you’re not just involving one group of people, you’re involving a lot of different voices. I also think that it’s really important to communicate with people and to let them know why you’re making the decision and also to listen to them. And I think that one of the things that’s really important is to really be open to feedback. And so for example, when we were making decisions about our technology plan, we actually had a lot of feedback from parents and from students and from staff and we actually made some changes based on that feedback. And I think that that’s really important is to really listen to people and to be open to feedback. I also think that it’s really important to make sure that you’re transparent and that you’re communicating with people. So for example, when we were doing our technology plan, we actually posted all the information on our website and we actually had a lot of people that were following the process and that were giving us feedback. And so I think that’s really important is to make sure that you’re transparent and that you’re communicating with people.

Steve Barkley: As a superintendent, how do you maintain a positive and productive working relationship with your school board?

Dr. Andrews: Yeah, great question. I think that one of the things that’s really critical is to make sure that you’re working collaboratively with your school board. And so for example, when we were doing our technology plan, we actually involved our school board in the process. We actually had our school board members on the committee that was making the decision. And so I think that’s really important is to make sure that you’re involving your school board in the decision-making process. I also think that it’s really important to communicate with your school board and to make sure that they’re informed about what’s happening in the district. So for example, one of the things that we do is we actually have a monthly update that we provide to our school board. And so we actually provide them with updates on all the different initiatives and all the different goals and all the different strategies that we’re working on. And I think that’s really important is to make sure that you’re keeping your school board informed and that you’re communicating with them. I also think that it’s really important to make sure that you’re working collaboratively and that you’re really building that relationship. And so for example, one of the things that we do is we actually have a lot of conversations with our school board members and we actually meet with them regularly to really make sure that we’re on the same page and that we’re working together.

Steve Barkley: Could you share a little bit about how you approach your own professional growth and development as a leader?

Dr. Andrews: Yeah, great question. I think that one of the things that’s really critical is to make sure that you’re always learning and that you’re always growing. And so for example, one of the things that I do is I actually attend a lot of conferences and a lot of workshops and a lot of seminars. I also do a lot of reading and a lot of research. I also think it’s really important to make sure that you’re networking and that you’re building relationships with other leaders. And so for example, one of the things that I do is I’m actually a member of a lot of different organizations and a lot of different associations. And so I think that’s really important is to make sure that you’re networking and that you’re building relationships with other leaders. I also think it’s really important to make sure that you’re seeking feedback and that you’re open to feedback. And so for example, one of the things that I do is I actually have a lot of conversations with my colleagues and with my mentors and with my peers. And I think that’s really important is to make sure that you’re seeking feedback and that you’re open to feedback. I also think it’s really important to make sure that you’re reflecting and that you’re taking the time to really think about your own practice and to really think about your own growth. And so for example, one of the things that I do is I actually journal and I actually take the time to really reflect on my own practice and to really think about what’s working and what’s not working and what I can do differently. And I think that’s really important is to make sure that you’re taking the time to really reflect and to really think about your own growth.

Steve Barkley: You’ve been a superintendent for quite a number of years and I’m wondering what advice you would give to aspiring or early-career superintendents?

Dr. Andrews: Yeah, great question. I think that one of the things that’s really important is to make sure that you’re always learning and that you’re always growing. I also think it’s really important to make sure that you’re seeking feedback and that you’re open to feedback. And so for example, one of the things that I do is I actually have a lot of conversations with my colleagues and with my mentors and with my peers. I also think it’s really important to make sure that you’re building relationships and that you’re networking. And so for example, one of the things that I do is I’m actually a member of a lot of different organizations and a lot of different associations. I also think it’s really important to make sure that you’re really focused on your goals and that you’re really clear about what you’re trying to achieve. And so for example, one of the things that I do is I actually have a lot of conversations with my colleagues and with my mentors and with my peers. I also think it’s really important to make sure that you’re really focused on your goals and that you’re really clear about what you’re trying to achieve. And I think that’s really important is to make sure that you’re really focused on your goals and that you’re really clear about what you’re trying to achieve.

Steve Barkley: Well, thank you so much for joining us today, Jason. This has been a really insightful conversation and I think our listeners are going to take away a lot of valuable information from your experience and your insights.

Dr. Andrews: Yeah, absolutely. Thank you very much for having me. It’s been a pleasure to be here and to share some of my thoughts and ideas.