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School Business Insider
Strengthening Leadership: The Superintendent, SBO, and Board Collaboration
01:02:25
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- [00:02]
John Brucato
You're listening to ASPO International's School Business Insider. I'm your host, John Brucato. Each week on School Business Insider, I sit down with school business officials and industry experts from around the world to share their stories and explore the topics that matter most to you. Find out what it means to be a school business official and get your insider pass on all things school business. Hello, and welcome back to another episode of School Business Insider. Today we're expanding on a presentation Dr. James Caishin and I gave at the 2024 ASBO International Conference and Expo. Dr. Caishin, Superintendent of Schools at Briarcliff Manor Union Free School District in New York, joins me to discuss leadership in education and the critical relationship between the superintendent, the Board of Education, and the school business official. In this episode, we'll delve into what it means to be a strong leader in today's educational landscape, how Dr. Cation weathered some difficult times at Briarcliff Manor and the lessons he's learned along the way. We'll explore how he built a relationship of trust with the Community Board of Education and his school business official and how that collaboration continues to shape the district's success. Jim, welcome to the podcast. I'm happy to have you.
- [01:22]
Dr. James Caishin
Thank you, John. It's great to be here.
- [01:23]
John Brucato
Yeah, great to have you on. And no stranger to podcasts, you have one of your own, which I hope you'll tell our audience a little bit about. But before we get into too much, can you just give our audience a little bit of your background and how you ascended to the superintendency here at Briarcliff?
- [01:36]
Dr. James Caishin
Sure. My path to education was not a straight line. As a matter of fact, I was working for Merrill Lynch, Pierce, Fenner and Smith as a young college graduate and was not very happy. I had a fiance at the time who is now my lovely wife who was teaching in New York City. She knew that I had always had thoughts of education, but being the child of two educators, I was talked out of going that route and was told to go make a little money for myself and enjoy my life. It was a difficult endeavor even back then, and my wife talked me into leaving Merrill lynch and going into I did not have any educational credentials, but I went into the city where they allowed you to work toward those credentials over the course of three years or so. And so I got my start in The Bronx at is 144, moved over to Bayside, Queens at Techardozo High School for several years, then made myself way into Westchester as A teacher, an administrator in Byram Hills. And I took a job as the middle school principal in Briarcliff about 24 years ago. Wow. And the rest is history.
- [02:46]
John Brucato
So you eventually ascended to the superintendency. Is that something you always had your eye on? Is that something you really aspire to be, or did it just kind of happen?
- [02:55]
Dr. James Caishin
Nope. Never envisioned it. Never thought I was capable of becoming a superintendent. Always looked at that as a position that was somewhat unattainable for someone as a classroom teacher, even a building administrator. But you learn as you move on that if you have. If you have something to offer and that people notice it, there are opportunities to elevate yourself in terms of where you stand in the organizational structure.
- [03:21]
John Brucato
So I do want to talk a little bit about your history with Briarcliff and Briarcliff in general. But when you think back to being a building principal and now being the superintendent, how has your relationship changed with the school business official? How has your interactions changed? How has your perspective changed in the process? Tell me a little bit about that.
- [03:40]
Dr. James Caishin
Well, I'm. I was the fourth superintendent in three years, and I'm actually talking to someone who is the fifth business official in six years, or six. Actually six business official in five years.
- [03:54]
John Brucato
A little bit of a revolving door, right?
- [03:56]
Dr. James Caishin
It is. It is amazing. And it had a lot to do with the finances of the district. It was on the heels of the financial collapse, and there was a lot of angst in the school community about how the district was spending its money. And in my opinion, there was an unwillingness to properly engage the community in those conversations. There was a lot of defensiveness, and there were a lot of practices that maybe had their time in years past but really needed to be changed.
- [04:24]
John Brucato
So what are some of those big challenges? When you first got into the superintendent's chair? What were you expecting? What was your reality?
- [04:30]
Dr. James Caishin
Well, when I first got into the superintendent's chair, it was because I was a known entity. It was because there were turbulent waters, and there was a lot of structural leadership change. And I think they wanted to calm things down. They had hoped I could gain the trust, at least internally, with the organization and hope that I could engage the community in a way that could garner their trust as well. Those things were a little bit easier for me. What was difficult for me early on was how important the finances of the district were to those in the community who did not trust the district and were challenging the board of education in terms of their decision making. And our board Meetings were often very lengthy and revolved around very finance specific conversations. So it became very apparent to me early on that I had to become knowledgeable, at least so that I could articulate where we were and where we were going from a financial perspective. But it was very difficult for me to join in conversations on the technical efforts of the district when often the challenges were back of the envelope. Sort of calculations were made by knowledgeable people in the private sector and who didn't really understand how public school financing worked. And I could not articulate on behalf of our business officials. And that was. That was difficult. So I knew that was an area that we really had to kind of find someone who could communicate to the school community and not only do the job well, but garner the trust and confidence that they were up to the challenge and could engage the community in a way that would garner understanding and trust.
- [06:15]
John Brucato
So because the focus was so financial in scope with the board and the community, what did you have to do as a superintendent to really get your chops with the finances? I mean, like you said early in your career, Merrill lynch, but very different than governmental finance. What did you have to do to kind of brush up on all that?
- [06:30]
Dr. James Caishin
Well, early on, I had to do whatever I could to learn about business, about the financial aspect of things. I mean, had a general understanding. I could talk about fund balance. I could talk about some of those things that do confuse the average person, but for school superintendent are relatively obvious. But I really had to. I had to go to conferences with business officials. I had to communicate with trusted business officials across the county, and I had to sit side by side with the business officials that we did have to create our budget and to respond to the questions. So I asked as difficult questions as were coming from the community and wanted to make sure that we could articulate them well to the school community. When we went to the dais to answer those questions.
- [07:13]
John Brucato
Was it tough in the beginning? Did you feel prepared? Did you feel underprepared when, you know, you're sitting at the dais during budget season in your first term of superintendent, what were your thoughts? What was going through your head back then?
- [07:26]
Dr. James Caishin
Yeah, I mean, unless you take the route as a business official, I don't know how you can be prepared for that. First. I mean, that was probably those early budget development processes and even those presentations, those recommended budgets early on were probably the most anxiety ridden experiences of my life because I knew what was riding on them. And it's not just about surviving. It's about what the future of the district would hold. So yeah, those were challenging things, but it really was about working hand in hand with the business officials. It was about challenging my own business officials privately so that that person had the confidence publicly to go out and have the conversations with the community to elicit that sort of respect and trust that they knew what they were doing.
- [08:17]
John Brucato
So I think that speaks to a strong leader, which I do want to focus a little bit more now on leadership. And if listeners haven't figured it out yet, I am your school business official and I say this objectively. You are one of the best leaders I've worked with and worked for. So I want to talk a little bit about your philosophy on leadership and kind of delve into that and what creates a successful leader. Not just as a superintendent, not just as a business official, but really as a functioning administrative team and a representation of the community. So, kicking that off, what do you feel the qualities that define a strong leader in education?
- [08:53]
Dr. James Caishin
Well, I think that they have to be open minded. I think they have to have a strong moral compass. And I'm not talking necessarily in the religious sense, but if you have a sense of, of what's right for kids, if you're in this job for the right reasons, then you need to have that strong moral compass because there's really no task that's too small. The day to day operations, you're flooded with a million different things to do. Some of those tasks seem inconsequential, but they really aren't. Everything that you do should be in line with your long term goals for kids. And if you operate that way, then it's a lot easier to keep track of what you're doing. Because you may be asked a question by someone who you admire in the organization you want to give a break to. But if you can't offer that same answer to that person that you can to the rank and file employee, that's where trouble starts to brew internally. So you want to be careful about. I told you the issue here was the external perspective on, I think, the good work that was happening in the district. But it's just as important to make sure you focus on the internal perspective that your staff have in terms of why and how decisions are made.
- [10:09]
John Brucato
So staying consistent, staying true to your moral compass and making sure you're not playing favorites or anything like that.
- [10:14]
Dr. James Caishin
Absolutely. I've had to tell people I adore no. And that's not an easy thing to do.
- [10:21]
John Brucato
So you're talking a lot about the qualities of strong leadership and what people should Embody in who they are. What happens when you're met with somebody that you work with that doesn't have those qualities? I mean, how do you address those issues with leadership? If someone is going off in a different direction than where you want to go or where you don't feel the district should be headed, how do you approach that?
- [10:42]
Dr. James Caishin
Yeah, that reminds me of the job I first took on here where I think there was an agreement that it was about kids and doing the right thing for kids was the spoken desire. But the way there wasn't a galvanizing philosophy, there wasn't a process in place that was clearly articulated in terms of what the professional expectations were. And there really was no direction for the district. So it was really hard to do anything but quote, unquote, trust the teachers in the classroom or trust those that everybody had good intentions when they came to the job. And there really wasn't a standard to hold them to, in my opinion. And I think that's part of the problem. So, you know, you have to have. You have to have clearly articulated goals along with clearly articulated standards. And then all you're doing is comparing the behavior, not the person, but the behavior, to those standards that you've established. And it becomes very easy. It becomes very apparent. As a matter of fact, 90%, in my opinion, 90% of the problems that you encounter will essentially go away. Because I do believe that the average person is self governing. I do believe the other average person wants to do a nice job. They just have to understand what defines good work.
- [12:03]
John Brucato
So it sounds like in the early years of your superintendency and prior, we were a little bit rudderless here in terms of vision and direction. And you said just kind of entrusting the teachers and hoping that everything is going well. How were you able to kind of implement that change? Because I feel like we are very much focused on where we want to be in the next five years. I mean, we have a strategic plan. How do you even begin those conversations and gain that support from not only your administrators, but the teachers at large?
- [12:26]
Dr. James Caishin
So interesting. I would say I just want to. Because it's so common for most districts. I kind of want to just comment on something you said and how you phrased that question. It wasn't so much that there was a lack of vision. The issue was there was a lack of strategy. And the vision was about an assumption that what we wanted to do is what is best for kids. But that was not clearly defined.
- [12:53]
John Brucato
Got it.
- [12:54]
Dr. James Caishin
And sometimes those decisions don't look in the initial stages, like you're doing great things for kids, you may be taking away, you may be removing some programming, you may be doing some things. We had a great angst about schedules and things like that, where kids were upset about some options that were changing. But we understood what we were trying to do for students. We persevered. We engaged students, families, faculty, the community in those difficult decisions because we had long term goals for kids that are now paying dividends.
- [13:28]
John Brucato
Right. So the role of a superintendent is multifaceted. How do you balance the leadership, managing day to day operations, but ultimately that long term vision we were just talking about, it's a lot to manage and you can get caught up in the tyranny of the urgent, dealing with fires from day to day. But how do you kind of keep the path, keep the course moving forward?
- [13:49]
Dr. James Caishin
Yeah, when I started as an administrator, just even here in the district, the Internet was somewhat new and two or three emails a day was a lot. Now it's literally hundreds of.
- [14:03]
John Brucato
It's commonplace.
- [14:03]
Dr. James Caishin
It's hundreds of emails. And you get people in their most vulnerable moments reaching out to you via email. I got an email the other day that was written 2:00 in the morning by an upset parent. You can only imagine what must be going on emotionally in that home. Home to write an email at 2:00 in the morning. Right. But that doesn't mean you dismiss it. That's important. And you could become awash in all of these, like I said before, small tasks. And if you don't have an organizing philosophy in terms of how you're doing, not only how you're responding, you clearly need to respond. You clearly need to take those concerns seriously. In my opinion, you know, it's that strong emotional connection that parents have with their children that makes schools successful, even though at times they create problems for districts. Because, you know, each situation with children can be emotionally fraught. But you have to have an organizing philosophy so that you handle things in a similar way. So it's almost with dispassion that I passionately lead this organization because I know where we're trying to go. I know that how I handle a specific problem has something to do with the direction of the district and the confidence that people have in this district that we're doing right by students and families.
- [15:31]
John Brucato
And so where does empathy fit into that process of dispassion? It's tough, it's very emotional. Like you said, parents are dealing with their children. It's kind of, you get one shot. Right. So where does empathy kind of fold into that?
- [15:42]
Dr. James Caishin
It's all about empathy. It's all about having an understanding of where parents are coming from, what their worries are. This is a very difficult world we're living in. The Surgeon General just released a report that says raising children is dangerous to your health.
- [15:56]
John Brucato
I can relate to that a little bit.
- [15:58]
Dr. James Caishin
Yeah. And as crazy as that sounds, these are tough times. This is the first generation of students who may graduate into a world where their lives are not necessarily going to be better. They're likely not going to be better than their parents by many economic standards. So you understand where the pressure comes from. So you really want to engage those parents with understanding. Often I get hit with emails that are all over the place, and you can sense the anger, you can sense the emotion, and maybe it's even nonsensical. But you need to engage. And if you engage and listen long enough, eventually the person writing you or the concerned citizen, the parent, the student, the staff member is going to reveal what really is the issue. And often when they get to what the real issue is, there's a lot of commonality in the kind of things that we all worry about. And therefore it's easier to respond.
- [17:00]
John Brucato
So when you're responding and communicating to parents or whoever's emailing you, and maybe it is one of those stream of consciousness emails, how do you effectively respond to that? Because a lot of the time it is emotionally charged. But how do you kind of bring it back down to earth, convey your message in a polite and meaningful way, but still putting the parent's mind at ease?
- [17:18]
Dr. James Caishin
Well, I cloak my response in our philosophy. You know, we're here, you know, I understand you have a problem. We're here to partner with you as a parent or a staff member or whomever may be writing to us, a student, we're going to engage the student and that we're listening. We may not necessarily ultimately agree in the end that. That they may have a suggestion that may not be practicable, but the feedback is really important to us. And usually somewhere in that conversation we reach common ground. Even if we agree to disagree, we've engaged the community with respect, We've maybe learned, we've taken some input, we've gotten some feedback, and we move forward. I'll give you a great example of how sometimes this helps reveal blind spots. Last year we had an emergency closing of the school district, and I get an email from a parent that says, why didn't you communicate this? And I could do the standard, well, we sent an alert we sent an email, we sent message, we did announcements, we did phone calls. We did all sorts of things to announce it. How did you miss it?
- [18:23]
John Brucato
Telling him everything you did do?
- [18:25]
Dr. James Caishin
Yeah. And the parent just said, why didn't you text me? And he's right. I'm like, why didn't we text them? So texting parents, which years ago, really was problematic. They didn't really want to get texts. And again, maybe that was because that was at a time when they didn't really have that great relationship with the school district.
- [18:45]
John Brucato
And maybe you were paying for minutes, too, right?
- [18:47]
Dr. James Caishin
Yeah. They might have had no unlimited plans back then. A dollar for the superintendent. Yeah. Yeah. And it really stopped me in my tracks. I'm like, oh, my gosh, you're right. So now text. Just straightforward te. No alert, no emergency, no signing up for an app or whatever that we once required teachers to do, parents to do, or community members to do is now just texted to them. And it was almost embarrassingly revelatory of how obvious that was.
- [19:18]
John Brucato
You say it out loud. It just makes so much sense.
- [19:20]
Dr. James Caishin
And I contacted that parent, gave them credit for great suggestions.
- [19:23]
John Brucato
That's great. So let's talk a little bit about transparency and how you communicate your processes. Maybe specific with the budget, maybe not. But when I started here In August of 20, I feel like I caught a little bit of the tail end of some of those tumultuous times that rested here in Briarcliff. Can you talk to me about the importance of transparency and communication and how effective leadership really bolsters those two?
- [19:51]
Dr. James Caishin
Transparency is really, really important. If you have a strong rationale for what you're doing, reveal it and then be ready to defend it. It's not about sneaking things by in the middle of the night. It's not about arcane rules or using the vernacular and board resolutions to kind of get things done. Really, anything of import should be out there and should be obvious to anybody who has an interest in the school district. I mean, it's hard to reach people who don't engage at all, but if they do, even if they watch a snippet of a board meeting or read one of the newsletters and catch something that they normally aren't paying attention to. You really want to be out there in a transparent way with why you're doing what you're doing. We're very transparent, for example, about how we budget. We're very transparent with our goals, with the budget. Obviously, the sequence is this. We design an educational program and try to come up with a sustainable way of financing that program. It's not the other way around. Here in Barclays, you know, we're blessed with the ability to do it that way. However, we are going to be very clear and transparent about how we're spending, where the money, where the money go. And you know that John, we not only put out five year projections so that you can see where we're going, but we do budgets to actuals, we do reports all year long. We're open about the finances and so the board can. Every district is idiosyncratic in terms of how they operate. There are best practices out there in terms of how boards function vis a vis their relationship with district administration. And in most cases it's really in the treasurer and the superintendent of the people who report directly to the board. In Brycliffe, we wanted the board needed to have access to the business official. So you know, you know as well as I, John, that any, any board member can contact you. And in some districts that's frowned upon and therefore and for good reason. But here we thought, you know, allowing the board to have access to you is really important. What's also important to note is that you'll let me know and that any board question that they have of you, they let the other board know. Board members know. They're asking. So there's transparency in that way as well.
- [22:17]
John Brucato
So how do you get to that point where you're comfort knowing that your administrative team and your board of education can communicate effectively, not leave you out of the loop and problems aren't going to arise from that? As you said, not all districts function that way. I've personally been a part of a district and leadership team where I wasn't allowed to talk to the board. Leadership changed then I was. It can waver back and forth. But in your opinion, how do you get to a point where you're comfortable knowing that your team can communicate with the board effectively?
- [22:47]
Dr. James Caishin
It takes a little time, but you have to witness it in progress. For Barcliffe, as I said, the emphasis really was on school financing for a very long time. I brought was fortunate enough to have your predecessor join us, who was strong, who unfortunately couldn't stay, moved upstate. So I could see the beginnings of what could happen when the board had confidence and he was willing to engage the community. He was a little more feisty than you, John, and he would admit that, but he was very direct and honest and transparent in terms of how we derive the budget or how certain arcane public school financing processes are. Requirements are and he was clear and able to do that. And I could see, based on the questions and the satisfaction on the board level, even if there were some community members who still didn't quite want to believe it or would still come up with their own numbers, I could see that the questions were being cogently answered. And that, for me is important in terms of recognizing that, okay, we're in a place where we're successful. But here's the more important thing. When I became superintendent, we talked a little bit about the number of transitions here at the district. We go over the HR side and we had just as many transitions. So by my nature, I am a control freak. And most people who are successful at administrative jobs in education have control over the details because they have to. As an assistant principal, you know, the tone and tenor of the building discipline, all of that stuff, the legal requirements in terms of all the processes you have to play, have to have in place. You know, you just have to control the details. But sometimes that has a debilitating effect in that you're not letting other people do their job. And as a result, you see a lot of burnout in education. And I have to tell you, I was not unsure. First of all, I was unsure I would survive my first year as superintendent. Fortunately, I did. I was the most surprised as anybody. But then after a few years, I wasn't sure I could sustain it anymore. And it became obvious to me that what I was trying to do by not letting anything thing fail was I was essentially coming in and rescuing everybody. And no matter what I did yet, it still reflected poorly on me. If the business official did a bad job reporting for the budget presentation or something, or answering a community question or whatever it may have been. But you have to understand that, especially a superintendent, that it may not work out in the long run, but you have to allow the organization to. You have to develop the capacity within your organization to lead. And that means they have to have autonomy in their roles and they have to be able to make decisions. Doesn't mean you can't intervene when necessary or when something unusual happens or when they come to you and they're looking for help, but you have to allow them to do that. So allowing. Allowing members of my administrative team to fail, not because I wanted to see them fail, I certainly did not. But allowing them to go through the process of trying to do, understanding what their role is and then trying to meet a goal or a standard or a task is really important in terms of their growth. So I think it's A combination of being able to be engaged to the degree that you can see when someone's successful and they're not, and evaluate that. But it's also about giving them the freedom to operate. And sometimes you'll find that. And now I find routinely with this leadership team that I have now they have much better ideas than I ever did. Right. So this may have. May I like to think this would have been a successful district if I was a tyrant and a micromanager, but I think it's a much better district because I'm not.
- [27:02]
John Brucato
So are you still a control freak? Your team has changed dramatically over the past few short years.
- [27:09]
Dr. James Caishin
I'm working on it. I'm working on it because I still have the compulsion to want to say things or suggest things, and I really work hard at it.
- [27:19]
John Brucato
Back to the transparency piece we were talking about a few minutes ago. You were talking about how when you're presenting the budget, presenting any information to the community, it's in public forum, and there may be disagreement with community members or board members. But if you know in your heart of hearts you're being as transparent and what you're delivering is the truth, how do you prove that negative? How do you get around the fact that maybe somebody is just going to disagree with you, regardless of what kind of data you present?
- [27:45]
Dr. James Caishin
I don't know that you get around it. I think you just have to acknowledge that that's going to exist. In the end, it's up to the community to decide. And. And it really comes down to whether it's a super majority 60% or just a straight majority 50%. Sometimes you're going to have close votes, and a lot of times it has nothing to do with the decision making you've engaged in in terms of budget development or what's best for kids. It may have a lot to do with what's going on in the broader community. As I said before, what really knocked this district for a loop was the financial cloud. We're in the shadow of New York City. We have a lot of finance people in the city. A lot of people lost their jobs during the economic crisis, and a lot of their bonuses and things like that that they depended on were curtailed. So people felt it in this community, and you can't really control that. And there's always going to be a level of skepticism that's out there. But again, when it reveals itself to the degree you can anticipate it, you try to communicate to anticipate it, because there's always a no vote out There. Right. But then you also just engage with those people honestly, and at some point, we agree to disagree.
- [28:58]
John Brucato
Did you ever find yourself taking it personally that you were being challenged like that when you knew you were delivering the truth? How do you silo that? If at all possible, it helps to.
- [29:08]
Dr. James Caishin
Have a short memory, a thick skin, and a small ego. Yeah, I've. Especially early on, I felt personally attacked with how could you think I would be creating a slush fund or padding the numbers or whatever? I don't operate that way. But that's the sort of climate we live in in terms of direct feedback from the community. And if you really stop to think about it, maybe 1 in 100 people might say something like that, but the other 99% are very respectful.
- [29:46]
John Brucato
So when you think back to those times and you think to where we are now, it sounds very much night and day. What were those challenges you faced and what was your approach from going personally attacked to smooth sailing in Briarcliff?
- [30:00]
Dr. James Caishin
Well, I never felt that it was a matter of me personally being attacked. It was a matter of just attacking the district for not really, you know, not knowing what it's doing, not handling the finances well without any direct evidence that. That there was something happening to the contrary. But as I said, it's a process. It's a process of you have to. Tough times are opportunities. They're opportunities. They're opportunities for you to rise above the noise. It becomes an opportunity for you to demonstrate how important you can be to an organization, how effective you can be as an employee and as a steward of the aspirations of a school community. And that's what a superintendent really is. So it's a challenge. And having gotten through those challenges now, I'm particularly proud of how we handled it. While we were going through it, we didn't resort to name callings or segregating people or ignoring people or castigating people. We engaged fully. We met in this very office with our most staunch opponents, too, to budgets or building projects, capital projects, you know, whatever we were trying to do that were really necessary to sustain the great effort that the district has historically put in place on behalf of kids.
- [31:27]
John Brucato
So when you think back to those times, what are some of those most important lessons that you learned? And if you could go back in time and give yourself a little bit of advice, what would that be?
- [31:36]
Dr. James Caishin
Gosh. So if my today self could speak to my younger self.
- [31:40]
John Brucato
Yeah, it is always a good one, right?
- [31:42]
Dr. James Caishin
Yeah.
- [31:42]
John Brucato
Not that you'd listen, but yeah.
- [31:46]
Dr. James Caishin
I think one might expect me to say, hey, you can survive it, you'll be successful. Just stick to your guns. That's really not what I would say. I would say that the beauty in this life of being an educator is interacting with the school community. And even though you may find an angry parent or a difficult situation intimidating, that's where the beauty is. Because if it's worth fighting for, if it's worth explaining and defending, then it's probably, and you have, as I said before, a strong moral compass and a galvanizing philosophy for the district and a direction and a vision for what's right, then those are wonderful battles. And when you come through on the other side, not necessarily as a loser or a victor, but when you come through knowing that you've engaged honorably in that conversation and those struggles, it's something to be proud of.
- [32:53]
John Brucato
So I have to imagine you've evolved over the past 24 years. How has your leadership style changed over that time from where you started to where you are now? And, and can you recall any specific changes you've implemented that you're proud of as a result of the evolution of your leadership style?
- [33:13]
Dr. James Caishin
Yeah, well, I alluded to it before and you know, you came at the beginning of the recovery, right? Like things had started. There was a. Like I said, you had a predecessor who was talented and knew what he was doing.
- [33:30]
John Brucato
Absolutely.
- [33:31]
Dr. James Caishin
And then you came in. It was still heavy, but you came in as I felt we were starting to emerge. And it only took a couple of board meetings. John, for you, watching you respond to the board's question, the community questions, engaging some of those community members who I had in this office multiple times in ways, and then inviting them to your office instead of mine. I was very proud of you. One check, right? There you go. This guy's a keeper. But you've seen it. You would probably agree that you probably saw a superintendent that was a little bit more concerned about the long term success. And now you see a superintendent who's sort of enjoying and reveling in absolutely what is a sustainable path of success for this district. And now rather than worrying about the day to day so much or worrying about some big event, I'm now worrying about the long term sustainability of this district. I'm thinking about the district beyond my superintendency. And that's a beautiful thing because I think what is perhaps most rewarding for me based on this long career I have had in education is the fact that I'm sitting here and I'm contemplating about, rather than some existential Threat, I'm contemplating what will my legacy be in terms of sustaining the good work that's happening here? And who are the good people that I can rely on or that someone else can rely on? And when I step away, it won't matter. It won't matter that the superintendent is a different person because the good work will continue.
- [35:30]
John Brucato
That's great. Let's talk a little bit about the relationship between the superintendent and the school business official. How important is that to a school district? And can you really talk about what a successful relationship between the SBO and a superintendent really looks like?
- [35:45]
Dr. James Caishin
There's nothing more important. There's nothing more important. I mean, how do you sustain your educational vision without the financing? And as I said, how do you get the financing if the community doesn't trust that the district knows what it's doing? So that relationship is going to be really important because I do believe that it's a symbiotic relationship. I think I've quipped before that it was getting pretty hot for me, four or five business officials in, when the board was beginning to look at me and say, well, it must be you, right?
- [36:25]
John Brucato
You're the common denominator.
- [36:25]
Dr. James Caishin
I'm the common denominator. Right. So thankfully, I found you. And now they're. Now I'm a great superintendent. Suddenly. This is crazy how it changes, you know, I'm amazing. Yeah. So. But. But what that speaks to is the fact that I'm the keeper of the educational vision for the district. Right. All that good stuff. What we do for kids, what we do for families, our results, our goals for future graduates. That's the rich, obvious stuff when you talk about education. But none of it's possible without it being financed correctly. And being financed is not just about a number or a total budget number. It's really about how you budget, where the money goes, how seamlessly things work. Because a lot of great ideas can be stymied by some arcane business process or by a business official who just says no, because they don't trust that we're going to get to the end of the year under budget or at budget, because maybe they don't understand what the goals are. So it really is important that there are conversations between the business official and the superintendent so that we are working toward a common goal. One is just trying to marshal the resources, the teachers, the programs that we have to do what's right for kids. And of course, the other is to finance those same things. And then it's always a living and breathing document because we're going to start talking about next year's budget now.
- [38:05]
John Brucato
Crazy thing. 2526 already, right?
- [38:07]
Dr. James Caishin
2526. And here we are. It's at the end of. We'll start talking about at the end of October into November. Things change and teachers end up. Teachers and building principals have great ideas that may not be budgeted for. And so you have to understand that you need to build a budget that, that can accommodate for that flexibility. Otherwise, teachers and building administrators stop communicating or stop exercising those good ideas. And again, as I said, if we were to control everything six or eight months in advance, I don't think our program would be as wonderful as it is.
- [38:44]
John Brucato
Right. You talked about being the keeper of the educational vision, building leadership and teachers coming up with new and innovative ideas. Where does the school business official kind of fit into that as a cohesive team member?
- [38:58]
Dr. James Caishin
Well, I think you have to give voice to those good ideas. Sometimes they're ideas that just aren't coherent in terms of what we're trying to accomplish. I'll give a great example. We're a Microsoft district and people have ideas with Google and we say, we don't do Google, we don't do it. And so initially that was tough, but now they understand and there are great opportunities and better ways to protect student data, in our opinion, the way we do it. And so you need to start to channel things in the direction that the district is going. You can't just be all things to all people. Again, having that galvanizing philosophy, having those processes and those understandings in place are important. So, yeah, it's not that you're going to say yes to everything, but you're going to channel it or you're going to start to guide it in the right direction and turn what can be an idea out in left field into an idea that really makes sense for the organization. So you have to be open to all of those things and you have to communicate to the school community where those opportunities are and how you finance things. Because sometimes things are budgeted and they don't really understand they have opportunities because they don't quite get the budgeting behind.
- [40:13]
John Brucato
Yeah, it's a complicated concept to explain to the layperson and to then kind of pull the veil back and talk to teachers and administrators about it gets even more complicated. And having to think 18 months out in advance just to maybe introduce something brand new. You can't just go to the store and pick up stuff and do a new program.
- [40:31]
Dr. James Caishin
I mean, imagine doing your whole finances that way.
- [40:33]
John Brucato
Yeah, it's impossible. Not impossible, but very difficult. So you've worked with many different school business officials. Can you provide some examples of how you've worked closely with school business officials to make critical decisions, especially during maybe some challenging times?
- [40:49]
Dr. James Caishin
Yeah, I think you develop a working relationship where, you know, like I said, there's no task too small. So even small things are discussed. There needs to be some formal times for communication. So we have, in our district, we have our blt, our baracklift leadership team.
- [41:06]
John Brucato
Which we still need to introduce at Bacon lettuce, tomato sandwich. I never understood.
- [41:10]
Dr. James Caishin
I'm always thinking of BLT, about BLTs because we meet 9 o'clock in the morning.
- [41:13]
John Brucato
That's the emoji on our group chat is a little sandwich.
- [41:16]
Dr. James Caishin
That's right. That's right. So we have our BLT meetings and that's a formal opportunity to kind of say, hey, what's on the agenda this week? And then we're all aware that's the entire leadership team. Right. And then we have our cabinet meetings with our building, all of our entire administration team. And then sometimes we bring up things that we've talked about because, well, we know and maybe they don't. We have a sense that it may not impact them directly, but they need to be aware. So to make sure that we're articulating very clearly regarding small issues and big issues, I think is really important. And then the informal opportunities. So it's not just enough to have your office next to mine. We have to have this relationship where we have conversations. So I'm walking into your office, getting a meal, we're talking about a grievance or talking about something like that. Those conversations will come up even though it may not have crossed your desk. Here are the implications.
- [42:12]
John Brucato
Keeping each other informed.
- [42:13]
Dr. James Caishin
Absolutely.
- [42:16]
John Brucato
I want to talk a little bit more about the relationship with the superintendent, the business official and the board of Education. You mentioned earlier how we have a setup here where I have direct lines to the board, the administration has direct lines to the board, and not every district has that. But can you talk about some common challenges that can arise with that relationship between the superintendent, board and the business official? And how can you really overcome those?
- [42:40]
Dr. James Caishin
Yeah, you have to be on the same page. I mean, there were times early on in my superintendency with members who served as my business officials, who I wasn't sure what they were saying or how it was being approached with the board. And that's a problem. And it becomes a bigger problem for both parties when a discussion that's been had privately gets to the dais and I'm either contradicting what was said or inadvertently undermining what was said or vice versa. That's important. And again, when you talk about building trust, it does nobody any good to have conversations, even if it's just a matter of interpretation or just perspective, to have these contradictions publicly. Because again, how is the board going to feel? I'm going to have members of my board of education who are more aligned with, hey, we want to do great things for kids. So I'm on the superintendent side and we're going to have members of the board of education who are like, hey, I'm all about finance, I'm all about accountability, financially speaking, and sustainability, financially speaking.
- [43:51]
John Brucato
And those two can be in conflict sometimes.
- [43:52]
Dr. James Caishin
Absolutely. But they can't be at cross purposes if what our goal is to educate students and take care of their educational needs to the greatest degree possible.
- [44:07]
John Brucato
Do you feel that if someone listening is aspiring or thinking about becoming a school business official, do they need to have somewhat of a political appetite?
- [44:16]
Dr. James Caishin
Yeah, I guess, yeah, they need to understand the political landscape.
- [44:22]
John Brucato
Because you're not sitting in an office crunching numbers anymore. Right. You're likely out in front of the board, in front of the community, having to present well, even if you are.
- [44:29]
Dr. James Caishin
Crunching numbers, because I imagine in some places you're crunching numbers. Right. But you're not necessarily. Yeah, you've used. Right.
- [44:36]
John Brucato
But twice a month I'm putting those numbers on display.
- [44:39]
Dr. James Caishin
Well, you're making meaning of those numbers. And when I have a half baked idea, I know you're crunching numbers that wasn't budgeted for. So I know that happens. But yes, you have to understand the political landscape may not be that you're directly involved in those. It depends on the district, how involved you are in those public discussions and how adept your superintendent is at handling financial questions. So it may vary to that degree, but you really need to understand, you need to understand the decisions you make are going to have political implications even in the best of times and that your decisions are going to require conversations at the dais that may require your input or certainly are going to require the superintendent's input from a political perspective on things. So yeah, you have to be aware. It doesn't mean you have to be a political animal. As I said, you can have a strong moral compass and you don't have to worry about being reelected every year. Right, right. You just have to worry about doing a really soft and being what is considered a capable and honest broker for the district from a financial perspective.
- [45:52]
John Brucato
So if someone listening today is wanting to really advance their leadership career in their district or maybe seeking other districts, what advice can you give to a school business official that wants to be more of an integral part of their leadership team?
- [46:07]
Dr. James Caishin
Well, two things. I think that I feel like there is no more important position in a school district in terms of its long term sustainability and success than the business officials. So I want my hats off to those people who are in this profession. You're really, really important to the organization and you're really, really hard to find. You know, so, you know, you have some power there. So I think it's about understanding that there will be opportunities for you if you're not happy where you're situated for whatever reason, or whether you want to step up in terms of maybe professional growth by moving somewhere, there are opportunities. So it would be about understanding how to articulate the nexus between finances and the day to day operations from an educational perspective with the superintendent and those you're interviewing with, but also be interviewing those places that you're going, making sure that you have somebody that when you look across the table you would feel comfortable working with, understanding that that person is going to be heavily reliant upon you so that you would be invaluable to them. But what is the reciprocation going to be like? Is it going to be something where, you know, you're going to come to these decisions together or are you somebody who's in a back room and maybe and there are people who are happy, you know, kind of being obscure in the back. Sure. Making those decisions? Or are you really going to want to be more of an active participant on the leadership team? You know, I think the latter is better, but I've seen it work both ways. But you should go in understanding that there are enough options out there for you that you can, you could, you should be interviewing them while they're interviewing you. Right.
- [48:01]
John Brucato
You want to make sure it's a good, good fit.
- [48:02]
Dr. James Caishin
Yeah. And I would encourage people to do it.
- [48:05]
John Brucato
And so for a new school business official, maybe just starting out in their career, or for a veteran business official starting in a new district, how does a school business official develop a strong relationship with their superintendent and develop a strong relationship with their board of education?
- [48:19]
Dr. James Caishin
Yeah, it just starts by understanding what the philosophy of the district is, understanding where they are in a point in time. You know, coming to Briarcliff today is very different than coming to Briarcliff in 2000, 10 years ago. So I think it's important to understand what you're walking into. It's important to get an understanding internally of what's going on, having conversations with people internally in terms of what the culture is like, and be very specific and clear about what you intend to do. It's never just about doing your job, particularly when you're in a leadership position. Your job is really to. To create a functional culture, to maximize efficiency, to improve the product. And there is always intense pressure on improvement, even when you think you're the best, or as soon as you think you're the best, you're on your way down. I think that's kind of the adage I'd like to use, but that's part of the territory. So creating a culture that's a joy to work in means that you've necessarily and inherently created a more productive culture and then hopefully a more creative culture, which means things that may have been, the district may have been restricted from doing in the past, they now can engage in. And that's the mark, in my opinion, of a great business official.
- [49:52]
John Brucato
You talked a little bit about legacy and how this district has evolved. Where do you see Briarcliff Manor going in the future?
- [50:00]
Dr. James Caishin
Well, we're very serious about a couple of things. You know, we understand we want to prepare students to be capable and confident young adults. And as the world changes, that means different things. Right. I think there was a time when it really meant they could really do well academically, no matter what college they go to or what vocational program they end up in or what walk of life they choose. It was more on test success, preparation, compliance, behavior, good behavior, quote, unquote. Right. And that's. That's been upended. Right. So now it's really about who are the high school graduates who can engage in complex problem solving, who are the college high school graduates who can collaborate and work well with others? Who are the citizens of this country that are digital and media literate? Right. And then who are the people who have a sense of agency, that they're not just kind of waiting for someone to tell them what to do or don't feel like, you know, their life is their own. And many of our kids suffer from that. They're very heavily scheduled and directed by parents and the pressures of this school environment, particularly here in Westchester. Right. So it's about a sense of agency. My ability to determine what I am interested in doing and how I want to live my life and still be an engaged, capable, and confident Citizen. So that's what we're looking to do. We're looking for students to be able to grapple with the world of work, the world of information that they are inundated with, and somehow come out on the other end feeling like they have a say in how they want to live their life and what they want to do and being capable and confident in that approach.
- [52:19]
John Brucato
And where do you see your administrative team fitting into that long term vision? What are your expectations and what do you hope you're going to be able to accomplish with them?
- [52:26]
Dr. James Caishin
Well, we can't just say it without allowing them to live it here in the district. And I think we've done that. I think we're doing that. Let's just say we haven't arrived, but we're still in the process. But I do think whether we're talking about classroom instruction and having students voice and choice and engaging them in critical thinking in the classroom and some of those skills that I just discussed, and then working their way up toward secondary level, the high school, those uneven years in the middle school, making sure that we're attending to their social level and emotional wellness at times, sometimes that's more important than the academics, but they are equally important. And then when they get to the high school, allowing them to exercise that autonomy, that agency, and we have an approach there, students select their courses when they're free. We just invested heavily in a capital project that creates a facility that allows students, students to get the supports that they need, regardless of what they are and whether that's working together, whether that's, you know, getting the support from the writing lab, math lab, support from a teacher, guidance counselor, you know, all of that, the tech department, the library, media specialist, I mean, all of that stuff is available to them. So they just need to take advantage of it. And anecdotally, what we hear from K kids is we're doing a good job with that because when they get to college, they not only feel well prepared, academically speaking, but well prepared to take advantage of the resources that are around them. So if they do struggle, even if they are an A student, there's nothing wrong with going to the writing or math lab, right? Or you know what, I have an issue or I have an idea, I can talk to my teacher. I had a student not too long ago who just graduated and she was attending university and I said, what are you doing this summer? Thinking she was going to talk about some vacation plans or something like that. She goes, oh no, I'm working in a laboratory at Yale. And I'm like, how did you get that? How did you make that connection? Thinking maybe that a parent had a connection because, oh, no, I made phone calls and I'm really interested in this. She did science research here in the district and she says, I wanted to continue my study. So. So I called around to see what labs would allow me to continue the research, and I found this.
- [54:55]
John Brucato
Talk about a sense of agency. Right?
- [54:57]
Dr. James Caishin
There you go. I mean, you can't express it any better than that. And that's what she wanted to. Nobody made her do that. She could have been doing like I did, just lazily playing baseball and laying on the beach or whatever I did all summer long. It's a different world. But she was thrilled. And that's an example of a student exercising that sense of agency.
- [55:16]
John Brucato
So today's conversation really came to mind because you and I, as I said at the top of the episode presented together at the 24 ACE, from a superintendent's standpoint, what'd you think? How was the conference for you?
- [55:29]
Dr. James Caishin
I thought it was great. Not only did we find a resource that I am thrilled about in terms of the use of AI that we're going to hopefully be piloting here in the district, and I am thrilled about it, but it was great to be exposed to business officials and some superintendents from around the country and understanding that a lot of the problems are the same regardless of where you are. I could be talking to someone in a small town in Oklahoma and we're talking about the same things, or grab that. Although culturally you might think never the twain's will meet, but really we're experiencing some of the same things, some of the same challenges, and essentially some of the same rewards. Right. So it doesn't matter really where you go. These challenges and these opportunities are very similar so we can learn from each other. And that was empowering. I also just really enjoyed presenting with you. I really felt like I was contributing to a broader conversation about best practices that I hope would help districts in New York and around the country be more successful.
- [56:46]
John Brucato
Well, you know, when you have a room of school business officials, you know, repetitively laughing at your presentation when we're talking about leadership and long range planning.
- [56:53]
Dr. James Caishin
Johnny, you're doing all right. Are you saying they're laughing at me?
- [56:55]
John Brucato
Laughing with us. Oh, with us. So winding down here. You know, I did mention you're no stranger to podcasts. Tell me about yours.
- [57:04]
Dr. James Caishin
Well, I have a podcast. It's something I started a couple of years ago. It's called Supercast With a K. With a K. Yeah. Yeah. All about promoting. Right. But it really is about highlighting and uplifting the voices of our school community and those who contribute to our school community. So we also interview local government officials and things like that. So it's great. I get to engage. Talking to kids about the great things they do with teachers and I said legislators and anybody of interest from the school district and around the region. It's just. It's a lot of fun. It's incredibly rewarding. I particularly like interviewing students. Cause they tell it like it is. And their sincerity and their optimism and their hope for the future is contagious. And you can't help but when you work with young people and really listen to them to be optimistic about the future of this country.
- [58:08]
John Brucato
Yeah. And just being a part of that from behind the scenes is just so inspiring to listen from students. And I think to your point, just hearing the unfiltered, raw, optimistic, emotional, just give it to you as they feel is amazing. There's no veil. There's just no smoke and mirrors. What you ask and what you receive is going to be just that. There's nothing in between.
- [58:29]
Dr. James Caishin
Nothing like interviewing a second grader. You're going to get it like that.
- [58:32]
John Brucato
The one of the elementary schools, the one at Todd, was great. It took a little meandering to get there.
- [58:37]
Dr. James Caishin
Oh, yeah. But that's. The joy is in where the story goes.
- [58:42]
John Brucato
Right. So, last question. You talked a little bit about burnout. Specifically, in your first few years of being a superintendent. What do you do when you take the superintendent's hat off? How do you achieve that balance?
- [58:55]
Dr. James Caishin
Well, I try to engage in things that are completely antithetical to being a leader. Because I think even being a manager of a softball team is just too much for me at this point. My local softball, which I've tried. Yes. And was not. Not enjoyable. But I, you know, I engage in some. I try to give back to my own school, my own community. I am a volunteer firefighter, which is something I love. I am not an officer. I am not a leader. I'm just one of the guys.
- [59:33]
John Brucato
Must be nice to not have to worry about.
- [59:36]
Dr. James Caishin
I can't tell you. I know exactly what everyone's going through. And to the degree that they know what I do, sometimes they'll seek my advice a little bit, which is affirming to me. But I'm not out there promoting it in any way, and it's great. And again, I work with. I am amazed at what we have a community service component in the school district, it's one of the. We were one of the first districts in New York State to have a. A graduation requirement, include a credit and community service. And we have kids doing amazing things. But so I'm out there in the community providing a service and I'm seeing what people are doing just out of a love of the community. We have paid firefighters working as volunteers in my hometown fire department. And they have tremendous leadership skills, tremendous dedication. 3:00 in the morning, you know, it doesn't matter what it is, there they are. And then they have their jobs on top of it.
- [60:35]
John Brucato
I mean, you've come into the office a little tired some days.
- [60:38]
Dr. James Caishin
Right. And smelling of smoke. Smelling of smoke, yes, that has happened. Yeah. And we have a multi. We have a number of things that our department does. I'm a member of our rescue dive team, which is great. I was diving in Sparkle Lake last night. So if I smell a little musty, it's not smoke today. Yeah, we did some. My first night dive, which was pretty cool, just as a training exercise. And then I'm a member of the Swift Water rescue team and Fast team. And it's great. It occupies my mind and my spirit in a way that's really rejuvenating. And then I have the energy even when I don't get some sleep, I'm still. My mind is ready to go when I get to work. And so I know I've found something that's great.
- [61:30]
John Brucato
And I can't end this without acknowledging you're a die hard Buffalo Bills fan too. So, you know, resiliency.
- [61:35]
Dr. James Caishin
Yes. And I was at the stadium. I was at the MetLife Stadium Monday night and our team emerged victorious, thankfully. Yes. So I'm very excited. So I'm also a little exhausted from that.
- [61:48]
John Brucato
Well, Jim, I can't. Thank you for joining me on School Business Insider. I just knew from the reaction we got from the crowd, it would be great to just kind of expand on what we talked about a little bit further today. So thanks again and it was great speaking with you.
- [62:01]
Dr. James Caishin
Yeah. Thank you, John. It was a pleasure.
- [62:05]
John Brucato
Thank you for tuning in to School Business Insider. Make sure to check back each week for your favorite topics on school business.