Career Transitions in School Business: Insights from Rubie Harris

Summary

School Business Insider: Career Transitions in School Business – Insights from Rubie Harris

Host: John Brucato
Guest: Rubie Harris, Assistant Superintendent for Finance & Management Services, Huntington Union Free School District (NY)
Date: October 21, 2025

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Overview

This episode centers on the personal and professional journey of Rubie Harris, who made a significant cross-state career move within New York’s education sector—from Niagara Falls to Long Island. Host John Brucato, a close friend and fellow school business official, explores Rubie’s path, the motivations behind her big transition, the leadership lessons she’s learned, and her reflections on work-life balance in a demanding field. The conversation combines candor, humor, and practical advice for current and aspiring school business professionals contemplating major career shifts.

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Key Discussion Points & Insights

Rubie’s Non-linear Path to School Business

• Origin Story: Rubie stumbled into school business after earning an accounting degree, landing her first job as a junior accountant at age 22 in Niagara Falls.
• Pivotal Guidance: Early mentorship drove her to complete the SDBL (School District Business Leader) program, which fast-tracked her into a business official role within six months.
  “I never even knew business officials existed, as most don't... I finished the SDBL program, and within six months, I was sitting in a business official role.” [02:16]

Motivation to Stay in School Business

• Impact Behind the Scenes: The draw was the ability to influence educational offerings for kids without being in the classroom:
  “Children are beautiful. I don't want to be in a room… This was my opportunity to really be involved, be the voice and change agent…” [03:40]
• Balance & Influence: Rubie appreciates the influence of the business official position—enough power to make changes, but not the front-and-center pressure of superintendent.

Defining Career Moments

• Relationships as Cornerstones: Instead of one-off achievements, Rubie highlights the relationships built across various districts as key to her growth and resilience.
  “Defining moments... have really been the relationships I've built... the pieces that have helped carry me right. In those moments where I think I'm absolutely insane for some of the decisions I've made.” [05:28]

The Big Transition: Moving from Western NY to Long Island

• Cultural & Logistical Shifts: Rubie details the daunting leap—from moving her entire life solo, to adjusting to regional differences in commute, community, and even real estate.
• Timing and Mindset: She delayed her move during COVID, ultimately allowing “the right time” to nudge her forward:
  “I needed a change... Our jobs are taxing... Let's try a new space.” [07:30]
• Keeping Plans Quiet: Rubie kept her search private to avoid negative projections from friends and family:
  “When people hear of the possibility... people tend to coddle you. They project that concern and that worry, and then it festers.” [09:32]

Challenges of Relocation

• Emotionally Charged Farewells: Telling her parents was particularly hard:
  “I'm their only kid and I'm picking my life up and I'm moving… That was tough.” [12:34]
• Unpredictable Housing & Geography: Learning regional quirks on the fly, questionable apartment hunting (“just looking at a map”), and high costs.
• Workplace Support: Supportive new colleagues helped her acclimate to the area and understand the local nuances. “The people at my district were very helpful… Chris Higgins helped a lot. I'd be like, I'm going to move to this area. And he'd be like, no, not a good area.” [16:11]

Entering a New District: Authentic Leadership

• Rubie describes entering her new district authentically, not trying to emulate her predecessor: “I’m very comfortable being me…I walk in as me. I give every person basically a clean slate to present themselves.” [18:00]
• She values transparency—even to the point of telling interview panels her intended time commitment was “three to five years”:
  “I should have kept that to myself a little bit. But in their world, they thought it was like, oh, well, she's like honest… intentional in it.” [21:05]

Evolving Leadership Philosophy

• From Overcompensating to Empowering: Early in her career, Rubie says she was more direct and sometimes overcompensated for her youth by being hard on mistakes. Now, she’s focused on support and measured accountability: “One mistake does not mean you can no longer do your job.” [31:47]
• Delegation Gains: In a larger, more complex district, she’s learned to delegate more and build staff confidence:
  “I delegate a lot better. I allow people to do their work and then I'm there to support them…” [29:21]

Advice for Big Transitions

• Patience and Realism: Rubie admits to underestimating how long it takes to feel settled—personally and professionally:
  “I thought I was gonna move, and within six months I'd feel settled. And… now telling me, yeah, you gotta give it [more time].” [32:02]
• Personal Networks: Establishing friendships as an adult, especially outside work, is challenging but crucial for grounding outside your professional circle.

Long-term & Short-term Goals

• Retirement Milestone: Rubie wants to reach 20 years with the Teachers Retirement System for financial security, but doesn’t see herself as a forever career business official:
  “There's so much I want to do and contribute to the world that is beyond this.” [36:01]
• Relocation Reflections: While Long Island is “now home,” Rubie is open to future moves and does not foresee a return to Buffalo, though family could always shift priorities.

Hindsight & Lessons Learned

• Career Pacing: Rushing into a demanding career young was financially great, but had lasting impacts. Patience and boundaries might have eased the way:
  “You don't realize, like, how long you'll be married to the job if you're gonna stick it out.” [38:47]
• Wholehearted Investment & Self-care: Rubie admits to pouring her heart into her work, sometimes to her detriment, and now values clear boundaries.

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Notable Quotes & Memorable Moments

• On early career surprises:
  “I thought I was going to be a doctor and perform surgery on people… Now I'm performing surgery on budgets and financial plans. But, you know, it comes full circle.” [02:19]

• On career influence:
  “You have enough power and influence to get things done. But the buck doesn’t necessarily stop with you…” – John [04:11]

• On moving cities for a job:
  “I was full force ahead initially. The only people that knew was my superintendent, my past superintendent… I wasn’t telling friends, family. Because… people tend to coddle you. They… project that concern.” [09:02]

• On new environments:
  “I had unrealistic thoughts of what this was gonna look like… I thought I was gonna move, and within six months I'd feel settled… you gotta give it [more time].” [32:02]

• On self-advocacy:
  “If only I could tell myself some things about myself… I put my whole heart into the work I do to the point that… that can be, like, literally sacrificing and heartbreaking in the journey.” [38:50]

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Timestamps for Important Segments

• Career Beginnings & Early Mentorship: [01:56–03:40]
• Staying in the Field – Motivation: [03:40–04:34]
• Defining Career Moments & Relationships: [05:15–06:58]
• Big Move: Why & How: [06:58–12:26]
• Challenges of Relocation (Clash of Expectations, Parent Reactions): [12:26–13:59]
• Adapting to Long Island & Culture Shock: [14:49–17:29]
• Leadership Approach in a New District: [18:00–21:49]
• Evolution in Leadership Style: [29:21–31:47]
• Advice for Career Moves & Settling In: [32:02–33:44]
• Making Friends & Work-Life Balance: [34:12–34:57]
• Long-Term Goals & Reflections: [35:10–37:31]
• Regrets, Hindsight, and Boundaries: [38:43–40:27]
• Closing Thoughts & Gratitude: [40:39–40:56]

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Tone & Style

• Open, Candid, and Relatable: The conversation is marked by humor, friendly teasing, and plain-spoken truths about the highs and lows of career transitions.
• Supportive & Empowering: Both host and guest emphasize community, mentorship, and the value of personal relationships—inside and outside the job.
• Realistic but Upbeat: Rubie doesn’t shy away from the emotional and practical challenges of moving but frames change as an opportunity for growth.

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For the Listener

This episode is a must-listen for any school business professional considering—or undergoing—a major career shift. Rubie’s honest reflections offer reassurance that while big changes are rarely seamless, they are survivable and even rewarding, especially with strong relationships and a focus on both personal and professional growth.

Transcript

[A]

You're listening to ASBO 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.

[B]

Industry experts from around the world to.

[A]

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.

[B]

Hello, everyone, and welcome back to School Business Insider. In this episode, we spotlight the professional and personal journey of Ruby Harris, Assistant Superintendent for finance and management services at Huntington Union Free School District, located in New York. With over a decade of experience in school business, Ruby, Ruby has established herself as a thoughtful, committed leader. Recently, she made a big move across the state to take on a new role, navigating both the professional opportunities and personal challenges that come with such a transition. We'll explore her career path, the lessons she's learned, what it takes to start over in a new district, and what she envisions for her future as a school business official. Ruby, welcome back on School Business Insider. How are you?

[C]

Good. How are you?

[B]

I am fantastic. We are here in Glens Falls for our leadership, and I thought, what an opportunity to bring you in and. And tell your story. You were one of my closest friends, so I appreciate you coming on the podcast and humoring me for the next 40 minutes.

[C]

I'm sure it's gonna be a great time.

[B]

Yeah. So I really wanted to take an opportunity to tell your story. I know it very well, and I think it's a unique one. I've kind of been with you throughout most of it, so I'm excited to kind of let everybody know what's been going on in your life. So can you just start by telling us your path in school business and how you landed where you are today?

[C]

Sure. So I never even knew business officials existed, as most don't. Right. And I applied at a local district, so this would have been when I lived in Niagara Falls, city of Niagara Falls, and I became their junior accountant. I was 22 years old.

[B]

You go to school for accounting or finance or.

[C]

Yes, I went to school for accounting. That kind of fell in my lap. That's what I thought I was going to do. I thought I was going to be a doctor and perform surgery on people, and that's not what I'm doing now. I'm performing surgery on budgets and financial plans. But, you know, it comes full circle.

[B]

Yeah.

[C]

Right. And I had a business official at that time that saw the potential there and encouraged me to go back to school and Literally, I finished the SDBL program, and within six months, I was sitting in a business official role.

[B]

Yeah, I think we kind of had a similar role where it was just you kind of show up and you're like, oh, now I'm doing the job. And I. You know, I think you being in the business office, you had a little bit of more kind of like Runway. Right. You kind of have an idea of what to expect.

[C]

Yes. I knew how to support the staff I was working with because I had worked in those positions or at least had really great relationships with the people that worked in those positions.

[B]

So what attracted you to kind of staying in the career? I mean, similarly, we both kind of just fell into it. But you've been doing this for almost a decade, or maybe over a decade now. What initially attracted you to being a school business official? Like you said, you're six months in. You're like, now you're. Now you're it. So what made you stick around?

[C]

I would say it's being able to have an impact on what is offered to students without having to be in a classroom. Children are beautiful. I don't want to be in a room.

[B]

You don't want, like, a classroom of, like, second graders running around?

[C]

No. I barely want to teach adults. And so this was my opportunity to really be involved, be the voice and change agent, which a lot of times requires you to be at the top, to be in the room, to have the voice for others.

[B]

Yeah, yeah. I always say, like, looking back at my career and just moving forward, I think the school business official position is, like, the sweet spot because you have enough power and influence to get things done. But the buck doesn't necessarily stop with you because you have your superintendent, you have your board. Has that been your experience?

[C]

Agreed.

[B]

Been able to kind of balance that a little bit?

[C]

Agreed. I love being in the spot that I'm in. And so I've had the conversation, and people continue to have this conversation of, this is just a stepping stone. You'll be superintendent next. And I'm like, nope, nope. That's a little bit too front and center. And being at the very top, I like where I'm at. I know the information. I'm able to support the person at the top, but I get to go home and shut off at moments as well.

[B]

Right, Right. So let's talk about and think back throughout your over a decade of being a school business official. Do you have any defining moments in your career that you want to share that have really kind of shaped who you are?

[C]

Today.

[B]

And what I didn't mention in the intro is that we serve on the ASBO NY board together. We've done a lot of leadership service together. But do you, when you think back, what are some of those defining moments for you?

[C]

I would say defining moments in my career has really been the relationships I've built, which may not sound like. For other people, like, oh, that's the defining moment. But for me, it has been. As you mentioned, I have transitioned. I've done a couple of transitions. Right. I've worked as a business official at a couple of different school districts in western New York. I'm now on Long Island. And in that, the relationships that have been built have really been the pieces that have helped carry me right. In those moments where I think I'm absolutely insane for some of the decisions I've made.

[A]

So.

[B]

So tell me about that transition. This was, what, a year and a half ago?

[C]

Two. Two years and three months.

[B]

Wow. Time flies. Two years and three months. Yeah. I remember you reached out to me, like, John, I'm thinking about moving downstate, which for us meant Westchester, Long island, because I had recently done that, and we were kind of going through the pros and cons. And before I knew it, you were interviewing near me down in Long Island. But tell me, it's like, New York's a pretty big state, very diverse. There's a lot of different things to consider when moving across New York, but you went from one extreme point to the other. How was that transition?

[C]

It was nuts.

[B]

Yeah.

[C]

So initially, if you remember, John, initially, right around Covid, when you had a lot of things going on, people were working remotely, you were already like, hey, rubes, I think you might like this. And Covid was not the time.

[B]

No, it wasn't. No. I remember because I remember I took kind of like a leap of faith, and I went downstate, and I fell in love with it. And I'm like, you know, this is kind of Ruby's vibe. I think she would appreciate just kind of like, the hustle down here.

[C]

Yes, I knew. And I'm glad I did not do it during COVID I think I'd have moved back. Covid was a hard time for everybody after when we started picking up those conversations again. I needed a change. When you start young, so I became a business official at, like, 26. Yeah, when you start young, it becomes hard to see how you're going to give somebody the next 20 or 30 years of your life. And our jobs are taxing. And so I had some moments where I was questioning the career choice, and I figured, let's try a new space where you know how to do the job. As you mentioned, I interviewed in the Westchester area. I didn't feel the connection there. You were there, and I love you, but you also have your. Your own life. You now have two kids and a wife.

[B]

So you're like, john, why can't you hang out anymore?

[C]

Right. John, why can't you go to a 9am party with me on a Saturday? Leave your kids and your wife at home. Let's go.

[A]

It'll be fine.

[C]

Right. So I wasn't connecting with Westchester, just in those couple of visits. Coming to Long island, you still have the access to the city. There's beaches. There's so many things to do. I did know a couple of people on the island, and the rest was just a leap of faith. Like, in all honesty, I was, what.

[B]

Else are you gonna do? Because there's no. I equate it to almost like when people told me how wonderful it was to have kids. There's nothing that I can associate with that and relate to. You just have to do it. And I think similarly, if you're gonna pick your life up and move for a job, there's nothing anyone can tell you. Cause it's all your own individual experience, you know?

[C]

Yeah. I was full force ahead initially. The only people that knew was my superintendent, my past superintendent.

[B]

Who you still maintain a relationship with.

[C]

Oh, yeah, he messaged me yesterday.

[B]

Brian Grah. Great guy.

[C]

Yes, great guy. And you knew. And I think at that time, James knew that I was looking and that was it. I wasn't telling. Friends, family. Because when people hear of the possibility that you're taking this leap, people tend to coddle you. They kind of. I know you think this is a great idea, but I'm worried. And they project that concern and that worry, and then it festers.

[B]

And they, you know, unsolicited feedback is like, I didn't really want your opinion on whether you think this is a good idea for me. This is like what I feel I need now. Right?

[C]

Correct. Correct.

[B]

One thing you said that I want to kind of go back to. You had mentioned starting out in your career at 26. We started out at a very similar age, being the chief sbo. What was that like for you, being so young? Because I think, at least when I call back to when we had started, we started pretty much at the same time. The average age was like twice our age. And we were like the kids. Right. We were the young ones, which On a side note is kind of depressing because I don't think that we can say that anymore. We're still the kids.

[C]

We're still the kids.

[B]

Yeah. We're always kids. Always kids. But what was that like starting out so young in an industry that wasn't necessarily representative of you or me at that time?

[C]

I would say it was like a culture shock. Walking into any organization and you're supervising people that are double your age, that have kids your age. And you're the leader. Right. You have to provide.

[B]

You're having to do a counseling memo on someone who's your dad's age.

[C]

Right. And you're giving direction and you're like.

[B]

Here'S how to be professional.

[C]

You're acting younger than I act. Like, grow up. So that part was a little bit of a struggle, just taking that on and feeling comfortable while doing it. But being in the environment of working with people that were older than me because I worked in the city of Niagara Falls, I have become accustomed to that piece of it. And you learn quickly and people will learn you quickly.

[B]

Yes.

[C]

I have a humorous side and I have another side.

[B]

I know both.

[C]

Yep, you do. I've gotten both. You have. So, like, when there are moments where you can connect and we can use humor and we're doing work, well, I'm there.

[B]

And that's what you hope for, right?

[C]

Yep.

[B]

Yeah. Yeah. All right, so tell me about the logistics of such a move for you. Back to your transition. I mean, you moved. I don't know how many miles it is, but it's a eight hour drive, so whatever that equates to. What was that like? Because you literally put your entire life in a U haul in a moving company, instructed across state. Solo.

[C]

Yes.

[B]

For all intents and purposes, right?

[C]

Yes, very solo.

[B]

What challenges did you face throughout that whole experience?

[C]

Every moment was a challenge.

[B]

Every awakening.

[C]

If there's ever a moment where you're like, if it goes to the left, I'm not gonna do it. I would have stopped at the beginning. Right. Every moment was a challenge. From expressing to my parents that I was moving. I'm. I'm their only kid and I'm picking my life up and I'm moving.

[B]

How did they take that?

[C]

Horribly.

[B]

Yeah.

[C]

Yeah. That was tough.

[B]

I remember your mom was having a really hard time. Really, probably, I think still is having a little bit of a hard time.

[C]

She's gotten better. She's gotten better with it, but it was just hard for her. Like, I've always been accessible. I've always Been.

[B]

You go back to Buffalo quite a lot.

[C]

Yeah, a lot. I try to explain to my mother how much I spend coming to visit her because she needs these moments of seeing my gorgeous face. So navigating that in itself was a challenge as well as just. You're looking for movers, moving, just getting a moving company, getting all the stuff packed, getting here was a disaster, right?

[B]

Were there ever a moment you're like, what the hell am I doing? Like, this is. I'm doing all this for a job. Is it worth it? Did you have any moments like that.

[C]

Where I didn't have the moments prior to moving because everything happened so quick.

[B]

It was, well, you, you, you signed the document. You're like, you gotta go, right?

[C]

So I knew in April, by the end of April, I knew I was taking the position. I was on their board meeting in May. I couldn't even go to their board meeting in May because I had my own board meeting the same night. And it's budget season, so I can't just be present. Right. And board meeting in May, flying down for what is 24 hours, looking for an apartment in June and moving in mid July and starting point.

[B]

That's just like the leap of faith, right? Cause you can't spend months shopping apartments. I need somewhere to rest my head next week.

[C]

Correct. And the timing was school year wise, it made sense. Life wise for moving to another area. Moving in the summer is the worst. Everything's inflated in cost and everybody wants to move when the weather is nicer. So, you know, you're stuck paying whatever rent, right? You're paying. And that was a culture shock too, because.

[B]

And if I recall correctly, you weren't like super familiar with the Long island area. So you were just like looking at a map like, here's where I work, here's what's like reasonable for rent. I guess we'll check this out, right? Is that basically like the logic you used?

[C]

That was the logic. So outside of coming for interviews, I had never been on Long Island.

[B]

That was the same for me for Westchester. I'm like, I don't know, I don't know.

[C]

Like, I don't know where things are. And so when I was looking for apartments, I'm literally thinking the way you work in western New York, like, if I put in how far is this from me? And it says, oh, it's a 30 minute drive. It's a 30 minute drive, right? That is not the case.

[B]

I will say as an aside, one of, I don't miss a lot about western New York. I miss my family and my friends and a couple little things. Maybe what I took most for granted is the ease of commuting and proximity to an airport.

[C]

Agreed.

[B]

Oh, my gosh. Because your point in Buffalo, New York, if it's 15 minutes, you might get there in 14.

[C]

Correct.

[A]

Right.

[B]

There's no, like, I have to leave early. Traffic doesn't really exist.

[C]

Right.

[B]

Oh my gosh. Like where Long island is insane. I'm in Connecticut and I commute into New York. 84, 684. If anybody listening understands that. Terrible. Like, it's just the traffic.

[C]

Right. So what was nice, though, is some of the people that are at my district were very helpful, especially Chris, who's our. He is our deputy superintendent. Now. He was in a heartbeat if I sent a text like, hey, I'm thinking this, he was willing to help. Chris Higgins helped a lot. I'd be like, I'm going to move to this area. And he'd be like, no, not a good area. And I'm like, it's right next door to the other area you said was fine. It's five minutes away. What does it mean?

[B]

He's on Long island, so he knows the nuances. And I mean, you know.

[C]

Correct.

[B]

The neighborhoods can change block by block, right?

[C]

Yes. So on a end of the evening, I'm leaving a board meeting. Let's say it's 8:30 at night. I can get home in 33 minutes on a. I'm leaving work at rush hour. I'm going to be in the car for an hour.

[B]

Isn't it amazing how quickly that changed? That's how. That's so. On a good night, like a board meeting, nobody's on the road. I can get home in 41 minutes. Rush hour, it's a good day, an hour, a bad day, an hour and a half. Like, if it's because if I'm going with traffic and everybody's heading out to the east coast for the weekend, like Friday afternoons, forget it. Like, it's just a nightmare.

[C]

Yeah, yeah.

[B]

So when you think back, you're settled. You're in Long Island. Not only are you in an unfamiliar environment, personally, professionally, it's just the same. So tell me about how did it work with you getting used to the existing culture at Huntington. What approaches did you take to kind of, I guess, assimilate to the district, but also kind of put your own stamp on. This is, you know, Ruby's business office. Now here's how I think we're gonna do things.

[C]

Gotcha. So one thing that I'm really appreciative of is. I'm very comfortable being me. So even going in new places, I'm not attempting to be my predecessor.

[B]

You were the most authentic individual I've ever known, so I can vouch for this statement. Everybody listening. What you see is what you get.

[C]

Thanks, John. I think that's a compliment.

[B]

It very much is a compliment.

[C]

So I'm very much me. I walk in as me. I give every person basically a clean slate to present themselves. I don't go based on what somebody else told me. Yeah, I have.

[B]

Is it hard to do sometimes? I mean, if. What if you have like someone you trust is like, I don't know about this person, like, kind of.

[C]

I stay mindful. Right. Because in this world you assume best intent and it's a professional setting. Now if we are talking on the side as personal items and you're like, yo, watch out for that one.

[B]

This is my cousin's cousin. Like, he's good. He's good.

[C]

That what you get in that world is very different because you are attempting to penetrate my personal life.

[B]

Well, the world of the school business official is small.

[C]

Right?

[B]

So like, so right. You got a good. It's easier to judge.

[C]

And I will say, coming in, I had heard wonderful things about my secretary Kim, who I love, Jorge, who's the accountant in my office. The people that were going to be right in that space with me, I had heard great things about their dad.

[B]

Was that kind of like a sense of relief because you never really know what you're walking into again? Totally unfamiliar personal and professional environment. Leap of faith? Thousand percent. At least you're hoping for a good business office. Was that kind of like, thank goodness, like, I have some good people to start with?

[C]

Yes. And they felt the exact same way. Like once you got to a place of everybody just being comfortable. We've had those discussions. Yeah, we've had the. What did I say in the interview? And had a moment of like, you thought this was funny. I had moments where I was like, oh, crap, I probably shouldn't have said that. In the interview process, is there anything you.

[B]

That sticks out to you that you got feedback later on? I have one thing I want to share after you that was so funny to me. But is there anything that when you had those conversations during the interview, like their perception of you and how it may be totally different or like what, What? Anything that stands out with those conversations.

[C]

So the one thing that I. When I left my first round of in person interviews, I actually called my Old secretary. And I said, oh, crap, I bombed that. And she's like, why? And I said, they asked me a question in regards to like moving. Right. Are you willing to move and everything? And then it was basically longevity. And I said, yeah, I can see myself doing this for like three to five years. And to sit back in that moment and be like, oh, crap, like, she's.

[B]

Only here for a few years.

[C]

Right. She's only here for a few years. Now the other side to that, in my mind, when I look at things, have to look at things in shorter spans of time, the longness of that gives me anxiety. Like, it's.

[B]

That's a lot I can commit, right.

[C]

So I'm thinking like, yeah, three to five. And I should have kept that to myself a little bit. But in their world, they thought it was like, oh, well, she's like honest, right? So if she's saying to you these different things, she's really thought about them and intentional in it.

[B]

That's how it worked out.

[C]

Like they, Well, I mean, they hired me.

[B]

Well, yeah, I guess, like, yeah, they.

[C]

Hired me and you know, I'll be at three years in.

[B]

So you were lying.

[C]

No. And really, it's been most of my career as a business official has been on the four to five year wave kind of cycle. It's not always intentional. It just kind of works out that way.

[B]

I found I get, I start to get bored around five years.

[C]

Yeah.

[B]

Like, I just, I start to get the itch to like, what's the next challenge? Like, it's. Our jobs, although challenging, are very cyclical and it's correct. You go in, you build something great, hopefully and you fix systems. And then by year five, it's like, all right, things seem to be running pretty well. Like, what's the next challenge? Do you. That's similar. Is that. Is that what's driving you to kind of look like and to move maybe? Or is it something else? That's like, after a few years, you're like, I don't.

[A]

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[C]

I think the other part was just me being very honest of where I was in life.

[B]

Yeah.

[C]

Right.

[B]

So more personally where you're at that's driving your professional.

[C]

Correct.

[B]

Yeah.

[C]

And so I was honest when. When people said, why Huntington? And. And what did you see that made you want to move to Huntington?

[B]

Why not?

[C]

Like, I was. I was very honest in saying it wasn't like, I looked at a map and pointed to Huntington, and I was like, ooh, I want to work for that district.

[B]

This is like my destination.

[C]

Right. I was. I said to them it was a life piece. Right.

[B]

Yeah.

[C]

I love the beach. I. I want to do more. I want access to more. And Long island provided that.

[B]

So you were. You were enhancing your personal life.

[C]

Oh, 100%.

[B]

Which obviously, hopefully would spill over to your professional life. Right?

[C]

Correct. The reality is, in the professional world, I had a great relationship with my superintendent. As you said, we still stay in communication, which I love, by the way. We literally did a podcast right before I was interviewing. Right. Together about the relationship of a SVO and a superintendent. So it wasn't that piece.

[B]

Speaking of which, tell me about that. I mean, relationships come and go. What was it like having to tell Brian that your previous superintendent, of which you still have a great relationship with? What was it like having to tell him not only were you looking for other jobs, but you accepted one?

[C]

That was hard. Not as hard as telling my parents, but up there in the list of.

[B]

Just being hard, because I know he has an immense amount of love and respect for you, so that must have been devastating for him to hear.

[C]

I'm sure. I'm sure. I say that and I laugh. And it was. It was hard on both of us. Because you're also saying to somebody that you've worked with for. How long was I at Grand Island? Four or five years. Yeah.

[B]

Yeah.

[C]

So he had been my superintendent the entire time I was there. So having him hire me. Us build such a wonderful relationship, and then to say, hey, I'm looking to never change.

[B]

Sorry. Do you remember that night we did interview prep for Grand Island?

[C]

Yes.

[B]

We were at this coffee shop that also served adult beverages.

[C]

That was a fun time.

[B]

We were getting animated about your interview. We were reviewing your slide deck. I forgot about that. That was so much fun.

[C]

I still have that.

[B]

Do you really?

[C]

Yes, I still have that. I still actually have the printed copy that I gave the school district.

[B]

I remember, like, you were downplaying yourself so much, and I was getting so annoyed. I'm like, ruby, no, that's not what you say in the interview. You know, more than this. Like, be confident.

[C]

Yes. Yeah. John encourages me to do a lot in life.

[B]

I do. I Do, whether it's moving across the state or otherwise, like, I'm here for you.

[C]

So, yeah, so that was difficult. He was supportive. I think the part that made it a little bit easier, because sometimes it doesn't go that well for people. I think the part that made it a little bit easier is he understood me picking up and moving. Right. It wasn't like, I'm going to.

[B]

You were leaving, like, disgruntled, right?

[C]

No, no, no, no. Not at all. And in any situation where I have left a district, I give 110% to the very end.

[B]

Right.

[C]

So my goal is never to leave people in a bad situation. If somebody reached out, had somebody reach out, like, hey, where'd you pull this report from? Here's the. Oh, all the time.

[B]

Yeah. So you've been at your Long island district for going on almost three years now. Beyond that, when you look back in your career, what leadership lessons do you think you've learned throughout your decade plus of being a school business official?

[C]

I think I've learned. The state has made me learn a lot. I have felt at every district that I've had something uniquely take place that is not the norm that I've had to navigate. I think the biggest thing is there's usually a solution for everything. Right. So don't lose your mind over it. You have helped center me in a lot of moments where I'm ready to pull my hair out. So just having having a solid support system in the actual realm that you work makes a heck of a difference. I can pick up the phone at any time.

[B]

The professional, personal network is so crucial. We talk a lot about that on the podcast. Like, it's. It's the people that make the difference, right?

[C]

Yeah. And I think for my staff, my staff would say the biggest piece that they value in my leadership is because I have worked in a lot of their lanes, I'm able to support them a lot better. So when they come in.

[B]

So you can walk the walk. You've done it before.

[C]

Yes. Even run payroll, but that is not something I want to do.

[B]

You know, I don't think I could do that. I wouldn't. I mean, maybe I could figure it out, but if it was the day of, I'd be calling you saying, ruby, I don't know how to do that.

[C]

Yeah. I had to run an emergency check for somebody who didn't have one. And that was fun. That was fun.

[B]

Hey, fun's different for everybody.

[C]

Yeah.

[B]

So tell me about you as a leader, though. How has your leadership style changed because if we go back through your career trajectory, you were at a small city school district in western New York. You went to a medium sized suburban district in western New York, a higher wealth district. And now what's Huntington beach? Kind of, what would you classify that?

[C]

Like, not Huntington Beach, I'm sorry, I.

[B]

Keep saying Huntington Beach Station. Now that you're there, like you've had a little bit of everything. How has your style as a leader changed? Because you're working with different people in all different districts. Culturally, across the state, it's very different. Like upstate is very, very different than downstate. I'm assuming you've had to adapt a little bit. How has your leadership style changed?

[C]

So I would say one of the biggest changes is trusting the staff more to do their pieces. Not to say I'd never trusted my staff in the past, but the workload, because of the size of the budget and the requirements of the district are heavier.

[B]

So you can't do everything yourself.

[C]

Correct. So I would say I delegate a lot better. I allow people to do their work and then I'm there to support them in the moments where there is an error. People constantly say to me, well, you didn't flip out or you didn't yell or you didn't scream. And that's not to say that was past administration either, but that's just not my style at all.

[B]

You're just screaming internally.

[C]

Sometimes. Sometimes it's those moments of like, I've.

[B]

Got bro, like how long end of day calls from you? Like, I've gotten the venting.

[C]

Yeah, like how long you been doing this? Like, how did that happen? But in the end, I want to make sure that I am making sure there are relationships that leave the door open for them to come have discussions. And I have had that happen. I had something recently in the last couple months happen that when it was disclosed to me in my mind, I was thinking, wtf in that moment for what that person received from me was, I'm glad you shared it with me. How do we move forward? Please ensure in the future these are the steps you take?

[B]

Has that always been your approach and personality to things? Like internally, like, what the hell are you doing? But. But externally saying, hey, appreciate you coming forward with this, or is that something you have learned through the profession and how to deal with people effectively?

[C]

I have learned it. In the beginning I was probably thinking, what the hell are you doing? And saying it, what the hell are you doing? That's just, I think just from being number one young and sometimes when you Start out so young, and you're leading people who are older than you, you think that they have more knowledge in that area than you do. So when they mess up, you're kind.

[B]

Of like you're overcompensating.

[C]

Are you serious right now? Whereas that's not really the thought. It's, you know, I'm gonna be a support now if this keep happening. You're gonna get written up. But it'll be a problem, right? It's gonna be a problem. But I trust you to be able to do your job. And one mistake does not mean you can no longer do your job.

[B]

Right. So for those listening who may resonate with some of what you've said, or more importantly, maybe considering a big professional move, what kind of advice would you give if someone's considering something like that?

[C]

Think it out, think it through. Not to say, don't do it. I would never say to someone, don't do it. I think one of the things that I was naive in my move, I had unrealistic thoughts of what this was gonna look like. I thought I was gonna move, and within six months I'd feel settled. And people are like now telling me, yeah, you gotta give it.

[B]

Like, do you feel settled 18 months later?

[C]

Not fully.

[B]

Not fully.

[C]

Not fully.

[B]

What's it gonna take?

[C]

Time.

[B]

Okay.

[C]

Time. Allowing myself that time and not believing that I need to be on a timeline or it looks a certain way.

[B]

Are you unsettled professionally, personally, or both?

[C]

That's a good question. Probably a little bit of both. I think you settle in a little bit more professionally once you have tenure, right. There's always that thing looming over your teeth, right? Never that. I'm worried that I'm not going to receive tenure, but just simply I picked my life up and moved it here, right?

[B]

Until you have it.

[C]

It's like, until you have it. And then personally, I have a lot of fun. I go to the city plenty. I am a beach bum. So when the weather is nice, not like it is today, raining, but when the weather is nice, I love to be laying on the beach. So those things are really great. But picking your life up, not knowing anybody personally, like, professionally, I knew people, but personally, personally.

[B]

In, like, sometimes your professional friends can be your personal friends, but not always. How have you been with making personal relationships? I mean, assuming you want personal relationships.

[C]

So funny enough, when I first moved, I just wanted a friend that I can go out with. And that's not what most people want in their 30s, right? They want, like, real friends. So people were Attempting to make real friendships with me. And I'm like, I got friends.

[B]

No, no, I got plenty of those.

[C]

I got friends.

[B]

You want to go out for dinner? I'll do that.

[C]

To enough people's problems. Yeah, I'm just listening, looking for somebody to like be running around outside in town with. So I've changed that mindset a little bit.

[B]

Okay.

[C]

But making connections as an adult and it not being the people that you're working with is difficult.

[B]

Sure.

[C]

But I'm making friends slowly.

[B]

Well, because not many people outside of school business understand what school business is.

[C]

Correct.

[B]

And it's tough to explain in a sense where people really only understand school as a student, not anything else.

[C]

Right. And also just people are at different places in life. Like I don't have kids, I'm not married. I have a lot of flexibility to come up with an idea and run with it. And I have to respect that people aren't there. They're also financially different. So as we said earlier, you just have to take those things into consideration.

[B]

Right. Well, not that we have to get into it, but you and I had a heart to heart earlier when we were killing some time. When you think long term and short term goals in your future, where do you see yourself?

[C]

So right now the focus, the most tangible thing that I feel when I talk about the future is I want to reach 20 years with the Teacher's Retirement System.

[B]

Why 20?

[C]

I don't. It's just. It sounds nice, sounds good. And I think there's some benefits financially with being at 20 years of service.

[B]

Yeah. There's less penalty for the retirement system.

[C]

Right. And me reaching that is five years from now. So I know.

[B]

How's that make you feel?

[C]

I know, well, what the hell. But me reaching that is five years from now. So really that is the thing that I focus in on when it's what do you want to do career wise? Beyond that. Do I see myself as a school business official? No.

[B]

Forever? No.

[C]

No.

[B]

I don't either. Like not me, but you. I don't see you as a school business official forever.

[C]

There's so much I want to do and contribute to the world that is beyond this. And some people, this is their forever thing and they'll retire from it. And yeah, not so much for me.

[B]

Do you see yourself moving again? Buffalo's a funny place where a lot of people that I know that started there somehow end up back there. It's just there's something that feels very home about Buffalo and I guess maybe you can make that argument for wherever you grew up. But, you know, do you consider Long island your home permanently now? Or is this just a stepping stone to maybe somewhere else permanently in the future? Maybe on the beach somewhere in the Caribbean.

[C]

Oh, that sounds beautiful.

[B]

Yeah, Especially like you said, it's raining out right now. It has been absolutely gorgeous for two months straight. And of course, the one time we have an ASBO thing, it's.

[C]

It's just pouring rain. So Long island is the now home, Right?

[B]

I'll be honest, moving now home suggests temporary.

[C]

Yes. But you have to understand, when I say now home, could it be now home for the next five years? Yes. Yeah, like, I don't mean like, oh, in six months I want to pick up Long Island. Moving was traumatic for me. Like, to the point that when I think of even looking for a new apartment, I'm like, nah, I'm gonna live here. I'm live here till I don't.

[B]

Yeah, yeah, that's it.

[C]

So beyond that, I'm open. There's places that I don't want to go, I don't want to do, like cold and dreary. Do I see myself moving back to Buffalo? Not really, but my parents are still in Niagara Falls. Who knows what all of that will be. When my mom asked me, it's still a no. I don't want to move back here. I don't regret the decision to move. I'm actually happy that I did it.

[B]

Well, we even said earlier, which is an interesting feeling, and I think we share this. Buffalo doesn't feel like home anymore.

[C]

No.

[B]

When you go back, you don't have that this is home feeling.

[C]

No, it's actually, it's great to see you guys. I'm ready to go home.

[B]

Yes. Hey, glad everything looks the same and everyone's doing well, but I gotta get back to my own life.

[C]

The thing I do miss is just being able to pop up and be like, going to a Bills game today.

[B]

I know, I know.

[C]

That's a little different.

[B]

I know. All right, so as we wind down here, Ruby, when you think back in your entire career, knowing what you know now, what do you wish you had known in the early stages of your career that maybe would have helped you along and made things a little less challenging?

[C]

That's a good question, I would say.

[B]

And would you listen to yourself? The answer is probably no.

[C]

Probably no. I'm so hard headed at moments like that. If only I could tell myself some things about myself. So I would say I just started early. You know, being 26 and becoming a Business official. I mean, financially, that was golden. I was, like, making money. Right. I'm making money. But outside of that, you don't realize, like, how long you'll be married to the job if you're gonna stick it out.

[B]

Yeah.

[C]

And there's just things that if I would have been a little bit more patient in that process, maybe I wouldn't have stumbled.

[B]

Yeah.

[C]

So much. Or maybe I'd be like, hey, I'm willing to give the next 20 because I didn't already give so many already.

[B]

Right.

[C]

Something else that I have let her know now that probably would have helped me then is just, you know. And you'll agree with this, I put my whole heart into the work I do to the point that that can be, like, literally. Yeah. Sacrificing and heartbreaking in the journey. So you guys won't experience me crying. But John has definitely.

[B]

There's been some moments for sure.

[C]

For sure of just, like, caring so much about the job, and that's okay to do. But you need to have a balance between that. You know, people talk about work life balance. I don't know really what that looks like. That's just a term. No, but boundaries have been something that I make sure, especially now at this age.

[B]

You're better setting those now.

[C]

A thousand percent. Yeah, a thousand percent. And if I could have did those, then I'm. I may feel differently about the profession and how much I give to it.

[B]

That's really interesting. It's a good point.

[C]

Yeah.

[B]

Well, Ruby, thank you so much for being willing to talk to me on a hot mic in a car ride to a brewery or something. I really appreciate it and I love you and I wish the best for you and you're going to do great things no matter what you decide to do, business official or otherwise. So thank you.

[C]

Thank you for having me.

[A]

Thank you for tuning in to School Business Insider. Make sure to check back each week for your favorite topics on school business.