Podcast Summary: School Business Insider Episode: Different Paths, Shared Lessons: Early Leadership as a School Business Official Host: John Brucato Guests: John Fink (Cornwall Central School District) & Chris Carballo (Highland Falls-Fort Montgomery) Date: December 23, 2025

Episode Overview

This episode explores the early years of school business leadership, emphasizing the realities of stepping into the School Business Official (SBO) role from diverse backgrounds. Host John Brucato is joined by John Fink, who transitioned from an instructional pathway, and Chris Carballo, who came from the private sector. Their candid conversation covers mentorship, work/life balance, building business office culture, navigating new relationships, and adapting to both planned changes and unforeseen challenges in their formative years as SBOs.

Key Discussion Points & Insights

Entering the SBO Role: Different Paths, Similar Surprises

• John Fink’s Journey (Instructional to Business):

  • Saw SBO as a far-off possibility when he first got certified.
  • Opportunity arose unexpectedly: “Superintendent uncovered that I had the certification... people with certifications were few and far between.” (02:30)
  • Jumped in as an interim, motivated by the urge to learn and model risk-taking for his sons.
  • Missed daily student interactions but had little time to dwell: “The cognitive level that I was operating at on a daily basis was incredible. I didn't have time to think about what I was missing because I was so focused on not missing anything here on the business side.” (03:31)

• Chris Carballo’s Journey (Private Sector to Education):

  • Discovered the SBO role after a COVID-induced career shift.
  • Family connection introduced him to the possibility: “My brother...said, ‘there is this role in school districts. It’s called a business official. They like, you know, they do some of the numbers…’” (05:05)
  • Challenges: the huge increase in regulations, tighter deadlines, and cultural differences—especially in communication styles.
  • On public sector email culture: “I get so many, like, ‘Hey, thanks for the info. Hey, that was great’...It’s so wonderful in a way… but I have a lot of emails I don’t need to open, but I have to open them.” (06:58)

Navigating Regulations and New Demands

• Regulation as Both Guide and Pressure:
  • Chris: “Having those guardrails is key… It adds a little bit different kind of stress though. You’re like, oh my God, if I miss the…September 1st deadline for my ST3…the whole world’s going to explode.” (08:02)
  • Importance of building a network: “You gotta be willing to pick up that Questar phone call or pick up a colleague that you met at an ASBO conference and just say, ‘Hey, listen, is it really due on the 15th or not?’” (08:23)

Early Struggles: Firehose Learning and Unforeseen Responsibilities

• From "Deer in Headlights" to Finding Confidence:
  • John Fink: Felt overwhelmed at ASBO’s SBMW training and leaned on other new SBOs for comfort.
  • “I went to the first workshop…sat there like a deer in headlights. I had no idea in this world…But you shared some of your being a new business official and what it’s like…and I’m like, okay, I’m not on John Fink island.” (12:16)
• Handling Surprises:
  • Brucato’s story: Opens with unexpected operational crises—e.g., fielding angry parent calls about transportation.
  • Chris Carballo handled difficult personalities in private sector, so didn’t mind operational headaches, but struggled more with the nuanced financial projections and adapting to school culture.

The Role of Mentorship & Building Professional Networks

• Mentorship as Lifeline and Confidence Booster:
  • Both guests credit mentors for supporting their transitions:
    • John Fink: “My insistence on having a mentor to help me…was huge.” (14:33) Continues informally seeking advice: “I don’t know if I’ll ever feel that way [not needing a mentor]…like, GASB throws something at you…you know, like, somebody help me out. I’m never gonna say I’m good.” (16:52)
    • Chris Carballo: Was provided a mentor by his district and maintained informal mentor relationships: “You just can’t be proud; go ahead and reach out to those colleagues you talk to…at a certain point you are giving answers as much as…you are starting to be one of the ones like, yeah, I’ve got a version of that you can take a look at.” (17:31)
  • Importance of peer communication (e.g., WhatsApp groups and email threads).

Building Trust and Healthy Business Office Culture

• Intentional Communication & Support:
  • John Fink: Regular meetings with directors, formalized and informal time to build relationships. “I needed to formalize it very quickly: what do I need to know, what do you need to know, and how do we move forward? …And then the personal side is…let’s get lunch, or I’m buying happy hour… I am so grateful for the work they do.” (27:50)
  • Chris Carballo: Stresses humility and respect—“People are people, right? ...if you’re respectful to people, treat them with just normal kindness and understand, like, hey, they’ve got certain skill sets that maybe you don’t have…” (29:38)

Navigating New Relationships with Superintendents, Boards, and Principals

• Adapting Communication Styles:

  • Chris: Advises formality, especially at the start, then building rapport: “You got to go from a standpoint of formality…as you craft that relationship, maybe you can get a little bit more relaxed.” (32:34)

• Switching from “Yes Person” to “No Person”:

  • John Fink: The transition from being a problem-solver on the instructional side to the SBO, often as the bearer of “no,” then learning how to become a creative problem-solver again: “You take on the no guy role…Now I’m trying to cool off of that…How do I become a good business official that’s not Mr. No guy? …We can make this work.” (34:26)

• Outsider’s Perspective Can Drive Creative Questions:

  • Chris: “My superpower is asking really dumb questions of really smart people.” (36:09)

Work-Family Balance in a Demanding Role

• Open Acknowledgement of Difficulty:
  • John Fink: “I have the greatest wife and kids for completely understanding…I was grinding 70, 80 hours a week when I first started…then it got to be a little too much, right?...Now, I do spend a lot more time with my family…There is a culture in my district…there’s not a lot of emails flying after 4 o’clock, 5 o’clock…Or on weekends. I’m not going to put that on my staff…” (39:16)
  • Chris Carballo: “Having great understanding from my wife and kids…You have to structure it yourself…carve out when, hey, look, I am done for this day…There’ll be days you go over past that, but prioritizing is key.” (41:00)

Lessons Learned & Advice for New SBOs

• Wish They’d Known (Early On):
  • John Fink: “Content. Like, I wish I was an AI machine four years ago where I could just crush the content…But in the end, I don’t regret any of that because I’ve learned so much. The learning curve went from the floor to the ceiling in seconds…” (42:30)
• The Power of Support Staff:
  • Chris Carballo: “I wish I’d really understood just how important those great key people in the support…roles are. You do need that payroll clerk, that clerical person…they’re the ones that are in the trenches doing the work…helping you to understand how to make the right decision…” (43:51)

Notable Quotes & Memorable Moments

• On mentorship and humility:

  • “I don’t know if I’ll ever feel that way, honestly, because, you know, like, GASB throws something at you … I’m never gonna say I’m good. There’s no way.” — John Fink (16:36)

• On building trust in the team:

  • “People are people, right? …if you’re respectful to people, treat them with just normal kindness and understand, like, hey, they’ve got certain skill sets that maybe you don’t have…” — Chris Carballo (29:38)

• On the culture shift from private sector to education:

  • “The best thing about this industry, this culture, is that…it’s about helping kids to prepare for their future…and the cool thing is that I would say so far 99% of the people I’ve met that do this, regardless of what they look on the outside, deep down, that’s what they believe and that’s why they’re here.” — Chris Carballo (22:13)

• On feeling overwhelmed but persevering:

  • “I equate my first year as a school business official…that meme with the dog sitting in the kitchen and everything’s on fire around him, and his caption’s like, ‘this is fine.’ That’s kind of how my whole first year was.” — John Brucato (13:26)

• On early learning curve:

  • “The learning curve went from the floor to the ceiling in seconds…And I really appreciate that.” — John Fink (42:42)

Timestamps for Key Segments

• [01:55] John Fink on why he transitioned to SBO and his early challenges.
• [04:23] Chris Carballo recounts entering school business after private sector challenges.
• [06:58] Culture shock: email overload & differences between public/private sectors.
• [08:23] The importance (and stress) of regulations—and leaning on your network.
• [12:16] John Fink’s deer-in-the-headlights moment at his first ASBO workshop.
• [14:33] Both guests discuss mentorship’s central role during their transition.
• [20:21] The value of building relationships with colleagues, BOCES, and state contacts.
• [27:33] John Fink on building trust in his new team through structured and informal strategies.
• [29:38] Chris Carballo’s approach—respect and humility.
• [34:26] John Fink on moving from “yes” to “no,” then back to creative “yes.”
• [39:16] Insights on work-family balance as a new SBO.
• [42:30] What they wish they’d known in year one.
• [43:51] Chris on relying on—and respecting—the power of the support staff.

Takeaways for Listeners

• There’s no perfect path to school business leadership—diverse experiences can both challenge and strengthen a new SBO.
• The learning curve is steep; mentorship and peer networks are essential for survival and eventual confidence.
• Humility, respect for team members, and a commitment to learning are critical.
• Formal relationships with superintendents, boards, and other senior educators require tact and gradual rapport-building.
• Burnout is real; setting boundaries and modeling healthy work-life balance can permeate the culture.
• The knowledge and commitment of support staff enable SBOs to succeed; never underestimate their contributions.
• No SBO ever truly feels like they’ve “arrived” or mastered everything—there’s always something new to learn.

This episode offers an honest, reassuring look at the early years in school business leadership, highlighting the value of candid conversations, embracing vulnerability, and relying on each other as “the only way through the firehose.”