Supporting a Chief Business Official (CBO) isn’t just about managing calendars or taking notes. It’s about being a strategic partner in a high-impact, fast-paced environment where decisions ripple across the entire school community.

But even experienced Executive Assistants can miss the mark in school business without the right guidance. Here are three of the most common mistakes—and how to avoid them so you can stand out and step up in your role.

1. Underestimating Their Strategic Value

The Mistake: Many EAs see themselves as “behind the scenes” helpers rather than key players in the success of their district’s business operations. They hesitate to speak up, ask questions, or take initiative—especially when it comes to budget cycles, board agendas, or interdepartmental coordination.

How to Avoid It:
Start by reframing how you view your role. You are not “just” support—you are a trusted partner who can shape how effectively your CBO leads. When you anticipate needs, proactively manage communications, and ensure priorities stay on track, you help your entire district succeed. With that in mind:

• Reframe your mindset: You are a strategic partner, not just support staff.
• Ask your CBO: “What are your biggest challenges this month?”—then look for ways to help.
• Take ownership of meeting prep, follow-ups, and communication flows.
• Stay engaged in cabinet and leadership meetings; jot down themes and action items you can help move forward.
• Use tools like shared agendas, project trackers, or internal dashboards to stay aligned with your leader’s goals.

“Once I started viewing myself as part of the leadership team, I gained the confidence to contribute more and my CBO noticed!”
—Past Participant, EA Micro-Certificate Program

2. Missing Critical Budget and Compliance Milestones

The Mistake: EAs may not be directly responsible for crafting the district’s budget, but they are instrumental in supporting those who do. Missing deadlines for board items, interim reports, or governor’s budget revisions can cause last-minute scrambles and costly errors.

How to Avoid It: Your role is not to master every fiscal detail, but to understand the flow of the year so you can support those who do. Knowing when milestones hit, what documentation is required, and who needs reminders ensures a smoother, less stressful process for everyone. Here’s how you can help:

• Learn the fiscal year cycle. Especially budget adoption, interim reporting, and audits.
• Build a shared calendar with reminders for key reporting milestones.
• Schedule prep meetings in advance for board deadlines, budget drafts, or revision windows.
• Use checklists to track the status of forms, approvals, and department submissions. Project management tools like Monday or Asana can really help you get organized!
• Communicate proactively with departments to collect input or confirm timelines.

“Now I know what the fiscal team is preparing, and when. I use calendars, check-ins, and dashboards to stay ahead of what’s needed.”
—EA Micro-Certificate Program Graduate

3. Failing to Navigate Confidentiality and Communication with Confidence

The Mistake: School business often involves sensitive information such as personnel matters, labor negotiations, compliance reviews, and more. EAs who aren’t trained in communication strategy or confidentiality protocols may accidentally overshare or stay silent when they should speak up.

How to Avoid It: You are often the first face or voice someone hears from in a crisis, a complaint, or a compliance inquiry. Knowing how to communicate accurately and with discretion builds credibility and trust. It’s not just what you say—it’s what you don’t say that matters too. Strengthen your communication confidence by:

• Clarifying early with your CBO: What is confidential? What’s okay to share?
• Creating templated language for responding to inquiries you can’t fully answer.
• Staying composed during crises; your calm presence is often the first point of leadership others see.
• Keeping notes secure, organizing files intentionally, and labeling sensitive materials clearly.
• Regularly scanning district updates, policies, and goals so you’re always prepared to communicate with accuracy.

“I used to be unsure of how to respond when people asked for information. Now I have a framework for communicating with clarity and care.”
—CASBO EA Cohort Member

4. Failing to Establish Trust with Your CBO

The Mistake:
Some Executive Assistants focus so much on task execution—emails, meetings, forms—that they miss the deeper priority: building trust with their Chief Business Official (CBO). Without trust, even excellent work can go unnoticed. When EAs don’t proactively align with their leader’s expectations, communication style, or goals, it can lead to tension, micromanagement, or missed opportunities to lead from behind.

How to Avoid It:
Trust isn’t built overnight, but it is built intentionally. Understanding your CBO’s working style, anticipating their needs, and communicating openly sets the foundation for a strong partnership. Here’s how to strengthen trust over time:

• Schedule regular check-ins, even 15 minutes a week, to clarify priorities and get feedback.
• Learn your CBO’s “non-negotiables” (like meeting prep or follow-through) and meet them consistently.
• Ask: “How do you prefer to receive updates or reminders?” and tailor your style to theirs.
• Anticipate problems before they reach your CBO’s desk. This builds long-term confidence.
• Practice discretion, transparency, and reliability in equal measure.
• Don’t wait to be told what’s needed. Offer solutions or draft options when appropriate.
• Celebrate small wins and reflect them back: “I know this was a big week for X. I’m glad I could help it run smoothly.”

“The more you show your leader that they can count on you, the more they’ll rely on your judgment. That’s when real partnership begins.”
—EA Micro-Certificate Program Facilitator

5. Letting Professionalism Slip in High-Visibility Moments

The Mistake: Some Executive Assistants underestimate how much their behavior sets the tone for the entire office. When professionalism slips it can quickly undermine trust. Letting personal stress show, using overly casual language, or overlooking district values in high-pressure moments sends the wrong message and erodes credibility, both personally and on behalf of the organization.

How to Avoid It: Professionalism starts with mindset and intention. EAs set the tone for many of the interactions across departments and with the public. Each email, each phone call, and each meeting is a chance to reflect the mission and values of your district. Here’s how to stay grounded:

• Walk into every interaction (online or in person) with positivity and integrity.
• Align your tone, language, and presentation with your district’s mission and public expectations.
• Practice active listening and neutral, respectful language, especially in tense conversations.
• Review district policies and goals regularly to communicate and represent them accurately.
• Model the mindset of “solution first” and others will follow your lead.
• Add value in small but meaningful ways (like preparing your leader’s workspace for a smooth start to the day or creating focus blocks on their calendar).
• Reframe difficult conversations with a question: “How can I make your day better?”

Build Confidence. Advance Your Career.

Avoiding these common pitfalls isn’t just about doing your job, it’s about growing your impact and career potential.

CASBO’s Executive Assistant Micro-Certificate Program is a 5-week, fully online course designed specifically for administrative professionals who support school business leaders. You’ll gain practical skills in:

• School district budgeting and compliance
• Meeting and event logistics
• Confidential communication
• Calendar and workflow management
• Real-world case studies and tools you can use immediately

Achieve a resume-ready certificate today!