How Women Are Navigating the Path to School Business C-Suite

In the world of school business, where budgets are tight and stakes are high, women often find themselves performing a second invisible job: tone management. One California school business leader admits she adds a smiley face to 20% of her correspondence just to ensure her intentions aren’t misinterpreted.

Her experience highlights a recurring theme for women in educational leadership – the exhausting effort to remain “friendly,” while being effective.

According to UNESCO’s Global Education Monitoring Report 2025 (Gender Report), female leadership is linked to stronger community engagement, more inclusive policies and collaborative school cultures. And in some cases, learning outcomes improve in schools led by women.

While women have made strides in school leadership, studies suggest there is still work to do. Women Leading Ed’s second annual insight survey found that women still lead only 30% of the nation’s largest school districts. Similarly, the UNESCO report found a 20% gender gap in secondary school leadership positions. Women Leading Ed also found that gender bias impacts women leaders’ physical and mental health, career pathways and compensation. According to 93% of women leaders, burnout is a major problem.

Given that women in leadership roles benefit organizations overall, how do districts ensure that conditions support not only their advancement into leadership positions but also their ability to thrive in those roles?

Beyond Expertise

Building expertise in your field is the No. 1 thing women can do to achieve and succeed in a position. But sometimes expertise is not enough. CASBO heard from many women in leadership who recounted instances of being passed over for a promotion by a male colleague with less expertise. Or being talked over by men in meetings. None wanted to go on the record for fear of offending their colleagues.

Candace Reines, assistant superintendent of business services at Perris United High School District, has focused on developing her ability to speak with confidence and authority. Reines, who became a business services director at 28 and a CBO at 31, appreciates direct communication.

“It comes down to being reliable and consistent,” she says. “Any of us can come off as abrasive to someone, but once they get to know you and what you are accomplishing, that will be forgotten.”

Besides expertise and public speaking, there are many skills women can lean into or develop that will serve them in leadership positions.

“Learning something new isn’t always comfortable. Part of growing in leadership is stepping into that discomfort.”

Jennifer Cassetta is the author of The Art of Badassery: Unleash Your Mojo With Wisdom of the Dojo. Cassetta says there are many skills that many women already have and can lean into for success. Those skills include empathy, inclusiveness, collaboration, emotional intelligence and leading with a purpose.

Many of us need to work on boundarysetting, communicating those boundaries clearly, using our internal voice to instill empowering beliefs and practicing selfcare. Michelle Howe-Kelton, director of f inancial services at Lemon Grove School District, found that, while she was conf ident in the knowledge she needed for her job, she was less confident in her ability to articulate that knowledge. Like Reines, she knew she needed to get more comfortable with public speaking, so she asked her CBO if she could start presenting at board meetings. In doing so, she “got comfortable with being uncomfortable,” she says.

Reach for a Stretch Role

There’s a lot of research showing that women tend to believe they need all the qualifications before even applying for a position, whereas men are more confident they will grow into the role. Jennifer Lewi argues that, “Learning something new isn’t always comfortable. Part of growing in leadership is stepping into that discomfort.”

Lewi is a former vice president of the School Nutrition Association; she’s now the founder of Design Your Next Step coaching. One of Lewi’s clients hoped to become a CBO. The position came down to two candidates, and the other person got it. Lewi encouraged her client to view the setback as a learning opportunity. She sought feedback on what she could have done better and realized that the other person was the stronger candidate. A few years later, she tried again and got the position.

“Seek feedback to learn how you’re being perceived and fix that,” advises Lewi. “We are often evaluated on where we are now. You may get rave reviews and wonder why you aren’t being promoted. It’s important to communicate the path you want going forward.”

Seek Allies

We all need a little help from our friends. That’s especially true in the workplace. Yet only 44% of women have benefited from mentorship and 22% from sponsorship, according to the Women Leading Ed study. Regardless of a formal mentoring or sponsorship relationship, finding allies who will support and advise you as you grow into your career can be immensely helpful.

Howe-Kelton has used CASBO to build her own personal board of advisers. She reaches out to her network daily. They often check in with each other when a big report is due to the state, bounce ideas off each other, recommend vendors and answer questions for each other. CASBO’s Women in Leadership Conference, held in February and returning next year, is a great place to build a network of women supporting other women.

Reines credits a mentor at the beginning of her career with influencing her trajectory. Early on, Reines was in a district with many dedicated people who had been there for a long time. She and her mentor, both newer to the district, wanted to push for some changes to make things work more efficiently. Reines learned from watching her mentor navigate the situation with skill and expertise.

Now, Reines runs a statewide school business academy where a cohort of applicants learn about school business to help them decide if it is the right career path. It’s also an excellent place to meet allies. “The technical competence is what gets us in the door,” says Reines. “But it’s the relationships that keep us at the table.”

As Reines discovered, acting as a mentor can be as helpful as having one yourself. That’s because we often learn through guiding others. Lewi teaches a framework called FRAME to encourage allies to empower each other.

FRAME stands for:

1. Focus. Be present for a conversation.
2. Recognize the implicit assumptions you’re making or the history you have with the person.
3. Ask open-ended questions and allow for silence.
4. Mirroring. Recap what the person said, and they can tell if you understand what they’re saying.
5. Empower them to come up with the solution.

A big benefit of the FRAME approach: It builds a network of people who can solve problems. One of Lewi’s clients had a fire in one of the schools in her district. Before following the FRAME approach, the client would have jumped in her car to put the fire out herself. Instead, she realized she had the right people in place to solve the problem at the site. She asked if there was anything her school nutrition director needed, offered some guidance, then let her ally solve the problem without getting in her way.

“When we learn to lead, we often think that we need to direct and guide people,” says Lewi. “That’s part of the job, but as you grow as a leader you need to grow other leaders by helping them find their own solutions.”

Take Steps to Avoid Burnout

We all want to go home from work fulfilled and satisfied that we are competently doing meaningful work. Sadly, that is not always the case. The Women Lead Ed survey found that 58% of respondents were contemplating leaving their field. Among those considering leaving, 88% think about it at least monthly. How do women in leadership avoid burnout and protect their own mental space?

Cassetta has some recommendations from the dojo:

1. Embrace the suck. We’re all going to get knocked down, but that experience expands our capacity to get through struggles.
2. When you get knocked down, how do you get back up?
3. Learn how to block attacks by setting boundaries and saying no to things that distract you from your purpose.
4. Pay attention to how you communicate with yourself. Use affirmative self-talk.
5. Identify what drains your energy and lean into what energizes you.
6. Practice mindfulness.
7. Be a teacher. Grow your skills by sharing them with others.

Howe-Kelton says finding allies both in her district and outside is key to cultivating a positive dynamic in the workplace. Another is agency, understanding what we can influence and what we can’t. She considers herself lucky that her CBO encourages her to continue learning and growing. Finally, aligning your purpose and goals with those of your district and co-workers creates a positive dynamic. Mostly, Howe-Kelton says, be true to yourself.

“Continue to speak your mind,” she says. “Your opinions matter and are worthwhile.”