School board promotes Harpswell native to permanent superintendent

The Maine School Administrative District 75 Board of Directors has chosen its interim superintendent of schools and former director of special education, Harpswell native Heidi O’Leary, to fill the district’s top post on a long-term basis.

The school board unanimously approved O’Leary’s appointment as superintendent of schools during a meeting on Thursday, Dec. 14. O’Leary, who led the district’s special education programs for six years, has been serving as interim superintendent since July 1.

The board approved a 3.5-year contract for O’Leary at an annual salary of $150,000. Her tenure will officially begin on Jan. 1.

O’Leary grew up on Orr’s and Bailey islands, where she said working for her father’s well-drilling and trucking businesses taught her vital communication and customer service skills. She vowed to usher in a new era of camaraderie and cooperation to the district, which has experienced a recent period fraught with discord and antagonism.

“From this day onward, I will take the opportunity to serve as a model,” O’Leary told the board immediately after its approval vote. “When disagreements inevitably arise, we can demonstrate how to bridge them through civil discourse and emerge the wiser.”

“Our students are always observing how we face conflict,” she continued. “I will approach divisions with openness, wisdom and integrity that sets a powerful example for our youth on the foundation of ethical leadership.”

O’Leary’s lengthy career in education has included stints as a substitute teacher, coach, educational technician, special education teacher, special education director and, most recently, interim superintendent of schools. She currently lives in Turner.

In addition to working for MSAD 75, O’Leary has served as an educator for Biddeford Schools and Waterville-area schools in the former Alternative Organizational Structure 92.

O’Leary’s appointment comes at a time when the district has struggled to hold onto a permanent top official.

MSAD 75’s most recent former superintendent, Steven Connolly, chose to resign effective June 30 after just one year in the role. His announced departure set up the district’s sixth executive leadership transition in as many years.

In a resignation letter dated Feb. 9, Connolly cited his own difficulty managing “the implicit divisions that exist (within the district) based on political, personal, and ideological beliefs” as the primary reason.

In September, Connolly told the Harpswell Anchor that “micromanagement” by board member Brandy Robertson, of Bowdoin, and former board member Eric Lusk, of Harpswell, had been a primary driver of his resignation. Robertson and Lusk disputed that characterization.

Since the retirement of Brad Smith, superintendent from 2011-2018, the district has often been forced to rely on interim leadership.

Interim superintendents Dan Chuhta and Bob Lucy split the 2018-19 school year. Shawn Chabot was superintendent in 2019-20 and much of 2020-21 before reporting for active duty as a National Guardsman. Lucy filled in for the rest of 2020-21 and all of 2021-22, then Connolly took over.

When Connolly announced his resignation, the board immediately selected a superintendent search committee made up of then-school board Chair Frank Wright, of Harpswell, and one board member from each of the district’s four towns: Harpswell, Topsham, Bowdoin and Bowdoinham.

In May, the committee’s top choice to become the next superintendent decided to withdraw, forcing the district to again turn to an interim leader — O’Leary — for the coming academic year.

But that has turned out to be a winning move, according to school board Chair Hutson Hayward, of Bowdoinham. He praised O’Leary as someone who “stepped up” in the district’s time of need and said the board has been “continually impressed” with her dedication to the role.

“Ms. O’Leary has been looking only to set the district up for success, regardless of who might be leading it,” Hayward said.

He said the school board became especially appreciative of her leadership when MSAD 75 was confronted with multiple bomb threats and a recent mass shooting incident in Lewiston that impacted the lives of many students who attend district schools.

“(She prioritized) student safety at all times, acting as a model communicator under turbulent circumstances,” Hayward said about O’Leary.

At Thursday’s meeting, several board members voiced their enthusiastic support for O’Leary, including Robertson, who had voted against her appointment to the interim position in June, citing her lack of prior experience in a top leadership role.

“I had my doubts … (but) I’m elated to say my concerns were unfounded,” Robertson said, adding that O’Leary is “the best superintendent we’ve had in a long time.”

Have a comment or news tip? Email J. Craig Anderson at craig@harpswellanchor.org.