The Untold Truths of the Superintendency

The Harvard EdCast

The superintendent’s role is challenging and always evolving but too often educators step into this leadership position not fully prepared for what’s ahead. As a position with high turnover and equally high isolation at times, Lindsay Whorton, The Holdsworth Center president, says we need to be more upfront about the role if we are to attract, support, and retain leaders.

“What we have to do is be honest but also be encouraging and celebrate what an incredible opportunity it is to be in these roles. Yeah, it's going to be hard and there's going to be these pressures. And it's a really complex, intellectually, emotionally, physically demanding job,” she says. “And it represents an incredible opportunity to facilitate a conversation in your community to help advance your district to do the right thing for kids and to really make a significant difference in the lives of both the students who are in your school system today and in the future.”

The transition to a superintendent role often surprises those coming from senior leadership, as it requires them to assume a broader, more public-facing leadership stance. Many new superintendents feel "discomfort" or even disillusionment when realizing how drastically their responsibilities have expanded, including heightened community visibility and accountability.

“What gets tricky is when that sense of discomfort turns into maybe I'm not capable, maybe I don't have the confidence, maybe this isn't something that I can do,” she says. “And so we think by helping people understand that it is normal to experience what we're calling a shift in professional identity, people can be a little bit less destabilized by that experience and can learn through it and get to the other side of feeling more prepared, more capable, more confident about the role that they have as a superintendent.”

Whorton explains that navigating the superintendency successfully demands strong relational skills, strategic vision, and adaptability. A key component to long-term success, she notes, is the ability to foster strong board relationships, even as boards may change or challenge the superintendent’s direction. Additionally, Whorton advocates for recognizing the superintendency as a role that requires community leadership and suggests a shift toward viewing superintendents as central civic figures.

In this episode, Whorton discusses whether the superintendent position has changed and why it’s necessary to reframe the role to inspire a new generation of leaders to step into this role.