School district leaders have had to navigate a new environment of constant change and uncertainty in recent weeks as a flurry of executive orders from President Donald Trump and new policy directives from the U.S. Department of Education and other federal agencies have left districts wondering what exactly they’re required to do.
But it’s also reminiscent of another unprecedented time not all that long ago, several superintendents said.
“It kind of reminds me of going through COVID all over again, when things were coming at us from all directions and changing constantly,” said Sharon Desmoulin-Kherat, the superintendent in Peoria, Ill., and a finalist for the 2025 national superintendent of the year award. “We were able to survive COVID so … I think we can do it.”
Since taking office in January, Trump has issued more than 70 executive orders, several of which directly affect education and schools, including one order that could affect how schools address race and gender and another that bars transgender girls from participating in girls’ sports. Trump’s Education Department, sometimes acting on these executive orders, has also announced a series of quick policy shifts for schools, including a directive to end race-based programming or risk the loss of federal funds and the return to an older set of regulations outlining schools’ obligations under Title IX, the nation’s law barring sex discrimination at federally funded schools. The administration also announced a funding freeze in its second week, forcing district leaders to question whether they could count on the federal funds Congress has appropriated for them, and revoked a Department of Homeland Security policy that generally kept immigration agents from making arrests and executing raids at schools.
Sometimes, the sweeping orders conflict with state laws, like in New Jersey, which mandates instruction on diversity and inclusion, a direct contradiction to Trump’s directive that schools cease race- and equity-based initiatives or risk losing federal funding.
Desmoulin-Kherat, who has been a superintendent for a decade, said the pace of the executive orders is “unique” and has not happened in the same way during other administration changes, a sentiment with which several other longtime education leaders agreed.
Patrice McCarthy, executive director of the Connecticut Association of Boards of Education, described the phenomenon to the news website CT Insider as a “fire hose of letters” coming from the federal government.
Trying to sort through those orders—while also keeping up with the normal, day-to-day demands of managing a school district—has posed a new challenge for leaders, who have in recent years lamented the infiltration of political issues into the classroom and central office operations. Many said they have spent a large chunk of their time in recent weeks working with legal counsel to parse the new federal orders, determine the potential impact on programs and budgets, and communicate with families and staff.
“It is incredibly challenging and very confusing, and it’s everything that we try to avoid as leaders in terms of trying not to instill chaos and confusion,” Desmoulin-Kherat said. “There’s a big push for school leaders to focus on their culture and climate and ensure that the angst and all of the contentions and unknowns are reduced to the extent possible so that we can really focus on the work. This is all very distracting from that goal.”
District leaders can lean on networks and professional organizations for help
Some worry about the financial implications of leaning more heavily on legal assistance to interpret and correctly implement the orders.
During a recent school board meeting about the Hanover, N.H., district’s diversity and equity strategic plan, Superintendent Jay Badams questioned how new federal directives, like changes to Title IX regulations and orders prohibiting DEI initiatives, will affect the district, according to New Hampshire Public Radio.
“All of those questions, they’re going to hit us, and we’ll be having conversations like this, I think, on a variety of topics through the remainder of this year and probably the next four,” Badams said at the meeting, following a state education department advisory telling Granite State districts to review and ensure compliance with the president’s orders. “I think we’re going to have a lot of legal bills just to get advice on things like compliance.”
Badams did not respond to Education Week’s request for comment.
The concerns are justified as new orders “impose significant legal obligations on school districts—or at least state that as the purpose,” said Sonja Trainor, executive director of the National School Attorneys Association.
“No one would expect a lay school administrator to be able to parse through what they mean, what their legal authority is, if and how they may conflict with their own state laws, etc., without consulting experienced legal counsel,” Trainor said.
She recommended districts invest in and nurture strong, trusting relationships with their school attorneys. Those attorneys should have the time and freedom to attend events with their professional organizations and networks to stay abreast of changes and their implications for districts, she said.
“The dollar amount a school district dedicates to preventative, proactive counsel from their trusted school attorney pales in comparison to costly litigation, which districts now face from many directions in areas where the law is unclear or unsettled,” Trainor said.
Desmoulin-Kherat, in Illinois, said districts like hers can also lean on partnerships with local professional organizations, like state administrator and school board associations, which can take the lead on assessing directives and give members guidance.
“This is all new for everybody, not just legal. We don’t necessarily have to rely on our legal for everything,” she said.
Mark MacLean, executive director of the New Hampshire School Administrators Association, also encouraged district leaders to rely on their networks to ease the burden and stress of trying to assess new orders and make consequential decisions alone.
NHSAA is a state-level association for school administrators that provides networking, guidance, and support to New Hampshire district leaders. There are similar groups in each state, and there is also a national-level group: AASA, The School Superintendents Association. Many district leaders are members of both their state associations and AASA.
Those groups are staffed with people—and legal teams—who are also analyzing new directives and pushing out both high-level and more in-depth information for their members, MacLean said.
“Instead of everyone having to respond in a silo, we’re able to … make sure that people are connected and having those conversations collaboratively,” MacLean said. “Embedded in all that, the advice is, rely on your peers and rely on your networks to make sure that you’re not responding without having folks to bounce ideas off of and get feedback and some additional direction from.”
Thoughtful and intentional communication can ease community stress
Like in 2020 when the pandemic threw K-12 education for a loop, school district leaders say they’re focusing on what they can control and on maintaining clear, consistent communication with families about issues that may affect them or their children.
For Debbie Jones, the superintendent in Bentonville, Ark., and another Superintendent of the Year finalist, that means responding personally to every email she receives from a concerned parent. It also means being a bit selective about speaking out.
“It’s not an abundance of communication, it’s thoughtful and intentional,” she said. “With my communications department, we have a saying: ‘It’s not our circus, not our monkeys,’ meaning we don’t try to play in other people’s circus when it’s not our issue. We stay well informed of the environment at all times, but sometimes it’s not our story to tell. By doing that, I think our community is more attentive when we do talk.”
It’s important, Jones said, that when she sends out messages on any topic—whether in an email or press release, or at an in-person meeting—she doesn’t insert political ideologies.
If she does, she said, “then I’ve lost 50 percent of my community either way.”
