How to Set Up and Then Evaluate School Initiatives

When Principal Scott Palladino assigned a faculty committee to reexamine Wareham High School’s cell phone policy, he assumed they would arrive at a cut-and-dried policy proposal: a blanket, all-day ban. Palladino was prepared to enforce that initiative—he saw the logic in it and was well aware of staffers’ complaints about how phones were interrupting learning at the Massachusetts school.

The committee returned with a compromise in which phones weren’t outright banned but needed to be placed in classroom cubbies during instruction. The proposal, which mirrors many other school districts’ approach to cell phones, wasn’t what Palladino expected, but he chose to follow the recommendation. A former teacher himself, Palladino had asked the committee to make a tough call, and they had put in the requisite time, effort, and research. If he didn’t listen to them now, why would they listen to him in the future when he made his own policy recommendations?

School leaders have countless things to consider when planning and rolling out a new initiative:

• Does the timing make sense?
• Are staffers aware of the initiative? Do they have a voice in how it’s instituted? Are they bought-in?
• Are there meetings on the calendar to monitor progress?
• Who’s delivering updates about the initiative?
• What happens if the initiative doesn’t work as intended?

These considerations require gut checks, adjustments, and transparency—not just with other administrators and teachers, but with students and their families, too. Without ample surveying, school leaders run the risk of announcing an initiative that lands with a thud. There are also scenarios in which a school leader and staff communicate harmoniously, meet frequently, and still run into a roadblock.

The key to executing new initiatives is having a rock-solid grasp of each step of the process—ideation and initial messaging, followed by collaboration and consistent communication—as well as how to handle unexpected issues that require pivots and even pauses.

Palladino and David Wiedlich, principal of Radnor Middle School in Pennsylvania, spoke with me about navigating new initiatives from start to finish. Here are their tips and some insights from business leaders who’ve written extensively about how they handle company-wide projects.

Don’t Bite Off More Than You Can Chew

First off, there’s a difference between strategic experiments and strategic initiatives, wrote HBR executive editor Ania W. Masinter. The distinction matters—it helps leaders set realistic expectations for themselves and for others. Experiments are about “discovery” and “should have explicit assumptions, hypotheses, and learning goals,” Masinter said, while “initiatives should have concrete success criteria.”

It’s fair to say the stakes are higher with initiatives, but only because they require more forethought, and unlike with experiments, the “desired outcomes ideally should have been laid out at the project’s outset,” Masinter noted.

In education, initiatives tend to affect a significant portion of a school, often for years on end—new course offerings, a cell phone ban, definitive AI guidelines, improved classroom aesthetics, those sorts of things. These are time-consuming ventures with potentially lengthy payoffs, which is why Palladino enters every school year with a realistic mindset about what he and his staff can accomplish.

“I’d rather focus on a handful of initiatives each year and do them well,” he said. “If you have some that are easier to attain, then that’s great. But you also don’t want to try and grab all the low-lying fruit just to announce that you met all of your goals.”

Palladino feels strongly that he and his staff “will never, ever bring in an initiative that we can’t support,” he said. He triangulates between his district’s strategic plan, a school improvement plan, and the recommendations of various departments.

That balancing act takes finances into account; Palladino isn’t interested in initiatives that are debuted on a shoestring budget. He cited Wareham High School’s recent addition of three new AP courses as an example of a well-thought-out, properly funded plan: “Through ongoing conversations at both the district and school levels, there was a shared understanding” that the initiative would ultimately be a net positive, he said.

Involve and trust Your Staff From Start to Finish

New initiatives have almost no chance of working out if they’re exclusively the brainchild of a single school leader. It’s crucial to work through policy ideas alongside teachers and faculty, as opposed to looping them in after the fact.

Wiedlich shared an example of how his school added more electives. Step one was just an inkling of an idea: Wiedlich wanted his students to be able to sign up for more classes that would make them genuinely excited. He went to his technical education teachers and asked for their opinions—what sort of content did they think was most important, and most interesting, for tweens and teens? He also wanted to know what the teachers were most interested in actually teaching.

After some brainstorming—and adjusting for statewide and Common Core standards—Wiedlich and the teachers shortened their list of possible courses so that it was increasingly relevant for middle school students. Next came a survey for students, to make sure the whittled-down list of potential electives looked intriguing. The entire process took roughly a year. There was no rush on making a final call or starting up the courses—Wiedlich’s aim was to keep talking to staffers so that there were no surprises or major frustrations.

“The teachers and the support staff, they’re the ones who are boots on the ground, they’re the ones who are constantly reflecting,” Wiedlich said. “You need to know them ahead of time, so when you look to change something, you may already know what some of the triggers are, as well as strengths. You’re not wasting people’s time, and you’re keeping things laser-focused on the task at hand more so than worrying about upsetting anybody.”

Palladino agreed that it can take “months and months” of steady communication with staffers to get an initiative over the starting line. At his school, teachers sign up for committees at the beginning of the school year via a Google Form. Each committee is tasked with exploring and planning one of the school’s most-discussed initiatives, and meets every three weeks to go over progress.

Unlike other faculty meetings, which are not always met with enthusiasm, these are pretty popular. “What I have found is by giving educators autonomy to come up with programs or even just to come up with a few options, the buy-in is so much greater, they’re invested, and then the word of mouth gets out,” Palladino said.

The consistency of the meetings is a great sign about staff buy-in, which is not a given. According to a June 2024 survey cited by HBR, “only 8 percent of organizations conduct monthly project reviews.” That lack of follow-through can be devastating—it leads to a lack of reflection about how initiatives are going, and it can also be a morale killer.

Don’t Be Afraid to Pivot or Pull Back—If You Really Know Why Change Is Needed

Some initiatives, like Wiedlich’s push for more electives, go swimmingly. Others do not. “We have tried different types of initiatives where I think it’s going great, or a committee thinks it’s going great, and we hit a roadblock,” Wiedlich said. For example, he and his staff weighed adjustments to Radnor Middle School’s master schedule—the number of academic periods and whether to integrate a period specifically for clubs and extracurriculars, among other changes.

With the help of a scheduling committee, Wiedlich gathered feedback from teachers, students, and community members. They reached a point where they were ready to “present some anticipated changes,” Wiedlich said, until they became aware of a district-led study that incorporated the scheduling strategies of high-performing schools around the country. Wiedlich opted to hit the pause button. “Rather than moving forward prematurely, we decided to wait for the study’s full results and then integrate those insights with the work our scheduling committee had already completed,” Wiedlich said. “Progress met a roadblock, but in a productive way.”

Wiedlich compared moments like that to taking the wrong dosage of a medication: You probably need to adjust the dosage, but you don’t necessarily stop taking the medication entirely. There are even scenarios where an initiative is pushed out and goes great… until it doesn’t anymore. That, too, requires a dosage adjustment—especially “in education, when you write curriculum or you create something, you’re dealing with different cohorts of kids every couple of years,” Wiedlich said.

Palladino similarly brought up making tweaks to policies as time goes on and the student body evolves. He mentioned a dual-enrollment program at a local college, in which high school students can knock out a bunch of courses before they even graduate. That program looks like a “totally different thing” than it did 12 years ago, he said. The tweaks have come from surveying teachers and students, which Palladino does every school year.

Palladino opts for radical honesty when he talks to staff about initiatives, regardless of whether the initiatives are in the planning stages or already active and in need of tweaks. He said that it’s exceedingly rare to complete all of the school improvement goals that he and his committees set at the beginning of the year, and that’s totally fine: “Sometimes it does take the principal to pull back and say, ‘You know what? We’re not ready for that this year.’ And then whatever you don’t complete, we bring back around again, and those are our first two goals for the next year,” he said. “It’s a marathon, not a sprint.”

When Palladino tells his staff that they’ll need to take an initiative goal into the next school year, they ideally aren’t surprised or disappointed. “There should have been some checkpoints throughout the year to see where you’re at,” he said.

There’s a big difference between exhibiting patience to get an initiative right and keeping it going indefinitely out of stubbornness or a lack of direction. HBR tallied up a list of benchmarks to guide leaders through challenging initiatives, three of which are especially applicable to principals:

• “Make continuation a conscious choice.” Don’t sleepwalk through an initiative for the sake of keeping it alive.
• “Spot weak projects early.”
• “Restaff your people to your most strategic projects.” Palladino, for instance, has reshuffled the number of staffers on his committees based on skill sets and competing priorities.

As noted in another HBR article about when to pivot, it’s not always easy to tell whether “the strategy is askew or the execution is poor—or if it’s some combination.” HBR contributor Ron Ashkenas recommends that you “take the time to ask yourself (and other stakeholders) where they see the flaws: Did you make some assumptions about the strategy that don’t seem to be holding true? Are there elements of the strategy that had not been tested previously and may need to be reexamined?”

Sometimes, the answer is simple: The initiative just isn’t working. If it’s wreaking havoc on staff’s schedules or causing other conflicts, it might not be worth the upkeep. “Just because you can continue to make the investment doesn’t mean you should,” wrote HBR’s Masinter. “The opportunity costs for strategic projects can be high in terms of time, money, talent, and executive attention.”

That’s certainly not an ideal outcome, but it’s inevitable, so how school leaders communicate about ending an unsuccessful initiative is crucial, both for themselves and for their staff. “You took an opportunity to change something” is how Wiedlich views it. “You want your teachers to take risks without the fear of being looked down upon if something doesn’t go right.”