In a recent episode of The Table, I sat down with Jenn Dubey and Kyle Conley to talk about something that’s been weighing on my mind for years: the isolation that school leaders experience and what we can do about it. Both Jenn and Kyle have spent decades working with educators across every school context imaginable (public, charter, independent, international), and their insights about supporting school leaders resonated deeply with my own experiences in education.
What struck me most about our conversation wasn’t just the challenges they named, but the solution they’re building through their organization, Building Leaders. Their approach centers on something surprisingly simple yet profoundly powerful: bringing school leaders together in judgment-free spaces where they can learn from each other, practice new approaches, and build networks that sustain them through the hardest parts of leadership.
The Leadership Preparation Gap Nobody Talks About
Kyle’s story about becoming a principal hit close to home. She described being asked to lead a turnaround effort at a historically struggling school, and despite looking ready “on paper” with all the right credentials and classroom experience, she felt underprepared for what actually unfolded. “The lived experiences and understanding the context was lacking,” she shared.
This preparation gap isn’t unique to Kyle. Research consistently shows that new principals often feel overwhelmed by the complexity of their roles, particularly when dealing with stakeholder management, organizational culture, and the emotional weight of decision-making that affects entire communities. The training programs exist, the professional development workshops are available, but something essential is missing.
Jenn named it perfectly when she talked about her own transition from teaching to school leadership. She attended numerous trainings on implementing programs with fidelity, staying in compliance, and managing her role. “But there was a real lack of leadership development and communities where I could be open and honest as a learner,” she explained. “Learning leadership in this new lens of school leadership, where I could be open and honest about what it looked like, what I needed, and what I was working on.”
What School Leaders Are Actually Struggling With
When I asked Jenn and Kyle what challenges educators are naming most consistently right now, their answers painted a picture that will sound familiar to anyone working in schools.
Jenn identified three major themes: isolation, overwhelm, and what she called “misalignment” (the exhausting gap between how leaders want to show up and what actually happens in their daily reality). Kyle added the challenge of short-term thinking that plagues school leadership. As she put it, “We’re worried about test scores this month, this year. We’re not thinking about what this student’s gonna look like five years from now, 10 years from now, 30 years from now.”
The isolation piece particularly resonated with both of them. Kyle described watching school leaders become “so insular that they can’t see beyond their own four walls.” This inward focus creates a kind of professional myopia where leaders lose perspective on broader educational trends, innovative practices happening elsewhere, and even their own blind spots.
But here’s the thing Jenn pointed out that I think we don’t talk about enough: this isolation doesn’t just hurt leaders personally. It affects entire school communities. When leaders are isolated, they make decisions in a vacuum. They can’t access the collective wisdom that exists across the education field. They burn out faster. And ultimately, the students and families they serve pay the price.
The Compliance Trap and Why It Matters
One of the most thought-provoking parts of our conversation was when Kyle talked about what she called the “compliance mindset” that dominates so much of education right now. She described it as a self-reinforcing cycle: schools focus on compliance, teachers are measured on compliance, and the whole system ends up oriented toward box-checking rather than actual learning and growth.
“If you can comply, you’re good to go,” Kyle said. “But that’s not real accountability. Real accountability is when I’m held accountable to the outcomes that matter, not just the outputs.”
This distinction between outputs and outcomes is crucial. An output might be “we implemented our new advisory curriculum with 100% fidelity.” An outcome is “students report feeling more connected to their peers and adults at school, and behavioral incidents decreased by 30%.”
The compliance trap affects school leaders in a specific way that Jenn highlighted: it shapes what kind of professional development they receive and what communities they’re invited into. If your school’s culture emphasizes compliance above all else, you’re more likely to attend trainings about program implementation than workshops about visionary leadership or building authentic relationships with families.
Why Traditional Professional Development Isn’t Enough
Both Jenn and Kyle were refreshingly honest about the limitations of traditional professional development for school leaders. The conference circuit, the one-off workshops, the webinars that promise transformation in 60 minutes—these all have their place, but they’re not solving the deeper problem.
Jenn described her breakthrough moment when she participated in a collaborative cohort at the University of Florida’s Lastinger Center. “Suddenly, I had that space to be in a room with other folks in my role, talking about our challenges, not worried about how the teachers we were coaching and developing were gonna receive what I was learning and working on. We could just be open and honest with each other as learners.”
That program got cut (as so many valuable programs do), but the experience showed Jenn what was possible. It also revealed what was missing from most professional development: psychological safety, ongoing relationships, space for honest reflection, and the chance to practice new approaches without the stakes of immediate implementation.
Kyle’s experience building global communities of practice for principals reinforced this lesson. She brought school leaders together to visit schools in different countries, then maintained virtual connections for months before visiting another country. “It was the first time I really saw the power of a cohort and the power of a community where the content learning isn’t the primary goal, but also the building of a strong network and a group of colleagues that is there for you,” she said. “That changed everything for me.”
What Communities of Practice Actually Look Like
So what makes a community of practice different from traditional professional development? Based on Jenn and Kyle’s description of Building Leaders and their broader work in this space, several elements stand out.
First, these communities are explicitly non-evaluative. Participants can share challenges, admit uncertainty, and try on new ideas without fear that their superintendent or board will hear about it. This psychological safety creates space for the kind of honest reflection that actually changes practice.
Second, they’re sustained over time. Rather than a two-day workshop where you collect some handouts and exchange business cards, communities of practice meet regularly (whether virtually or in person) and build relationships that extend beyond the formal programming. Members become resources for each other.
Third, they’re grounded in real contexts. Kyle and Jenn’s model includes school visits where leaders can see different approaches in action, talk with practitioners about what actually works, and observe how various contexts shape leadership decisions. This experiential learning is far more valuable than PowerPoint slides about best practices.
Fourth, they’re designed for perspective-taking. By bringing together leaders from different school types, regions, and contexts, these communities help participants see beyond their own “fishbowl” (Kyle’s term) and recognize that the same challenge can be approached in multiple ways.
The Power of Getting Out of Your Building
One thing that came through repeatedly in our conversation was the importance of physical proximity to other schools and other ways of doing things. Kyle made the case that site visits and immersive learning experiences offer something you simply can’t get from reading case studies or watching videos.
“When you can walk through a building, when you can talk to students, when you can observe a staff meeting or see how a school handles morning drop-off or manages advisory time—that’s when ideas really stick,” she explained. “You’re not just learning about a practice, you’re experiencing it in context.”
Jenn added that these visits also have a humanizing effect. “When you meet leaders who are facing similar challenges but approaching them differently, you realize that your way isn’t the only way. And that’s liberating. It gives you permission to experiment.”
This reminded me of something I’ve observed in my own consulting work: school leaders who regularly visit other schools tend to be more innovative, more open to change, and more resilient when their initial approaches don’t work. They’ve built a mental library of possibilities that they can draw from when facing new challenges.
Building Leaders: A Case Study in Supporting School Leadership
The organization that Jenn and Kyle are building offers a concrete example of how to structure these communities of practice. Building Leaders brings school leaders and aspiring leaders together for school visits, helping them step out of their everyday environments to learn and reflect alongside peers from different contexts.
Their model addresses several of the gaps they identified in traditional professional development. The school visits provide that crucial real-world context. The cohort structure builds sustained relationships. The focus on reflection ensures that participants don’t just collect ideas but actually process how those ideas might apply in their own settings. And the multi-day immersive format creates space for the kind of deep conversations that rarely happen during the school day.
What I appreciate about their approach is that it’s not prescriptive. They’re not telling leaders “here’s the one right way to do advisory” or “this is the curriculum you should adopt.” Instead, they’re exposing leaders to different possibilities and then supporting them in determining what makes sense for their own communities.
As Jenn put it, “We’re passionate about bringing people together in communities of practice, helping them get out of their everyday environment into new schools and perspectives and places to learn and reflect and to bring back practices for their own leadership and practices for their schools.”
The Hopeful Part: It’s Already Happening
Toward the end of our conversation, I asked Jenn and Kyle where they find hope in education right now. Their answers were grounded in real examples rather than platitudes, which I appreciated.
Kyle talked about seeing communities starting to reimagine what education should look like for their specific context. Rather than accepting one-size-fits-all solutions, these communities are asking fundamental questions: What is the purpose of education here? What do our students need? How do we measure whether we’re actually serving them well?
“This is the first time we’re really doing a much better job of listening to communities and reimagining the role that they play in determining the outcomes for their students,” Kyle said. She gave the example of a community that realized its STEM program wasn’t accessible to all students and course-corrected to make those experiences available across the board.
Jenn found hope in the incredible leaders she knows who are doing this work with purpose-driven curiosity rather than just responding to compliance pressures. She mentioned specific schools (Edgecombe County in North Carolina, Kapo Community School in New Mexico) that are asking those fundamental purpose questions and building programs around genuine community needs.
“There are folks out there who are gonna do whatever it takes, and they’re doing it,” Jenn said. She was quick to add that we need to talk about supporting these leaders in ways that don’t burn them out, but the commitment and creativity exist.
What This Means for You
If you’re a school leader reading this and feeling isolated, overwhelmed, or stuck in short-term thinking, here’s what I want you to take away from this conversation:
First, you’re not alone in feeling this way. The challenges you’re facing—the isolation, the compliance pressures, the misalignment between your aspirations and your reality—these are systemic issues, not personal failings.
Second, there are alternatives to the traditional professional development model that doesn’t quite meet your needs. Communities of practice exist, and more are being built. Organizations like Building Leaders are creating spaces specifically designed for judgment-free learning, honest reflection, and sustained peer support.
Third, if you can’t access a formal community of practice right now, start building informal connections. Kyle’s advice was to “look beyond your immediate fishbowl.” Visit schools in other districts. Connect with leaders working in diverse contexts. Join online communities where school leaders share challenges and solutions. Diversify your perspective and your ideas.
Fourth, advocate within your own organization for the kind of professional development that actually supports leadership growth. Share what you’re learning about communities of practice. Make the case for sustained cohort experiences rather than one-off workshops. Help your superintendent or board understand that investing in leadership development pays dividends across the entire school community.
The Bottom Line
The work of school leadership has always been complex, but the challenges facing today’s leaders feel particularly acute. The isolation, the compliance pressures, the overwhelming pace of change—these aren’t going away anytime soon.
But neither is the dedication and creativity of school leaders who show up every day, determined to do right by their students and communities. And, as Jenn and Kyle demonstrated in our conversation, people are building infrastructure to support those leaders in sustainable, meaningful ways.
The question isn’t whether school leaders need communities of practice. The research and lived experience make it clear that they do. The question is how quickly we can build those communities and ensure that every school leader has access to the kind of sustained, judgment-free support that allows them to grow into the leaders their communities need.
As Kyle said, “If you are a school leader who is feeling isolated, please reach out. Feel free to look beyond your immediate fishbowl because there really are different ways of approaching the same challenges.”
And as Jenn reminded us, “You are not alone, and folks are there to support and work with you and to also cheerlead you and to help you see the incredible things that you’re doing every day that you’re probably not giving yourself enough credit for.”
That feels like the right note to end on: You’re not alone. The support exists. And your community—whatever form it takes—is worth finding.
Want to learn more about Building Leaders and their school visit opportunities? Visit their website at building-leaders.org to find details about upcoming experiences and how to connect with this community of practice.
