By Ben Berger and Shuki Taylor
This article was originally published in The Chronicle of Philanthropy. See the published article here.
Professional development has long followed a predictable formula: Junior staff members learn from senior team leaders, managers enroll in structured programs, and organizations invest in top-down training efforts. These methods have their merits, but they often overlook one of the most powerful and underused tools for leadership growth — peer learning.
Job shadowing is typically seen as a tool for those early in their careers, an opportunity for emerging professionals to observe and absorb knowledge from those above them. But what happens when two senior leaders step into each other’s worlds to learn, not as mentors and mentees but as peers?
As leaders committed to professional development, we wanted to push beyond traditional models and try something different: peer shadowing on the job for high-level executives. Unlike mentorship programs or executive training, this wasn’t about following a curriculum or receiving instruction. There was no clear “teacher” or “student.” Instead, it was an immersive experience requiring international travel and a week outside of the office — no small commitment. But it allowed us to learn from each other with openness, curiosity, and a willingness to rethink how we lead.
Rooted in the Jewish tradition of havruta, a centuries-old model of paired learning that values both challenge and support, our experience revealed some critical insights that challenge many of the dominant assumptions about how professionals at the highest levels should grow.
Here are five key things we learned.
The goal of partnership is mutual growth
Collaboration in leadership is often framed around achieving shared goals or outcomes, such as launching a joint initiative, securing funding, or driving a project forward. But true partnership isn’t only about what gets accomplished.
It’s about how both parties grow in the process.
When we embarked on this peer-shadowing experience, we weren’t trying to build something tangible together. The value came from something deeper: seeing our own leadership through someone else’s eyes. Watching how another senior leader navigates challenges, engages with a team, and makes decisions forced us to reflect on our own habits and instincts in a way that traditional leadership training rarely does.
This idea is backed by studies on peer coaching in the military that show how structured peer relationships help leaders become more self-aware and open to new ways of thinking. For example, one of us left this experience rethinking how to best structure daily priorities after observing the other’s approach to calendars and task management. The lesson here wasn’t about overhauling a system but adopting subtle changes that helped us feel more proactive and less reactive in managing time and responsibilities.
We also explored real-time examples of how AI can be used to streamline tasks, brainstorm, and solve problems, which opened new possibilities that we’ve both integrated into our daily workflows with excitement and impact.
Even more unexpectedly, the experience shaped how we think about our lives outside the office. We both travel frequently for work, and a single conversation about how to explain that to young children — shifting the focus from absence to purpose — left a lasting impression. This simple reframing prompted both of us to be more intentional in how we communicate with our families the meaning behind our work and why it sometimes takes us away from home.
Professional development should be actively shaped
Leadership training often treats development as a passive process achieved by attending workshops, taking courses, or receiving mentorship. While these approaches have value, they reinforce the idea that learning is something to be absorbed rather than created.
When we set out on our peer-shadowing experience, we weren’t looking to be taught — we were looking to learn with each other. From the start, we aimed to create a shared learning opportunity in which both of our perspectives carried equal weight, mirroring the havruta model.
Instead of passively receiving insights, we actively shaped the experience in real time, making the learning more relevant, immediate, and deeply personal. One of the most meaningful parts of that process was taking time each evening to debrief. A simple check-in — “What are you noticing?” — led to reflections that revealed far more than either of us could have seen alone. Observations about how meetings unfolded, how listening happened (or didn’t), and how ideas were either affirmed or questioned became powerful points of reflection. These conversations helped surface patterns we weren’t always aware of and offered a rare chance to see ourselves, including our habits, instincts, and blind spots, through someone else’s eyes.
This kind of dynamic two-way learning is not only more engaging but more effective. Studies show that when people act as both teachers and learners, they gain deeper understanding and retain knowledge longer.
Outside perspectives fuel leadership growth
Leaders often work in environments in which they are expected to have answers — not questions — and where their habits, decision making, and leadership styles go largely unchallenged. Self-reflection is difficult in isolation, yet leadership requires self-awareness. Without external perspectives, blind spots remain hidden and opportunities for growth can be missed.
Peer shadowing on the job disrupts this cycle by providing a way to see one’s work through the eyes of another leader. When we committed to this experience, we knew we’d be stepping into unfamiliar territory, but we didn’t anticipate just how much it would challenge our own self-perceptions. Subtle but meaningful insights emerged, like how to better structure our time and tackle difficult conversations, such as explaining work-life balance to our children. These moments sparked deeper self-examination and led to more intentional leadership choices. This kind of outside perspective is rare for senior leaders, but it’s invaluable.
Authentic partnerships require trust and honest dialogue
Professional growth happens when leaders feel safe enough to be honest yet challenged enough to evolve, more than in carefully controlled environments. Peer learning works only when both parties commit to authenticity, setting aside egos and competition in favor of real, unfiltered exchange. This requires a foundation of trust and a willingness to be seen, not only as accomplished professionals but as leaders still refining their craft.
Our peer-shadowing experience wasn’t built on formal vetting or strategic alignment. It started with intuition, an instinct that there was something to learn from one another. Because of that, we were able to have vulnerable conversations about the challenges we face, from managing team dynamics to making high-stakes decisions. Over the course of the week, we explored several early-stage concepts each of us was developing. Discussing them revealed things we had overlooked, surfaced new connections, and, at least in one case, unlocked a shift in perspective that has shaped every discussion since. The ability to let go of perfection and invite real feedback made this experience far more valuable than any leadership seminar could be.
Generosity fosters deeper collaboration and shared success
Leadership can often feel isolating, especially in industries where competition — whether for funding, talent, or influence — is ever-present. Too often, leaders keep insights and strategies to themselves, fearing that openness could weaken their position. But true leadership involves sharing knowledge in ways that strengthen the entire field.
Our peer-shadowing experience challenged the instinct to guard our work. Rather than keeping internal strategies private, we openly shared our approaches to leadership, fundraising, decision making, and problem solving in our roles. This helped deepen our collective understanding of what it means to lead. And though it wasn’t our original intention, that openness led to something unexpected: We began co-creating some new initiatives together. It’s the kind of collaboration that simply wouldn’t have happened in a more guarded or competitive setting.
This mindset of generosity didn’t dilute our influence; it strengthened it. By offering transparency, we built trust, gained new outlooks, and walked away with fresh programs and strategies that benefited both of our organizations.
Leadership is a shared journey
Peer shadowing helped us remember that lasting growth happens when we step beyond our own expertise and invite the fresh perspectives of those who walk the leadership path alongside us. When senior leaders embrace learning as a dynamic, reciprocal experience rather than a fixed destination, they don’t just become better at what they do — they cultivate a professional culture of curiosity, generosity, and continuous evolution.