When I was director of the teaching and learning center at an all-girls school, I often encouraged students to try new test-taking strategies. For example, if a physics test previously resulted in a student getting a disappointing grade, I’d challenge them to experiment with a new study technique. I’d suggest that they make a practice test similar to the original and complete it under the same time constraints as the actual exam. Another approach was to solve the problems in order of difficulty, tackling the tougher ones first and saving the easier problems until the end to maximize their time.
Most of the time, my students were apprehensive about trying these strategies. They feared that if the new approach didn’t yield better results on the following test, they’d receive another poor grade that could put them into a hole they wouldn’t be able to get out of. I would then coach them through this fear, reminding them that they have the space to make a mistake and still make an incredible comeback.
As educators, we often emphasize to students the importance of practice, trial and error, and using mistakes as learning opportunities. We encourage them to “use their erasers” and correct mistakes, and we celebrate their progress. However, in leadership, this kind of grace is often absent. Like learning, leadership—whether as a teacher leader, team leader, department chair, senior administrator, or head of school—requires time, patience, and grace.
Yet, how often do we give teachers and school leaders the opportunity to get it right, knowing that, like students, everyone learns at their own pace? As school leaders, it’s crucial to create spaces where team members can take risks, make mistakes, and still feel valued. This culture is especially important for leaders who may already feel scrutinized, such as women and leaders of color, and fostering a space that normalizes growth through mistakes is essential to their retention and success.
As we consider the sustainability of our schools and the retention of school leaders, we must ask ourselves: How can we support leaders learning and growth and offer grace in moments where they may not get it “just right” the first time—or even the second or third time?
What Does This Look Like
In many organizations, including independent schools, there are multiple stakeholders and various priorities that can differ among teams, departments, and divisions. As a result, it often takes time for new leaders to understand these priorities and develop the skills necessary to navigate communication, strategy development, and buy-in with each constituency group. People often need the chance to practice these skills, and with that practice, missteps are inevitable. Support from colleagues is essential.
Last year, I started at a new school in a leadership role I had not entered before, and that first year was filled with exciting growth and learning—and support. I was fortunate to be in an environment where the sentiment was, “We’ve got you.” I felt confident that I could take the time to learn my role and, if I made a mistake, my colleagues would have my back. I realize not every school, community, or team offers this level of support.
School communities must understand that making mistakes is not only acceptable, but also an important part of leaders, especially new leaders, building confidence, gaining expertise, and growing personally and professionally. Early on in a new role, receiving negative reactions from supervisors or colleagues can undermine the sense of belonging a person might feel in the community. This can lead them to feel a decreased sense of confidence and hesitancy to take initiative, execute ideas, or invite collaboration.
Building a “we’ve got you” environment involves creating regular opportunities to connect with those who are new to their leadership roles. Such connections allow for a deeper understanding of each person’s unique learning pace.
Supporting and Modeling Growth
Throughout my career, I’ve seen several successful growth strategies in action that made the difference for new leaders, whether they’re new to leadership or their position.
One effective approach is highlighting team members’ contributions during meetings. This practice can boost morale and strengthen the sense of community within the school. This might include shoutouts for colleagues making strides in their work or having department/division leaders share updates on their projects. This approach celebrates small wins, ensures all voices are heard, and makes individual efforts more visible. By identifying the areas of their roles and responsibilities where they are already demonstrating growth, we can celebrate progress over perfection.
For instance, sharing feedback like, “It was great to see your outline and begin implementing the initial stages of that project…” validates their efforts and highlights their contributions. Recognizing and affirming each step taken helps to build confidence and encourages continued development, fostering a supportive environment for growth.
Regular check-ins—ranging from 15–30 minutes weekly—between leaders and their supervisors create a proactive feedback loop. These brief, ongoing touchpoints provide steady coaching and support, laying a foundation for growth over time instead of waiting to address concerns reactively.
Focusing on solutions when mistakes happen, rather than assigning blame, can foster trust and collaboration. For example, if division heads note a lack of alignment in programming, a director might say, “While we couldn’t coordinate formats this year, let’s consider sharing our draft plans next year to balance distinct divisional needs while presenting a complementary approach for families.”
Using helpful frameworks like “start, stop, continue” encourages team members to reflect on practices and discuss possible adjustments collaboratively. It invites colleagues to ask: What should we start or try next time? What should we stop? What should we continue? This practice fosters a collaborative approach to growth.
Encouraging direct conversations when questions arise fosters an environment of trust and mutual respect. When a team member faces repeated challenges, their colleagues can take time to understand the underlying issues. For example, if someone new is struggling with deadlines, it’s helpful to ask, “What barriers led to needing more time on this project?” This kind of dialogue offers valuable context for future planning.
For new leaders, finding supportive networks outside their school can provide valuable affirmation and a space for vulnerability. This is especially important as they may not feel comfortable sharing challenges with immediate colleagues or supervisors. Women school leaders, for instance, may benefit from joining female-centered collectives or aspiring heads or heads networks with a clear focus on the unique challenges of women.
Faculty and staff can support new administrators by giving them time to learn before delving into detailed queries. For example, rather than immediately asking a new head about their vision, allow time for listening sessions to grasp the community’s existing priorities first.
Leaders themselves need to practice positive self-talk, particularly when mistakes happen. Reassuring themselves with phrases like, “I was hired because of the value I bring to this community,” or “I am not my mistakes; I am the lessons I learn and the strength I gain from them,” can bolster resilience and maintain a growth-focused mindset.
Maya Angelou said, “I can be changed by what happens to me, but I refuse to be reduced by it.” Embracing mistakes as a leader—acknowledging them with humility and using them as opportunities for growth—demonstrates self-awareness and a commitment to continuous improvement. When leaders openly own their mistakes, they foster mutual respect and trust within their teams.
In striving to create this environment, we work toward a deeper sense of belonging where colleagues feel comfortable coming to leaders with complex situations they need help navigating. Just like students, leaders need time, reflection, and grace to grow and improve. Let’s make it a priority to extend this grace to those we lead—and to ourselves.