Leadership Monograph

The theories I use to inform how I lead.

Lead with Confidence

I often reflect on how I enter a room and how I’m perceived by others. As a young Black gay cis-man in independent schools, much of my early professional career was painted with self-doubt, fear, and feelings of inadequacy. I used to always play it safe, and try not to ruffle any feathers. But as I’ve grown, learned, sharpened my skills, explored, and built my network, I now enter a room with confidence. Not only did I gain confidence over time, but my definition of confidence evolved. In discussing metacognition, people often understand confidence as a way to “self-evaluate one’s knowledge” where one’s relatively high confidence was used as a “‘no need to learn further’ strategy.” (Son et al, 3). With this definition, as confidence increases, people typically feel less inclined to do more or learn more. In some ways, high confidence equates to having it all figured out. When speaking about self-confidence, however, I disagree with this definition.

In speaking with a former Head of School in the Boston area, his approach and understanding of confidence is more in line with my evolved definition of the word. He said, “confidence is being willing to make mistakes. Arrogance is not being willing to make mistakes.”

I’ve also learned of other frameworks for understanding confidence by watching a TEDTalk by Brittany Packnett. “We make it easier in this society for some people to gain confidence because they fit our preferred archetype of leadership. For some of us, confidence is a revolutionary choice, and it would be our greatest shame to see our best ideas go unrealized and our brightest dreams go unreached all because we lacked the engine of confidence.” (Packnett, 07:45). Brittany goes on to list the three things confidence requires: permission (births confidence), community (nurtures confidence), and curiosity (affirms confidence).

So as I reflect on my leadership style, I proudly created this leadership memoir: “Confidently Leading with Care and Intention.” I have given myself permission to make mistakes and not be afraid of taking risks. I’m diligently working toward broadening my community of people who are different from me, but support me. I know that there are so many ways in which students can learn and I’m excited to explore how learning needs evolve in order to prepare students for an everchanging world. But in my leadership journey, I know that I must also prioritize and take care of those around me in my ambitious pursuits.

“Without confidence, we get stuck. And when we get stuck, we can’t even get started.” (Packnett, 07:10).

Utilize the Power of Our Stories

My all-time favorite quote is from Audre Lorde, “If I didn’t define myself for myself, I would be crunched into other people’s perceptions of me and eaten alive.” This quote informs my interactions with students and guides my understanding of the environments in which everyone learns best: spaces where we can honor and harness the power of our own stories and identities.

Culturally responsive teaching requires educators to engage all students in their classrooms that address their behavioral, emotional, and cognitive needs. And while these may seem like independent tasks, they’re interdependent. “The more students are emotionally engaged in school, the more easily they can focus their attention and direct their behavior toward learning…. Teachers can promote engagement…by figuring out what it is that students need.” (Allensworth et al. 3, 5). Additionally, culturally responsive teaching asks teachers not to ignore their cultural positions in favor of the student’s but to “reflect on their cultural position and adapt their practice to leverage students’ cultural and linguistic resources as assets to build upon.” (Allensworth et al., 7). In essence, to do this work well, we have to deeply understand ourselves and those we’re tasked with educating.

So how do we do that?

How we speak to and about students and how we frame the value of our institutions has a significant impact on the student experience. In a keynote presentation, Dr. Jeff Duncan Andrade talked about the need for educators to “stop telling children that education can be the conduit for them to escape their circumstances.” When that language is used, we rob students of their humanity and paint a picture of their home life as something that must be escaped or inherently wrong. For children, their surroundings provide them with the very things they hold near and dear to their hearts. When we use language about “escaping poverty,” we do not allow students to tell their stories. Duncan-Andrade goes on to say that the purpose of education is “not to escape poverty, but to end poverty,” and that is the frame of reference we should take as educators that create environments where our students feel safe and seen.

Affinity spaces also provide spaces where identities and experiences are nurtured, valued, kept safe, and seen. Students gain convictions and support from others with similar identities. Outside of these spaces, students are challenged by the views and beliefs of others. They then use their newfound self-understanding to engage in meaningful conversations to better society, the classroom, the lives of those around them, and their learning.

Celebrate and Disrupt

Many independent schools do many things well. Like most organizations, however, there is always room for improvement. As new leaders enter new schools with their hopes, visions, and goals, it’s essential to acknowledge that schools have their own cultures and values. As a leader, I aim to celebrate our institutional achievements, but I will always focus on disrupting systems that need improvement.

In his presentation to a class of Klingenstein graduate students, Dwight Vidale, Assistant Head for Equity and Belonging at Collegiate School, talked about understanding the need to have both connectors and disruptors. Connectors typically focus on belonging, affirmation, empathy, and recognition. I was particularly intrigued by disruptors, which he categorizes as those who “understand that inequitable environments stifle us all.”

Part of disrupting environments is making sense of what needs to be disrupted. “Rather than immediately jumping to solutions, we must start with collecting data and scrutinizing it for trends and patterns that point to better solutions; rather than ignoring warning signs of failure, we should learn from others what those warning signs might be.” (Ancona et al., 34). In essence, you must first learn what’s happening and how it currently impacts all relevant stakeholders before making any changes. Successful sensemaking doesn’t happen in silos, either. It, in and of itself, is a way of disrupting people’s understanding of how to make change meaningful. The people tasked with disrupting must start from a mindset of learning and asking questions. As the questions are answered, and the findings are discussed, it’s essential to refer back to the original area of improvement and “update the map and move on from sensemaking to creating a new vision.” (Ancona et al., 38).

Vidale emphasizes that disruption is more than just addressing systems that impact an individual. Disruption “shifts our attention from the individual to the environment.” So as we walk through spaces, craft curricula, or publish our admission application, we have to ask ourselves what stories are being told, who is telling the story, and what voices are being ignored. When we get in the habit of asking questions, leading with understanding first and action second, we create a culture of disruptors and celebrators.

Using Restorative Practices and Care to Rebuild Community

As a leader, we’re constantly confronted with a problem and asked to come up with a solution. Most decisions become so routine that we don’t often think twice about the solution. But every now and then, we’re confronted with a problem that requires our undivided attention. In those moments, we reference our student handbook, research any institutional precedent, think about the potential lawyer fees if we mishandle the situation, meet with our team of administrators, gather information, etc. At some point a decision has to be made and all eyes are on you. And while the outcome may not be in favor of the student, a leader’s decision should always keep in mind the potential harm students may suffer and that students are able to, in most instances, be provided with an opportunity to restore any harm they may have caused to the community.

One of the worst things a school can do, outside of causing harm to students, is causing moral injury to its faculty and staff. Levinson defines moral injury as, “the trauma of perpetrating significant moral wrong against others despite one’s wholehearted desire and responsibility to do otherwise.” (Levinson, 1) As a school, we have to provide our educators with opportunities in which they feel like they are able to act justly.

One can create a just community through adopting restorative practices also. Restorative practices allows all members impacted by the harm to enter a space to discuss the harm and hopefully come to a resolution as to how that harm can be resolved. Through these circles, students see how widereaching their actions were and provides them an opportunity to reflect and acknowledge the damage they have caused the community.

Radical care is another framework educators have used to help avoid unintended harm to students (especially students of color). The framework has five tenets: “(a) adopting an antiracist, social just stance; (b) cultivating authentic relationships; (c) believing in students’ and teachers’ capacity for growth and excellence; (d) Strategically navigating the socio-political and policy climate; and (e) Embracing a spirit of radical hope.” (Rivera-McCutchen, 257). And while radical care is more converntionally presented in Black and Latinx environments, embracing this framework helps all educators. Critical care in leadership allows leaders to intentionally address racism that exists in our spaces.

Works Cited

Ancona, Deborah, et al. “The Overlooked Key to Leading Through Chaos.” MITSloan Management Review, vol. 61, no. 1, 2020, pp. 34–40.

Allensworth, Elaine, et al. “Supporting Social, Emotional, & Academic Development.” UChicago Consortium on School Research, Oct. 2018.

Duncan-Andrade, Dr. Jeff. ELC 2014 - Keynote. YouTube, uploaded by YaleSOMELC, 1 May 2014, https://www.youtube.com/watch?v=iUe85I4xNoM&t=851s.

Levinson, Meira. 2015. “Moral Injury and the Ethics of Educational Injustice.” Harvard Educational Review 85 (2) (June): 203–228. doi:10.17763/0017-8055.85.2.203.

Packnett, Brittany. “How to build your confidence and spark it in others” YouTube, uploaded by TED, 17 Jun. 2019 https://www.youtube.com/watch?v=b5ZESpOAolU,

Rivera-McCutchen, Rosa L. “‘We Don’t Got Time for Grumbling’: Toward an Ethic of Radical Care in Urban School Leadership.” Educational Administration Quarterly, vol. 57, no. 2, 2020, pp. 257–289., https://doi.org/10.1177/0013161x20925892.

Son et al. “Metacognition: How to Improve Students’ Reflections on Learning” Retrievalpractice.org, 2020