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The Power of Reflective Moments

When I started working with Felicia Owo-Grant and Ayinde Spradley in fall 2021, they wanted to go big. From our first coaching conversations as part of CityBridge’s Design Fellowship program, they made clear that their ultimate aim was to build an in-house professional learning institute to support educators across the entire 16-school network of Friendship Public Charter Schools. 

The challenge they framed early on was that—for all the strengths of the professional development offered to leaders of Friendship schools—principals and academy directors (the Friendship term for assistant principals) did not have a way to get continuous leadership development and professional learning. 

My desire in coaching teams is to help them make big, transformational changes, so it feels counterintuitive, maybe even wrong, for me to look at seasoned leaders like Owo-Grant and Spradley and say, “I want you to start small.” But in Design Fellowship, starting small is one of many strategies to help teams learn about and reshape complex challenges in public education. 

By pausing to reflect on what they knew about how to meet the needs of leaders at their schools, a pathway came into focus for Owo-Grant and Spradley. This pathway still leads to the institute they imagine—the “Friendship Learning Lab” for leadership and professional development. But the forks, curves, and crossroads along that winding track are reflective moments that generated significant learning for this team. “I used to think that we would not be able to identify an area small enough to pilot,” Owo-Grant wrote at the end of the second Design Fellowship workshop in October. “Now I see the benefit in narrowing the focus and how it can yield better understanding for even initiatives with large, lofty goals.”

My learning, as a designer of the Fellowship program itself, is that reflective moments generate the insights designers need to better understand the challenge, the experience of stakeholders in their community, and the next best step on their pathway to a potential solution.

CALL OUT: Our team at CityBridge has refined a set of tools, workshop sessions, and coaching strategies over the course of multiple years to support educators and teams in redesigning public education. As part of our commitment to sharing that work more widely, we are presenting a first version of our “Incubator Toolkit,” which is designed to help teams go from a first hunch about an education challenge to those critical reflective moments that come after implementation of a pilot test.


With their long-term vision for a Friendship Learning Lab in mind, Owo-Grant and Spradley started where we encourage all Design Fellowship teams to begin: by talking with those closest to the problem. While they had hunches and anecdotal data about the gaps in professional learning for Friendship leaders, particularly academy directors, their empathy interviews and survey research crystalized how those leaders experienced the challenge.

As they sifted through their interview and survey data, Owo-Grant and Spradley had an important reflective moment. For all the technical and adaptive skills these leaders wanted to learn, they also wanted to be able to show up as their full, authentic, and vulnerable selves in leadership development environments. For a group of rising and established school leaders, nearly all of whom are Black, it was the need for a safe space to feel like they could take risks and talk about their own biases—where it was okay to not be an expert and to admit to missteps—that was important. By using empathy research tools and pausing to reflect, Owo-Grant and Spradley crystalized an important insight that shaped the piloting work that followed.

CALL OUT: The empathy interview tools included in our Toolkit foreground two equityXdesign principles: designing at the margins, by connecting with those who have been excluded from a community; and starting with yourself to unpack the biases, power, and perspectives you bring to any interview.


In their theory of change, Owo-Grant and Spradley identified a “home-grown learning institute” as their long-term goal. The theory of change also included a list of preconditions that would need to be true in order to enable the success of what would eventually become the “Friendship Learning Lab” and another layer of “inputs” necessary to realize those conditions.

I got to engage in several heady and jargon-filled conversations with Owo-Grant and Spradley as they drafted their theory of change. But for all the theoretical and technical detail we nerded out on, the crucial reflective moment was when they realized their key question: did the training they offer create brave spaces for leaders of color? They needed to pilot a professional learning environment “where leaders can bring their authentic selves and feel vulnerable to not be the expert.”

CALL OUT: A theory of change, or TOC for short, is a process and a product for strategic planning and thinking. The version of TOCs that we offer in the Toolkit is a simple graphic organizer for teams to write down the causal links between the actions they take and the outcomes they’re aiming for.


It was time to build and run a first pilot. Starting small meant planning a single morning of professional learning for a group of academy directors. This right-sized pilot would test several important questions, including: Was it feasible for Owo-Grant and Spradley to collaborate with their colleague, the deputy chief academic officer in the Friendship central office, on the design of the session? And to what extent were the participants able to focus on self-reflection and to interrogate personal biases in a brave space?

These types of questions can seem pint-sized next to the goal of developing an institute aimed at supporting hundreds of educators. But small learning questions embedded in a pilot like this are connected to the larger challenge. Spaces of psychological safety and belonging for Black and Brown educators to get personal as they grow as leaders are not just nice to have—they are necessary. Further, they hypothesized that de-siloing leadership development work required that they develop these learning opportunities in tight collaboration with Friendship colleagues.

The results of the pilot affirmed their hypotheses. During the session, academy directors readily leaned into the novel opportunity to talk about personal bias and how those intersected with real challenges facing them at their schools.

When Owo-Grant and Spradley reflected on the results of this first test afterward, they developed another insight: not only was the content of professional learning sessions like this important, but so was the collaborative process of creating the workshop itself.

CALL OUT: Pilots are experiments, big and small, that are systematically designed to answer a set of questions. Through pilots, which we see as low-risk opportunities to learn, innovators are able to “try-on” a solution aimed at addressing inequities within our education system. Our Pilot Plan template provides a highly specific framework for guiding designers through a pilot.


The conclusion of that first pilot was another key moment for reflection. The final section of the pilot plan document asks designers: What did you want to learn? What is your emerging answer? And what are the implications and next steps? At this point, those simple questions appeared before Owo-Grant and Spradley after the bend in a lengthy path. 

One of their learning questions for the pilot was this: To what extent was it feasible for them to collaborate effectively with their colleague, the deputy chief academic officer? The answer that emerged was that it was more than just feasible; it was hugely beneficial to the creation of a powerful professional learning session.

That insight around the need for new ways of de-siloing work across the Friendship organization guided them through the crossroads. They had affirmed the importance of creating spaces for self-reflection on biases in leadership. Now they saw the opportunity to develop ways of collaborating with colleagues to meet the various other learning needs school leaders said they had, like budgeting, instructional planning, and management.

The next pilot Owo-Grant and Spradley are working on involves the creation of a scope and sequence for professional learning for any leader at Friendship Public Charter Schools. But what they are testing next is the collaborative process of creating that document and the related PD opportunities that will form the foundation of the Friendship Learning Lab. 

At this point, I don’t have a conclusion to Owo-Grant and Spradley’s story, since they are still on the journey. But getting to the end doesn’t feel like the point. Rather, it’s about getting to moments of reflection. We challenge teams in our Incubator programs, and in Design Fellowship in particular, to do a lot: empathy research, theories of change, multiple pilots. There is great value in the process of learning and leveraging each of those tools. But the most crystalized insights from the process come at the pause points at the end of each cycle work with these tools. The insights that emerge swing their compass arrow in the direction of a new path. And off they go in pursuit of new questions, new solutions, new learning.

This post is a part of The Rewind, our month-long highlight reel sharing what we’ve learned and spotlighting the leaders and ideas we’ve supported from 2020-2022.

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