When I first started thinking about the strategy of schools, I was reading A.G. Lafley’s Playing to Win. I hadn’t really thought of a school district as needing to win per se. I thought schools were on a mission for equity and touted that “everyone is a winner and capable of excellence” kind of stuff. However, in Kentucky at least, I found that the incentives for school funding can drive competitive behaviors between districts. Income from the number of students in attendance is a significant revenue stream. In the game of education, this is a big deal especially if you are in a town with a stagnant or declining population. And while I give some credence to the saying “90% of success is just showing up,” in this case it seemed like a marginal way to qualify winning in 21st century education. I began to wonder where else we might stake our claim to winning. With a human centered design lens, I needed to better understand the end-user of our services. To answer my question about what it meant to win, I needed honest conversations with parents and students. Only this would uncover their perspectives. I also wanted to know what value we were bringing to families who opted to send their children to our school from outside our attendance area. Knowing where we were winning as a district, and more importantly, for our students became the foundation to our strategy. My initial research took two paths. First, I made calls to families that opted into our district. I was looking for their entry point and motivation. I needed to know what made their child’s experience with us so valuable that they would jump through all the extra hoops. These conversations also gave me a sense of the culture that was attractive to these particular parents. Next, I developed a survey for parents, staff, and students. This process took a couple of months to execute but was absolutely critical in helping design our winning aspiration. Our focus was able to switch from the shallow, attendance-driven model to a deep dive into the needs, hopes, and aspirations of our parents, students, and community. The insight gleaned from conversations before, during, and after the survey helped shape our understanding of what the community needed to grow and what the students needed to stay engaged. Surveying the staff was helpful in two ways. It communicated the strategy building process as well as provided time for co-designing. It also allowed us to have staff look at those they were serving from the unique lens of their neighborhood/school culture. We presented the feedback from the surveys from both an overall district perspective and then from their school. This gave staff a glimpse of the big picture and their role in developing that picture. We shared community economics and demographics and conducted small group SWOT’s looking at strengths, weaknesses, opportunities, and threats. These SWOT analyses allowed time for listening to, engaging with, and synthesis of all the data. It got everyone aligned in their thinking and informed about the intentions of the district to figure out how to play the game so that ultimately our students would be the winners.