Becoming a school principal is not an obvious path to take out of business school. How does the role draw on the skills of an MBA?
Principals have enormous management and leadership responsibilities, especially in Chicago, where individual schools have more autonomy than in many other districts. In my first job as an elementary school principal, I had a budget of $4 million and 35 educators I was responsible for evaluating—as well as cafeteria staff, custodians, engineers, and all the other important people who make a building function. I had to think about how to create strong teams, elevate teacher voice, and bring people together around common goals.
Budgets in Chicago are based on the number of students enrolled in the school. In order to build a more sustainable budget, I worked to increase the student population by about 60% over my six years as principal. Marketing became an important part of the job. We reached out to the community, held open houses, and gave tours. I worked hard to understand what mattered most to families when making a decision about where to send their child to school and became really clear about the value proposition of the school. I also had to think about how to include parents in the school in intentional ways, address family concerns, and keep families enrolled through eighth grade. Unlike companies, schools don’t have a head of development or head of government relations. As the principal, you are doing those things. Starting as a school leader two years out of business school, I had much more responsibility than many of my peers in different fields.
You’ve spent your whole career in education, starting as a teacher out of college. Why did you choose this field?
I grew up in Washington, D.C., and had the privilege of going to an amazing independent school. At the same time, in high school, I worked at an after-school program serving kids in low-income housing near my home. I got to see the difference in the educational experience I was having compared to that of other kids growing up close by. I became interested in ways I could work to address the economic disparity, particularly in urban areas, that I witnessed growing up in D.C. And as a 21-year-old, I felt like I could graduate college and immediately have an impact as a classroom teacher.
I’ll always remember my first day teaching first grade. I spent such a long time planning lessons for the day—and within an hour, I had one student under a chair mooing like a cow and another who had peed on their seat. I wasn’t prepared to deal with either of those things, but that was where I started to build the leadership skills that have sustained me throughout my career. My students taught me the importance of preparation, but also how to read a room and be ready to pivot. They also showed me the importance of bringing joy into my work: They did better when I was having fun and making the learning fun, and it turns out that’s true with adults as well.
In my early jobs, I noticed that many principals got to that role by being a good classroom teacher, but those jobs require very different skill sets. I felt that the ability to bring out the collective knowledge of teachers working with students every day was missing.
What did you learn about school leadership from your early days in the classroom?
As a new teacher, I found it was really hard to have a say in what was happening at the school. So when I finished Teach for America and got the chance to be a founding teacher at a charter school in D.C., I was excited to think through how we could make school a better place for kids.
We spent a lot of time on big questions, like what math curriculum we were going to use. I also learned that little decisions—like recess activities and supervision—can be equally important. Our building was under construction, which meant that outdoor space was unavailable, and we didn’t have a great plan for who would watch kids during recess. But recess has a huge impact on what happens for the rest of the day. If kids are upset after recess, they’re not going to learn math, no matter what curriculum you’re using.
Did you know you wanted to become a principal at that point?
In my early jobs, I noticed that many principals got to that role by being a good classroom teacher, but those jobs require very different skill sets. I felt that the ability to bring out the collective knowledge of teachers working with students every day was missing. That’s what drove me to SOM. I was committed to urban education, and I felt there was an opportunity to bring insights from other sectors into that space to build stronger leadership.
I did my summer internship at Chicago Public Schools (CPS), where Arne Duncan, the CEO at the time, was bringing in a lot of people with business backgrounds. After graduating, I joined a venture philanthropy firm that raised money from Chicago’s business community and invested it in new public schools. What I learned from that experience was that there was no shortage of ideas about what good schools could look like; there was a shortage of really strong leaders. Visiting schools made it clear to me that the most important factor in a school’s success is the caliber of the leader. You can have the best ideas and strong financial backing, but without a strong leader, you can’t create positive outcomes for students. I realized that no matter what I wanted to do in education, I needed to understand the lens of a school leader. I didn’t know it was going to be my favorite job in the world.
As a principal, how did you ensure teachers had a say in the school, the way you wanted in your early jobs?
Working with teachers was one of the many things I loved about the role of principal. When you’re in the same space every single day, you can really build the relationships and trust to create effective teams.
One thing that’s very personal for teachers is curriculum adoption. When we were in the early stages of choosing a new math curriculum, I knew that it wasn’t going to be effective to make a top-down decision. As with many other things, the best way to convince teachers to do things is to have them hear from other teachers. I identified the teachers who were most interested in trying out something new and worked closely with them to identify and pilot the Eureka math curriculum. We spent a lot of time learning from what they were doing, and they were able to share with the teachers down the hall, “This has been my experience, and this is why we should move forward with this.” That process of building buy-in—going slow in order to go fast—was so critical to the long-term success of the initiative.
As a principal supervisor, it was a little more difficult—how do I bring principals together across 25 elementary schools? How do I elevate their voices? Again, my strategy was to build them up as experts for each other so they’re learning from each other more than they’re learning from me. The most effective way to help a teacher who is struggling with something is to connect them with another teacher who is doing that thing really well. I don’t need to be an expert in everything; I just need to be an expert in the strengths of the team around me.
As you pointed out, principals have to work with a lot of stakeholders. In Chicago, every public school has a Local School Council (LSC), an elected governing body that includes parents, students, and other community members. How did you approach making important decisions with your LSC?
The LSC is responsible for hiring and evaluating the principal, as well as approving the budget and school improvement plan—all the largest drivers of success for a school. It’s very unique to Chicago. But principals didn’t get any training on how to work with an LSC. The work of managing a LSC can be challenging.
In 2013, CPS was in a dire financial situation, and we knew our school-level budget was going to be cut. I wanted to make sure the LSC, made up of many people who had never worked in education, was armed with the right information to be able to make really difficult decisions about cutting positions. I started doing classroom visits with the LSC. We created a rubric so they could capture their observations, and tied each visit to organizational goals so they could see how we were or weren’t meeting them with the resources we had.
When budgets tighten, one position that often gets cut is an interventionist—someone who provides extra academic or behavioral help to students who need it. Parents of students who aren’t struggling may never interact with an interventionist or understand why this role is so critical to the success of the school. When we named as a goal focusing on students who were furthest from opportunity and making sure they get to grade level, that provided a powerful lens for LSC members when they went into classrooms. People got to really understand what an interventionist does, and those visits were the key to us preserving the position going forward. We ended up making huge gains toward grade-level proficiency, which we wouldn’t have been able to do without that resource.
You eventually became a principal supervisor overseeing the leaders of 25 Chicago elementary schools. How did the leadership challenge evolve as you moved up the ladder?
The biggest thing is that you move further from the classroom. That’s a challenge for me because I love being with students and teachers in the classroom, but also because the work becomes less effective if it is disconnected from the daily experiences and needs of students. When you’re not in those spaces daily, it’s harder to identify the opportunities and get the immediate feedback from students and teachers on the strategy. You’re working across many more departments and priorities, with many more stakeholders. You need to be really thoughtful about instituting systems and structures to get the feedback to prioritize and plan for change management across the organization and 600 schools with intention. It’s even more important to set a clear vision and purpose for the work, to help people row in the same direction and come together to be more impactful.
The COVID pandemic struck a few years into your tenure in that role. What does leadership look like for a principal supervisor at a moment like that?
Schools felt COVID so acutely, because suddenly we had to become much more than schools. We were distributing meals and technology; we were helping some families get wireless connectivity for the first time ever. Staff members were being asked to do this while going through their own challenges.
As a leader, I tried to be aware of that and strategic about supporting people in showing up every day for our students and families, while also knowing that they’re struggling.
When we were gearing up to welcome kids back in January 2022, there were so many unknowns. Which teachers and kids would show up? What are the health precautions and would people follow them? What if a kid won’t wear a mask? I spent that first week after students returned teaching a preschool class that didn’t have a teacher. It wasn’t my expertise at all, but it had a big impact on the leaders I supervised. They knew I was willing to do the work with them hand in hand, especially during the most difficult times. It also helped me be a better leader, because I was reminded of my own experience—of the large and small challenges in a building during this time of transition.
You finished your tenure at CPS as chief of teaching and learning for the entire district. What does that role entail?
The chief of teaching and learning is responsible for the planning of academics from kindergarten through 12th grade. That includes 18 departments and 270 employees supporting all content areas—reading, literacy, math, social science, science, arts—and programmatic teams for gifted, STEM, and Montessori offerings. Chicago is one of the few districts in the country that creates its own curricula, so I oversaw the curriculum department, as well as a professional learning team that supports about 23,000 teachers and creates pipelines for teacher leaders.
There’s a lot of additional complexity that comes with overseeing different departments that work in a fairly siloed manner. During COVID, the district saw a huge influx of federal ESSER funding to help respond to the pandemic. As soon as I started in the position, I had to start thinking about the budget crisis that would come when that funding ended. I started building a more sustainable infrastructure by centralizing resources, finding efficiencies, and renegotiating contracts. This helped prepare the department, so we didn’t have to face such a large fiscal cliff all at once. Instead, we had a careful plan over two and a half years to decrease our spend and prepare for the end of federal funds.
We also had to deal with challenges that none of us had ever considered before. As a sanctuary city, Chicago saw an influx of newcomers starting in 2023. Around 10,000 English learners enrolled that school year. School leaders were welcoming students who didn’t speak English, many of whom had been out of school for a year or more. Many schools did not have bilingual staff members or resources for students. The strategy and leadership courses I took at SOM helped me during unprecedented moments like these. As a district leader in this situation, I focused on the things I could control, like listening to leaders and staff and trying to provide clear communication. I advocated for decisions that were in the best interest of students and provided resources as strategically as possible across the district. As a large urban district, we also worked across different city agencies and community organizations to leverage resources and supports on behalf of our new students.
What are you most proud of from your time as chief of teaching and learning?
One thing I was really proud of was our work to elevate student voice in decision-making across the district. Our office instituted a district-wide student survey on classroom conditions that every student from 5th through 12th grade completed twice a year. We supported teachers in interpreting that data and having authentic follow-up conversations with students about their experiences and needs so that teachers could work to improve the daily classroom experiences based on direct feedback from students.
We also set up student roundtables that brought kids from different schools to advise the central office. Students gave feedback on the academic calendar, proposed changes to the high school promotion policy, and helped create the first-ever middle school strategy for Chicago Public Schools. After talking to students across the city, we learned middle-school students wanted more opportunities to mentor younger students, take on leadership roles in the building, and have middle-school electives, sports, and after-school clubs.
When there was a lot of federal agent activity, especially near schools, students expressed fear and concern over the safety of students and families in their communities. We wanted to give them the tools to support themselves, their peers, and their families. So the Office of Student Voice led a series of Know Your Rights campaigns that trained students to lead sessions in their school communities.
Elevating student voice has been a throughline for me since I was a student myself. I’ve come to believe it’s one of the clearest measures of whether a school, or a system as large as CPS, is working. It’s important both that kids learn and that they have a real say in their own education. That’s the same conviction that motivated me to move from the classroom into leadership roles. Education is one of the most powerful levers we have for expanding who gets real choices in life, and I’ve tried to spend my career making sure more students get to be part of deciding what those choices look like.
“The Yale School of Management is the graduate business school of Yale University, a private research university in New Haven, Connecticut.”
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