Day in the Life: Q&A with Program Chief of Staff Selina Eadie Dhillon

How would you describe your role on the Senior Leadership team? 

I serve as EA's Program Chief of Staff and work closely with our Chief Program Officer (CPO), Jami O'Toole, and support the Vice Presidents leading our Engineering, Data Science, Implementation and Services, Product, and Business Strategy divisions. 

A big part of my role is helping EA deliver on its long-term priorities. At some point, strategy always runs into calendars, budgets, staffing capacity, dependencies across teams, and the occasional “wait, who owns this?” question. My role is to help bring enough structure and clarity that leaders can make decisions and the work can keep moving.

One of my favorite aspects of being Chief of Staff is the vantage point it provides. I get to see across many different streams of work happening throughout the organization and understand how they relate to one another. Because most teams are understandably focused on the priorities directly in front of them, part of my role is helping leaders recognize dependencies, opportunities, and challenges that cut across teams and determine the best path forward.

What interested you in working at EA? 

What drew me to EA was the opportunity to help solve challenges that many education organizations share. Before graduate school, I worked for school-based nonprofits through AmeriCorps, and when I started my Master's in Public Affairs at the University of Wisconsin-Madison, I thought I was headed toward a career in federal education policy. Over time, I realized I was less interested in working within a single district or state agency and more interested in tackling the kinds of challenges that cut across organizations and systems. When I discovered EA, it felt like a direct line to the work I cared most about: helping education organizations use data and problem-solving to improve student outcomes at scale. 

One of the reasons I've stayed at EA for more than a decade is the opportunity to grow alongside the organization. As EA has expanded its work, I've had the chance to wear many different hats, from data strategist to program operations leader to Chief of Staff. I've joked that I've had several different careers without ever changing employers. 

But the biggest reason I've stayed is the people. I work with some of the smartest and most mission-driven people I've met. After more than a decade, the relationships I've built here are just as important to me as the work itself. 

We know that every day is different, but what would a typical day at EA look like for you? 

A typical day at EA starts very early my time. As one of our West Coast employees supporting a largely Central Time organization, I'm usually up before the sun, making a bougie latte, walking my dog Tecolote, and trying to game plan for the day ahead before it's time to wake up my two- and four-year-old and welcome the morning chaos. 

I'm also probably more enthusiastic about productivity systems than the average person), so I often use that quiet morning time to update Slack agendas for 1:1s, schedule reminders for things I don't trust myself to remember and check my automated to-do list to see what's coming up. 

Once the kids are off to school, the day can really be a mix. I might be in a 1:1 meeting with our CPO or our divisional leads to discuss priorities, facilitating a larger stakeholder meeting like our Quarterly Program Business Review, or diving into a specific initiative. Some days I'm focused on big-picture strategy and organizational planning. Other days I'm trying to untangle a surprisingly complicated operational question that nobody realized was connected to three other things. On a really good day, I've also carved out an hour of uninterrupted focus time. 

And, of course, no day is complete without checking in on some of our more important Slack channels, like #ea_snack_reviews and #bingo. Whether I'm weighing in on a new LaCroix flavor or lamenting that the one bingo square I needed wasn't called, it's one of the many ways our remote culture stays fun and connected. 

What skills do you possess that you find helpful in your role? 

One thing that's been helpful in my role is knowing the difference between needing an answer and needing to ask a better question. I work across a wide range of topics and functions, so I've learned that asking a good question is often more valuable than having a quick answer, and that jumping to solutions too fast can mean solving the wrong problem entirely. 

I also spend a lot of time paying attention to how people are framing problems. Sometimes people are much closer to an agreement than they realize, even if they're using different languages to describe the issue. Making that visible helps teams spend less time debating the 95% they already agree on and more time tackling the handful of issues that are  holding things up. This is a skill that's taken practice to develop, especially when the problems don't come with clear owners. 

What is your favorite project that you’ve worked on at EA? 

One of my favorite recent projects is an internal one. Over the past six months, I've worked closely with our Business Operations team and Chief Talent Officer, Gabe Rosen, to improve the quarterly reporting tools our divisional leaders use to review progress and make plans. 

What I've enjoyed most is thinking through what information is most useful for those conversations. How do leaders know whether things are on track, where risks exist, and what deserves attention? I find those questions fascinating. 

I also love this work because it allows us to benefit from the same expertise we provide to our partners. EA has incredible talent in data systems, analytics, and dashboard design, and it's been rewarding to see those capabilities applied to improve how we operate as an organization. 

If you had to choose a different team to work on at EA, which team would you pick and why? 

If I had to choose a different team, I'd probably pick Business Strategy. The truth is that we have so much talent across the organization that I could make a case for almost any team. 

What appeals to me about Business Strategy is that the team must understand both the work we're doing today and the possibilities for where that work could go next. They're part of conversations about the future of education data, interoperability, workforce development, AI in K-12, and other emerging opportunities, while also staying grounded in the realities our partners face every day. I think it would be fulfilling to explore how emerging needs intersect with the skills, products, and services we have at EA and where we have the opportunity to create meaningful impact. 

What changes do you anticipate in your field in the next year? 

I think we'll continue to see growing expectations around interoperability, broader implementation of standards like Ed-Fi, real-time access to information, and the ability to connect data across systems in ways that help organizations make better decisions. Many education organizations have access to more information than ever before, but the challenge is turning that information into something actionable and useful. 

I also expect conversations about AI to continue accelerating. One of the most exciting possibilities is the ability to put insights into the hands of educators, students, families, and leaders more quickly than ever before. At the same time, AI doesn't eliminate the need for high-quality data. If the underlying systems aren't connected, the data isn't reliable, or the methodology behind the analysis isn't sound, AI can simply help people get to the wrong answer faster. 

That's why organizations like EA remain important. The better these tools get, the more important it becomes to have confidence in the underlying data, systems, and methodology. 

What is something you enjoy in your free time? 

One of my favorite activities outside of work is improv. Since 2019, I've been taking classes and now perform on several teams in San Diego, including a musical improv team called Basic Pitches and a duo called First Child. This August, we're performing at the San Diego ImprovCon alongside some of my improv heroes, which is both exciting and a little surreal. 

What I love about improv is that it forces you to get out of your head. You can't plan ahead, and you can't control where a scene is going. The only thing you can really do is listen carefully, accept what your scene partner is giving you, and build from there. As someone who is naturally a planner and probably a little Type A, it's been a wonderful counterbalance to my tendency to plan ahead, and it brings me a lot of joy.

Not to make everything about work, but improv has also made me better at my job. It's helped me become more comfortable with uncertainty, more willing to adapt when things don't go according to plan, and, most importantly, a better listener. For someone who enjoys planning as much as I do, it's probably the healthiest hobby I could have picked. 

When you were a kid, what did you want to be when you grew up? 

I wanted to be an actress (those that know me well are not shocked by this answer whatsoever) and then later, a judge. I have been able to scratch my performative itch through my extracurriculars, and I get to play lawyer, judge and juror in the courtroom of my two kids (the case of “who was playing with the ball first?” is currently under litigation). 

What is something that you would tell your younger self about your career? 

I would tell my younger self not to let my assumptions about what I was good at limit what I was willing to try. Growing up, I loved reading, writing, and public speaking, and I had a pretty clear picture of where my strengths were. 

Some of the most important growth in my career came from stepping into roles and projects that required skills that didn't feel particularly natural to me at first. Economics, statistics, operations, and even some aspects of leadership felt outside my comfort zone, but they became areas where I developed real confidence over time. 

Looking back, I'd encourage my younger self not to rule out opportunities simply because they felt unfamiliar. Some of the most valuable experiences I've had came from giving myself permission to be a beginner at something and trusting that competence would follow.