Steven Eskay

Steven Eskay resides in Silver Spring, Maryland, where he serves as an educational leader with a decade-long tenure in the field. Embracing progressive educational ideals, Steven currently holds the esteemed position of Principal within the DC Public Schools system. Influenced by civil rights icons, he strives for representation, inclusivity, and enhanced accessibility for all students under his purview.
Steven Eskay’s journey into education commenced with a strong emphasis on personal academic growth. Graduating with a BA in English from The College of William and Mary laid the groundwork for his subsequent achievements. Seeking further expertise, he pursued a Juris Doctorate in Law (JD) from UDC, David A. Clarke School of Law, followed by a Magna Cum Laude Master’s in Education from American University.
His professional odyssey began as an Educational Consultant and Advocate, a role he adeptly fulfilled from 2011 to 2019. Providing educational testing, consultation, and advocacy services for students aged 5-12, Steven’s dedication was palpable. Concurrently, he assumed the responsibilities of a Part-Time Teacher at Model Learning Center (MCPS) in 2009, teaching English, History, and NSL Government, a role that eventually evolved into a Special Education Teaching position from 2013 to 2019. Noteworthy achievements during this period include significantly enhancing student performance metrics, notably increasing Math passage rates from zero to forty percent for students with Individualized Education Programs (IEP).
Transitioning to DC Public Schools in 2019 as the Manager of Specialized Instruction, Steven implemented data-driven instructional practices. Subsequently, he served as an Assistant Principal, where he spearheaded the development of comprehensive support systems, including a Summer Academy, After School Acceleration Academy, and Saturday Arts Academy.
Currently, as Principal of a DCPS Elementary School, Steven oversees the institution’s instructional and operational facets, managing a student body of over four hundred and a staff of sixty. Under his leadership, the school has achieved a historic high reading proficiency rate of 87%, alongside the establishment of the “Innovation Lab,” a beacon of STEM education excellence. These initiatives have contributed to a notable increase in enrollment, reaching a five-year peak.
Beyond education, Steven is passionate about art and soccer, recognizing their capacity to foster creativity, community, and collaboration. He envisions these pursuits as instrumental in nurturing well-rounded, expressive, and informed future generations.
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What is your typical day, and how do you make it productive?

My day begins at 7 am. I have to get two girls off to school and then I head into work. I work on two different campuses so sometimes I am at Trinity College and other days I am at the high school. As the director of an early college academy, I am interacting with professors, support staff, and students all day. I make my day productive by keeping a very tight and organized calendar of events and being prepared for all my meetings.

How do you bring ideas to life?

I bring ideas to life through collaboration with others. I like to use questions and a Socratic style to get the most out of my team members. I view myself as someone who helps to build consensus around ideas and gets all members of the team to contribute.

What’s one trend that excites you?

I am excited by how politically involved all the young people in our country seem to be. I love that they are passionate and issue-driven about big problems that need big solutions. I think the level of advocacy that our younger generations are showing is exciting and I hope that they continue to push for important ideas to make the world a better place.

What is one habit that helps you be productive?

One habit that helps my productivity is that I never procrastinate on big deliverables. I always start on projects as soon as they come in the door. This buys me time on the back end to finesse and add depth to the project or task as new ideas come into play. It gives me control over deadlines.

What advice would you give your younger self?

I would tell my younger self to think strategically about all my interactions with persons in the professional environment and to always remember to keep a positive, upbeat attitude.

Tell us something you believe almost nobody agrees with you.

I think that we should reduce the power of the federal government and return some of it to the states.

What is the one thing you repeatedly do and recommend everyone else do?

I always tell my students to calendar their lives and take an hour a week to look ahead at their schedules so they can take control of their workload so that it does not control them.

When you feel overwhelmed or unfocused, what do you do?

I step back, put the work away for an hour, and go for a walk.

What is one strategy that has helped you grow your business or advance in your career?

I have always put in the extra hours to prepare for meetings and always volunteered for extra work or assignments when on the job. I have moved up because I was willing to learn the new job before I applied for it.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

One failure was losing the trust of some staff due to how I was communicating my vision to them. It taught me that change leadership can be very challenging and that it must be undertaken with great care and attentiveness to the myriad of issues that come up in a complex, relationship-driven institution.

What is one business idea you’re willing to give away to our readers?

I think that someone could make millions of dollars coming up with a platform for educational administrators that organized all of their data, meetings, and schedules for all the staff and students in the building.

What is one piece of software that helps you be productive? How do you use it?

I really like Microsoft Office and all the suite of applications it has to offer.

What is the best $100 you recently spent?

I took my wife out to a very nice dinner that definitely over $100 but it was amazing.

Do you have a favorite book or podcast from which you’ve received much value?

I recently read Trust by Hernan Diaz. It was the Pulitzer Prize winner. Deep, complex, interesting, and emotional. Highly recommend!

What’s a movie or series you recently enjoyed and why?

I recently watched Mr. and Mrs. Smith on Amazon. It has a great mix of action and smart dialogue. Donald Glover is a genius!

Key learnings:

• Self-Reflection is important
• Optimism is crucial to success
• Be strategic with people and aware of where they are coming from
• Stay organized and attentive to details