Name: Richard M. Gordon

Title: Assistant Superintendent

Organisation: School District of Philadelphia

Richard M. Gordon IV is a nationally recognized, award-winning educator who has spent over a decade transforming education in underserved communities. Known for his visionary leadership, Gordon served as Principal of Paul Robeson High School for Human Services in Philadelphia, where he led the school through a remarkable turnaround, increasing graduation rates to 95% and earning the title of Most Improved High School in the city.

In 2020, he was named Pennsylvania Principal of the Year, becoming the first recipient from the School District of Philadelphia in its 207-year history. Gordon has also been honored three times as National Principal of the Year. Currently, he serves as Assistant Superintendent in the School District of Philadelphia, overseeing 15,000 students and continuing to champion community collaboration to address systemic issues such as poverty, mental health, gun violence, and the impact of COVID-19 on education.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Richard's answers will encourage you in your leadership journey. Enjoy!

Cheers,

Jonno White

1. What have you found most challenging as a leader?

As a leader in urban education, one of the most challenging aspects has been balancing the immediate, tangible needs of students and staff with the long-term vision for systemic change—especially when working within the complexities of the 8th largest educational bureaucracy in the country.

In the schools I’ve served, and now leading the largest high school learning network in the School District of Philadelphia, the challenges are multifaceted: academic underperformance, safety concerns, unhealthy building conditions, teacher shortages, overcrowded buildings/classrooms, and issues of poverty and mental health. These are issues that disproportionately affect our most vulnerable minority communities, and yet, I believe we have to address both the short-term needs and the long-term cultural transformation necessary to create sustainable change.

The daily pressures of improving test scores, graduation rates, and student engagement can often feel overwhelming, but they can’t overshadow the necessity of shifting broader educational and social systems that impact our students. These systems have devastating implications for their futures, and they require a leader who can navigate the tension between short-term solutions and long-term vision.

Leading in an environment with limited resources, while also dealing with intersecting crises like poverty, mental health and wellness, gun violence, and the lingering effects of COVID-19, is incredibly demanding. What makes this even more challenging is the pace of response from the larger bureaucracy.

I tend to be someone who thrives on action and urgency, so patience—especially with the systems that govern large districts—is not always my strongest virtue. However, I firmly believe in the sense of urgency required to address immediate needs. It's crucial not only to engage students and families in activities that inspire them toward achieving their dreams but also to ensure that our teachers, administrators, and staff are fully aligned with our mission.

We are in a race to support and nurture our students and staff, and we cannot afford to slow down. This means balancing the need for higher academic achievement with the imperative of a strong social-emotional support system. Keeping morale high and ensuring that everyone—students, teachers, staff, and families—feels supported and part of the mission is something I work hard to maintain every day. It’s a constant challenge, but one I am deeply committed to navigating.

2. How did you become a leader? Can you please briefly tell the story?

My leadership journey was never part of the plan. It was a series of unexpected opportunities and reluctant decisions that led me to where I am today. After seven rewarding years of teaching in Maryland and Washington D.C., where I earned recognitions like two Baltimore City Mayor’s Citations and the Baltimore City Distinguished Teacher of the Year Award, I returned to Philadelphia and took a position in the School District of Philadelphia’s central office.

My original goal was to move up within central administration, and I had no interest in school-based leadership. I had seen firsthand the struggles of school leaders I worked with—overwhelmed, stressed, and seemingly unhappy in their roles. I thought school leadership wasn’t for me.

But in 2004, I was invited to join a joint educational leadership program through Lehigh University and the district, and that’s when my perspective on leadership began to change. Upon completing the program, I hoped to move forward with my central office career, but when that opportunity didn’t materialize, a friend and classmate who had recently been hired as an Assistant Principal recommended me for a second Assistant Principal position at the same school. Initially, I was hesitant and had no interest in taking on the role, but after some encouragement, I reluctantly accepted. This decision marked the beginning of my seven-year tenure as an Assistant Principal at three different high schools.

One pivotal moment came while I was at George Washington High School in Northeast Philadelphia. I worked closely with my mentor, the school principal, and was given the responsibility of overseeing school climate and student discipline for a school of 2,500 students. My role required knowing each student’s name, profile, and background—something I took great pride in. This work caught the attention of Superintendent Arlene Ackerman, who visited the school and was impressed by the positive environment we had cultivated. After her visit, I received an unexpected call from her office, which led to a meeting where I was offered my first principalship.

I initially turned down the offer due to family considerations—my son was about to be born, and the timing was difficult. To be honest, I had never aspired to be an assistant principal, let alone a principal. But less than two weeks later, the district called again, this time offering me the chance to lead Roberts Vaux High School, a smaller school with only about 300 students. Despite my initial hesitation, Dr. Ackerman and her leadership team insisted they saw something in me that I didn’t yet see in myself. After much thought, I accepted the challenge.

That first principalship was a formative experience. Leading a small school in a challenging environment was an eye-opener. While the district ultimately decided to close Vaux, the lessons I learned there laid the foundation for everything that came next. After Vaux, I moved on to lead Paul Robeson High School for the next ten years, where I had the opportunity to apply all that I had learned and lead the school through a remarkable turnaround. During my tenure, we saw unprecedented success at the local, state, and national levels, which marked the pinnacle of my professional journey.

After ten years of transformative leadership at Robeson, I was contacted by Dr. Tony Watlington Sr., the current Superintendent of the School District of Philadelphia, who invited me to leave my principalship and join his leadership team. While I was deeply attached to my school community and reluctant to leave, I knew this was a chance to make a broader impact on the education landscape in Philadelphia. I ultimately accepted his offer, and I was promoted to my current role as Assistant Superintendent.

Looking back, my leadership journey wasn’t one I ever planned—it was shaped by unexpected opportunities, challenges, and the guidance of others who saw potential in me when I couldn’t see it in myself. I’m grateful for every step of the journey and for the chance to continue leading and making a difference in the lives of students. That’s been my journey in school leadership: one rooted in service, a commitment to student success, and an unwavering dedication to transforming urban education.

3. How do you structure your work days from waking up to going to sleep?

My workdays are a blend of strategic planning, school visits, and the daily responsibilities of overseeing a large school network. While no two days are the same, I’ve developed a routine that helps me stay focused and prioritize what matters most—for myself, my family, and the students, families, principals, and educators I serve. I typically wake up around 4:00 AM. The early morning hours are my quiet time, where I focus on reflection, planning, and reviewing important updates or reports for the day.

This helps me prepare mentally for meetings, challenges, and decisions that lie ahead. By 4:45 AM, I usually get in a brief workout, whether it's a morning run or a quick exercise routine. I believe strongly in maintaining both physical and mental well-being—it’s key for staying energized and sharp in such a high-pressure leadership role. By 5:30 AM, I begin getting my three children ready for school—making breakfast, checking their outfits, and organizing their snack and lunch bags. By 6:00 AM, the household is up and moving. We all get dressed, finish packing, and leave the house by 7:30 AM.

After dropping them off, I typically arrive at my first meeting of the day by 8:45 AM. During the weekdays, I prioritize school visits, aiming to visit 2-3 schools per day (Monday through Thursday). Fridays are typically my office hours. These visits often involve a mix of one-on-one check-ins with principals, observing classrooms, data reviews, and reviewing school climate. I also meet with district leaders and community partners to stay aligned with our long-term learning network goals.

In between school visits, I’ll attend numerous meetings—some in person, others via Zoom. I try to maintain a visible presence at the schools, as I believe leaders must engage directly with the school community to understand the unique challenges and successes they’re experiencing.

Throughout the day, I meet with principals, district leaders, and community partners to strategize and discuss urgent issues. I’m deeply committed to staying closely connected with my principals, as their feedback and insights are essential for driving our collective success. The constant flow of meetings and school visits is a balancing act, but I always make time to engage with teachers, students, and staff.

I see my role not just as a decision-maker but as an active participant in the educational experience, fostering strong relationships across the district. In the afternoons, I focus on strategic planning, reviewing upcoming initiatives, and collaborating on district priorities. This could include reviewing curriculum implementation, analyzing student outcome data, or working with academic partners on supporting school-based initiatives. I also allocate time to mentor emerging leaders, as I’m committed to building the next generation of educators and administrators.

By 5:00 PM, I wrap up my official workday. Between 3:00 PM and 5:00 PM, I check in with my Executive Assistant to ensure no open items are missed and to review what’s ahead for tomorrow. I make it a point to reflect on the day—what went well and what could be improved. As much as I’m focused on leading others, I’m always looking for ways to grow personally and professionally.

At 5:30 PM, I pick my children up from their grandparents’ house, where they’re usually picked up after school. We return home, have dinner, review homework, and engage in our evening routines. I strongly believe in work-life balance, so evenings are reserved for family time and personal reflection. While I try to disconnect from work, it’s sometimes difficult, as the nature of my role means that emails and urgent matters can arise at any time.

On the days I’m not on "Daddy Duty," I use that time to catch up on work or engage in professional networking opportunities to secure resources and support for our schools from both the public and private sectors. Before bed, I take a few moments to review any remaining emails, reflect on what I can improve for the next day, and unwind with a bit of television. It’s my way of mentally preparing to tackle another busy day ahead.

Though every day brings new challenges, I’ve learned the importance of structure and intentionality in my routine. By maintaining a clear schedule, I’m able to manage my responsibilities effectively while staying grounded in my vision for education and my commitment to serving students, families, and the community.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

A recent lesson I’ve been reminded of is the importance of embracing vulnerability and authenticity in my leadership. Throughout my career, I’ve prided myself on being solution-focused, driven, and results-oriented. While those are essential traits in leadership, I’ve come to realize that there is tremendous power in being open about my challenges and uncertainties—especially in a role like mine, which is high-stakes and filled with complexity. As a second-year Assistant Superintendent, I’ve found myself facing new frustrations and challenges, particularly in collaborating within the slower-moving bureaucracy of the district.

I’ve had to make decisions and execute professional duties that I don’t always agree with, and I’ve had to navigate the tension between what I know is best for our schools and the constraints imposed by district mandates. The reality of district leadership is much different than school-based leadership, where you have more autonomy to act and respond swiftly to student and staff needs. I’ve come to understand that, as part of a larger district system, I am not an island unto myself, and the decisions I make must be seen through the lens of the entire district and state policies we must adhere to.

A few months ago, we faced a particularly complex issue in one of the schools I oversee. It revolved around teacher professionalism, and despite our best efforts, the solutions I was directed to implement weren’t producing the results I hoped for. I found myself questioning whether I was missing something or if I was even the right fit for this role. I could feel the frustration mounting not just within myself, but among my principals as well. The district mandates we were forced to implement were frustrating, and I could see how they were creating roadblocks in our schools.

Instead of just providing feedback and following up with directives, I decided to be more honest and transparent with my principals about how I was feeling. I shared my concerns, acknowledged the shared frustrations we were facing, and admitted that I didn’t have all the answers. I encouraged an open dialogue where we could discuss the barriers we were facing and work together to find solutions.

The result was unexpected and powerful. The honesty and vulnerability I showed created space for my principals to share their perspectives and frustrations. It allowed them to express the support and grace I didn’t even realize I needed. They didn’t just listen; they engaged deeply, contributing creative solutions and fresh ideas that ultimately helped refine our approach. This experience reminded me that leadership isn’t just about having all the answers or making tough decisions—it’s about creating an environment where everyone feels heard, valued, and empowered to contribute.

This process reinforced for me that leadership is as much about building relationships and fostering collaboration as it is about making tough calls. Embracing vulnerability doesn’t weaken authority—it builds trust, strengthens connections, and nurtures a culture of shared ownership and accountability. It's a lesson that I’ll continue to carry with me as I navigate the complex and ever-evolving challenges of educational leadership.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

As a reader and advocate of advancing public education, it is extremely difficult to limit the impact that the written words of colleagues—especially those with whom I’ve had the privilege of working or sharing presentations—have had on my professional journey.

The three books I’ve had the honor of reviewing and contributing the Foreword to—Why This, Why Now? by Emily Woods, New Principal, No Problem: Leading a Winning Organization Without Losing Your Mind by Dr. Elvis Epps, and Building School Culture by Dr. Joel Bratton—have all played pivotal roles in shaping my leadership practice.

Each one has not only expanded my understanding of effective leadership but also reinforced my commitment to creating learning environments that are inclusive, supportive, and transformative for both students and educators.

Why This, Why Now? by Emily Woods In Why This, Why Now?, Emily Woods provides a comprehensive exploration of the transformative potential of Community Schools. Her book helped me think about schools not just as places of academic instruction but as centers of community support and action. The emphasis on integrating essential services like healthcare, mental health support, and career readiness into the school environment opened my eyes to the importance of holistic approaches to student success.

This book reinforced my belief that schools should serve as the backbone of a community—providing students and families with resources that go beyond textbooks. In my current work, I prioritize creating partnerships between schools and community organizations to address the social, economic, and health challenges that many of our students face. Emily’s call for grassroots involvement in education resonated with me deeply, and it has shaped the way I approach collaboration with local stakeholders. The book also reminded me of the immense power of community in driving long-term change, which I now actively incorporate into our district’s work.

New Principal, No Problem: Leading a Winning Organization Without Losing Your Mind New Principal, No Problem: Leading a Winning Organization Without Losing Your Mind by Dr. Elvis Epps’ New Principal, No Problem was a transformative read for me, particularly in the way it emphasized the human side of leadership.

As someone who has worked closely with new and emerging leaders, I have come to appreciate the complexities and emotional toll that leadership can take. Dr. Epps does an exceptional job of unmasking the often-overlooked emotional and mental struggles that come with school leadership. He writes not only as a scholar but also as someone who has lived through the ups and downs of leadership, which adds a unique level of authenticity to the book.

Dr. Epps' focus on self-reflection, accountability, and managing the stress that comes with leadership helped me navigate my leadership challenges. It reinforced the importance of supporting and mentoring new leaders, especially as they face the daunting and often isolating realities of school administration. The practical strategies and frameworks provided in the book are invaluable, and they’ve impacted how I coach and mentor the emerging leaders in my district, encouraging them to not just lead with vision but to also prioritize self-care and emotional resilience in the process.

Building School Culture by Dr. Joel Bratton Dr. Joel Bratton’s Building School Culture has profoundly shaped my approach to leading schools. His book emphasizes the significance of school culture in driving educational success, and it underscored for me the critical role that culture plays in creating safe, inclusive, and academically rigorous environments for all students. The focus on building relationships—between teachers, students, families, and the broader community—resonated with me deeply.

One of the most impactful lessons from this book is that the culture of a school can either support or hinder student success. I have seen firsthand how a positive, inclusive school culture can drive significant academic and social outcomes, while a negative culture can stifle growth and achievement. As a leader, I now place an even greater emphasis on fostering an environment where everyone feels valued, respected, and supported, and where diversity is celebrated.

Dr. Bratton’s insights on the complexities of school culture have also helped me guide schools through significant cultural shifts. I’ve used his strategies to help schools assess their current culture and implement changes that foster inclusivity, belonging, and academic excellence. The book provided me with both the theoretical understanding and practical strategies I needed to tackle culture change in our district—something I now see as foundational to long-term success.

Impact on My Leadership Practice These three books have profoundly impacted my leadership philosophy and practice. From Why This, Why Now?, I learned to view schools as central hubs of the community and to prioritize holistic approaches to student success. From New Principal, No Problem, I gained a deeper understanding of the emotional complexities of leadership and the importance of mentorship and self-care. From Building School Culture, I reinforced my commitment to creating positive, inclusive school cultures that support the academic and personal growth of every student.

Together, these books have expanded my approach to leadership beyond just focusing on academic outcomes. They have deepened my understanding of the power of community, the importance of mental and emotional resilience, and the critical role of school culture in achieving lasting educational success. I continue to draw on the wisdom and insights from these texts as I work to create a school system that is not only effective in terms of academic outcomes but also supportive, inclusive, and transformative for the students, families, and educators we serve.

6. If you could only give one piece of advice to a young leader, what would you say to them?

If I could give just one piece of advice to a young person who aspires to be a leader, it would be this: Always keep your focus on what truly matters. For me, that focus is on the people you're leading—the students, the teachers, and the community you're a part of. Leadership isn’t about titles, accolades, or climbing the ladder; it’s about service and making a meaningful impact on the lives of others.

Throughout my career, I’ve had the privilege of working alongside some of the most successful and knowledgeable school leaders in Pennsylvania. Much of my growth has been supported by incredible mentors who have consistently provided me with guidance. But the most impactful piece of advice I received came from a former high school principal during my second year as an administrator.

He said something that has stuck with me ever since: “Take care of your students, your school, and your community first. Do what is right for them, because they are your priority professionally. Let the chips fall where they may with everything else. And if that’s not good enough for anyone supervising you, then they can come get my keys to the school building. Tell your own story, because no one will tell your story better than you, nor will they be as interested in telling your story more than you.”

This advice, though seemingly two pieces of wisdom, is deeply intertwined and has served as a guiding principle in my leadership journey. First, it underscores the importance of remaining grounded in your core values and ensuring that the people you serve are always at the center of your decisions. As a leader, you’ll inevitably face moments where external pressures, organizational constraints, or even internal expectations challenge you.

But if you stay true to your role as a servant leader—putting students, educators, and the community first—you’ll always know you're on the right path. It’s about making decisions based on what’s right, not what’s easy. When your foundation is built on a commitment to your people, even the toughest challenges become opportunities to live out your leadership values.

Secondly, this advice is a powerful reminder that no one knows your journey, your struggles, or your successes like you do. It’s your responsibility to own your narrative. In leadership, this means advocating for yourself, sharing your perspective, and ensuring that your values and intentions are understood. Too often, leaders hide behind assumptions or let others shape their stories for them.

But by telling your story authentically, you set the tone for others to do the same, creating an environment of transparency, trust, and empowerment. Your voice matters—it’s the key to shaping the culture you want to lead. When you share your challenges and triumphs openly, it not only permits others to be themselves but invites them into your shared mission. It makes you relatable and trustworthy.

Putting people first and owning your story work hand in hand. When you put your people at the center of your decisions and lead from a place of transparency, you build a culture where people feel empowered and engaged. By staying true to your values and sharing your authentic self, you create a space where others feel safe doing the same. That’s when real transformation begins. Leadership is about modeling the way and empowering others to find their voice within the shared mission.

It’s this balance of self-awareness and servant leadership that will keep you grounded and focused, even when the road ahead feels uncertain or difficult. So, as you continue on your leadership journey, remember that serving with integrity and owning your narrative are the twin pillars that will guide you to success.

In short, this advice isn’t just about leadership in the traditional sense; it’s about integrity, resilience, and the courage to remain true to your mission—even when it’s hard, even when it means challenging the status quo. Keep your focus on the people you serve, protect what truly matters, and always be the storyteller of your journey.

This advice wasn’t about defying authority or being stubborn; it was about having the courage to prioritize what’s truly important. It’s about standing up for your values and for the people who rely on you. As a leader, you’ll face challenges, encounter obstacles, and at times, even find yourself in conflict with others in positions of authority. But if you’re grounded in the belief that your primary responsibility is to your people—those you lead and serve—you’ll always have a clear sense of direction.

Stephen Covey once wrote, “The main thing is to keep the main thing the main thing.” And that’s what I would say to any young leader: Stay focused on your purpose. In education, that purpose is helping students succeed, supporting teachers to do their best work, and building a community where all can thrive. It's easy to get distracted by the noise—meetings, emails, or the pressure of external expectations—but as a leader, your role is to protect the core of what matters most and ensure that nothing pulls you away from that.

So, as you begin your leadership journey, remember to always place people first, make decisions with integrity, and be bold enough to do what is right—even if it’s not the easy path.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

One of the most meaningful stories from my journey as a leader is deeply personal and rooted in love—a love for my students, for the communities I serve, and for the idea of getting our students, families, and communities to love school in return. My leadership is not just about creating opportunities for others; it’s about ensuring that those opportunities are built with the same love and dedication that I would want for my child.

Having my daughter attend the very same school I helped build—a school that, at one point, wasn’t supposed to exist—is a reflection of who I am, where I come from, and the kind of future I want to build for all of us. If it was good enough for my child, I knew it would be good enough for others.

As a leader in urban education, I’ve always believed that love is the foundation of everything I do. Love for the work, love for the mission, and, most importantly, love for the people. This love has allowed me to build educational programs that are not only changing lives but also defying the odds in a system designed to fail so many.

One of my proudest achievements is the fact that the programs I helped create will allow my daughter to graduate as the Valedictorian from a school that, against all odds, has become one of the best in Philadelphia and even recognized across the country. And for two years, I had the honor of being my daughter’s principal. Now, she will graduate as the Valedictorian of the Class of 2025 from the school I helped shape.

When I reflect on my work in education, it’s about far more than titles or accolades. It’s about the lives we’re transforming, one student at a time. I see my journey in every student I serve—their struggles, their resilience, their potential. I grew up in Camden, New Jersey, once known as the country’s murder capital and one of the poorest cities in America. My family lived through the kind of hardship that many of my students experience today—hunger, instability, violence, and systemic inequity. I know what it’s like to feel like the world is working against you, but I also know how education can be the tool that changes everything.

When I was eight years old, after my parents’ divorce, I lived with my father until I was twelve, when he was incarcerated. My brothers and I moved into a one-bedroom apartment with our mother in Philadelphia—no separate bedrooms, no beds, just the love of an amazing woman setting the standard for the love I have for my children and my students. Despite those challenges, I knew that the way out of poverty was through education.

And that’s why I dedicated myself to learning, to growing, and eventually to becoming a teacher, an administrator, and now, a leader. What drives me every day is not the title I hold or the recognition I receive; it’s knowing that the work I do has the potential to change the trajectory of a student’s life.

I see my own experience reflected in the faces of the students I serve. I know what it’s like to feel invisible in a system that doesn’t believe in you, to grow up with the odds stacked against you. But I also know what it means to rise above, to persevere, and to create opportunities for success, even in the face of adversity.

One of the most powerful moments for me was when I realized that I was not just a leader in my community—I was also a role model for my daughter. As she watched me build programs and as she walked the halls of the school I helped shape, she learned what it means to fight for something bigger than yourself.

She’s witnessed firsthand how love and commitment can transform lives, how education can break the cycle of poverty, and how, despite the odds, we can create something beautiful and lasting. But the work I do is not just for my daughter or my students. It’s for every young person who feels like they don’t have a chance, for every family struggling as mine once did. I am a reflection of them.

I was once that child growing up in Camden, surrounded by poverty, violence, and hopelessness. Now, I stand at the front of the classroom, leading with love and showing my students what’s possible. This work is not just about fixing a broken system; it’s about building something new—something that reflects the true potential of our children and our communities. My daughter, who will walk across the stage as Valedictorian, is proof that love and education can conquer even the most entrenched challenges.

As a father, a leader, and a product of these very communities, I will continue to fight for that future—for her, for my students, and for every child who deserves a chance to succeed. In the end, it’s not just about creating opportunities—it’s about showing up with love, every single day, and being the change that we wish to see in the world. When I look at my daughter, I know that my work is far from over. It’s only just begun.