Building Stronger Teams with Sean Brown
In February, we welcomed Sean Brown, Chief Advancement Officer at St. Andrew’s School in Boca Raton, Florida to The Huddle. With a decade of experience at The Frederick Gunn School in Connecticut, Brown shared his firsthand insights on assessing and strengthening an internal team—an essential skill for school leaders navigating transitions and seeking to foster a high-performing culture.
Leading with Authenticity: Know Yourself First
One of the most compelling points Brown emphasized was the importance of self-awareness in leadership: “You can’t lead, if you don’t know who you are, or if you don’t know what you stand for.”
Before assessing others, leaders must reflect on their own values, leadership style, and what they bring to the table. Establishing trust starts with demonstrating authenticity, and a clear sense of purpose serves as a foundation for meaningful team engagement.
Assessing and Aligning Your Team
When stepping into a new leadership role, it can be tempting to jump right into making structural changes. However, Brown strongly advised against immediate restructuring. Instead, he recommended an intentional assessment process, starting with reviewing job descriptions and conducting one-on-one interviews with every team member.
“Not only do you need the right people on the bus, but you need them in the right seats,” Brown said. By gathering intel on strengths, interests, and individual motivations, leaders can begin to see where gaps exist and where talent can be best leveraged.
The key takeaways here? Listen first. Observe. Understand what each team member values in their work and how they see themselves contributing to the organization’s goals. Then, align individual roles with both team and institutional objectives, ensuring that each person is positioned to succeed.
Creating a Culture of Trust and Accountability
Leadership is not just about setting expectations—it’s about providing the support and autonomy needed to achieve them. Brown underscored the value of continuous feedback, stating, “I strongly believe that no one should ever be surprised by anything that they learn in a semi-annual or annual review.” Regular check-ins, open communication, and clear accountability measures ensure that employees know where they stand and have the opportunity to grow.
Additionally, he emphasized the importance of fostering a team culture that prioritizes collaboration and transparency. Borrowing from sports analogies, Brown encouraged leaders to create touchpoints that remind employees of their shared mission. Whether it’s a “Believe” sign on the office wall (à la Ted Lasso) or an all-in mentality akin to Clemson’s football team culture, these symbolic gestures reinforce a collective commitment to success.
Managing Challenges: Difficult Conversations and Organizational Buy-In
Of course, not every transition is smooth, and not every team member is an easy fit. A question from The Huddle audience brought up a common challenge: How do you hold team members accountable who say they’re on board but don’t follow through? Brown’s advice was clear—set explicit expectations and provide a continuous feedback loop. If someone is actively sabotaging efforts, address it directly, and if necessary, adjust their responsibilities to play to their strengths (or limit their impact on others).
Another hot topic was managing up—ensuring alignment with supervisors, especially when they lack a deep understanding of certain leadership areas. The solution? Leaders must frame their department’s work within the larger institutional vision, making a compelling case for their strategic objectives in a way that resonates with leadership.
Final Takeaways: Becoming a Leader Others Want to Follow
Brown left us with a simple yet powerful reflection: Leadership is about giving credit and taking responsibility. It’s about building trust, modeling integrity, and empowering others to do their best work. He reminded us that the best leaders don’t just manage—they mentor, develop, and ultimately create future leaders.
Want the Full Playbook? Get the Recording
The blog captures some of the highlights, but the full Huddle recording is packed with actionable insights you won’t want to miss. Brown breaks down a structured team assessment process, shares real-world examples of handling difficult team members, and provides practical frameworks like SMART goals and 4 Disciplines of Execution for aligning and motivating your team. Plus, his candid discussion on managing up, leveraging development committees, and the growing role of executive coaching offers a deeper dive into the leadership strategies that truly make a difference.
If you're a school leader navigating team transitions, looking to refine your leadership, or simply seeking fresh approaches to accountability and team culture, this session is for you.