#TheLeaderInside

As a principal, I often find myself dreaming big. I thrive on the grand visions, the Moonshot thinking, and the aspirational moves that inspire transformation. I envision a schoolhouse where many hands work together, creating a masterpiece of learning. But here’s the thing: while I may live in that realm of possibility, I know not everyone shares the same bandwidth or sense of urgency. We all move at different speeds, and it’s our responsibility as leaders to gauge where our teams are. To lead effectively, we must be visible, be present, and most importantly, listen. It’s through this intentional awareness that trust is cultivated.

In the past year, I’ve found a renewed appreciation for the power of small wins, a lesson beautifully captured in two books that have become cornerstones of my leadership practice: Legacy of Learning by Meghan Lawson and The Leader Inside by Lauren Kaufman. Both authors remind us of the importance of celebrating small moves as stepping stones to greater heights. They offer a powerful perspective on how small, intentional acts can build momentum, nurture growth, and foster a culture of progress.

Embracing the Power of Small Wins

In today’s educational landscape, many of us are feeling the weight of the pandemic’s aftermath and the uncertainties of new challenges. I see it daily in our school—a fatigue that cannot be lifted by a Jeans Day or a Donut Party. We need more than quick fixes or temporary boosts. As leaders, we must make deeper, more intentional moves that celebrate small wins and bring joy back into our school communities.

One way I’ve embraced this approach is through curating Images of Possibility. I’ve been using Wakelet to capture and share snapshots of the good happening in our schoolhouse—students smiling, engaging in hands-on learning, or experiencing new adventures like a virtual field trip to Alaska via Nearpod. I sent this Wakelet collection to our staff with a simple note, inviting them to pause and savor these moments. It was a small gesture, but it created a powerful ripple of positivity.

During a recent focus group with our teacher assistants, I shared the Wakelet collection and asked them to reflect on the small wins they’ve witnessed. One TA’s words resonated deeply: “A small win is just that—a win. And a win is a win.” Her comment sparked a wave of sharing, as others opened up about personal victories and classroom successes. It was a moment filled with belonging, connection, and most importantly, hope.

Building Delight Through Intentional Leadership

Reading Unreasonable Hospitality by Will Guidara has also shaped my perspective on leadership lately. Guidara talks about building delight, not through grand gestures, but through thoughtful, intentional moves that show we care. This idea has inspired me to rethink how I approach small wins, not as fleeting moments, but as opportunities to build delight and create lasting impact.

We, as leaders, are called to cultivate hope. We must lift each other up, recognizing that our presence and our voice are catalysts for the hope our students need. It’s about finding the small wins, tuning into them with intention, and amplifying them with purpose.

Four Action Steps for Building Delight and Celebrating Small Wins

Curate Moments of Joy: Start a collection on Wakelet to capture images and posts that highlight the everyday successes in your school. Share these with your staff regularly, creating a visual reminder of the good happening in your schoolhouse. It’s a simple yet powerful way to inspire and uplift.
Begin Meetings with Small Wins: Kick off your meetings by inviting staff to share a recent small win. This practice sets a positive tone, fosters a sense of accomplishment, and encourages a mindset of celebration. It’s a small step that can create a big impact.
Build a Culture of Sharing: Encourage your staff and PLN to use the hashtag #SmallWinsEDU across social media platforms. By sharing small wins, we create a dialogue of support and inspiration. Let’s celebrate each other’s victories and build a network of hope together.
Celebrate Progress, Not Just Perfection: Make it a point to notice and celebrate progress, even if it’s incremental. Acknowledge the effort and the journey, not just the final outcome. When we focus on progress, we create a culture where every step forward is valued and celebrated.

A Call to Action

As school leaders, we have the power to shape the narrative. Let’s tune into the small wins, build delight, and create a culture of hope. Let’s support each other in this journey, lifting each other up through the small yet powerful moves we make every day. Together, we can make a difference, one small win at a time.

So, let’s start today. Share your small wins using the hashtag #SmallWinsEDU and let’s create a collective space of inspiration and support. After all, a small win is still a win, and every win deserves to be celebrated.

Keep dreaming big and finding joy in the small moments. We’ve got this—together.

When I was a young adult, I used to shudder at the statement, “Be yourself.” It seemed like a trite sentiment, almost painfully obvious. Of course, one would want to be oneself. Why wouldn’t that advice make sense? Now, in my later years as a school principal, I have a much deeper appreciation for those words.

During my early years as a principal, I believed I had to conform to the image others had of a school leader. I modeled myself after the austere principals I saw in films like Lean On Me. I thought I needed to wear a three-piece suit, keep my shoes polished, and stride through the building with a Morgan Freeman-like swagger. For those who know me, that’s not the character I am in the story I’m writing as a leader. I quickly learned that those I served could see through the facade and empathized with my internal struggle. I was pretending to be something I wasn’t, and I needed to return to my core values as a leader.

Seeking advice from the best leader I know, my father, I was reminded to hold my head high and stay true to my values. With his guidance and the support of a leadership coach, I was able to reflect on my core values and not only articulate them but also act with authenticity. It was a long journey of reflection and discovery, but it was worth it and helped shape the leader I am today.

We all have a story we are composing that serves as the architecture for our life’s journey. Early in my leadership as a principal, I learned the importance of carrying your values with courage, passion, and humility. My good friend, Lauren Kaufman, beautifully explores the significance of storytelling in unleashing one’s leadership potential in her recent book, The Leader Inside: Stories of Mentorship to Inspire the Leader Within. The inspiring Baruti Kafele, also known as Principal Kafele, emphasizes the importance of staying true to your leadership core. Your leadership core is the DNA of your momentum as a leader. It embodies the values that drive your vision and mission.

In the latest edition of Ryan Holiday’s The Daily Stoic newsletter, Holiday underscores the absolute importance of being yourself and embracing who you are. This resonated with me and highlighted the essential move of embracing our leadership core. We must remain true to ourselves as leaders and individuals. There will be naysayers who try to divert you from your core, and sometimes you may be your own worst critic. This self-doubt cannot be tolerated. Questioning your core and the goodness within leads to a path of devastation filled with Imposter Syndrome and personal well-being fractures. Trust me, I’ve been there and know the negative effects. I’ve seen it ruin leaders.

Stephen M.R. Covey’s pivotal book, Trust and Inspire: How Truly Great Leaders Unleash Greatness in Others, talks about the need for a new type of leadership in our ever-shifting global landscape. Covey challenges leaders to shift from a “Command and Control” style to one rooted in the ethos of “Trust and Inspire.” To flow as “Trust and Inspire” leaders, we must take stock of our authentic selves and connect with others. Remember, leadership is not about getting others to follow but rather about amplifying and encouraging the unique strengths of others.

Whether you are a leader returning to an assignment or starting anew, who you are matters. Your leadership is needed for a reason. Don’t shortchange your passion or compromise what inspires you. If you are an unabashed Taylor Swift fan and that inspires your leadership, then share it and incorporate it into your daily banter. If you are an avid, amateur geologist, then let rocks and soil be part of your faculty repertoire. By embracing the light of your leadership core, you build a culture of trust and inspire others to do the same.

I often sign off on the #PrincipalLinerNotes podcast with the following thought: “Don’t forget to share with the world your dreams, ideas, and insights because the world needs them, and you help make the world a better place for others.” This rings true for leaders grappling with expressing their authentic selves. You have value, and your leadership core will ignite gifts in others, making your school or organization a place that will better our world and community. Illuminate your core and let its light inspire others to do the same.

Action Steps for Leaders

Reflect on Your Core Values: Take time to deeply consider what values are most important to you as a leader. Write them down and think about how they influence your actions and decisions.
Seek Authentic Feedback: Engage with a mentor or leadership coach who can provide honest feedback and help you align your actions with your core values.
Embrace Your Passions: Integrate your personal interests and passions into your leadership style. This authenticity will resonate with and inspire those you lead.
Create a Culture of Trust: Foster an environment where others feel safe to express their authentic selves. Encourage and amplify the unique strengths of your team members.

Leadership Liner Notes: Sean Gaillard

Built on Connection. Tuned for Impact.

Celebrating Small Wins and Building Delight in the Schoolhouse