What separates a group of talented people from a truly great team?
In Episode 301 of Leaning Into Leadership, Darrin sits down with executive coach and global educator Gaby Jordan to explore what it takes to build what she calls champion teams—teams grounded in connection, honesty, trust, and a shared commitment to something bigger than themselves.
Gaby brings a unique perspective to leadership. After practicing law for 15 years in Midtown Manhattan, she transitioned into business, executive coaching, and eventually education. Today, her work spans corporate organizations and educational settings from K–12 schools to universities. Across all of those environments, she has discovered one important constant: leadership is always human work.
Darrin and Gaby dig into why relationships matter so much to team performance. High-performing teams don't have to be made up of best friends, but people do need to know one another, understand one another, and be willing to have honest conversations. Gaby shares how learning someone's origin story—and even acknowledging our own vulnerabilities and imperfections—can completely change the way a team works together.
They also explore one of the biggest threats to healthy teams: the stories we create in our own heads. Darrin shares a story from his school leadership days about a colleague whose "thinking face" he initially interpreted as frustration or disagreement. That simple misunderstanding becomes a powerful example of how easily assumptions can turn into narratives—and how those narratives can quietly damage relationships.
Gaby introduces the idea of Champion Conversations, intentional conversations designed to help people address unresolved issues rather than carrying old transgressions forward. She explains why teams sometimes need to clear the air before they can create a meaningful vision for the future.
The conversation also explores agency, vulnerability, silos, honesty, and why leaders can't simply pile a new strategy on top of unresolved team dysfunction. As Gaby puts it, you can't create a compelling future "on top of the muck."
If you lead a school, district, organization, department, or leadership team, this episode is an important reminder: the strength of your strategy will always be limited by the strength of the people trying to execute it together.
In this episode:
Connect with Gaby Jordan
Learn more about Gaby's education work through Human Better EDU. You can also find Gaby on LinkedIn and Instagram and learn more about her corporate leadership work through Source Elements Group.
This Episode Is Sponsored by HeyTutor
HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.
Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com