Leading Together

Mike Grossman has spent more than 30 years leading venture-backed technology companies through growth, uncertainty, and acquisition. In this episode, we explore what it takes to build high-performing organizations and leadership teams that thrive over time. We discuss the difference between strategic identity and cultural identity, why great companies intentionally define and measure their values,...

When team tension and conflict arises, it's often because something significant is unclear. Team Agreements can go a long way towards driving clarity and alignment. In this episode, we sit down with organizational consultant and Deliberate Works founder Sam Spurlin to explore the practices that help teams work better together over time. We discuss team agreements, team charters, operating rhythms,...

What if one of the most powerful leadership skills isn’t giving better advice, but helping people feel truly seen and understood? In this episode, we sit down with psychologist and author Caroline Fleck to explore the practice of validation and why it plays such a critical role in leadership, teamwork, trust, and psychological safety. Caroline shares how validation differs from agreement, why lead...

What does it take to scale an organization without losing your culture? In this episode of Leading Together, we sit down with Leisle Chung, CEO and co-founder of Vanguard Skin Specialists, to explore how mission, identity, and leadership evolve as organizations grow. From starting a medical practice to leading a team of 150+ employees across 10 locations, Leisle shares candid lessons on building a...

What does it take to rebuild a broken leadership team? In this episode of Leading Together, we sit down with Phyllis Snodgrass - former CEO of Habitat for Humanity Austin and longtime executive leader - to explore what it really takes to turn around struggling teams and build high-performing leadership groups. Drawing from decades of experience stepping into complex, often broken organizations, Ph...

In this episode of Leading Together, Shaun sits down with Brian Francis - former executive director of three Texas state agencies, author, speaker, and poet - to explore what it really takes to build a high-performing leadership team. Brian shares practical insights on leading with trust, vulnerability, and intention - from giving away decision-making power to creating a culture where feedback, ac...

In this episode of Leading Together, Shaun Lee and Joe Olwig sit down with Alistair Deakin, founder of SigBee, to explore what truly makes teams thrive. From the power of simple daily check-ins to the importance of clarity and honesty in leadership, Alistair shares lessons from decades of leading organizations and building high-performing teams. The conversation explores why so many teams struggle...

What does it really mean for people to feel like they matter at work - and why does it have such a powerful impact on performance? In this episode, Shaun and Joe sit down with researcher and author Zach Mercurio to explore the science and practice of mattering in leadership. Drawing from his research and his book The Power of Mattering, Zach explains how feeling seen, valued, and needed shapes eng...

In this first episode of the Leading Together Interview Series, Shaun and Joe welcome former NFL running back and ESPN analyst Fozzy Whittaker for a powerful conversation on leadership, energy, and influence. Drawing from his experiences in college football, the NFL, and life beyond the field, Fozzy shares how contagious joy, encouragement, and conditioning shaped his approach to leadership. Toget...

Most teams put their energy into planning synchronous time such as meetings, offsites, and Zoom calls, but real collaboration actually happens asynchronously in Slack threads, shared docs, and decision logs. Without clear design, async work often devolves into scattered updates, missed handoffs, and interruptions. In this episode, Shaun and Joe share four practical asynchronous hacks that help tea...

What makes a team brave? In this episode, we explore James Clear’s quote, “We don’t rise to the level of our goals, we fall to the level of our systems,” and ask what it really means for leadership today. With help from a powerful clip featuring Brené Brown and Adam Grant, we dig into the idea that courage is not just personal. It is structural. Well-designed, collaboratively built systems increas...

In this special episode, we pull back the curtain to share our own journey, sharing how two different paths led us to the same vision. Shaun reflects on his early experiences in AmeriCorps and nonprofit and entrepreneurial leadership, while Joe shares how his time in Teach for America and later as a principal shaped his calling. Together, we talk about how we met, why we built the 6 Levers Framewo...

In this episode, we unpack the leadership lessons from The Bear, Season 2, Episode “Forks.” It’s the story of Cousin Richie, a guy stuck in old patterns, bitter and defensive until one week at a world-class restaurant changes everything. By the end, he’s energized and full of purpose. We explore how this transformation shows the power of team culture: Why excellence only lasts when anchored in pur...

One-on-ones are a staple of leadership, but when they become the primary place for real conversations, teams pay the price. In this episode, we unpack why leaders over-rely on one-on-ones, the risks of pushing too much problem-solving into private meetings, and how to redesign them for genuine connection and development. If you want your team meetings to be more than status updates and your one-on...

Too many leaders are overwhelmed not because they care too much, but because they’re carrying too much. In this episode, we explore the mindset of shared ownership and why it’s one of the most powerful traits of high-performing leadership teams. Through the story of Didi from The Man on the Inside (brought to life by Stephanie Beatriz), we unpack what happens when leadership is isolated, and how t...

If we want a culture of trust and belonging, accountability can’t be the thing we avoid. In this episode, we explore why even the most well-meaning leaders struggle to address underperformance, and what’s really going on under the surface. Using insights from Self-Determination Theory, we unpack the psychological barriers to accountability, what’s at stake when we delay, and how to step into these...

A mission statement on a wall doesn’t shape culture - an activated identity does. In this episode, we explore what it means to have a truly alive organizational identity, using Costco as a gold-standard example. We unpack why identity must go beyond words, how leadership teams can activate it through decisions and systems, and why a clear sense of purpose creates resilience in the face of pressure...

In this episode of Leading Together, Shaun and Joe explore the importance of conflict in building great teams. Join us as we discuss how effective conflict can serve as a catalyst for engagement, creativity, and stronger relationships among team members. We dive into the concept of conflict competence, emphasizing the need for psychological safety and open communication. We share practical strateg...

In this episode of Leading Together, we delve into the critical issue of organizational silos and how they hinder growth and innovation. Join me, Sean Lee, as I discuss with co-host Joe Ulwig the findings from a recent Bain & Company study that reveals half of all managers struggle with bureaucratic barriers that stifle collaboration. We explore how these silos often originate from leadership beha...

In this episode, we explore the deep connection between psychological safety and high performance, through the lens of one of the NBA’s most admired teams: the San Antonio Spurs. Honoring the legacy of Coach Gregg Popovich, we examine how his philosophy of "people before players" and his modeling of vulnerability helped create a culture of trust, belonging, and sustained excellence. We unpack prac...

In this episode of Leading Together, I engage with co-host Joe Ulwig to tackle the critical yet often overlooked issue of organizational systems. We explore the tendency to blame individuals for performance problems rather than examining the underlying systems that shape their work. Through a compelling example from our book, At The Heart of Work, we reveal how miscommunication and unclear priorit...