Leading Together

What happens when you step into the top leadership role and realize how much you still have to learn?

For Jechane Reyes, becoming executive director of Community Integrated Support Services meant succeeding the founder she had worked alongside for years—and discovering just how much "invisible work" came with the role.

In this episode, Jechane joins Shaun for a candid conversation about growing into executive leadership. She shares how she's learned to recognize where she needs help, surround herself with subject-matter experts who are willing to teach rather than simply do, and build an empowered senior leadership team that shares responsibility for the organization's future.

It's a conversation about humility, confidence, succession, and recognizing that becoming the leader doesn't mean you suddenly need to have all the answers.

Connect with Jechane on LinkedIn here: https://www.linkedin.com/in/jechane-reyes-30bb27242/

Meetings are where decisions get made, alignment takes shape, and organizational culture is built—or broken. So why do we put so little thought into designing them well?

In this episode, Shaun and Joe sit down with organizational behavior expert and Your Best Meeting Ever author Rebecca Hinds to explore why so many workplace meetings aren't working and what leaders can do differently.

Rebecca shares practical strategies for treating meetings like a product: designing them intentionally, eliminating unnecessary attendees and agenda items, creating clearer outcomes, and experimenting with new approaches rather than defaulting to the way things have always been done. The conversation also explores one-on-ones, asynchronous collaboration, meeting size, better agendas, and why sometimes the best way to fix an overloaded calendar is to start over completely.

If your calendar is packed but your team still struggles to find enough time for the work that matters most, this conversation offers a practical path toward fewer—and much better—meetings. Learn more about Rebecca and purchase her book at www.rebeccahinds.com.

In this episode of Leading Together, I sit down with Daniel Caridi, co-founder and CEO of Kibu, a technology company revolutionizing support for disability service providers. Daniel shares the inspiring story of Kibu's evolution from a volunteer fitness class in 2019 to a powerful platform that enhances the lives of individuals with disabilities. We discuss the challenges of navigating rapid growth, the importance of fostering a culture of curiosity, and the need for continuous improvement in both product and processes. Daniel emphasizes that true innovation comes from understanding user needs and anticipating their future requirements, providing insight into how Kibu is shaping its mission to empower direct service professionals. Tune in for valuable lessons on leadership, vision, and the impact of technology on community care.

What happens when teams avoid the conversations they most need to have?

Gustavo Razzetti, CEO of Fearless Culture and author of Forward Talk, calls the accumulating cost conversational debt - the price teams pay when important issues go unaddressed, conversations stay on the surface, or people stop speaking up because they no longer believe anything will change.

In this episode, Gustavo joins Shaun and Joe to explore why psychological safety alone isn't enough to get people talking, how avoidance, blame, and groupthink keep teams stuck, and why healthy tension can actually make teams stronger. They also unpack the "alignment trap," the role leaders play in creating more candid conversations, and practical ways teams can surface tension before it becomes something much harder to solve.

If your team has ever danced around an issue, mistaken agreement for alignment, or left an important conversation for another day, this episode offers a practical path forward. You can buy Gustavo’s book, Forward Talk, here: https://gustavorazzetti.com/books/

What does it take to build a team that doesn’t just perform, but wins together?

In this episode of Leading Together, Shaun Lee and Joe Olwig sit down with Andrie Leday, III, U.S. Commercial Vice President of Joint Reconstruction Enabling Technologies at DePuy Synthes, to explore the leadership practices behind high-performing teams.

Drawing from more than 20 years of leadership and sales experience, Andrie shares lessons from his own journey, from achieving success as an individual contributor to leading teams and organizations at scale. He discusses why great leaders hire people who are smarter than they are, the importance of creating space for different personalities and strengths, and what he calls the “A-Team effect”: bringing together people with distinct capabilities to achieve something greater together.

The conversation also explores how trust is built through action, why leaders should look for “opportunities for greatness” to invest in their people, and how a clear definition of winning can move teams from individual silos toward shared ownership and teamship.

If you’re working to build a more aligned, trusting, and high-performing leadership team, this conversation is full of practical lessons on what it takes to truly win together.

What separates healthy nonprofit boards from dysfunctional ones?

In this episode, Shaun sits down with governance expert, former CEO, board chair, and author Kurt Senske to explore what makes CEO-board relationships thrive. They discuss trust, role clarity, board culture, executive onboarding, strategic partnership, and why healthy governance can become a competitive advantage for any organization.

Whether you serve as a CEO, executive director, board member, or board chair, this conversation offers practical insights for building stronger partnerships that help organizations accomplish their mission.

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, how executive teams create alignment through operating rhythms, and why leaders should focus on process rather than outcomes they can't control.

Mike also shares lessons from his new book, Failure Is an Option, including the importance of psychological safety, healthy accountability, storytelling, and building teams that put the organization ahead of individual success.

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, retrospectives, decision-making, psychological safety, and why trust is built through meaningful shared work.

Sam shares lessons from his work with the Ready where he worked with fortune 500 companies in several industries, including how teams can create greater clarity, strengthen connection, improve accountability, and build the habits that sustain long-term performance.

If you're part of a leadership team, executive team, or any group working to improve how you collaborate, this conversation offers practical insights you can put into practice immediately.

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 leaders are often quick to jump into problem-solving, and how helping people feel heard can actually make them more open to feedback, growth, and change.

We also discuss the connection between validation and psychological safety, how validation helps teams avoid groupthink, and practical ways leaders can begin incorporating this skill into everyday conversations.

Whether you're leading a team, coaching others, or simply trying to build stronger relationships, this conversation offers a powerful framework for creating environments where people feel seen, valued, and empowered to contribute their best.

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 mission-driven organization that stays aligned through growth, challenge, and change.

We explore:

- Why fast growth can weaken team engagement—and what to do instead

- How doubling down on mission and values can strengthen culture

- What it means to lead an “integrated life” and bring your whole self to work

- How to create shared ownership across teams at every level

- Lessons from navigating crisis and leading through uncertainty

If you’re leading a growing organization or trying to strengthen alignment across your team, this conversation offers practical insights you can apply right away.