In this episode of Beneath the Transaction, Chris sits down with Vanessa Plant, Executive Director of the Alku Foundation and an experienced leader in Boston’s nonprofit and philanthropic space.

Vanessa has spent her career helping organizations move beyond traditional, transactional approaches to fundraising and into more relational, trust-based models of giving. Her work centers on building authentic partnerships, strengthening organizational culture, and creating lasting community impact.

Together, Chris and Vanessa explore what it looks like to move beneath the transaction in philanthropy—shifting from control and metrics to trust, relationship, and shared purpose. They discuss the principles of trust-based philanthropy, the role culture plays in nonprofit effectiveness, and why meaningful impact begins with how we choose to relate to the people we serve and support.

At its core, this conversation is about more than giving. It’s about the kind of leadership required to build trust, foster connection, and create change that lasts.

Because when philanthropy becomes relational, impact becomes transformational.

CHAPTERS

00:00 Introduction to Beneath the Transaction Podcast 01:45 Exploring Philanthropy: Intent vs. Transaction 04:19 Historical Context of Philanthropy 09:04 The Transactional Nature of Fundraising 12:05 Trust-Based Philanthropy: A New Approach 18:29 Power Dynamics and Fears in Philanthropy 25:36 Helping Organizations Find Their Own Answers 30:13 The Importance of Culture in Nonprofits 33:35 Investing in Culture and Human Connection 39:12 The Importance of Employee Retention and Culture 41:09 The Soil of Organizations: Culture vs. Outcomes 46:41 Building Authentic Relationships in Philanthropy 51:00 Leveraging Influence Capital for Community Impact 55:25 The Power of In-Person Connections 01:01:05 Authenticity as a Key to Meaningful Relationships

In this episode of Beneath the Transaction, Chris and Kenzie explore the role purpose plays in real transformation—both in our leadership and in our lives. Too often we focus on achievement and external success, but lasting transformation begins when we slow down long enough to ask deeper questions about who we are becoming and why we do what we do.

Joining the conversation is H Hassan, who has spent more than 21 years serving in public safety. Throughout his career, H has taken on a variety of roles, including training and developing law enforcement professionals and helping officers strengthen both their physical and mental readiness. He currently serves as a Firearms Training Coordinator, where he brings together discipline, leadership, and mentorship to help others grow in demanding environments.

In this conversation, H reflects on his own leadership journey and the impact of discovering and defining his “why.” Together, Chris, Kenzie, and H talk about the difference between surface-level change and true transformation, the role intentionality and commitment play in personal growth, and what it means to live and lead beneath the transaction.

At the heart of the episode is a powerful idea: purpose is the mortar of transformation. When purpose becomes clear, leadership moves beyond achievement and into the deeper work of becoming.

In this episode of Beneath the Transaction, Chris sits down with Olivia Hickerson, founder of EmpowerTactics, to explore the often unseen work of creating psychologically safe organizations.

Olivia has spent her career helping mission-driven organizations strengthen the systems behind their impact — from governance and organizational infrastructure to the cultures that shape how people show up at work. Her work focuses on translating values into structure so that culture isn’t left to chance.

Together, Chris and Olivia explore why psychological safety is not simply a leadership buzzword but a daily leadership responsibility. They discuss the unique pressures nonprofit leaders face, the emotional weight of mission-driven work, and how burnout often grows in environments where safety and support are lacking.

The conversation also unpacks the complex dynamics between executive leaders and boards, the courage required for vulnerable leadership, and how small, intentional actions can transform the environments people work in every day.

At its heart, this episode is about leadership posture — the way leaders show up, listen, and create space for others to thrive.

Because the cultures we build aren’t accidental. They’re shaped by the environments we intentionally create.

Key Themes in This Episode:

• Why psychological safety is foundational to healthy leadership

• The hidden burnout dynamics inside mission-driven organizations

• The relationship between board leadership and organizational culture

• How vulnerability strengthens leadership rather than weakening it

• Small leadership actions that create meaningful cultural change

• Why intentional structure protects culture from becoming accidental.

Guest Introduction:

Olivia Hickerson is the founder of EmpowerTactics, where she partners with mission-driven organizations to strengthen the systems behind their impact. She specializes in organizational infrastructure, governance clarity, and psychologically safe workplaces, helping teams move from reactive problem solving to intentional design.

Olivia is known for bringing steady strategy, thoughtful challenge, and practical clarity to complex leadership environments.

🎙️ Listen to the full conversation on Beneath the Transaction, and follow the show for more weekly conversations about life, leadership, and the work happening beneath the surface.

Chapters

00:00 Introduction to Psychological Safety 02:22 Olivia's Journey in Nonprofit Leadership 05:55 Experiencing Burnout in Nonprofit Work 12:32 Navigating Board Dynamics and Leadership Challenges 22:49 Creating Safe Spaces in Leadership 28:40 The Importance of Sequence in Organizational Culture 30:01 The Power of Vulnerability 32:28 Creating Safe Spaces in Leadership 35:19 Building Relationships with Board Members 39:05 The Ripple Effect of Change 52:04 Transformational Leadership and Human Connection

In this episode of Beneath the Transaction, we sit down with Kate Westerman, Senior Director of Operations Learning & Development at UNFI, to explore what truly shapes growth inside organizations.

Kate has built enterprise-wide training systems across complex operational environments — but what stands out most isn’t her portfolio. It’s her posture.

Together, we talk about why so much of what we call “development” becomes transactional — compliance-driven, checklist-focused, and disconnected from the people it’s meant to serve. Kate shares how suspending the ego, seeing learners as gifts, and cultivating accountability inside belonging changes everything.

This conversation is about more than training. It’s about the kind of leadership that forms people — not just processes.

If you care about building cultures where transformation is actually possible, this episode invites you to slow down and reconsider how you develop others — and how you show up in the process.

Because transformation isn’t delivered. It’s cultivated.

Thank you for listening! We don't believe transformation is a solo act. Follow along and join a community practicing what it means to Live Beneath the Transaction.

CHAPTERS

Chapters

00:00 Introduction and Context of Transformation 03:13 Kate's Background and Philosophy on Training 06:05 The Role of Ego in Leadership and Training 11:58 Transactional vs. Transformational Training 19:01 Creating a Culture of Accountability 27:57 The Importance of Relationships in Leadership 34:46 Rituals and Practices for Growth 40:04 Reflections on Personal Growth and Future Directions 56:53 Conclusion and Key Takeaways

Welcome back to Beneath the Transaction.

This week we’re joined by Sean MacMillan, VP of HR for Captain D’s and a leader deeply rooted in applied organizational and behavioral science.

Sean has spent years helping executive teams build leadership pipelines, strengthen employee experience, and translate culture work into measurable business outcomes — especially in high-pressure, frontline environments.

But this conversation isn’t about HR trends.

It’s about relationships.

Together, we explore:

• The difference between transactional and relational leadership

• Why transparency and emotional sharing build trust

• The role of vulnerability in shaping culture

• How small cultural gestures carry deep meaning

• The power of storytelling in connecting people

• Why consistency builds credibility

• And why growth always requires discomfort

Sean reminds us that culture isn’t shaped in grand declarations — it’s formed in daily interactions.

You can’t build trust from a distance. You can’t outsource vulnerability. And you can’t create accountable people without first creating safe, relational space.

If you’re serious about leadership, culture, or personal growth, this episode will push you to examine how you show up.

Because before strategy, before systems, before outcomes —

You have to go relational first.

It takes a Tribe to practice transformation. Let’s practice this together.

Chapters

00:00 Lost Footage and New Beginnings

01:07 Introducing Sean MacMillan

01:48 The Scope of HR at Captain D's

04:00 Passion for Culture and Human Experience

05:10 Transactional vs. Relational Dynamics

07:05 Building Trust and Relationships

09:34 The Importance of Vulnerability

12:36 Cultural Gestures and Their Meanings

15:14 The Breath of Life: Aloha and Connection

17:53 Transformational Leadership and Personal Growth

24:35 The Power of Storytelling in Leadership

29:12 Consistency and Emotional Sharing

34:10 Navigating Difficult Conversations

40:18 Embracing Discomfort for Growth

45:05 Overcoming Limiting Beliefs

48:59 Closing Thoughts on Potential and Best Efforts 49:37 podcast close 2-.mp4

Welcome back to Beneath the Transaction.

This week we sit down with Alix Prassas — an organizational effectiveness leader with more than two decades of experience in People & Culture, global organizational development, DEI, and change management.

But this conversation isn’t about frameworks.

It’s about the moments that shape culture quietly and powerfully.

Alix shares her journey from working in a family business to leading large-scale transformation efforts, and what she’s learned about trust, vulnerability, and accountability along the way.

Together, we explore:

• Why culture is formed beneath the surface

• How small leadership moments shape belonging

• Why vulnerability is a prerequisite for trust

• What accountability looks like when it’s rooted in relationship

• Why conversations around diversity require courage and openness

• And what it means to “have the conversation anyway”

This episode is honest. It’s practical. And it reminds us that transformation isn’t about bold declarations — it’s about consistent courage.

It takes a Tribe to practice transformation.

Let’s practice this together.

CHAPTERS

00:00 Introduction to Culture Change

01:58 Alix's Background and Journey

06:32 The Importance of Culture in Retail

14:34 Building Trust and Vulnerability

20:25 Navigating Difficult Conversations

30:58 The Role of Accountability in Leadership

40:28 Personal Stories and Lessons Learned

50:11 Final Thoughts on Culture Transformation

Welcome to Beneath the Transaction.

This episode marks a new beginning—not just for the podcast, but for how we want to show up in these conversations moving forward.

We start by naming something we’ve both been feeling for a while: how quickly life moves, and how easy it is to slip into a way of living and leading that’s driven by efficiency, outcomes, and transactions rather than relationship and meaning.

From personal moments of reflection to experiences that reshaped how we understand community and leadership, we share why this work feels urgent—and why transformation can’t wait until “someday.”

We talk about indigenous wisdom that has deeply influenced our thinking, including the idea that transformation is shared, breathed in together, and sustained through community. This is where the language of Tribe comes from—not as a buzzword, but as a reminder that none of us are meant to do this work alone.

We also introduce the Seven Conditions of Transformation, which guide much of our work and will continue to shape future episodes:

• Purpose

• Commitment

• Common Language

• Vulnerability

• Consistency

• Deep, Trusting Relationships

• Safe Space

These aren’t steps to complete. They’re conditions we return to again and again—at home, in leadership, and in community.

Throughout the episode, we reflect on the small moments that often get overlooked, but quietly shape who we’re becoming. The conversations we avoid. The relationships we rush past. The opportunities we have—right now—to choose intentionality instead of autopilot.

This podcast will feature conversations with leaders from organizations, communities, families, and faith spaces—but it will always come back to the same question: What’s being formed beneath the transaction?

• Why this podcast needed a re-beginning

• How transactional living slowly disconnects us from what matters

• Why transformation is a journey, not a destination

• The role of community in sustaining change

• How the Seven Conditions show up in everyday life

• Why urgency doesn’t mean panic—but presence

• What it means to build a Tribe rooted in belonging

This episode ends with an invitation—not to have it all figured out, but to begin paying attention. To stop wasting minutes that matter. To practice living beneath the transaction together.

If something in this conversation resonated with you, we hope you’ll stay with us. Share it with someone in your Tribe. And join us as we continue this journey—one honest conversation at a time.

Chapters: 00:00 A New Beginning 03:51 Life Is Moving Fast 09:18 Breaking the Transactional Cycle 12:48 Indigenous Wisdom & Shared Breath 16:11 The Seven Conditions of Transformation 21:01 Transformation as a Journey 25:03 The Power of Human Connection 41:37 An Invitation to the Tribe

Thank you for listening to The Rooted Leadership Podcast!

Today, we are honored to have Ryan Marshall with us, an experienced school counselor and dedicated advocate for student well-being. With a deep commitment to supporting students and educators through the challenges they face, Ryan has been at the forefront of crisis response and transformational leadership in his school district.

His work emphasizes the power of relationships, vulnerability, and truth-telling in the education system, and he’s been a key figure in driving meaningful change to better support both students and staff.

In today’s episode, Ryan will share his insights on navigating crises in schools, the shift from transactional to transformational approaches in education, and how the Groundwork program has played a role in enhancing the outcomes for educators and students alike. Get ready for an inspiring conversation that delves into the heart of what it means to connect, grow, and lead through times of fear and grief. This conversation explores the themes of crisis response in education, the importance of transformational leadership, and the need for deeper relationships between educators and students.

Chris and Ryan discuss the impact of recent crises on their school community and how their experiences have shaped their understanding of grief, loss, and the necessity for effective communication and support systems. They emphasize the importance of equipping educators with the tools and time needed to foster meaningful relationships with students, ultimately leading to better educational outcomes and community engagement.

Thanks for watching!

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