Beneath the Transaction

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.

Because when philanthropy becomes relational,

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00:00 Introduction to Beneath the Transaction Podcast

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.

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

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.

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

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.

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.

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 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:

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.

Chapters:

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!

🚀 Ready to Ignite Your Leadership Journey? 🚀

At Groundwork Leadership Institute, we’re all about transforming leadership to create a real impact. 🌟 

Our vibrant courses and local cohorts in Salem are designed to supercharge your growth—whether you’re aiming to elevate your personal leadership or boost your organization’s potential.

🔥 Exciting News! We’re launching a brand-new cohort on October 25th! This dynamic hybrid program kicks off with an in-person, one-day transformational workshop, followed by 5 powerful coaching calls. Get ready to start the new year with unstoppable momentum and transformative goals!

💥 Dive into our self-driven Transformational Leadership Accelerator course, uncover the SECRET to unlocking your best leadership self, and build a foundation for lasting, positive change. 

Don’t miss out—join us and share this episode with a friend who’s ready to take their leadership to the next level! 🙌✨

In this conversation, Chris and Jason discuss the importance of philanthropy and the impact it can have on individuals and communities. Jason shares personal stories of how he was influenced by his parents and early experiences to care about doing good and helping others. They explore the challenge of maintaining the essence of philanthropy as it evolves over time and generations. They emphasize the need to stay connected to the people being helped and to avoid turning philanthropy into a transactional process. The conversation highlights the transformative power of philanthropy and the joy that comes from giving and serving others.

We hope you liked this episode! Please like and share to support our show. You can also watch some of our most recent episodes here on our youtube channel @groundworkleadership under Rooted Leadership Podcast Highlights.

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Thanks for watching!

Exciting News! Our TEDx Talk on Transformational Leadership Drops This Month – Stay Tuned!

Check out another series on my youtube channel: Life and Leadership | Chris Pineda, Groundwork Leadership https://www.youtube.com/playlist?list=PL1GuQtiEuoFzThLWg-bhKijGzbW09rR18. Chris Pineda Keynote Speeches https://www.youtube.com/playlist?list=PL1GuQtiEuoFxx-CEiBPcTMtiG0RiQfs1R. The Rooted Leadership Podcast Highlights https://www.youtube.com/watch?v=s5nk5lqfZBw&list=PL1GuQtiEuoFxA6LOsow8SdRKDPZg2Ln3e. Groundwork Leadership's Client Success Stories https://www.youtube.com/watch?v=DsY_liF4qw4&list=PL1GuQtiEuoFwMy3QjRVhOEMAPsyfPm_4b. __

Over the span of 5 years Groundwork Leadership has been working with local leaders across industries (philanthropy, faith, government, education, non profit, and business) to raise the tide of leadership in our community. Our services include: Local Leadership Cohorts, Business Retreats, Full-Day Workshops, One-on-One Coaching, Organizational Assessments, Online Courses, and Large Keynote Speeches.

I am Chris Pineda and I am the CEO of Groundwork Leadership. Our mission is to help individuals, organizations and communities grow a more collaborative culture and break free from transactional behaviors and mindset.

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Follow us on Facebook at - Groundwork Leadership Follow us on LinkedIn at - Groundwork Leadership, Chris Pineda Follow us on Instagram at - @groundworkleadership, @transformwithchris Follow us on TikTok at - @transformwithchris, @groundworkleadership Download our Podcast - The Rooted Leadership Podcast found on apple and spotify! Visit our Website - www.groundworkleadership.org

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If our message resonates with you please reach out to [email protected].

Thanks for watching! Please help us share our message by sharing this episode with a friend.

Exciting News! Our TEDx Talk on Transformational Leadership Drops This Month – Stay Tuned!

The Rooted Leadership Podcast explores topics of leadership, culture, and conflict. The host, Chris, and guest, David Whippy, discuss their friendship and background in peacebuilding. They emphasize the importance of creating safe spaces for dialogue and learning in conflict resolution. They also highlight the need to understand the root causes of conflict and address the underlying needs and values of individuals involved. The conversation touches on the significance of recognizing expertise on the ground and involving stakeholders in the process. They discuss the concepts of Talanoa and Veivosaki-yaga, which involve open discussions and in-depth conversations to build relationships and address conflicts. The conversation explores the importance of having a common language in conflict resolution and creating a culture of peace. Indigenous practices are highlighted as valuable tools for building understanding and connection. The speakers discuss the significance of language and values in creating a common ground and fostering effective communication. They also emphasize the role of individuals in being the solution to conflict and the importance of honoring and learning from indigenous cultures.

New to Groundwork Leadership? 

Over the span of 5 years Groundwork Leadership has been working with local leaders across industries (philanthropy, faith, government, education, non profit, and business) to raise the tide of leadership in our community. Our services include: Local Leadership Cohorts, Business Retreats, Full-Day Workshops, One-on-One Coaching, Organizational Assessments, Online Courses, and Large Keynote Speeches. I am Chris Pineda and I am the CEO of Groundwork Leadership. Our mission is to help individuals, organizations and communities grow a more collaborative culture and break free from transactional behaviors and mindset.

Like and share our podcast!

You can find highlights of this episode on our socials below.

Follow us on Facebook at - Groundwork Leadership

Follow us on LinkedIn at - Groundwork Leadership, Chris Pineda

Follow us on Instagram at - @groundworkleadership, @transformwithchris

Follow us on TikTok at - @transformwithchris, @groundworkleadership

Download our Podcast - The Rooted Leadership Podcast found on apple and spotify!

Visit our Website - www.groundworkleadership.org

WE ARE LOOKING FOR PARTNERS! If our message resonates with you please reach out to [email protected].

Join us for a captivating episode featuring Chad Ford, esteemed global mediator and bestselling author of "Dangerous Love." With unparalleled experience in resolving conflicts across the globe. We also have two new guests on the show: Jessica Otjen and Hassan Hassan who are alumni of Groundwork Leadership.

Our alumni are going to have the privilege of asking Chad some interesting questions about his work around the globe as a conflict mediator and professor. He shares profound insights from his book, Dangerous Love and the lessons he's learned from different cultures around the world, specifically the Pacific Islands. Prepare to be inspired and enlightened as Chad's wisdom encourages you to cultivate intentional relationships and embrace the transformative power of empathy and understanding. Tune in for an unforgettable journey towards greater compassion and connection.