A Conversation About Emerging Leadership with HLG’s New COO, Shanon Olsen
Photo Credit: J.M. Jardine
We’re entering an exciting new chapter at Henley Leadership Group—and who better to help shape this moment than our newly appointed COO, Shanon Olsen? In a candid conversation, Shanon muses about the complexity of the COO role, the deep trust and mutual respect that ground Henley’s work and her vision for cultivating ease, flow, and joyful growth in the midst of these deeply uncertain times. She also shares her insights on what emerging leaders need to thrive, her own path to leadership development and the wisdom she’s gained from mentors like Dede Henley and Carol Zizzo throughout her long history with the company.
You’ve been part of the HLG for years. What has surprised you most about stepping into the COO role?
To be transparent—maybe even too transparent—I wasn’t necessarily called to this role. Yet, when I looked at what the business needed in this moment of transition, I found myself saying yes. I also know that, as leaders, this is what we do. We find ourselves taking on roles not because they’re a perfect fit, but because we care deeply about the work, the people, and the mission. We step in where we’re needed, trusting that we’ll find our way as we go.
As for surprises? It’s the sheer scope and complexity of what I’m holding. Trying to get my arms around the entire business—as small as we are—has been no small feat. I’m also holding the majority of sales and marketing and doing my best to keep my eyes and heart on everything.
What do you think is core to Henley’s DNA — and what are you excited to grow or change moving forward?
At the core of everything is a deep, internal trust. No matter the circumstances—and we’ve weathered plenty, from the exciting to the traumatic to the uncertain yet inspiring—there’s always been this steady belief that we’ll figure it out. That trust extends to one another on our team. There’s a deep mutual respect among us. We don’t always have a clear roadmap, but we trust the process and our ability to find our way together. We trust that if we keep doing meaningful work with our clients—and within ourselves—clarity will emerge. Looking ahead, I’m focused on a simple question: How do we engage with this business with as much ease, flow, and joy as possible?
When I think about growth, I want a grounded and meaningful reason to expand. Growing just to grow doesn’t appeal to me. I know that when growth isn’t sourced from a clear purpose, you will experience loss of culture, burnout, and effectiveness. So I’m paying deep attention to the ways we might be working that no longer serve us—and how we can shift as we expand our work in the world. We’re in a season of paying close attention to what sustains us and pushing against norms and beliefs that have outlived their purpose.
We’re in a season of emerging leadership within Henley and across the world of work. What do you think is most needed from the next generation of leaders?
I see something remarkable in Millennials and Gen Z: they’re motivated by a desire for meaningful work, fulfilling lives, and enriching experiences. They want their time to count—and I deeply respect that. I hope they continue to grow into strong collaborators, thoughtful challengers, and partners within their organizations. Wanting change is powerful, and real impact comes from staying engaged through the often tedious season of transition to shape the culture you are most committed to. Each generation brings something valuable to the table. My hope is that emerging leaders continue to invest in their own development and remain committed long enough to leave a meaningful mark.
What helped you step into leadership when you were emerging in your career?
Back when I started as a subcontractor at Henley, I carried an entrepreneurial spirit. I approached the work like a leader of this company, holding myself accountable and generating new ideas to move this amazing place forward. I was fortunate to have mentors like Dede Henley and Carol Zizzo, who saw and nurtured that passion. The work genuinely mattered to me. I was given autonomy, room to be creative, and the freedom to lead. My ideas were welcomed, and I was treated like a future voice of the business, long before any title or role made it official. That experience left a lasting impression. It’s something I believe all senior leaders should consider: Are you listening to your emerging voices as if they are the future of your organization? Because they are.
Was there a moment when you felt the baton was passed to you?
When Dede had to step away suddenly due to a family emergency, I found myself in a co-leading partnership alongside Carol. This moment had nothing to do with title or role, but rather a keen awareness of what was needed and a dedication to ensuring that this company continues to provide the transformational work it is called to do. One of the values we’ve recently defined for Henley Leadership Group is generosity on behalf of what’s possible in the future. That’s what I did—I offered my time and energy because I believed in what we could become.
You’ve worked closely with both Dede and Carol. What have you learned from them that you’ll carry into your own leadership?
Carol is incredibly steady. When a hard decision needs to be made, she slows everything down until the most compassionate and kind approach becomes clear. Carol insists on aligning with values before acting. Dede is a relentless learner—she’s been in personal and professional development her whole life. She modeled what we encourage in executive leaders: if you’re leading, you should be learning—always. She still is!
Henley talks a lot about leadership from the inside out. How do you personally ground yourself in your values and purpose as a leader?
I’m a sensing, intuitive, feeling, instinctive person. I know I’m out of alignment with my values or our mission when I’m crabby, tired, cynical, or questioning everything. That’s a signal I’ve lost my connection to the “why.” So I do my best to stop and get curious about what I need to return myself to what is possible. I need that space to get quiet, and reconnect with the big picture. One of the best ways for me to reconnect is to be with clients. When I’m in the room, engaging in our work, it’s impossible to be disconnected from Henley’s purpose and values. Even our First Friday webinars help me get grounded.
What are you most hopeful about right now — for Henley, for the world of leadership, or for yourself in this new chapter?
I’m excited about building a strong community—both within our team and with our clients. In a world that feels disconnected, community is a powerful answer. It provides support, learning, and growth. I want us to double down on that sense of connection in the years to come. I’m also excited to see who will join us next, especially younger talent who will bring fresh perspectives. I love the idea of being part of something that evolves, that can shift and adapt quickly—like a jet ski rather than a slow-moving barge. That sense of agility and possibility keeps me energized.
What’s something people might be surprised to learn about you, either at work or outside of it?
I’ve been in the learning and development space since I was 14 years old. I immersed myself in transformational learning from a young age, thanks to my family. Early roots in learning, development, and transformation attracted me to a wide variety of things I’ve done for the sake of transformation: the Camino {de Santiaga} in Spain, a 10-day Vipassana retreat, traveling alone, weird workshops, fortune tellers, marriage, parenting, dancing! It’s all interesting, and what I long for most is radical experiences of change. I love things that make me feel different on the other side. Why not? Give it all a go!
Shanon’s reflections remind us that leadership is both a responsibility and an opportunity, anchored in trust, shaped by self-reflection and learning, and connected to purpose and a bold vision. She rarely takes the easy path, choosing instead rigorous soul-searching, unflinching truth-telling, and always asking the hard questions that build a stronger, more intentional future.
Shanon’s story reflects the kind of leadership we nurture—honest, human, and deeply committed to impact. If you’d like to learn more, we invite you to subscribe to our newsletter, join our (free!) First Friday webinars, and connect with a community that’s redefining leadership, one conversation at a time.
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