Meet Derek Olsen

What called you into this work?

Who I am and how I serve have been shaped by transformation. My own journey began in 2001 with what seemed like a simple desire: to get sober. That path led me through challenges that demanded more courage than I thought I had and revealed more strength than I knew I possessed. I learned how to ask for help, be honest and vulnerable, and embrace both the best and worst parts of myself. That experience clarified my purpose: to be as much of myself as possible, in service of others.

I empower people who empower people. Since joining Henley Leadership Group in 2008, I’ve had the honor of working with thousands of leaders across industries and at every level—from the C-suite to the front lines. I lead large-scale leadership development programs, facilitate team development and offsites, coach small groups, and work 1:1 with clients to help them grow.

What is your approach to coaching and leadership development?

Leadership is an act of faith, a belief in a better future, a commitment to possibility. It requires us to surrender to uncertainty, to lead with love, and to stay open to transformation.

In my work, I focus on helping clients stay present and mindful of their impact. We all lead, consciously or unconsciously, through every interaction, either building or eroding trust, either empowering others or giving them reasons to protect themselves. Leadership is about taking responsibility for both your intended and unintended impact.

When leaders deepen their awareness of themselves, they naturally shift how they relate to their teams and systems. That creates more resilient, more connected, and ultimately more human organizations. With greater courage, authenticity, empathy, and vulnerability, leaders become the people others want to follow.

What qualifies you to do this work?

• Certified Professional Co-Active Coach, Coaches Training Institute

• iEQ9 Integrative Enneagram Practitioner (individuals & teams)

• The Empowerment Dynamic & Triple Impact Practitioner

• B.A., University of Southern California

• Plus: countless workshops, retreats, trainings, counselors, and therapists; each one a chapter in my growth
  
  

What are you exploring and learning these days?

I’m committed to examining systems of oppression and my role as a privileged, white male in creating liberation, equity, and well-being on a larger scale. Over the last two years, I’ve read one book a month by authors from non-dominant cultures with Henley’s book club, participated in Whiteness @ Work, and deepened my listening to leaders whose voices are often marginalized.

What are you proud of personally?

I’m proud of the home my wife and I have created for our family. I’m proud that I can say I’m proud of myself, that I haven’t given up, and that I haven’t settled for what’s safe or familiar. I’ve worked hard to be who I am today, and I’m surrounded by people who’ve stayed with me on that journey. That’s everything.

What are you proud of professionally?

I’m proud of the moments that don’t show up on a résumé. Clients who found the courage to say the hard thing. Clients who set boundaries, spoke their truth, and stepped into roles that aligned with their passions. Clients who mended relationships or formed new ones. Clients who came out, brought their partners to work events, and let their teams know who they really are. I’m proud of clients who were willing to be uncomfortable in the name of growth and freedom.

What grounds your work?

A quote I return to often is from Rachel Naomi Remen:
“When you help, you see life as weak. When you fix, you see life as broken. When you serve, you see life as whole… Service is not an experience of strength or expertise; service is an experience of mystery, surrender and awe.”

That’s what this work is for me; a humbling, awe-filled invitation to serve.