James-Olivia Hillman


  • Coach
  • Speaker
  • Workshop Facilitator

James-Olivia Hillman is a relational leadership speaker, a nurturer of disobedience and regard, and a facilitator of exquisitely uncomfortable conversations. She brings relentless compassion, an unusual perspective, and an eclectic variety of tools to the conversation of expanding our lives and leadership beyond personal development and into relational thriving.


Difference & tension hold possibility. Right Relationship nourishes. More you is better.

Authentic Leadership Emotional Intelligence Emotional Intelligence and Empathy Empathetic Leadership Empathy Speakers Equity Consciousness Interpersonal Dynamics Latinx/Hispanic Speakers Leading with Vulnerability Speakers LGBTQIA+ Speakers Negotiation and Self-Worth Personal Empowerment Relational Leadership

Popular Talks

Supremacy Culture’s impact on our most important relationships

Skills for relating competently to difference when the stakes are high

Congruence: Bringing yourself (and staying with yourself) in challenging conversations

Workshops & Coaching


Skilled & Sovereign
A relationship skills intensive for humans who want to connect deeply, interrupt their own relational fuckery, communicate cleanly, be more themselves, and relate competently when difference is present and the stakes are high… at home, in their organizations and businesses, in community, in conflict and in love.

Supremacy Culture & Relational Fuckery
A slow, two-day, intimate, in-person conversation exploring the ways we perpetuate supremacy culture in our most important relationships — and what we can do to uproot contempt and create more peace & joyful connection and less suffering in our communities & organizations, friendships & families, our partnerships, parenting, politics, and professions.


The most accurate descriptor comes from a client who wrote: “These are the best conversations I ever have with myself.”

“James-Olivia is who you want to work with when you want to be LOVED, HEARD and GUIDED into understanding the intersections of disconnection we’re ingrained in — fully and deeply. They are incredibly gifted at listening to the experiences of your life and helping you dissect and dismantle the lies of limitation and cultural programming that separate you from moving towards embodying your realness in our society.”
— Ash Johns

“It’s always amazing to talk to James-Olivia. They tell you the truth, they are always surprising, and they’re willing to hold your hand while leading you into places that may be uncomfortable for you. If you want truth and surprise, without being pandered to, these are conversations you need to have.” is what I would say to other people. But for me, I basically just wish these conversations would never end.”
— Tiana Dodson

“James-Olivia and I met in 2010 and I am forever grateful for the ongoing opportunity to learn and grow alongside this humble and hungry soul. I found James-Olivia at a time where my mind and body were experiencing a disconnect. James-Olivia has the skill to guide one’s inquiry inside and utilize personal accountability to motivate change, empowerment and balance. I continue to lean on James as part of my village. I cherish the unfiltered perspective, transparent communication and humility they brings to our shared space.”
— Christina Garcia, Co-Founder C Scape Foundation

"I immediately felt at ease with James-Olivia, even though we were virtual strangers."

James-Olivia Hillman teaches skills for relating competently to difference and facilitates and mediates uncomfortable, necessary, life-changing conversations with people who want more joy and connection and less suffering in their most important relationships—with themselves, their loved ones, their organizations, and the world.

They come to the work of living and leading relationally with the lived experience of moving through life in the U.S. as an autistic, multi-racial and sometimes white-presenting “other” with many other intersecting privileges and marginalized identities.

James-Olivia brings relentless compassion, an unusual perspective, and an eclectic variety of tools to the conversation of expanding our lives and leadership beyond personal development and into relational thriving.

She is “learning and unlearning alongside you. I make mistakes and dissect them openly. I give zero fucks about goodness (yours or mine), and have far more interest in the full spectrum of our humanity and our ability to be with, celebrate, and discover possibility in discomfort, uncertainty, and difference.”

Let’s collaborate to ensure a transformative experience.