DEI Journey: Interview with Willie Jackson

Willie Jackson

Willie Jackson

The DEI Journey series spotlights the folks behind the work here at ReadySet. The team comes from different backgrounds and areas of expertise, and we’re excited to share a bit more about ourselves with you.

What do you bring to your work as a DEI practitioner?

My approach to DEI is deeply grounded in my identity is a black man. And the journey of learning, understanding, and exploring what it means to have the identity that I have continues to this day. Sitting with the paradox of having a historically marginalized identity while also moving through the world with a tremendous amount of freedom and privilege allows me to cultivate ever more compassion and empathy for others.

What has most surprised you in your DEI work and journey?

Doing the internal work allows you to hold space for others that can’t be replaced by intellectual knowledge or a general concern for your fellow man. Beyond an awareness of history and culture, an understanding of how trauma (and adaptations to it) are passed along from generation to generation is invaluable. The story of mankind over time is at bottom a story of overcoming and resilience and an orientation towards the power structures present in any given society. Understanding the embodied aspects of this work and also the historical, sociological, and anthropological implications of the human experience can be a superpower.

What might surprise folks to learn about you?

Despite making a living in some fairly extroverted ways—leading workshops, giving talks, and so forth—I’m a card-carrying introvert and quite shy in some contexts. It helps that I love people and come alive with a microphone, but I enjoy retreating into a dark corner after I deliver a workshop or talk.

What book or books should folks read in order to better do this work?

  1. Slavery by Another Name by Douglas A. Blackmon

  2. The Half Has Never Been Told by Edward E. Baptist

  3. Lies My Teacher Told Me by James W. Loewen

  4. The Fire Next Time by James Baldwin

  5. The Case for Reparations by Ta-Nehisi Coates

  6. Childhood Disrupted by Donna Jackson Nakazawa

  7. Hillbilly Elegy by J.D. Vance

  8. Tribe by Sebastian Junger

  9. Just Mercy by Bryan Stevenson

  10. The War of Art by Steven Pressfield

What’s something that’s often overlooked, but important for companies and organizations to get right?

In addition to support from the top, you need courage and vision to do this work. There are fundamental best practices that DEI practitioners can generally abide by when looking to maximize the impact of their work, sure, but many of the skills needed to advance inclusive programs require a strong resolve and a clear understanding of what animates your motivation—this work takes guts, and every battle isn’t worth fighting.

What are you most proud of?

Learning to be kind to myself. Self-compassion allows me to extend goodwill towards others.

What worries you?

I think there’s a felt sense among educated professionals that the passage of time is synonymous with societal progress. The more I study history, the less I’m convinced that this is true.

What’s your superpower (or area of expertise) as a practitioner in this space?

Driving and facilitating conversations that are both challenging and accessible to a wide range of audiences. That’s my jam.

How can leaders better support DEI work and initiatives?

There are obvious things that anyone will tell you—more budget, more headcount, more trust—but I think more leaders need to become students and ground themselves in the practice separate from their operational roles in organizations.

You need to be a skilled operator and an expert and interpersonal dynamics for sure, but you also need to understand what it’s like to hold space for folks day in and day out.

Who or what inspires you?

Ralph David Abernathy, Sr. There would have been no civil rights movement without him, and not enough people know his story.

Willie Jackson