When the world feels divided and uncertain, great leadership matters most. In this episode of The Space In Between, tech CEO and leadership wisdom-keeper Everett Harper joins me for a candid, deeply human conversation about leading with integrity in challenging times. Everett reflects on his journey as a trailblazer in sports, college, as an African American tech CEO, and on his track record of innovation in his remote-first company, Truss. He shares insights from his book Move to the Edge, Declare It Center, along with practical tools like the “pre-mortem” that help leaders navigate complexity, build trust, and connect across differences. We also explore ways leaders can improve effectiveness by making time to center and ground ourselves using simple, non-time consuming practices. This conversation is both practical and inspiring—a guide for leading with courage, clarity, and purpose in challenging times.
From Lifetime of “Firsts” to Pinnacle of Leadership
Everett’s passion for navigating complexity stems from a lifetime of being “the first or the only” in many spaces—whether as the first Black student in a class, the first in his family to attend college, or one of the few Black tech founders in Silicon Valley. These experiences built his ability to detect patterns, connect across differences, anticipate and adapt to shifting organizational and societal dynamics, and hone his ability to build deep connections with a wide range of people.
His experiences also formed the genesis of his leadership philosophy which he captures in his groundbreaking book —Move to the Edge, Declare It Center—. We explored the title and what it means and Everett broke it down into two, simple concepts:
- Move to the Edge → refers to stepping beyond your comfort zone into the space where learning and innovation happen. This might mean trying a new business model, experimenting with a process, or collaborating across divides.
- Declare It Center → refers to once you find something that works, build the repeatable systems and cultural practices that make it sustainable.
This philosophy is as relevant to teams and organizations as it is to personal growth, and we discuss some examples of how each work.
Our conversation deepens as we reflect on how the world feels even more uncertain and polarized today than it did during COVID. Everett emphasizes the critical importance of leaders making time—every day—to center themselves, focus on the few issues that matter most, and avoid getting swept up in the intense fragmentation around us. The practices in his book, and those we discuss in the episode, offer practical tools to do exactly that.
Methods are Practices: Try the Pre-Mortem
One standout tool from Everett’s playbook is the pre-mortem—imagining a project has failed, then working backward with your team to uncover what went wrong. We discuss how he has used this with Truss project teams and even with clients and learn how what can initial start out as ‘oh no, that would be horrible’ actually transforms into a powerful, and practice way to drive alignment and energize participants. The reason is that a pre-mortem, done well, surfaces risks early, when they’re easier to address. The conversations also build trust by allowing people to name fears openly. And, it fosters agency and creativity, even in while considering high uncertainty.
The take away: a pre-morem is a deceptively simple way to replace fear with problem-solving energy.
Lessons in Making Remote Work more “Human”
Long before COVID, Everett’s company, Truss, was remote-first. The challenge wasn’t just about technology—it was about culture. Practices like Being Humans Together sessions (casual video calls for sharing personal stories) helped humanize the team and build deep trust, even without an office. These sessions were initiatied by employees and they remain a staple of Truss’s culture.
Everett notes a few other practices that help with remote work, and acknowledges that there are times when face-to-face is invaluable. All companies are unique and should assess their needs in terms of remote-first, or partially remote.
When the ‘Center’ is Expansive
Leigh and Everett discuss how the ‘center’ isn’t a static place but rather should be where systems and processes are used, adapted, and innovated on. Leaders who cling tightly to their “center” undermine ability to learn, adapt and collaborate across differences.
Shared goals—even between unlikely allies—can create surprising coalitions. The space between perspectives is often where the most powerful innovation emerges.
Bright Spots in a Fractured World
I asked Everett about places where he gets personally bolstered and inspired and he gave two examples. The first is with his work as a board member at CARE, which is a prominent and impactful global NGO that does work to help build communities, especially by empowering women and girls, as a path to stability and peace. He noted that the board is made up of democrats and republicans and they don’t have ideological ‘hats’ on during their work together. Instead, they follow the data and tried and true programs that lift communities in sustainable ways. CARE is a model for all organizations to follow.
He also pointed to the work his company has done with the IRS Direct File project. IRS Direct File is a government service build by Truss that made tax filing simpler, faster, and free, building trust that the government can have modern, adaptable and helpful online systems for citizens. The platform is free which means folks don’t need to pay money to get helpful tax help, and for many people saving the $100 that a vendor like Turbo Tax might charge results in very concrete, tangible progress. While the new administration may end up cutting the program, Everett still sees the platform as an example of how the government can bring cost-effective ways to serve people.
A Wish for Leaders Everywhere
Everett’s parting advice is refreshingly simple:
- For daily practice: Start small—write down three things you’re grateful for each day for a month.
- For catalyzing change across systems: Create communities where our edges are dynamic, our centers are expansive, and collective wisdom can flourish.
Leadership in uncertain times isn’t about having all the answers—it’s about staying open, building trust, and creating systems that help people thrive. As Everett shows us, when we move to the edge and declare our center with intention, we create not just stronger organizations, but stronger communities.
📖 Learn more in Everett Harper’s book Move to the Edge, Declare It Center.
