HELLO

Rickie Singleton 

He/Him

LinkedIn

 

Meet the Leader

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Rickie Singleton is a Future of Work strategist, program management executive, and AI ethics advocate who bridges operational excellence with inclusive leadership. He helps organizations and communities think critically, adapt to rapid change, and design futures that are both innovative and equitable.

 

Restorative Leadership Interview Questions:

 

Question 1: What helps you stay creatively courageous when the world feels threatened/like it’s on fire?

 

What keeps me creatively courageous when the world feels like it’s on fire is remembering that world threats aren’t new. Humanity has faced disruption before, and with it comes the possibility of renewal. Crisis doesn’t weaken imagination; it forges it.
For me, courage shows up in how I lead. I don’t focus on the systems that are crumbling; I focus on the future we’re building. In my work at the intersection of AI ethics, critical thinking, and the Future of Work, I see every disruption as an invitation to respond differently, think differently, to create differently.

The real work is resisting the pull to shrink, to conform, to let urgency dictate every move. Instead, I protect space for possibility, for myself, anyone I work with, and my community. That’s where radical imagination lives. And when we choose to hold onto it in the middle of a crisis, we’re not just surviving the fire, we’re shaping what comes next.

 

Question 2: Describe a time when your imagination helped you move from fear into action.

 

When I was asked to build a new IT services group with zero revenue on the books, the fear was real. What if I failed? What if the vision didn’t take hold? But instead of letting fear freeze me, I leaned into imagination. I asked myself: What if we could create something that doesn’t exist yet? What if this challenge is an opening to reimagine how services are delivered? That shift unlocked bold action. We built a PMO from scratch, cultivated a culture of resilience, and within three years scaled that vision into a $500M business unit. That moment taught me that fear points to where imagination is most needed. Even now, whether I’m leading conversations on AI ethics or rethinking the Future of Work, I treat fear not as a barrier but as an invitation to imagine bigger.

 

Question 3: What does growth and holding space look like for you after a loss or rupture? 

 

Growth after loss starts with slowing down. Too often we rush to fix, but I’ve learned the first step is making space, space to name what was lost, space to let people feel it, space before moving forward. I don’t see ruptures as the end of the story. I see them as places where resilience can be rebuilt. In practice, that has meant creating circles of listening after hard transitions, spaces where people could be honest about the pain before we started talking about the future. At a former company, this approach helped open the door for deeper equity work after difficult moments. For me, holding space isn’t passive. It’s a deliberate act of leadership, honoring what was broken while daring to imagine what could be built in its place. That’s where true growth begins.

 

 Question 4: How do you protect space for imagination in your team or community? 

 

I treat imagination like oxygen, not optional, but essential. The challenge is that a created sense of urgency often tries to suffocate it. So, I intentionally create pauses where imagination has room to breathe.
In team settings, that has meant carving out time where efficiency isn’t the goal, openness is. At one of my last companies, I hosted listening sessions where people could surface bold ideas without fear of judgment. In my mentoring work, I encourage people to dream beyond the limits they’ve been told to stay within. In my AI ethics discussions, I ask teams: What future would you design if nothing stood in the way?
Protecting imagination means drawing boundaries around time, modeling vulnerability, and showing that creativity isn’t a distraction; it’s the work. And when people feel that safety, they start to imagine not just tweaks, but whole new futures.

 

Question 5: What rituals or practices help you (and/or your team/community) name what hurts while still holding on to what’s possible? 

 

I’ve learned that one of the most powerful practices is naming both truths at the same time, what hurts and what’s still possible. That balance keeps us honest but also keeps us moving.

In practice, I use tools like listening sessions and reflective exercises. At one of my former companies I worked at, we asked people directly: What’s weighing on you right now? And what do you still hope for? Writing those answers side by side created a powerful shift; people could see that hurt and hope weren’t opposites; they could coexist.

That’s how I approach leadership in any space: give people permission to tell the truth about their pain, but also give them permission to imagine beyond it. When both are held together, imagination doesn’t feel naïve; it feels necessary.