In the last 10 minutes of an executive session I was leading, I had to make a decision. I wanted to tie a nice bow around the morning and give the group a preview of what our following conversation would entail. But I couldn’t.

“Is this working for you all? It doesn’t feel like this is worth your time.”

You could hear a pin drop.

We still had several more sessions left in our contract, and few leaders wake up in the morning expecting their trusted advisor to try and fire themselves. I gave them a moment to process, and several of them thanked me for having the courage to speak up and invite some real talk before we dismissed.

In the immediate aftermath, several team members went out of their way to ensure I didn’t feel discouraged about the progress of our work. But the truth is that I had never felt more confident in my work and ability to make change.

I’ve been a consultant for my entire career, and I’ve been facilitating executive sessions for nearly a decade. What comes with that experience is a clear understanding of when and where my work is most effective. A lot of it has to do with personality fit, but other factors are equally important: how the team make decisions, how comfortable they feel speaking up, and how open they are to change.

I went in with high hopes, but sometimes our ambitions don’t survive contact with reality. That’s normal. What we do with this realization is up to us.

It would have been a lot easier not to rock the boat, but I was unwilling to trade short-term comfort for long-term misalignment. The outcome? We decided to repurpose the remaining sessions for work with their people managers—work that everyone is excited for me to deliver.

What’s more: the client sees me embodying my values of authenticity, speaking truth to power, and being open to finding creative solutions.

I went to school for Information Technology, and I was among the first to graduate from FSU’s College of Information with that degree. Previously, it was the School of Information, focusing on Library and Information Science. I had good timing.

My first love was medicine—my mom was a nurse, and I still fantasize about completing a medical anthropology doctorate—but my father wisely nudged me in a more practical direction, aligning with my aptitude for technology. In truth, I had no idea what the pursuit of medicine required at the time, and tech was undoubtedly the right specialization for me.

I’ve always been fascinated by web publishing, and I recall looking up williejackson.com in school to see how much it would cost to register the domain. It was an eye-popping $500 for some reason, but I checked back regularly and managed to snag it for a much more reasonable $50 months later.

I still remember my first website and my obsession with the HTML and CSS that brought it to life. I turned that obsession into a freelance web design business after friends coveted my shiny new web presence. I never made retirement money, but I learned about sales, marketing, pricing, and eventually web hosting, which ultimately led to a Director of Web Optimization role. Invaluable.

Anyway, I recently overhauled my website after putting it off for years, and I’m really happy with how it’s coming together. It’s not “finished”—websites are never finished—but it’s live, and I’m happily neck-deep in details that most people will never notice or care about.

And that’s fine by me, it’s just great to be back at it.

Earlier this year, I was facilitating a session on authenticity—a squishy and nebulous term that I had seen used unhelpfully for years. My workshop was well-researched, and I felt prepared, but I still had more than a few misgivings about the topic going into it.

On a lark, as I was putting the session together, I included quotes on authenticity from three very different people. And for reasons unknown, this really section struck a chord with the audience. You could palpably feel the excitement and engagement growing in the room. The session had come alive. The room had come alive. People had a lot to say.

This isn’t an uncommon experience, but it’s always a turning point when I’m presenting something new. I never know when the moment will come, but it’s always a relief when it does. Yes, it felt validating for my experiment to pay off. But the real magic was learning from the audience what authenticity meant to them.

The not-so-secret secret that teachers know is that what looks like the sharing of knowledge is actually them saying, “Here’s something interesting that I’ve learned, what do you think? Is there something interesting here for you?”

There was. There usually is.

About a decade ago, I was meeting with a new client in Manhattan about a project. We were similar in age, shared hundreds of mutual friends, and the project had all the trappings of an experience that would forge a lasting relationship.

There was a lull in the conversation as our kickoff meeting was winding down, and to my utter bewilderment, he started making a series of racial jokes. Not in an exploratory, test-the-waters kind of way—it was a rapid-fire I’ve-been-waiting-for-this-moment vibe.

The jokes weren’t especially offensive, but they were nonetheless shocking and unwelcome. The client happened to be a white guy, but equally important is the fact that this was our first meeting. We had nothing close to the kind of rapport that would make his comments okay.

I didn’t have the patience or sophistication to address it diplomatically, so I asked him what the hell was going on. His face sank as he turned fire engine red.

He sheepishly explained that his primary exposure to black men was as a high school football player, and their way of relating to each other was to crack predominantly racial jokes. He assured me that no harm was intended and that he only meant to poke a little good-natured fun.

Finally, it made sense. Bless his midwestern heart.

Understanding his point of reference and intent allowed me to soften my reaction and view him with compassion; he was doing the best he could using the tools he had and simply trying to connect with me.

It’s easy to believe that people around us harbor animus and overt bias—we’re all living through a destabilizing period of polycrisis—but this makes the need for connection, courage, and community even more urgent.

This week, I delivered a Global Black History Month session for a client I’ve been working with since 2022. The story goes back to 2020, when many organizations were dealing with the racial reckoning following George Floyd’s murder. Sarah saw my MAKERS keynote about the ally skills framework I helped create and reached out on LinkedIn, thinking she’d never hear back. We had our first call 10 days later and our first project 60 days later.

My work as a speaker, consultant, and facilitator isn’t possible without partners advocating for me in rooms I don’t yet have access to. And it’s not like I’m speaking about standard business topics like sales and marketing—I’m often steadying the hand of leaders looking to navigate the tumultuous terrain of race, gender, and difference more generally.

I could write a manifesto on the role an external speaker like me plays when being brought in to deliver a timely message, but here are three that have served me:

• Know your audience: When working with an array of constituents across an organization, I will show up differently in a meeting with the CEO than in a meet-and-greet with the organization’s Black ERG (Employee Resource Group). I’m not a different person on these calls, but the message I’m bringing has to address a different set of unspoken needs.
• Share the spotlight: in my address this week, I asked for brief, recorded videos of two employees in the NYC and London offices talking about their career highlights and challenges. The audience loved this format from a stagecraft perspective and in providing global visibility for people who had the courage to speak personally about their professional experiences.
• Read the room: the worst thing you can do as a speaker is offend your host, and the second worst thing is being forgettable. Dancing without a net is my specialty; audiences appreciate it when you take risks.

But mostly, my job is to make the people who hired me 1) look good and 2) feel glad that they brought me in.

Today marks my 40th revolution around the sun. To celebrate this milestone, I’m launching something new. But first, a story.

In 2016, I lived in Harlem and ran a small media company. I had been at it for a while and the daily grind of publishing other people’s writing for a living was losing its appeal—to say nothing of selling sponsorships against that writing to keep the lights on. I was bored and desperately needed a new challenge.

Around the same time, I learned that WeWork was opening an office in the neighborhood. It was long before the company’s spectacular implosion, and the news of their arrival had the streets buzzing: one of the hottest and fastest-growing startups was descending upon Harlem, replete with all the uncomfortable racial and economic optics one would expect.

I met with the team leading the charge and they were armed with well-rehearsed talking points about looking to build with Harlem. To soften the landing, they were clearly looking for some socially connected locals to partner on a few events with. At the time, WeWork was producing tens of thousands events around the world, and had it down to a science.

I pitched my idea, and we executed my vision in fifteen days. It was a flat-out sprint. Boredom: vanquished.

I wanted to showcase Harlem’s rich history and dynamic residents, so I decided to moderate a panel. I assumed that many of the people I asked to sit on the panel would be out of town, uninterested, or unavailable, so I made eight simultaneous requests. They all came back in the affirmative, so after weeping silently as my inbox produced a rapid stream of excited yeses, I prayed to Oprah and strapped in for the grand social experiment that I had inflicted upon myself.

Two weeks of pure adrenaline ensued, culminating in an oversubscribed event with nearly 300 RSVPs. We had to turn off reservations because the venue couldn’t accommodate more people. New and used friends came from as far away as California for the evening, and I still vividly remember the energy in the room. It was electric.

The upshot is that we took the Harlem WeWork office from 50% to 75% sold with that one event. The stress was astronomical, and I remember lying on the floor and vibrating with overstimulation that night when I got home. In retrospect, I was merely dehydrated, but I reported back to my advisor in a dramatic fashion the following week that I was getting out of the events business. I shared that I didn’t enjoy the experience and wanted to stick to publishing.

He looked at the event photos and the scale of my accomplishment and dismissed my complaint. “The event wasn’t for you. And what you did was hard.”
“No kidding,” I said to myself in French. But he was right. And I was hooked.

Over the years, I’ve produced and hosted events that reached thousands of people across four countries, from informal meetups in Argentina and intimate dinners in Paris to sponsored rooftop mixers in Oakland and networking events on Wall Street.

“To achieve great things, two things are needed: a plan and not quite enough time.” —Leonard Bernstein

After leaving my job last year, I had some big decisions to make—not just about what I wanted to do for a living but also how I wanted to spend my time. But instead of seeking out something new and novel, I noticed my instincts in the immediate aftermath.
I started writing, making introductions, and planning events to host. Absent the familiar routine of a job to create imaginary obstacles, I found myself putting pen to paper and laying the groundwork for…an events company?

Introducing Power Circle Events

Power Circles create the conditions for people to connect more deeply than they typically do. Magic happens when a group of people give generously of their time and attention, looking for ways to advance a conversation, someone’s journey towards a goal, or simply being more present to what someone has to say.

And a memorable experience can reliably take shape with careful planning and facilitation. Based on 15 years of bringing people together, here are three essential elements of a Power Circle:

• Connection: we’re social primates hardwired for connection—meeting the right person at the right moment can shift the arc of our lives
• Community: finding our place and voice in the world—even and especially among people we may disagree with—can clarify what we stand for and what’s worth doing
• Courage: the stakes may feel higher than ever, but showing up despite this inspires others to do the same

If this sounds like your kind of party, drop me a note and subscribe.

After six tremendous years, I’ve stepped away from ReadySet—the company I’ve helped build over the last six years and longest job I’ve ever held.

I moved to the San Francisco Bay Area in 2017 after four years of running a small media company in Harlem, eager for a change of pace that didn’t involve commercial publishing. I loved writing the newsletter and producing live events, but I grew weary of selling sponsorships for a living.

In 2016, I spoke at a conference in Berkeley and was subsequently recruited by a fellow panelist—an Oakland-based founder whose B2B SaaS startup was hiring. Candidly, it didn’t take much convincing to trade my dwindling savings for a Bay Area-based startup and all the attendant trappings. I was thrilled.

But neither startup wealth nor professional stability befell me in San Francisco. Within two months, I returned my laptop and paid back my relocation advance—a story for another day.

Things were bumpy in the immediate aftermath, but I had the good fortune of crossing paths with a fledgling diversity strategy firm called ReadySet while consulting for a competitor and eventually joined as their third hire. I started as a generalist but learning and development quickly became my focus and specialty. I thrived.

For a while, I had a fairly ideal flywheel. My conference talks were well-received and resulted in media, sales, and more speaking. I was in an average of two cities per week for nearly two years until the pandemic, and I loved the work. It was a formative time, and I blossomed as a speaker and team leader as ReadySet grew.

But companies evolve and so must their leadership. When what the firm needed from my role diverged from my zone of excellence, I decided to step away. The decision wasn’t difficult thanks to supportive partnership and great coaching, and my resignation was sent (and received) with gratitude.

“There are years that ask questions and years that answer.” —Zora Neale Hurston

So what’s next?

Aside from leadership development consulting, I’m organizing a series of events for executives in the NYC area. If you’re subscribed, you’ll be the first to know.
But mostly, I’m excited to write—there’s so much I have to catch you up on.