One of my first high-stakes facilitation assignments was an engagement outside of Santa Barbara, California. I was facilitating a Leadership Lab, with “My Beautiful Story,” an activity I created, serving as the centerpiece. The client had rented a stunning mansion for the offsite and all of their high-potential leaders were invited.

At the time, ReadySet had a small office in what used to be a mall that had been converted into a coworking space. I was meeting with my CEO about the engagement before I flew out, which I expected to be a formality. The meeting, as it turned out, was not a formality.

She asked me to review my opening remarks and share how I intended to introduce the activity. And not just voice over my plan, she wanted me to stand up and role-play my opening remarks for her as if there was an audience present.

I clicked my heels, hoping to find myself in Kansas, or at least somewhere other than that meeting, but when I opened my eyes again, five excruciating seconds had passed, and I was still very much sitting across from my CEO in Oakland.

I stood up and offered a miserable, stuttering first attempt. Y-Vonne mercifully stopped me and calmly said, “Start over.” I looked down and still didn’t see any sign of a yellow brick road, so I took a breath and tried again.

She interrupted my second attempt by offering better phrasing which I graciously received while feeling confident that I could face a firing squad with more equanimity.

But on we went like this for what felt like an hour, and by the end of the exercise, I felt confident and prepared. I felt better aligned with how the session and the activity fit into the broader arc of the client’s programming, and I felt better prepared to showcase the growing canon of dynamic organizational interventions our firm was developing.

The preparation paid off, and we continued working with the client for five years.

The experience showed me the power of combining the power of preparation the with art of improvisation. Many of us who facilitate, speak, and perform in front of audiences have to adapt to things in the moment, but it’s the practice behind the scenes that makes the performance look effortless.

Every time I publish a piece of writing here, I feel both relief and regret. Relief that for another day, I showed up, published something that I believe, and offered a bit of myself to be judged by friends and strangers alike. I also regret not publishing something better, longer, and clearer.

But that’s a tradeoff I’m willing to make, because the point of the writing practice isn’t to change your life right now—it’s to change mine. I’m having a conversation with myself, out loud, and bringing others along for the ride.

Will the nature of what I share change over time? Of course. But for now, I’m embracing the imperfection.

In 2019, while working for ReadySet, I got an email offering us a sponsorship opportunity for From Day One’s upcoming event in San Francisco. ReadySet was based in Oakland, and we were eager to showcase our work, but we weren’t in a place to invest in the sponsorship with the ROI being unclear.

But where there’s a Will, there’s a way.

My friend Maurice was a DEI director with a substantial budget, so I pitched him on sponsoring the breakout and co-facilitating it with me. He was on board.

The breakout was well-received and well-attended—people were standing in the doorway and sitting on the floor in the aisle which of course wasn’t a fire hazard. Afterwards, Nick, the co-founder of the conference, asked me if I would deliver that same content at their upcoming event in Brooklyn. I agreed.

Nearly 200 people attended the Brooklyn session. The content landed, and so did my jokes. A colleague in attendance took me to lunch afterwards and tried to poach me. Something was happening.

I formalized the partnership with From Day One, and we took the show on the road. I served as the closing keynote speaker for FD1 conferences in Atlanta, Boston, Dallas, Los Angeles, Miami, Philadelphia, and Seattle. I leveled up and business grew. The ROI was clear.

And then 7,000 miles away, something weird happened in China, and I stopped traveling, just like everyone else. Things got quiet for a few months, but after a police officer in Minneapolis knelt on George Floyd’s neck with the world watching, things got decidedly less quiet.

The seeds planted in those sessions across the nation bore fruit, and business exploded. We had more work than we knew what to do with, and I delivered two to three virtual workshops a day for weeks. Maybe months.

Looking back, the From Day One partnership was one of the most economically and professionally rewarding relationships of the past decade. It altered my professional trajectory in ways I’m still benefiting from. What a ride.

I had reached a career pinnacle—making partner at a firm I helped build—but I had never felt more adrift and unmoored. Two of my super-powers are facilitation and business development, and I have a history of combining these passions to great success. But these things weren’t my priorities at the time.

The challenge is that the company needed a “strategic executive” in the Head of Growth seat to which I had been promoted. I spent months trying to figure out what that meant in practice. It felt like putting business words about the future into documents and decks, and what I really wanted to do was close business and perform The Willie Jackson Show on stages every week. Tensions grew.

When I brought the issue to my executive coach, he listened patiently while I spent our call tying myself in knots. As the call ended, he issued me a simple challenge. He said, “If you’re going to be there, act like you want to be there.”

It was comical in its simplicity, but it completely interrupted my unproductive rumination. The following week, I hijacked a meeting with my CEO and COO with an insight that Stevie Wonder clearly beheld: this isn’t working.

The response was validating and relieving: “We agree, and we’re so glad you said something before we did.”

***

Exactly one year ago today, I submitted my resignation, and the process couldn’t have been more supportive and straightforward. I’ve learned and grown so much in the past year, in ways I’m still noticing.

Living in alignment with your truth isn’t always convenient or easy, but it’s worth it.

Yesterday’s post made me think of two experiences I’ve had as a manager that stuck with me over the years.

The first is thanks to Shaila, who was a trusted collaborator and co-facilitator for several workshops. I once asked Shaila for feedback, and she delivered it with such care, thoughtfulness, and truth that it deepened the level of trust between us.

She didn’t shy away from the truth, nor did she deliver it flippantly. The feedback was fair, direct, and considered. Instead of the instinct to secretly convince myself of how wrong she was or to defend myself, I basked in the power of the truth delivered with care.

By contrast, I’ve seen and experienced feedback that causes irreparable harm to relationships, either because of the shaky relational foundation that couldn’t bear the weight of the truth or because of the careless way in which the feedback was delivered.

Good feedback, delivered well, at the right time, from a trustworthy source, is a gift.

The second experience was when I worked with Erika, who brought such depth and creativity to the work that I got off our calls thinking, “So that’s what excellence in my role could look like.”

Erika and I collaborated on large-scale training rollouts, where we had to consider factors such as geography, language, dialect, class, psychological safety, and dozens of other elements that contribute to delivering effective global training programs.

And even though the experience she brought to the table could have made me feel like an intern on my first job, the grace and playfulness she brought to bear always made me feel like a peer.

I used to joke that my manager could give me any feedback she’d like as long as she started by telling me that I’m doing a great job.

And by “joke” I of course meant it sincerely.

Some people thrive on feedback and want as much of it as possible. Some people despise feedback and need it to be delivered in writing. Some people would much rather walk the plank than receive feedback at all, and most everyone else is somewhere in between.

The broader takeaway here’s that it’s okay—essential, even—to treat different people differently.

At the height of my people management responsibilities at ReadySet, I managed a team of 11 people. That was probably nine too many, but the point is that each one of them had their preferences for everything from feedback to accountability to scheduling. And it was my job to keep track of these things.

One of the most effective tools for managing individual preferences on teams is the Personal User Manual, which can cover things like your working hours, how you like to receive feedback, what energizes you, and what you value.

I gave a talk on Giving & Receiving Effective Feedback in Miami that you might find helpful, or at least amusing. Enjoy.

In yesterday’s post, I said:

Managers have a significant impact on your career and work experience. They can eliminate obstacles in your path, offer timely guidance on things you’re not seeing, and put in a good word for you with the right people.

I did things the hard way that summer. Don’t be like me.

Bring your people along.

My friend Sana asked in response:

“Would your advice change if your manager wasn’t generally helpful or lacked the skills to be?”

Yes.

The bedrock of any healthy management relationship is trust, and not everyone is afforded this luxury. Managers are people, and people are sometimes toxic. This toxicity can permeate the culture of a team and organization in a way that leads to a lack of psychological safety for its people.

Mentors, advisors, and colleagues are vital members of our extended network. We can lean on them for guidance, in addition to honing our judgment and intuition along the way. And these decisions are deeply personal—they connect to our feelings of worthiness, self-image, and confidence.

Over the long arc of your career, you’re likely to have managers you’d work for again, and managers you’d be delighted never to see or hear from again. I hope you have more of the former than the latter.

During the summer of my sophomore year, I secured an internship at Convergys in Jacksonville, with the goal of receiving a full-time offer upon graduation. I was an IT major and looked forward to putting theory into practice at my first corporate job.

Upon arrival, I learned that my internship project was decidedly non-technical in nature. The people I was working with were lovely, but technologists they were not. To make matters worse, I was earning a full $5/hour less than my intern friends in other departments and companies. Not good.

I’ll spare you the details of my first project—an FMLA data consolidation and documentation project I affectionately called “alphabetizing paperclips”—but I was highly motivated and made the most of my two summers with the company.

To wit, I networked and took on extra work like a madman.

I helped organize the inaugural intern symposium at the company headquarters in Cincinnati, met with executives across the firm, and ultimately secured an extension on my internship that was in line with my professional ambitions.

There was just one problem. I hadn’t told managers what I was doing.

My immature calculus was as follows: I was solely responsible for my success. And I didn’t want to rock the boat. However noble my self-sufficient intentions were, the impact is that I came across as unfocused and secretive.

I still cringe when I met with my managers at the end of the summer to share the news of my internship extension. Awkward doesn’t begin to describe it. They knew, but they were annoyed and confused by how I went about it.

The team at headquarters was excited about this motivated intern down in Jacksonville who had dreams of a thriving career with the company, but the team I worked with every day had to find out about my ambitions through their colleagues.

I didn’t realize that my team could have been a force multiplier for my efforts. They already knew all the people I was meeting. My “win” felt hollow, and I strained relationships I valued.

If I could counsel my young, ambitious self, I’d say something like this:

Listen, Will. I know you feel like you need to hustle and make something happen here, but the real work isn’t the outcome of the internship. It’s how you move through it.

Your manager is here to support you, and if something isn’t working as you had hoped, schedule some time on her calendar and ask for advice. You don’t have to do it alone.

Work with the system—not around it—and watch doors open that you didn’t know were available to you.

Managers have a significant impact on your career and work experience. They can eliminate obstacles in your path, offer timely guidance on things you’re not seeing, and put in a good word for you with the right people.

I did things the hard way that summer. Don’t be like me.

Bring your people along.

I was rounding the final corner on my walk to the gym in downtown Brooklyn when a baseball fell from the sky and thudded onto the sidewalk in front of me.

Across the street was a recreational field where someone had accidentally hit a ball over the twenty-foot fence. I looked over, and a guy with a baseball glove looked on curiously to see if I was going to spare him an inconvenient walk to retrieve the product of his son’s athleticism.

Secretly delighted, I dropped my backpack and wondered if I could at least get the ball over the fence and in the general direction of my new teammate.

Baseball never excited me growing up, I was a basketball guy through and through—blame it on the whole 6’3 thing. I played baseball during PE classes in elementary school, sure, but basketball was my chosen sport.

I sent up a silent prayer to Roberto Clemente and let it fly.

The ball sailed over the road, cleared the fence, went between the trees where the guy was standing, and he caught it—he didn’t even have to move. I played it off as if it wasn’t a big deal, but I felt like Neo in the Matrix when he learned that he could dodge bullets.

It’s been at least a year and a half since my moment of spectacular arm cannon excellence, but I still smile every time I think about it. In my storytelling workshop called My Beautiful Story, I describe everyone as the hero of their own journey, and how this posture is a catalyst for connection and empathy. I definitely felt like a hero that day.

We all have experiences and accomplishments that we fail to or forget to share with others, and it’s a gift to create the space where people have an excuse to share them.