Turning Life Experience Into Your Strengths with Executive Coach Karl Stewart

Karl Stewart believes we each have a Purpose built in and that we can collaborate with a diverse system of support to achieve great outcomes. Through his executive coaching business, Work Well Groups, he helps leaders do just that.

What is executive coaching? “We’re all executives, every human being,” Karl says. “Executive coaching is about helping each individual on the planet build up their executive function.” 

Though Karl came to coaching after a 20-year career in human resources, he brings a broader perspective to his work as a coach — from his training as an actor and dancer to his lived experience as a gay Black man in America. 

“I get to bring all my experience to bear on this one hour of being with this person as they unlock their authentic leadership playbook,” he explains. 

In this article, Karl shares his journey to executive coaching, the growing popularity of coaching, and a framework anyone can use to show up more impactfully within their organization or community. 

How an introverted actor became an executive coach

Karl says that his mother was his first coaching client. “She made major calls in our family, and she had a lot of anxiety about it,” he explains. “She would turn to me.” 

Though Karl was always emotionally intelligent, a career that requires public speaking didn’t always seem like a natural fit. “I’m actually a high introvert,” he says. 

His training in theater and dance — Karl has an MFA in acting in addition to his master’s in organizational psychology — helped him become comfortable engaging with groups. It also helped him navigate the dichotomy he experienced as a Black man living in New York in the eighties. 

On one hand, Karl says, “When I would step onto a subway, white women would clutch their purses.” He responded by contracting himself to make his six-foot-tall presence seem smaller. At the same time, he says, “on the streets, I protected myself by pretending that I had nothing to steal.” 

As he progressed through a career in human resources, Karl worked to integrate the diverse aspects of his identity and experience in his personal and professional life. Eventually, he discovered executive coaching. 

“My background is perfect for executive coaching,” he explains. “My experience has created somebody who can deeply listen to somebody else’s story.” 

Helping individuals and organizations build inner resilience

By the end of 2022, Karl had a vision for an independent career that would bring together his experience in dance, theater, organizational psychology, and competing in triathlons. 

“I could bring all of it together,” he says. “All the work I had done in therapy to bring myself to a mental health homeostasis.” 

In January 2023, he formally launched his business, Work Well Groups, with a mission of helping senior Afro-Latina leaders in media, technology, design, and education lead their teams fiercely. Today, he’s led more than 300 one-on-one coaching sessions, as well as group sessions on emotional intelligence, radical candor, and positive intelligence. 

Karl is part of a global trend: according to the International Coaching Federation, the number of professional coaches grew 54% worldwide from 2019 to 2022. 

He chalks this up to two factors: the growing number of HR professionals who are leaving W-2 roles — and the growing number of people seeking support in an increasingly chaotic world. 

“John Maeda says that we’re all experiencing trauma,” Karl explains, referencing the work of the technologist behind the Resilience Tech Report, which explores how people and organizations respond to adversity. “His work suggests that the cadence of trauma is getting higher and higher, and the ups and downs are more of a whiplash.” 

Karl sees coaching as a way for people who have a stable mental health baseline to process their experiences and gain traction into their lives productively and sustainably. 

“We all have the opportunity to use whatever it is that’s happened to us in our lives and turn it into gifts and strengths that help us going forward,” he says. “But it requires intentionality, and that’s what coaching does.”

A 5-step framework to help anyone transition from problem to action

One of Karl’s favorite tools to use with his coaching clients is the Positive Intelligence framework. 

“I love this framework because you’re tapping into the joy of exploration,” he says. “There are old management philosophies around fear… this shifts it all to the love of being in community, service and enjoying each moment, day by day.” 

Here’s how to use the 5-step Positive Intelligence framework to approach any challenge or conflict. 

1. Explore

Start by looking at a situation from different perspectives. “Ask the neurodiverse person, the remote person, the CEO, the board of directors, the introvert,” Karl says. That way, you’ll get a fuller picture of what’s going on. 

2. Empathize

“Now that you’ve looked at the data, go to the heart,” Karl says. He encourages people to look at a situation the way a 5-year-old would, with the assumption that everyone deserves unconditional love. 

3. Navigate

“20 years from now, what do you want to say about this challenge or this situation?” Karl asks. He likens this step to the Distant Mountain exercise that Pollen Expert-in-Residence Austin Church runs during his quarterly planning sessions for Pollen members. 

The goal is to understand what’s truly important about a challenge — what you’ll care about in the long term. 

4. Innovate

Now, it’s time to brainstorm. With empathy and sensitivity, having looked at many different perspectives, you can start to throw out ideas. “The trick here is to pick the 10% you like out of an idea and build on that,” Karl explains. This makes the innovation process more collaborative than competitive. 

5. Activate

The final step is about clear, laser-focused action. This is where you might create a Gantt chart or assign next steps to identify who’s responsible for what. 

Karl says this framework works because “human beings love clear responsibility connected to a bigger picture.” He recommends it as a tool both for meetings and for individuals to make decisions or action plans. “It’s easy and it’s fun to do,” he says.

Finding community as an independent

Though Karl runs an independent business, he doesn’t describe himself as a “solopreneur.” 

“One of my dearest mentors once said to me, I never want to hear you say the word solopreneur,” Karl says. The “entre” in “entrepreneur” translates to “between,” in Karl’s thinking, and Karl believes that’s a more authentic way to describe how we rely on others to help us succeed. 

“I  think an avenue for us to evolve as a species is to just bring more ideas, thoughts, feelings, ways, approaches, paradigms to the table and see what we get in the mashup,” he explains. 

Karl has been deeply influenced by the ideas and paradigms he’s encountered in the Pollen community. In particular, he appreciates what he’s learned about communicating a purpose and vision to prospective clients. 

Thanks to Pollen, he says, “I’ve transformed the way I communicate about the work I do. The way I wake up and show up in the world is different because of that.” 

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