Michael Kester had sketched out a career in public service or public office, but the study of philosophy and leadership broadened his horizons
Michael Kester knows when to shift gears. He was a first-year business student at the University of Colorado Boulder in the early 1990s when he took an introduction to philosophy course and was hooked.
“It just felt right. It felt like this is what the college experience should be,” he recalled recently. “It forced me to think differently, to challenge my own biases, ask myself questions I wouldn’t have otherwise asked about the world and about myself. It was just fun.”
So much fun that he switched majors and graduated in philosophy summa cum laude in 1996. His openness to change was no fluke, as his résumé shows:
After graduating from Harvard Law School, Kester became co-president of a leadership consulting firm, and before that served a stint as a Wall Street financial analyst. Last year, he launched Lead Belay, an affordable “peer-based leadership experience” for millennials.
None of that was in the original plan, either.
Great people leadership is about enlisting people to a vision."
As he graduated from CU Boulder, Kester won a Truman Scholarship, a premiere graduate fellowship for those pursuing careers in public service. His aim was to work in the private sector before going into public service, perhaps running for office.
But when he joined Lehman Brothers in New York, Kester quickly discovered it was “a misfit.”
“Everything I had been taught about leadership just seemed to be completely ignored, and I felt completely out of place there,” Kester said. He’d learned about leadership in the CU Boulder Presidents Leadership Class (or PLC).
Harvard Law School was invigorating, he said. “But I wasn’t as compelled by the practice of law. It just didn’t seem to fit with my own personal sense of purpose, mission and direction.”
So he became an analyst at McKinsey & Company, a global management-consulting firm, a position he enjoyed. And when he had the opportunity to help a friend launch an e-learning company, Kester took it.
That business eventually became part of The Regis Company, which creates custom leadership programs for large corporate clients. Kester helped lead Regis until May 2020, when he launched Lead Belay.
When he was at CU Boulder, where he served as a student-government legislator and executive, leadership development “didn’t register to me as an industry,” Kester said. “So, no, I wasn’t thinking about it as a career path.”
“It made sense in the end, but it wasn’t my original intent.”
At CU Boulder, Kester joined PLC mostly because it was “the place to be if you want to accomplish things.” But leadership, like philosophy, seized his attention.
“Great people leadership is about enlisting people to a vision. It’s about getting them to coordinate and work together with a real sense of purpose and mission-related vision.”
At Lead Belay, Kester discusses leadership through three lenses: psychological safety, communication and alignment.
“If people don't feel safe, which includes a sense of connection and belonging within their organization and within their team, they’re not going to be able to perform at their best. Frankly, they’re not going to be tied in and necessarily want to stay very long.”
Communication, he added, “is really all about what it is that you want from one another.” Often, for instance, colleagues make a “non-request”—like “someone should fix problem X”—rather than ask someone to complete a clearly defined task by a specific date.
“We communicate in code and aren’t very direct about requests, so how do you hold people accountable without eroding psychological safety? That’s central to most leadership challenges today.”
The third lens, alignment, “is about making sure that everybody within the team understands what one another is doing, how it relates to your goals as the team leader and to the broader organization, how all this connects,” Kester said, adding:
“And if you take it to another level, how does it all tie back to each individual’s own sense of mission, of values, of self.”
Kester says much of one’s growth as a leader “is about discovering your own style and finding your own path” rather than being told what to do. “We’re not trying to develop people into a specific mold as leaders, but really to introduce them to a number of topics that they can reflect on and think about their own style.”
One reason Lead Belay focuses on younger leaders is that workers leave jobs and switch careers at a much-faster rate than did previous generations, and employers are thus less likely to invest in leadership training.
So millennials are “kind of left out in the cold to figure things out by trial and error.”
Learn to write. Learn to critically think. Those are the most important skills.”
The name Lead Belay utilizes terms for rock climbing and was suggested by an employee who is a climber; using a rope, leverage and friction, the person who belays protects a lead climber from catastrophic falls.
“If you’re belaying somebody, you’re helping them rise to new heights and take risks,” Kester said.
“So we’re belaying the participants in our program. They’re belaying one another. And then as leaders, they’re belaying the members of their team,” he added. “It’s a powerful analogy for what modern leadership and, I think, effective human leadership looks like. It’s not about you as a leader.”
Studying philosophy prepared him well for his career, Kester said, praising “the logic skills, the communication skills, the precision of your thinking that was kind of forced by the curriculum.”
“Having an academic foundation that orients you toward challenging your own hypotheses, your own biases, is a huge leg up in the world today,” he said. “We all suffer from tremendous cognitive bias, confirmation bias being one of the greatest drivers of problems we see in society today.”
His advice for students now enrolled at CU Boulder: “Learn to write. Learn to critically think. Those are the most important skills.”
“There’s such a focus on technical skills, and if you’ve got the aptitude for them, you’re going to pick those things up,” he said, adding: “It’s more important today to learn how to learn, meaning we’ve got to learn, unlearn and relearn things faster and faster and faster as a society and as individuals.”