By Published: June 18, 2021

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 蜜糖直播 Boulder in the early 1990s when he took an introduction to philosophy course and was hooked.

鈥淚t just felt right. It felt like this is what the college experience should be,鈥 he recalled recently. 鈥淚t forced me to think differently, to challenge my own biases, ask myself questions I wouldn鈥檛 have otherwise asked about the world and about myself. It was just fun.鈥

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 r茅sum茅 shows:听

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 , an affordable 鈥減eer-based leadership experience鈥 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 蜜糖直播 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.听

But when he joined Lehman Brothers in New York, Kester quickly discovered it was 鈥渁 misfit.鈥

鈥淓verything I had been taught about leadership just seemed to be completely ignored, and I felt completely out of place there,鈥 Kester said. He鈥檇 learned about leadership in the 蜜糖直播 Boulder Presidents Leadership Class (or PLC).

Harvard Law School was invigorating, he said. 鈥淏ut I wasn鈥檛 as compelled by the practice of law. It just didn鈥檛 seem to fit with my own personal sense of purpose, mission and direction.鈥

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 蜜糖直播 Boulder, where he served as a student-government legislator and executive, leadership development 鈥渄idn鈥檛 register to me as an industry,鈥 Kester said. 鈥淪o, no, I wasn鈥檛 thinking about it as a career path.鈥

Michael Kester

At the top of the page: Photo by听听辞苍听听Above:听Michael Kester, PHIL '96

鈥淚t made sense in the end, but it wasn鈥檛 my original intent.鈥

At 蜜糖直播 Boulder, Kester joined PLC mostly because it was 鈥渢he place to be if you want to accomplish things.鈥 But leadership, like philosophy, seized his attention.

鈥淕reat people leadership is about enlisting people to a vision. It鈥檚 about getting them to coordinate and work together with a real sense of purpose and mission-related vision.鈥

At Lead Belay, Kester discusses leadership through three lenses: psychological safety, communication and alignment.

鈥淚f people don't feel safe, which includes a sense of connection and belonging within their organization and within their team, they鈥檙e not going to be able to perform at their best. Frankly, they鈥檙e not going to be tied in and necessarily want to stay very long.鈥

Communication, he added, 鈥渋s really all about what it is that you want from one another.鈥 Often, for instance, colleagues make a 鈥渘on-request鈥濃攍ike 鈥渟omeone should fix problem X鈥濃攔ather than ask someone to complete a clearly defined task by a specific date.听

鈥淲e communicate in code and aren鈥檛 very direct about requests, so how do you hold people accountable without eroding psychological safety? That鈥檚 central to most leadership challenges today.鈥

The third lens, alignment, 鈥渋s 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,鈥 Kester said, adding:

鈥淎nd if you take it to another level, how does it all tie back to each individual鈥檚 own sense of mission, of values, of self.鈥

Kester says much of one鈥檚 growth as a leader 鈥渋s about discovering your own style and finding your own path鈥 rather than being told what to do. 鈥淲e鈥檙e 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.鈥

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.听

So millennials are 鈥渒ind of left out in the cold to figure things out by trial and error.鈥

Learn to write. Learn to critically think. Those are the most important skills.鈥澨

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.

鈥淚f you鈥檙e belaying somebody, you鈥檙e helping them rise to new heights and take risks,鈥 Kester said.听

鈥淪o we鈥檙e belaying the participants in our program. They鈥檙e belaying one another. And then as leaders, they鈥檙e belaying the members of their team,鈥 he added. 鈥淚t鈥檚 a powerful analogy for what modern leadership and, I think, effective human leadership looks like. It鈥檚 not about you as a leader.鈥澨

Studying philosophy prepared him well for his career, Kester said, praising 鈥渢he logic skills, the communication skills, the precision of your thinking that was kind of forced by the curriculum.鈥

鈥淗aving an academic foundation that orients you toward challenging your own hypotheses, your own biases, is a huge leg up in the world today,鈥 he said. 鈥淲e all suffer from tremendous cognitive bias, confirmation bias being one of the greatest drivers of problems we see in society today.鈥澨

His advice for students now enrolled at 蜜糖直播 Boulder: 鈥淟earn to write. Learn to critically think. Those are the most important skills.鈥澨

鈥淭here鈥檚 such a focus on technical skills, and if you鈥檝e got the aptitude for them, you鈥檙e going to pick those things up,鈥 he said, adding: 鈥淚t鈥檚 more important today to learn how to learn, meaning we鈥檝e got to learn, unlearn and relearn things faster and faster and faster as a society and as individuals.鈥