Lessons in Leadership

Stephen Bailey was championing greater diversity and inclusion in business years before it became a more commonplace topic in the wake of the racial unrest sparked by the events of 2020. The former lawyer helped launch ExecOnline, aiming to diversify business leadership development through online learning, back in 2014.

“We were talking about these issues, and we were really driving this mission of equity in corporate America, long before the murders of George Floyd or Breonna Taylor,” he says, welcoming the greater attention being given to the issue. “No one was saying, ‘I don’t care about it,’ but they weren’t putting their dollars where their statements were, and now we have seen that shift. Our goal is how do we make it sustainable and not just something that’s a flash in the pan and then people move on to something else.”

ExecOnline partners with a dozen of the world’s top business schools to help develop leaders from diverse backgrounds, to bring other than white-guy faces to the C-suites and boardrooms. It offers university-certified programs in strategy, innovation and operations, with participants working on real-life projects applicable to their everyday work.

Among ExecOnline’s clients has been athletic and activewear company Lululemon, which announced its IDEA (Inclusion, Diversity, Equity and Action) stand in 2020. The firm turned to Execonline for help through a three-week Fostering Inclusion and Diversity experience co-created with the Yale School of Management.
Some businesses (like Lululemon) have embraced equity and inclusion because they recognize it’s the right thing to do, Bailey notes. Some—though they are becoming fewer, he says—don’t care. Then there are a lot of organizations in the middle who recognize “this can help them improve their bottom line, and that’s why they’re committed to it.”

Businesses that have become more inclusive report “a huge impact,” particularly now, in a tight labor market. “If you’re just recruiting from a narrow set of pipelines, you’re not going to be a successful company in the future,” Bailey says. “You’ve got to broaden your pipelines and that’s about gender, that’s about race, that’s about first-generation college students, geographic diversity.

“You’ve got to broaden out and organizations who understand how to be inclusive and distribute opportunity can hire from anywhere and they can retain the people that they hire. And that’s the big difference we’re seeing from a business impact perspective.”

Opening up the room
If Bailey is all about getting organizations to think outside the box, it may have something to do with the fact that he has never felt comfortable in one himself. A high school debater, he saw himself working in politics when he got older. But after earning a B.A. in history from Emory University and his J.D. from Yale Law School, he soon realized “law firms weren’t creative enough for me… and it turns out I’m not very good at working for other people.”

He left law for Frontier Strategy Group, a software and information services business focused on international markets. After five years there he co-founded ExecOnline, where he is CEO. His passion for helping “democratize” leadership development was fueled by some of his own experiences with the lack of diversity and representation in the corporate world as he raised millions of dollars of venture capital for the new initiative. People would want to pigeonhole him as “a Black entrepreneur” and assumed he had expertise regarding the urban market.

“I can tell you a lot of interesting things that you might not know as a white male in venture America, but it doesn’t just have to be about the urban market,” he says. “It can be about leadership development and leading institutions and how to build a B2B sales organization.”

Online programs have exploded since COVID-19 emerged, but they were central to ExecOnline from its launch. “When you make leadership development purely an in-person enterprise it tends to be exclusionary because not everyone can participate and the people who get access to the best opportunities and get tapped on the shoulder, so to speak, are often individuals that are in certain networks, that have certain backgrounds,” Bailey explains. “And typically, you see rooms full of largely white males.”

Having said that, the coronavirus has “created a tailwind” for the company, he recognizes, affirming its long-held conviction that leadership development should and would move online. Bailey believes that it’s important to measure progress. So, for example, he can report that women’s participation in ExecOnline programs has risen from around 29% at the company’s launch to the mid-40s.

The power of three
Bailey doesn’t subscribe to the view that some people are born leaders and then there’s the rest of us who should “go find something else to do.” He thinks that’s an “exclusionary” perspective. Leadership is about influencing and supporting people to achieve a common goal, and “all of us have that capability,” he says. “I believe there are many different leadership styles. What we’re born with might dictate the type of leadership style that we might express, but we can all be leaders in our own way.”

Having said that, natural leadership traits and capabilities still need to be developed. “You’ve got to cultivate it in order to express it effectively, but it is there for all of us to achieve if we so choose.” It is important to distinguish between leadership and management—knowing the right thing to do and doing the thing right. If leadership is about influencing and supporting people toward a common purpose, then management is “the blocking and tackling and the skills around how you actually lead a team or an organization day-to-day.”

Bailey is a big believer in the power of three—whether that’s goals or metrics—because you can be specific without getting overwhelmed with too much detail. So, he offers three principles for anyone wanting to grow their life.

First, define your purpose: why are you here? “I think we’re all on this earth for a reason, but I don’t think we often reflect on why… What are you passionate about? I think we’re great when we pursue the things we’re passionate about, because that’s what we’re going to be best at.”

Second, “surround yourself with people who share your passion.” If you look around and realize no one cares about what drives you, why are you there? “That can mean a job change, that can mean broadening your friendship circle, joining different organizations, but really affirmatively surrounding yourself with some people who share your passion.”

Third, go for it. “Unleash your inner leader, recognizing that you have the ability. Once you surround yourself with people with a shared purpose, to actually influence those people you don’t have to be their manager, be their friend, but you can influence people toward that shared purpose and mission.”

Bottom-line, he says, don’t let anyone else define you. “It doesn’t matter who that is. Could be your parents, your friends, a boss, but in life it’s really important to go on a journey of self-discovery and self-definition that ultimately connects you to your passion and your purpose.”

From an interview with Louis Carr