How a Serial Entrepreneur Unexpectedly Became the COO of Elite Leadership Group YPO

Sean Magennis is a lifelong entrepreneur. In the early 1990s, he started a business consulting firm and an executive search business that has served clients across the United States, Canada, and Mexico. But, as I quickly discovered in our conversation for the Second in Command Podcast, Sean is also passionate about fostering relationships among ambitious entrepreneurs.

Early in his professional journey, he joined the Entrepreneurs’ Organization and immediately began volunteering in a peer group of young entrepreneurs. He quickly became, as he puts it, “addicted to volunteering.” He later joined YPO, a nonprofit networking group for CEOs that has 27,600 members in 135 countries, and a robust 70-year history. He’s been a YPO member since 2007.

But membership wasn’t enough for Sean. After years serving as the first in command of his own ventures, he took on his first COO role in 2013 when he joined the leadership team at YPO.

He shared how his professional background informs his work at YPO and his philosophy on leadership.

Human first, business second

Sean and I spoke at length about the investment that YPO members make in one another, beyond their professional development and into their personal lives. But Sean acknowledges that comfort in that personal communication takes time to develop, and that’s a lesson he wishes he could have learned earlier in his career.

“In the old days, it was ready, aim, fire, one thing to the next,” he recalls. “What happens with that is you lose connectivity and you don’t establish relationships.” Business will always be messy, he explains, but caring for business colleagues as humans first goes further in building the trust and respect that’s so necessary in a business environment.

“The best CEOs are the ones that can clearly articulate their own personal values and show up as authentic human beings,” he says. “Human first, business second.” Of course, there’s a line between the professional and the personal. But Sean says the amount of time colleagues spend together in an organization demands that caring for one another at the human level be a core value.

It has even informed a mantra that guides him: “Operate as a leader with a servant heart and a business mind.”

Great employees don’t stay forever — and that’s OK

Part of caring for the human first is recognizing that no one will be a part of an organization forever. That creates opportunity, he says, to foster talent when it’s present.

Sean stresses the importance of keeping employees engaged, especially those closer to the beginning of their careers. When a new hire joins the organization, “It’s very important to understand what they come in with and what their desires are for future contribution,” Sean says.

Employees may join an organization knowing their job duties and create a plan for their first year or two with their manager. But Sean says to push beyond that surface level planning. It’s essential to understand what an employee wants to do, not only in the organization but beyond it, he says. Then, the manager’s challenge is to help them create the conditions for that growth.

It can be challenging when an organization is relatively flat, Sean says, without a ton of room for growth in a three-to-four year span. “The key is to maximize that time they’re there with you,” he says. That requires frequent and continuous feedback to ensure that employees are supported in their role, maximizing their skills and also that they’re feeling fulfilled.

“I find that a lot of younger people today will not work for an organization unless they’ve clearly aligned their value set with the purpose and values of the organization,” Sean says.

“So often we think that you’ve got to pay top dollar,” Sean says. But it’s not always about money. If your values are a fit, “If [a staffer does] leave because there isn’t a role for them in the organization, you’ve prepared them so well,” Sean says. “You’ve given them the tools, you’ve given them the right examples, they’ll go on and be your advocate way longer past their employment with you than you will believe.”

How Sean shifted from CEO to COO

Sean believes a good executive is constantly learning, and in his first role as COO, he continues to focus on his own growth. “When you have somebody like me who was a complete entrepreneur, I had to retool some of those skill sets,” he admits. One of his greatest lessons? Parking his ego at the door, especially when it comes to the relationship between the CEO and the COO. 

Sean and YPO CEO Scott Mordell have a baseline agenda for their one-on-one meetings. “We share our views openly without critique. We agree to disagree, but when we leave that room, we’re 100 percent aligned,” he says.

And they’re always clear on their roles. Sean says he’s there to amplify the CEO’s vision and execute it. “I’m not in the limelight,” he says. “I am not the ultimate accountability individual.”

That shift took some getting used to after 25 years in the top executive position at his own companies.

“Part of the integrity of leadership is also not necessarily taking the credit even though you’re the deciding force and the buck stops with you,” he says. “In my case, the buck stops with Scott.”

And on the occasions when Sean doesn’t have all the answers he needs to serve Scott well, he has the peer mentors and friends he’s made in the YPO community through the years. “I’m blessed with an incredible group of individuals that I can go to for advice from their experience,” he says.

That, perhaps, best highlights his passion for seeing an entrepreneur as a human first, before an executive.

This article is based on an episode of Second in Command Podcast, where your host Cameron Herold interviews the chief operating officer behind the chief executive officer to learn their tips, systems and insights from being the second-in-command of an amazing growth company.