Doing the work of a CEO is one thing; feeling like a CEO is a whole different ballgame

We hear that sentiment a lot at Aileron, especially from young leaders who are fresh in their roles. While imposter syndrome – the self-limiting belief that you’re not as capable as you are – can contribute to not feeling CEO-ready, other factors, namely not knowing how to work on the business instead of in it, can also make for a tenuous role change.

In 2019, RetireMed’s founder and CEO Don Mackos announced his plans to retire and began preparing the company for his successor. Marisa O’Neill, the company’s Chief Growth Officer at the time, was identified as the next CEO and began growing into her role nearly two years before the official hand-off in January 2021. Here are a few insights from her journey from team member to CEO.

Getting away from the business to work on the business

“When you work in something all the time, you don’t typically get an opportunity to step back. It’s like if you go to the doctor and they say these are your numbers, we’ve got to talk about your cholesterol. It forces you to talk about things you can gloss over in the day-to-day.”

This thought – that a company and a team needed regular time and space to step back and check in on the business – is how RetireMed initially started working with Aileron. The company began using Aileron’s campus as a place to step back from the day-to-day hustle with facilitated strategic planning. Through this initial work, their Aileron Business Coach grew to understand the intricacies of RetireMed’s team and business model.

“Our business changes very quickly. It’s Medicare, so it’s based on the government. We can’t have a five-year plan. It just doesn’t work for us. Having dedicated time off-site with a guide to help direct us through strategic planning made a big difference,” said Marisa.

That occasional strategic planning facilitation turned into four years (and counting) of RetireMed working closely with their Aileron Business Coach as he supported the business through Marisa’s transition and ongoing strategizing.

“By having a guide who sits with us during strategic development, there’s the opportunity to poke holes in what we’re doing and challenge it. We’ve been working with our Business Coach for so long now, he deeply knows our business. It’s been a huge asset to us, especially as a fairly young leadership team, to have someone we’ve worked with for a while who understands our business, but who is also outside of our work enough to see all the elements with clarity and help hone our focus. It forces us to address all parts of the business where we might otherwise be too deeply involved to see clearly.”

Seeking clarity with outside perspective

“It’s valuable working with people who have seen similar situations who can push back. They hold you accountable and push you in the right direction.”

Even the most seasoned CEOs crave community; hearing from people who have been in the same role, faced the same challenges, and felt the same pains can be comforting, eye-opening, and inspiring. For Marisa, having a community of guides and peers she can lean on has been instrumental as she has grown into her role.

“My Aileron Business Coach and Leadership Coach clearly had successful careers. They have the real-life experience from their life and their business to apply, as opposed to someone who only reads a lot and has theoretical knowledge. First-hand experience really makes all the difference. The fact that they have these big careers and now they’re also working with people in the thick of things, that’s what makes Aileron different.”

The power of the Aileron community isn’t limited to coaches. Marisa has also met other business owners who have faced similar situations.

“They’ve led to really interesting conversations and connections,” said Marisa.

Growing the business by growing the team

Years before she filled her current role, Marisa and a colleague took Activating Professional Management (formerly called the 2-Day Professional Management Workshop) at Aileron and were introduced to core professional management concepts; she didn’t know it yet, but that work would serve her well over the next few years when she was identified as the next CEO.

Today, Marisa is focused not just on growing her own leadership skills, but on growing the company’s entire leadership team. In addition to continuing her work with her Leadership Coach, she’s also investing in other leaders at the company; various RetireMed team members have started Leadership Coaching with Aileron as well.

“I look at our Chief of Staff, our COO, and our Director of Marketing who are all working with Leadership Coaches from Aileron. They have changed a lot. It’s made a big difference,” said Marisa. “We’re so lucky to have a facility like this here; as a company of a hundred people, we aren’t going to get that guidance internally. But I trust everyone at Aileron, so why wouldn’t I lean on them for that resource?”

“I think the fact that I’m getting the other leaders in the company Leadership Coaching opportunities helps me balance my personal and work life. If I have other good people around me, it takes some pressure off me.”

Marisa says not only do those who participate in Leadership Coaching benefit from the experience, but other people internally take notice, too.

“The business as a whole really respects that as an organization we are committed to bettering ourselves and continuing to take the company to the next level. Our people are all we have. We don’t sell products; we have a service. If we don’t have good people, we’re not going to provide good service.”

That leadership transition – from doing the day-to-day work to managing the business and the growth of the team executing the work – isn’t easy for most people. After all, the reason many CEOs are promoted into that role is because they were so good at doing the work itself. It’s often a different skillset to work on the business: to set strategy, lead a team, shape culture, and chart a vision for the future.

We’re shining the spotlight on our community and sharing the stories of our members. Are you interested in sharing your Aileron journey? Reach out to us.