Respect and asking for help

Powerful Insights and Wisdom from Top Middle-Market CEOs: Leading an Experienced Team with Respect and the Power of Asking for Help

In Leadership Resources by Brandt A. HandleyLeave a Comment

On ROI’s Into the Corner Office podcast, we have interviewed over 150 leading middle-market CEOs from companies across industries, and the advice and wisdom they have shared with us is unparalleled. We are excited to share some of these insights with you in a new form!

When I interview my podcast guests, I always ask how their leadership has grown throughout their careers. I ask them to describe some of the early struggles they faced when they first began managing people or leading a team. Interestingly, one of the most common threads I hear is the challenge of leading a team of people who are older and more experienced felt daunting when they were young leaders. 

Titles do not Eclipse Respect or Experience

Tom Troy, CEO of CSAA Insurance notes, “The more experienced person has a deeper knowledge base, and for that reason in many cases tends to be older than the people that they’re managing.” But he also told me that it’s become increasingly common for team leaders to be younger, and that was the case for him. His advice? Be humble and clear. Stay out of the way of the successful members of your team. When I asked him how he handled it, he said, “I wanted to make sure I was impressing upon my team that I didn’t question that they had a deeper knowledge base about the specific work that we were doing, but that my role was to do more the administrative, leadership-oriented tasks and not get in the way of their technical expertise.”

Lindsey Ueberroth, CEO of Preferred Hotels & Resorts, described the virtues of listening to her team, relying on their experience, and the importance of asking them how she can help. She says the process might seem slow, but it’s worth it. Lindsey remembers that she learned, “You just have to listen a lot and understand what the complaints are and then figure out how to get over that obstacle. But it [can take] a lot of patience. It [takes] a lot of time.” She also recognized that she was hired for a reason, and had her own skillset and strengths. So, her advice is to discern “How do you partner to figure out how to leverage the best of both skillsets?”

Tom Schmitt is CEO of Forward Air Corporation, and he was in a similar place when he took over a leadership role. As a young man, he moved from Europe to Cleveland to manage BP retail locations. His previous role with BP had been “lots and lots of math on a computer” dealing with very high-level spreadsheets, so the shift from managing numbers to managing people was already a challenge. When he arrived, he jumped right in because, “One of those lessons clearly is well, just roll up your sleeves and do your very best because right now you are needed here.” The other thing, Tom said, is “You always have to add value. Don’t go and rely on your title right away … make sure you leave a place better than you found it.” Sound advice from a leader who is so obviously respected and loved by his team!

Most Leaders Cannot Lead Alone

As I’ve mentioned before, leadership is often perceived as an intrinsic skill or quality but is actually a learned skill for most people. One of the skills that many leaders must hone is how to ask for help. The inclination can be to handle as many tasks as possible. “If you want a job done right, do it yourself!” right? In most cases, that is actually not the best way to go about it!

When I interviewed Paul Macaluso, now CEO of Another Broken Egg Cafe, he told me that early in his career, he was very focused on “Doing everything [himself] and figuring out how [he] could do it and not asking for help.” As he notes, however, asking for help is a valuable skill that can change the trajectory of your career. It’s also a valuable skill to teach your team. “It has really accelerated my career in the last ten or so years as I learn that skill and also is important to me as I talk to more junior people in my company today on making sure that they know that and use that and develop that skill.”

Sometimes asking for help includes bringing in a third party to offer outside perspective and insight for how to improve things. When Michael O’Neil, Founder & CEO of GetWellNetwork, first started the company, he says his leadership style was “Very personality-based, and it was based on [his] personal experience and [his] instincts on the product.” After bringing in an executive coach who pushed him to move to a commitment-based organization, it’s been possible to scale the company more effectively. “We really began to talk very openly about who the stakeholders are, what our commitments are, and make sure we filter all of our key decisions to these commitments. And it’s really served us quite powerfully.”

Mutual Respect and Teamwork

Top leaders recognize that leading companies and people requires mutual respect and teamwork plus having shared goals and commitment. To read more leadership stories, see more articles here. You can find the full archive of Into the Corner Office podcasts episodes here, or wherever you listen to podcasts. 


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