My Four Biggest Mistakes as CEO of an INC. 500 Company

By the time I took on my first “real” CEO job, I was ready for it. Most of it, anyway. And I emphasize “real” because prior to founding my start-up I had spent nine years as division president of a large communications company. That job helped me learn strategic planning, employee relations and team building, operations, finance, and all the rest. But there was always someone above me to hold me accountable.

That safety net disappeared when I started my own business.

As we grew I built an excellent leadership team, which was one reason we were able to ascend to #129 on the INC. 500 list. But we could have done better. I could have done better. Now, with the wisdom of hindsight, here are what I consider my four biggest mistakes as CEO.

1) I assumed being the leader meant I had to go it alone

Let me be honest about this — when you get your first job as a CEO, whether you create it in a start-up or you’re hired for that position — it’s pretty cool. It’s a rush. It means that you’ve risen to the top of your snow globe.

And, it also means you’re alone at the top. Rarely are there two CEOs. The buck stops with you, as the saying goes.

Looking back, I probably would have thought it was a sign of weakness if I looked for guidance. I mean, I was CEO. Wasn’t I supposed to have all the answers? Admitting that I didn’t know what to do would be — gasp — expressing vulnerability. I couldn’t do that!

But I should have had the courage to be vulnerable. I should have recruited one or more guides or mentors to not only coach and listen to me, but do one more thing I sorely needed. To hold me accountable when I was pursuing cross-country and international acquisitions. Or offer guidance when we were raising millions in financing for the first time.

2) I was accountable to no one

Sure, I had an executive team and a board of directors. But I hired the executives and I chose the board members.

This lack of outside perspective and having a resource to hold me accountable for results had negative consequences. We made poor acquisitions because I “justified” them. We wasted time and money by expanding our geographic footprint too quickly. We developed client concentration issues with too much revenue being generated by a few large clients. We spent heavily expanding into online offerings when it wasn’t our core competency (this was at the height of the dot-com bubble).

Bottom line? I was too focused on top-line growth at the time. Now, in retrospect, I regret not having had someone on the outside checking my actions against my goals.

3) I didn’t place enough importance on developing leaders

My business grew from a one-person start-up to 450 employees in five years. As you know if you’ve taken a business from very small to mid-size, the leadership requirements evolve. The job of an operations manager of a 10-employee small business bears little resemblance to that of a VP of Operations of a 450- employee business with multiple locations. Yet, we had start-up personnel who ascended into these roles. But they didn’t really “grow” into these roles because we didn’t invest in their development. Rather, we (I) expected them to keep pace and grow.

Looking back, I was too immersed in expanding the business and making sure IT grew rather than focusing on whether my LEADERS grew. 

Shame on me for that.

4) I didn’t place enough importance on developing myself as a leader

If I didn’t take the time to make sure my most important people developed leadership skills it should come as no surprise that I treated myself the same.

Prior to my start-up, I had gone through all kinds of training in my Fortune 500 job. Every year. Leadership skills, total quality management (TQM) and Six Sigma training, employee relations training — even taking week-long MBA sabbaticals at places like the University of Michigan. But once I sat down in the hot seat, isolated, it all stopped.

Reaching the job of CEO isn’t “the end.” It’s the beginning of that job. Of that responsibility. So it’s critical to commit to the ongoing development of your skills because the job changes over time as your company grows and the market evolves. Just look at hiring and supply challenges that exist today that were non-issues a few years ago. 

Do you really want to tackle those immense challenges in a vacuum? Wouldn’t it be smarter to have a peer group that has your back to help you navigate these challenges?

I think so. I know so.

The job of a CEO is critically important. We’re talking about creating jobs here, and making the world a better place with our products and services. In some cases, saving lives. Most CEOs aren’t prepared for the job they’ve taken, particularly new CEOs. They need help, and they need to know it’s okay to ask for it.

With the benefit of experience, I know this now. It’s the reason why I’m doing what I chair a CEO Peer Group at Peernacle so I can facilitate an environment in which CEOs and business leaders can succeed.

Wherever you are, if you’re running a business, or if you endeavor to, be sure to invest in yourself. Not just event-based training, which wanes over time. But, more importantly, in belonging to a group of peers who care about you and your success. As the African Proverb states, “If you want to go fastgo aloneif you want to go fargo together.

As CEOs, we confront critical choices – growth strategies, succession planning, employee engagement, leadership development…the list seems endless. The weight of these decisions can feel exhilarating, yet also stressful. And lonely.

Even though I started an INC. 500 company, I spent too many years trying to navigate it all solo. I’ve learned every CEO needs a community of peers who understand the unique challenges we face.

Peernacle is a private peer advisory group where leaders in southern Virginia come together and help one another to make better decisions and grow as leaders. If you’re looking for a community where you can gain insight from others who have sat in your seat, explore Peernacle group membership.