4 Lessons I Learned in My First Year as a First-Time CEO

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During my first year as a CEO, I experienced countless emotions—excitement, pride, apprehension—but the feeling that loomed the largest for me was fear. Fear of failing a team committed to the business’ success, fear of failing a founder who had entrusted me to take his baby from adolescence to adulthood, fear of failing our customers who love our brand.

Today, a little over a year later, that fear has been replaced by something else: a quiet confidence that I have what it takes to lead.

When people ask me about the last year, I compared it to boot camp. It was an intense 12 months, and I still need to keep training, but I feel like I’ve reached a base level of fitness to continue leading this team and pushing the business forward.

Much like with exercise, there may not be a shortcut. I think you need to learn by doing and building muscle memory as you go. That said, I wanted to share my greatest lessons from the last year in case it’s possible to cheat your way there faster.

You’re only as good as your team

A team that has clear and complementary strengths and skillsets, that knows where each role ends and the next begins, that can communicate clearly and, more importantly, can debate openly is the foundation for a successful organization. This takes time and will likely never be perfect (we are human, after all), though.

What I didn’t know was, as CEO, you can never stop communicating or tying everything back to your vision, strategy and plan.

There are a few actionable things we’ve done to drive toward this, like over-interviewing new hires. We joke that getting a job at Bonobos feels like getting a job at the FBI, which I used to be embarrassed by but now see as a point of strength both for us and the candidate.

People pay more attention than you think

Just when you think no one is listening, they are. This lesson took me a while to realize, and it was only when I heard someone repeat something I had said in passing that I realized my whisper is a shout. An even more surprising learning from last year is the impact my physical bearing can have.

When we were in Wyoming at a company retreat last summer, we did a horse whispering exercise. The goal was to enter the corral and get to know the horses. I walked up to the first horse with my trademark enthusiasm and positivity, which made the horse back away. But as soon as I slowed my breath and movements and simply held out my hand, the horse approached me. The metaphor was not lost on me. The way I carry myself can have a meaningful impact on any given situation.

Find your joy

There is a lot involved with being a CEO, and not all of it sparks joy. Over the last year, I learned to schedule time to do the things that bring me joy, energy and clarity. For me, that includes spending more time in customer-facing scenarios. I try to spend at least one day per month either in our stores or shadowing our customer service agents. Not only do I enjoy it, but it also keeps me close to our customers.

I also spend time telling our story externally, whether at public events or industry gatherings. In the telling and retelling of our story, I remind myself of why I love this brand, business and our team. It also helps me step back from the day-to-day and gives me perspective around our biggest wins and greatest learnings.

Communicate, communicate, communicate

I intrinsically know as a marketer that you need to keep your message consistent and repeat it a few times to make sure it’s remembered and understood by teammates. What I didn’t know was, as CEO, you can never stop communicating or tying everything back to your vision, strategy and plan. Communication drives alignment, and alignment drives team effectiveness, which is crucial in this industry.

This first year has been both exhausting and exhilarating. But now, a year later, I’ve realized that while the responsibility is great, the rewards are greater. I also realized that I have a unique opportunity to pay it forward and share what I’ve learned. So, this summer, together with my executive coach, I will be hosting a retreat in Wyoming for other first-time CEOs or those transitioning into that role. Maybe that’s the shortcut. Here’s to year two.

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