Lessons I’ve Learned As A CEO

I’m someone who moves too fast. I run as fast as I can, and I break things. I make decisions quickly, I’m sarcastic, and I had virtually no internet presence before taking on this role. Those are all things I am adjusting and balancing as a CEO. I've learned a lot of lessons in this position. Some were things that I expected, while others were a bit more of a surprise. I want to share some of the most important lessons I’ve learned as a first-time CEO, and whether you're a CEO or not, I hope you'll find these lessons useful.

The responsibilities of A CEO:

I was given a book at the beginning of all of this called Hot Seat: The Startup CEO Guidebook by Dan Shapiro. It contains six things a CEO has to own, that they can’t delegate.

1. Building the team

2. Keeping the vision

3. Chief strategist

4. Managing investors/board

5. Critical relationships

6. Maintaining Culture

In my experience so far, I find this to be true, along with a seventh (and arguably the most difficult) task, and that’s to be healthy. None of the other six tasks can be accomplished if you’re not a healthy leader to begin with.

Lesson #1: Decision fatigue is real

I was on holiday with my wife shortly after becoming a CEO. My inbox and Slack were empty, and I had no meetings. You’d think I’d be able to relax, but my mind was racing. No one was waiting on me to do anything, so I thought “why do I feel this way?” You see, what used to weigh me down were tasks and checklists, but what was now weighing me down were decisions, and decisions are a lot less tangible.

The burden of leadership includes: 

1. Revenue 

2. Customer success

3. Culture

4. Cash/payroll

5. Friends & family’s investments

I had the realization that, previously, I didn’t have to solve the big problems. I would move fast, solve the little problems, and send the big problems “upstairs.” I realized that, as the CEO, I now had to solve the big problems, and that’s what was causing my decision fatigue. It highlighted how big the gap was for me in effective decision making, and the learning curve that I needed to overcome. Now, I delegate the smaller problems and tasks to make space for the big decisions that need to be made, and I trust my team to handle the things I’ve delegated to them.

Lesson #2: Balancing authority with leadership

Everybody wants to be a CEO or an entrepreneur, but nobody wants to lead. They want to be CEO because they want to be the boss, and they want people to just do what they say. 

The trick is, there’s a difference between being a boss, and being a leader. 

-Bosses take advantage, where leaders empower. 

-Bosses command, where leaders ask. 

-Bosses say “go,” while leaders say “let’s go.” 

What I’ve learned when it comes to balancing authority is that yes, I’m the CEO, but the best ideas will always win. And those ideas don’t need to come from me. The best ideas have to win, if the company is going to be successful, and that means empowering my team to lead with the best ideas.

Balancing the responsibilities and burdens of being a CEO requires adapting a new and unique skill set, but the privilege of leading others is the real measure of success. 

These are just a few lessons I’ve learned in the first year of being a CEO, and I’m more excited than ever about what’s ahead.

MT

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