12th January 2023 | Written by

3 Lessons I Learned as a CEO

Being a CEO sounds like a great gig, right? Maybe not – 40% of new CEOs are deemed failing in their first 18 months, according to the Center for Creative Leadership. I’ve been lucky enough to serve as a CEO throughout my career, and the lessons I’ve learned have helped me become a better leader, and more importantly, a better person.

So, here they are. The top three leadership lessons I’ve learned from my time as a CEO.

Lesson One: Company culture starts with the CEO.

It shouldn’t come as a shock to you that most successful companies have core values—big pillars they stand behind that focus their efforts around who the company really wants to be. Roughly 50 percent of those companies have at least one core value that’s centered around trust, honesty, or transparency.

While that sounds nice, those are often the most difficult values to pull through your culture. It has to start from the CEO level. The “trust” pillar often ends up compromised and undermined because, for top CEOs, it feels nearly impossible to be authentic about messing up. When you can’t be honest about your weaknesses, that core value of trust & transparency goes out the window.

Take it from me: if you want your people to do it, you have to do it first. I always say that great leaders go first. Be authentic and vulnerable. Start the process with yourself by using the Three Principles:

  1. Practice Rigorous Authenticity: When you admit what you don’t know, you instantly make it a safe place for everyone to admit what they don’t know.
  2. Surrender the Outcome: What’s the worst thing that could happen? Identify that it’s unlikely and that it’s also out of your control. Put the outcome aside, and lead on with a clear conscience by doubling down on what you can control: your words and actions.
  3. Do the Uncomfortable Work: Say No to all the things that don’t serve your highest goals and move your company forward. Make it the standard operating procedure of your company to give permission for your team to do the same.

Do all of the above with vulnerability, in front of everyone. Let them see how you lead yourself, and they’ll start to lead themselves the same way.

Lesson Two: When you’re scaling, focus less on “How do we grow?” and more on when to Say No.

Companies start with one word: YES. Someone says yes to a product, investors say yes to funding it, customers all say yes to buying it, and suddenly a business is off the ground.

But what about the growth stage? The fact is companies need one word to scale, and that’s “NO.”

Think about it. Growth happens when we:

  • Say No to potential poor-fit customers, so we can target the exact customer we need.
  • Say No to building all the products, so we can build the right product.
  • Say No to 99% of all that’s possible with a business, so we can focus on the 1% that we’re truly good at.

Most companies and their employees are hooked on “yes.” That’s what today’s culture has taught us. That growth and success only happen from a place of saying yes. But that just isn’t true. With a “say yes to everything” mentality, things get out of control—quickly.

  • Low-value tasks add up
  • Unnecessary meetings are constantly on the calendar
  • Unreasonable timelines are assigned
  • Difficult conversations are avoided
  • Morale plummets
  • Performance suffers
  • Your big goals to scale and grow are stalled

These are all things that hold a company back. And they can be avoided by teaching people the power of No.

As hard as that is, Addictive Leadership helps people feel good about Saying No as it equips them with a system to methodically Say No to the wrong things in order to make space to Say Yes to the right things.

Lesson Three: Honesty (aka Rigorous Authenticity) is still the best policy.

Once, I was the CEO of a 30-40 person company that my business partner and I decided to sell. I was incredibly anxious about the process, and I didn’t want to tell my team about it. So, when our investment firm told us we weren’t allowed to tell anyone about the pending sale, I was relieved . . .

Relieved, until I felt like a fraud.

Every day I was showing up to work and meeting with my team, making big plans and long-term goals . . . while never communicating that this company might be very different by the end of that timeline. I felt like a traitor and a liar.

As a recovering addict, I couldn’t live like that – hiding and lying are the exact opposite of the behaviors you need to stay in recovery. I needed to practice Rigorous Authenticity and be fully transparent with my team if I wanted to sleep at night.

So, I went against the wishes of the investment firm. They said, “No one does that! Don’t do that! You could blow the sale!”

I’ve been around long enough now to know that 99 percent of the worst things that could ever happen to us . . . only happen in our head. Yes, I could blow the sale. Yes, people could quit en masse. Even so, I Surrendered the Outcome, committed to Rigorous Authenticity, and did the Uncomfortable Work of coming clean to my employees.

What happened when I was transparent with my team?

  1. Every night I went to bed with a clear conscience. I was a better leader and co-worker during this time of change. I knew I did what was right.
  2. My openness gave my team permission to offer the same. We were able to dialogue about fears and concerns, which gave us the ability to actually resolve challenges and retain the people we needed by having Uncomfortable Conversations.

And I didn’t lose a single employee I wanted to keep.

Selling a company was one of the more challenging times in my experience as a CEO, but because I put an emphasis on honesty, some of the richest moments of my professional life happened in those complicated conversations.

CEOs have quite the job, there’s no disputing that. But the lessons learned and experiences gained are so valuable to collect – and reflect on – along the way.

There’s so much more to take away from the Addictive Leadership program, our step-by-step structure equips your team with the same time and cost-saving framework used by CEOs and leaders at Dell, Global Payments, Google, and the State of Colorado. Start today by subscribing to our newsletter to receive monthly action items and insights.