5 Things I've Learned About Being a CEO by NOT Being the CEO

I have not been a CEO, but I have been the #2 guy several times over – in nonprofits, in consulting, and in two tech startups. I like being the #2. I like enabling CEOs to thrive. I like playing up their strengths and helping manage or compensate for their weaknesses. I like bridging the vision of the CEO with the team who needs to execute it and customers who need to buy it. I find it a creative sweet spot for me. I have no interest in being a CEO.

So, I thought I’d share 5 things I’ve learned about being #1 by being #2:

1.There is no perfect CEO.
Every CEO I’ve worked for has been different. A CEO is only as good as his/her match with the company: with its stage, its product or service, its customers, and/or its growth trajectory. Some CEOs are great in the messy early stages but struggle to operationalize the early creativity into a growing company. Some have great industry knowledge but don’t know what it’s like to build an early team or sell an incomplete or inadequate first product or service. Some are masters of business and process but struggle to adapt in the absence of the ideal. Some thrive on the energy of the business but lose the people in the process. Some thrive on the people and lose the business. So, a CEO’s success is often a function of their match with the business need and opportunity – and the right #2.

2.The glory isn’t worth the pain – unless you really are a CEO.
Being a CEO sucks, unless you are really a CEO. It’s in your wiring. The time commitment, the burden, the responsibility, the relentlessness of the business, the personal and family sacrifices: these aren’t for everyone. I’ve seen the wear-and-tear first-hand and, because I was always #2, I often recognized it in my CEO before they fully saw it in themselves. Don’t get me wrong, the #2 has wear-and-tear too, but it’s different. The best CEOs aren’t CEOs because they wanted to be a CEO. They are a CEO because of something deeper.

3.The best CEOs recognize leadership is a team sport.
I’ve been fortunate to work exclusively with CEO’s who believe this and believe it deeply. I suppose a CEO who didn’t believe it would never have hired a #2 like me. They welcomed someone who would challenge them. They welcomed someone who could step up and do what it takes in the moment regardless of complexity or audience or function. They welcomed someone who proactively took things off their plates. They welcomed someone who owned the vision with them, but knew how hard it is to be a CEO. They welcomed anyone who made them better and made the team better.

4.The best CEOs know their weaknesses and look out for their blind spots.
You have to be supremely confident as a CEO but also know how to check your ego at the door. The CEO sets the tone and the standard for the rest of the company. So, a CEO who wants people to learn has to be willing to openly make mistakes. A CEO who wants his team to own the vision has to be willing to give all the credit for its realization. A CEO who wants a company that treats its customers well has to build a company that treats each other well. It’s far more effective for the CEO to show all the ways he’s not perfect than to create an illusion otherwise.

5.The best CEOs have the best #2’s.
I am not saying I was the best #2 or that my CEO’s were necessarily the best. Rather, I believe the proof that you’re up to the task of being the CEO is that you are willing to hire someone as a CFO or COO or CHRO or otherwise who you trust and empower to lead the company with you. The role of the CEO is inherently lonely. Good CEO’s don’t double-down on that by making it about them but rather enlist true partners in the work. 

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