Being a CEO Is a Brutal and Lonely Job, But It Doesn’t Have To Be

The Thinker - Auguste RodinWho gets their head “chopped” if a company can’t get traction, hit their sales numbers, find enough financing, or retain their high-performers? Who has to be the chief recruiter, fundraiser, strategist, and often makes the most expensive mistakes? Who has to listen to endless opinions and filter out all that noise? The answer is simple – the CEO!

As many of my friend CEOs would attest to, being a CEO is a brutally hard and very lonely job! Add family, personal relationships, and other responsibilities to the mix and you understand why CEOs yet to cross 3-0 mark are already developing gray hair. But it doesn’t have to be this way.

I have spent a decade and a half being part of these tag teams with several CEOs. I love this role because my protective “I will fix it” personality allows me to be their consigliere and chief of staff. I know my counterparts feel no differently, so I really speak here from our collective experience.

The CEOs who have matured, understand how powerful their partnership with their second in command can be. This role has many titles like COO, VP of Operations, President, Managing Director, or co-founder. Whatever the title, the essence of this role is being the multiplier and enhancer in the leadership team.


Two years ago I wrote an article “What To Look For In a Chief Right Hand Person“. This article is the next iteration of what I shared with you then.


So what does it take to turn this business relationship into a powerful tag team?

It takes personality fit. We often like to hire people like ourselves, when in reality we should be looking for someone different. We have to find someone who will compliment and magnify our strengths. Two pure visionaries will not get along, two executors will butt heads, two data geeks will overanalyze, two product people will fight over features, two technologists will squabble over platform choices, two disciplinarians will kill creativity, two pragmatists will limit risk-taking, etc. etc. etc. Many great leadership tag teams fall apart because of this misfit. We should be looking for something that could be described as Yin to our Yang. And yes, I absolutely don’t buy the “in a professional relationship personality should not matter” statement. This is something people who have no real world experience being part of a successful leadership team say.

It takes complete vision alignment. Since the accountability of the CEO to the shareholders can result in Chief “Ultimately Will Get His/Her Head Chopped if Things Go Wrong” Officer, the direction of the ship and final calls always go to the CEO. You have to be able to have a relationship where you can question your CEO’s judgment, data, logic, etc., with the right context of helping him/her make better decisions, but in the end you genuinely need to respect the calls he/she makes. If you can’t do this, you need to move on.

It takes an unprecedented level of trust. Even the best delegators have a hard time relegating control. But you can’t scale if you can’t let go and trust others to multiply your impact. Vision alignment coupled with trust is what makes this truly possible and effective. My counterparts and myself have several tests to see how strong the trust bonds are in our tag teams, but the ultimate test is how effective we are in helping lead our companies and taking care of our employees and customers. In my best tag team relationships, I had to spend very little time syncing with my chief. I knew the calls my CEOs would’ve made in almost any situation. I knew when I was the multiplier.

Bottom line: these are all AND not OR conditions. All conditions must be met/worked-out or this tag team will not live up to its full potential. Unfortunately, no amount of personality, skill testing, reference checking, track record matching, etc., will help ensure a 100% fit. It can get you 51% there, but the rest can only be discovered by working together. It is huge risk for both parties and should not be rushed into.

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