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

by Aug 23, 2012Operations Leadership

Who loses sleep and years of life if a company can’t get traction, hit the sales numbers, find enough financing, or retain its 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 the 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 different, 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 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 complement and magnify our strengths. Two pure visionaries will not get along, executors will butt heads, data geeks will overanalyze, product people will fight over features, technologists will squabble over platform choices, disciplinarians will kill creativity, 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.

It takes complete vision alignment. Since the CEO’s accountability 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 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 they make. 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 I 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 CEO. I knew the calls my CEOs would’ve made in almost any situation. I knew when I was the multiplier. And the times it did not work out? Micromanagement was unbearable.

Bottom line: these are all AND not OR conditions. All conditions must be met/worked-out to make this tag-team work. 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 a huge risk for both parties and should not be rushed into.

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