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Dear Founder,

You may be grappling with one of the hardest issues any leader faces—when do you put the company’s intended destiny above your own needs?

Being the CEO of a company sounds like a great job—until you actually have to perform the actual work and you soon find that this work must come before your own personal desires. You’ll find that when you take on the chief leadership role of any entity you have to put that entity’s mission ahead of your own goals. It can sometimes be a huge wake up call.

At least it was for me. I’ve always pined for leadership roles. When I became a manager at IBM, I realized how much more responsibility I had than when I was an individual contributor. Comments that I used to make in jest were interpreted with fear (“Is my job in jeopardy?”). I also found out very quickly that employees expected me to fix the concerns they had about the department. This was my first experience understanding the broader role of a leader versus what I had been in the past, an individual team member.

As my career progressed I landed new jobs and I kept getting excited about bigger and bigger roles, including CIO jobs, a COO role and a CEO role. I took on board roles and became Chairman a couple of times. There were countless times when I had to do something for the good of the entity at a personal sacrifice to me. As a matter of course, I would often take less compensation for myself to ensure that my stars could receive more. I canceled family vacations, including turning around one time on the way to an airport. I once was asked to spend almost half a year in China away from my home and family to help turn around eBay. This was during my son’s final year in high school and in the middle of building our dream home. Meg Whitman asked me to grade, on a scale of 1 to 10 (with 10 being the highest), my enthusiasm for the assignment. I answered honestly, “a ‘1’ or a ‘2’”. I was told, “You’re going anyway.” And so, I went. I did my best to put my heart and soul into fixing things at the company, but it came at big family cost. (In hindsight this was worth it, but in the moment I was not so certain, nor was my family.)

A year later, when my daughter was about to enter her senior year, I was asked to transfer to Europe to run Skype. This time I put my family first, but also knew that decision meant it was time for me to leave eBay. It’s not that eBay required that; it’s that it highlighted to me that I was unwilling to put the mission above my personal desires, which felt wrong as the #2 person at the company. I have never regretted the decision to not move and the subsequent decision to leave; it was the right call because of what I was willing to give at the time.

There are all sorts of leaders, from command and control leaders who bark orders and expect everyone to toe the line, to inspirational servant leaders who put the entity’s needs above their own. The most inspiring are the CEOs who are committed to changing the world, but who are able to do so by putting the destiny of the company ahead of their own ego or needs. (Where it gets really tricky is being able to simultaneously take care of all the entities they are part of—their company, their family, their team.)

Much of this is personal, so don’t let anyone else decide how you want to deploy the CEO role at your company. There are many successful CEOs who do the role in different ways. But in order to determine if they still deserve the role, I think every great CEO needs to periodically ask themselves:

  • Am I driving/leading the company forward or holding it back?
  • What unique contributions am I making to the success and future of the company?  Would I rehire myself as CEO? Why?
  • Am I getting managed into compliance by the Borg?  Or am I challenging the Borg to get to previously unimagined capabilities?
  • When I do challenge the Borg and look at it in hindsight, was it the right thing to do or did it cause unnecessary churn and not achieve the desired result. Why?

Sometimes, when you’re tired or overwhelmed, you need to harden your resolve and dig deeper. I have a lot of belief in founders and their willingness and commitment to do the unthinkable. But, if you no longer have the burning desire to take on the challenges and responsibilities that come with the top job, you may need to put the company’s success ahead of your own. And, that may mean stepping aside.

Being a leader is hard work and it requires tons of personal sacrifice. You have to manage your employees, your customers and your board and investors.  The founder of TPG categorized it once to me as playing 3-dimensional chess. It’s insanely difficult.

You have the toughest and the coolest job on the planet. I wish you strength and peace.

All the best,

Maynard