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TechCrunch: What’s The Most Difficult CEO Skill? Managing Your Own Psychology.: By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology. Organizational design, process design, metrics, hiring and firing were all relatively straightforward skills to master compared to keeping my mind in check. Over the years, I’ve spoken to hundreds of CEOs all with the same experience. Nonetheless, very few people talk about it, and I have never read anything on the topic. It’s like the fight club of management: The first rule of the CEO psychological meltdown is don’t talk about the psychological meltdown. ....... this is the most personal and important battle that any CEO will face. ..... no CEO ever has a smooth path to a great company. Along the way, many things go wrong and all of them could have and should have been avoided. ..... If CEOs were graded on a curve, the mean on the test would be 22 out of a 100. This kind of mean can be psychologically challenging for a straight A student. It is particularly challenging, because nobody tells you that the mean is 22. ...... At a certain size, your company will do things that are so bad that you never imagined that you’d be associated with that kind of incompetence. Seeing people fritter away money, waste each other’s time, and do sloppy work can make you feel bad. If you are the CEO, it may well make you sick. ....... Every problem in the company was indeed my fault. ....... Being responsible for everything and getting a 22 on the test starts to weigh on your consciousness. ....... CEOs often make the one of the following two mistakes: 1. They take things too personally 2. They do not take things personally enough ...... Ideally, the CEO will be urgent yet not insane. She will move aggressively and decisively without feeling emotionally culpable. If she can separate the importance of the issues from how she feels about them, she will avoid demonizing her employees or herself. ...... In your darkest moments as CEO, discussing fundamental questions about the viability of your company with your employees can have obvious negative consequences. On the other hand, talking to your board and outside advisors can be fruitless. The knowledge gap between you and them is so vast that you cannot actually bring them fully up to speed in a manner that’s useful in making the decision. You are all alone. ....... asking oneself anything 3,000 times turns out to be a bad idea ...... if you don’t like choosing between horrible and cataclysmic, don’t become CEO ...... Make some friends ..... it is extremely useful from a psychological perspective to talk to people who have been through similarly challenging decisions. ...... Get it out of your head and onto paper ..... I wrote down a detailed explanation of my logic ...... Focus on the road not the wall—When they train racecar drivers, one of the first lessons is when you are going around a curve at 200 MPH, do not focus on the wall; focus on the road. ........ A Final Word of Advice – Don’t Punk Out and Don’t Quit As CEO, there will be many times when you feel like quitting. I have seen CEOs try to cope with the stress by drinking heavily, checking out, and even quitting. In each case, the CEO has a marvelous rationalization why it was OK for him to punk out or quit, but none them will every be great CEOs. Great CEOs face the pain. They deal with the sleepless nights, the cold sweat, and what my friend the great Alfred Chuang (legendary founder and CEO of BEA Systems) calls “the torture.” Whenever I meet a successful CEO, I ask them how they did it. Mediocre CEOs point to their brilliant strategic moves or their intuitive business sense or a variety of other self-congratulatory explanations. The great CEOs tend to be remarkably consistent in their answers. They all say: “I didn’t quit.”