The vast majority of my mentees are what I would consider self-confident: they believe in themselves and their ventures, but despite typically stellar academic and business credentials, I’ve only found two in eight years of mentoring that drove the meter into the conceited or arrogant end of the scale.
The telltale sign is that a founder considers themselves uniquely talented beyond anyone else in the world. This is a dangerous delusion at best, because what I have found is that founders with this belief tend not to listen. They are “know-it-alls” versus “learn-it-alls” in the words of Microsoft CEO Satya Nadella.
It’s virtually impossible to mentor someone who doesn’t listen, so fortunately for me in both cases the mentee made it possible for me to exit the relationship.
But it’s worth going beyond self-confident into a quality that I think really makes for a good CEO: charisma.
charisma |kəˈrizmə|
noun
1 compelling attractiveness or charm that can inspire devotion in others:
Beyond the dictionary definition, I think another element in charisma is self-confidence. Another is that when a charismatic individual talks with you you get the feeling you are the only person in the world at that moment. Their full attention is focused on you in a way that escapes even the most self-confident individuals.
Obviously “inspiring devotion in others” comes in very handy as a CEO and part of what separates leaders from managers. I only met Steve Jobs once very briefly when I was at MIT and he paid us a visit before a Boston Computer Society meeting because we were selling his NeXT machines in the MIT computer store. But it will come as no surprise to anyone that he tops my CEO/charisma scorecard.
Other charismatic CEOs that come to mind that I’ve known include the late Wayne Oler, of Addison-Wesley Publishing Company and Mitch Kapor, founder of Lotus Development. (While Mitch didn’t enjoy the CEO role and eventually stepped down in favor of Jim Manzi, Mitch was the prime move of the company as it took off like a rocket.)
So charisma is at one end of the scale, conceit at the other. What we should be looking for is a strong degree of self-confidence in founders, as doing a startup is very hard and has its ups and downs. Without self-confidence a founder won’t survive the down times.
A good example of conceit and arrogance and how it can hurt you comes from the recent Super Bowl:
Kyle Shanahan Must Own His Mistakes to Succeed as an NFL Head Coach – Bleacher Report by Jason Cole.
People who know Kyle well will all tell you that he’s arrogant,” said an executive to an NFC team. “He talks down to people, and he doesn’t listen. He thinks that he knows better than anybody else…and he likes to prove that.”
His two play calls when the Falcons were within easy field goal range demonstrate how arrogance can cause failure at the most critical times.
Mentorphile 
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