3 Wonderfully Negative Traits of Successful Startup CEOs

So much is written about the positive attributes that successful CEOs have. We are usually given a list of adjectives such as confident, passionate, tough-minded, intrepid, etc.

Basically, the successful CEO has been molded into an inaccessible superhero full of traits that are about as commonplace as Barbie’s anatomy.

In my career working with dozens of CEO’s hailing from a range of companies — from leading financial services brands, to scrappy tech startups — I do agree that there are a healthy percentage of executives that do posses many of these traits.

What I disagree with, strongly, is the way we’ve been made to think that leaders have to have bulletproof personalities in order to be successful. In fact, I would say that some of the most successful CEO’s that I’ve worked with possessed traits that would be seen as the antithesis of the CEO archetype that is so prevalent today.

MIT researcher and creator of ideonomy, the study of ideas, Patrick M. Gunkelof, created a list of 292 possible personality traits. Within this list there are three groupings, Positive, Neutral and Negative. In my experience some of the most successful CEO’s that I have worked with had three main personality traits that all fall in the negative grouping.

Fearful:

Fear is a miraculous thing. It is both a best friend and worst enemy. Something that can bind us like a straight jacket and also propel us like a rocket ship.

CEO’s with a high degree of fear tend to have a higher degree of drive as the latter is often driven by the former. I am no psychologist and won’t begin to assume where this fear comes from as it is certainly different person to person, but the underlying fear of failure can be a tremendously beneficial asset. In the startup world, where failure is lurking around every corner, this is exceedingly true.

Naive:

Naive can mean a lot of things, but in this case I’m using the definition inexperience. Now I’m not suggesting that CEO’s should be completely wet behind the ears, but I am saying that low mileage can give you a longer lifespan. In the startup world it’s not uncommon to come across battle seasoned CEO’s who are on their third or fourth startup tour, embarked on yet another war to defeat startup failure.

While this experience can provide a degree of wisdom that can help you navigate the landscape more effectively it can also have a wear and tear affect.

Let me use another analogy. I have a family member who is currently in tryouts with several NFL teams. One would assume that this person must have spent his whole life training for this moment, grinding day in and day out. Actually, he walked on his college football team as a junior and has only ever played two years of competitive football. Yes, he has the intangibles and natural gifts that separate him from 99% of us, but he has something else that teams are intrigued by, inexperience or naïveté. If he has gotten to this point so soon in his career, imagine what an NFL team could help mold him to be — and all while having near zero mileage on his body.

Insecure:

This might be the least intuitive trait. Whenever we think about CEO’s one of the first traits we think of is an unflappable sense of confidence. In my opinion, confidence is one of the most overrated and dangerous traits.

The overconfident CEO — someone who I’ve met many times before — is perhaps one of the most insidious dangers to any startup culture. This person is drunk on the company Kool Aid — which more than likely was entirely created by them — and is someone who is immutable, combative and hardly a leader at all.

Recently we were working with an incredible startup, backed by a who’s-who of investors. We had secured the CEO’s first ever live broadcast interview and he was terrified. He made no secret of it either. After a good amount of preparation, the interview ended up going just fine. Yes, they looked nervous at first, but nervousness is an authentic trait. And so is insecurity. If there’s anything customers want and expect today it’s exactly that: authenticity.

CEO’s are like you and me — we are all different. I have a problem with people glorifying traits that are mostly just masks or facades anyway. I think we need to do a better job of celebrating the traits that we consider weaknesses and talk about how they can be strengths.