If you’re trying to assess someone to see how entrepreneurial they are, try to evaluate their honesty first. It’s hard to do this when everything is o.k., dishonesty is easy to mask when there’s no pressure, but when there are major problems people’s true colours come out.
Entrepreneurs think differently than regular old managers. They welcome risk, collaboration, new ideas, iconoclasts, unusual thoughts. They’re more open to having very intelligent people around them, because they’re an entrepreneur, not merely a supervisor or a manager of people.
If you’re a non-entrepreneur wanting to make this transition, this is some of the retraining you’ll have to do — risk, new ideas, smarter people telling you often what you don’t want to know, the brutal truth. These are good things to an entrepreneur.
Most CEOs are entrepreneurs and most entrepreneurs naturally rise to the level of CEO or similar. Most, in fact almost all, entrepreneurs (and CEOs) that succeed are also honest. They like to controllability that honesty brings, the consistency, as outlined in the prior section. Their ego is evolved past the stage where they need to lie or obfuscate to be able to operate.
Watch for it, if you see a dishonest CEO, they probably aren’t an entrepreneur or a CEO, and they will fall eventually. Zuckerberg is an anomaly, but he will go too, eventually.
I’ve seen CEOs change from entrepreneurial and honest to egotistical, dishonest, insecure. They say that pressure can do that to someone with an ego weakness –– everything smooth until things get tough.