When I was figuring out which company I wanted to join following my first (of what will be many) ill-fated forays into entrepreneurship, the CEO question loomed large in my mind. It is not my natural inclination to follow, so choosing the right person to work for is a pretty complicated decision. CEO is always an important role, but in startups the leader is going to be pretty make or break. You essentially end up betting the trajectory of your career on the person in question. You know, no big deal.

So…what did I consider relevant in making the decision you ask?

Clarity of Vision

A lot of folks just look at the ”vision” box and check it off. I’ve found that to be a relatively poor means for distinguishing between folks I’d want to work with. There are a lot of funded companies headed by people with grandiose ideas, but I’ve found very few with a very clear understanding of how those ideas will operate in the circumstances they find themselves in. It takes a person with vision to start a company, but clarity of vision is what will make it successful.

Clarity is about a concrete understanding of the major features of the vision and a firm belief in the proper approach to those features. If your goal is to “redine social,” how would you break that down into an articulable strategy? What happens if core assumptions are incorrect? How sure are you about those assumptions? This can go on for a while.

The CEO will speak with many people, and all of them will have very different ideas. A CEO without a strong grasp on the “enlightened path” will be swayed often, causing a pivot whiplash for the company as it goes in any number of directions. Things like feature creep and bloat are symptoms of a CEO without clarity. Dangerous stuff for a startup.

Sophistication

Sophistication is all about a nuanced comprehension of the details of the industry the person occupies. Vision can be enough in the right hands, but CEOs with a solid understanding of the inner workings of their industry instills a bit more faith in me.

I normally measure sophistication by spending an enormous amount of time studying the space and then asking a lot of questions. I don’t really expect the CEO to think of everything the same way I do (otherwise I wouldn’t bring much value to the table), but the level of knowledge and analytical framework is very important. Particularly around key areas for the success of the company. For example, I find it alarming when the CEO of a mobile game company doesn’t have a solid grasp of the UA pipeline, the relative merits of the major platforms or the game mechanics/systems. I find it hard to believe that a person that doesn’t fully understand these things will be inclined to make the best decisions regarding them.

Compatibility

This one is pretty simple: I want to like the person. It’s very hard to convince me to join a company where I haven’t had some history of positive interaction with the person. In the case of PlayMesh, I got to know the founders over the course of a year and the CEO and I spend a fair bit of time playing video games together. Not only do I respect his play within the games, but I genuinely enjoy interacting with him on a personal level.

Sometimes it’s hard to get that level of relationship with a person before working with him or her. I’ve found the best way to move things forward quickly is by being blunt. I try to be up front about what I care about and what motivates me, knowing that it may not be exactly what they want to hear. I’d rather give them a fair opportunity to evaluate me and react on that basis than try to ingratiate myself with platitudes. If people are unwilling to be forthright, it’s very easy to end up with miscommunications and mismatches.  Alas, PwnLaw is occasionally an acquired taste.

I also think its worthwhile to try and find common ground. If you share no interests beyond mutual professional goals, it’s a lot harder to make things stick. There needs to be something beyond the project if you’re going to spend 70 hours a week with someone. At PlayMesh, we spend a lot of time playing games – Magic: The Gathering, Call of Duty, Valor, League of Legends and so forth. There are other options, but the fact that I can interact with the CEO on a personal level is important to me.

Ability to Lead

You don’t need to be a full-bore extrovert to inspire the people around you. I want someone who can capably lead. All of the things outlined above are important to leadership ability, but more than anything I find it’s a matter of effectiveness in communication. People who communicate well are understood easily. This is the hallmark of a good leader. Vision is not very useful if the people cannot understand it. Being able to connect to a group of people as well as one-on-one conversations is an incredibly valuable trait.

A clear communicator can set the tone for a company and ensure everyone understands the strategy and core values of organization. This isn’t about marketing, it’s about being understood.

Everything Else

There’s a lot more that can be heaped on top of stack – presence, intelligence, charm, etc. Honestly, they’re all pretty much covered under the things above. A good communicator has presence. It’s tough to have sophistication without intelligence. So on and so forth. There is no need to make this overly complicated. If you want someone to lead the way, it seems reasonable to focus on the things that matter: vision, depth of knowledge, ability to communicate that knowledge, and your desire to spend time with that person.

JM: This is an essential analysis in establishing your own job satisfaction and by proxy your success in your career. This model of considered evaluation of course scales up and down the org. Up, as a CEO working with investors and board members, and down as employees in a larger company in terms of assessing your boss as well as the CEO and exec team. Any way you look at, your career is in your own hands, you are ultimately responsible for what happens in your life. By that measure, your hands are never tied, you always have the leverage to select your CEO or boss.