The intuitive view is less certain, encompassing subtle, non-verbal cues which are coupled with what they say and how they say it. Books have been written about body language and detecting lies and surfacing their true feelings and intentions; these are all relevant. I try to take it all in and this builds the intuitive view of a person.
All this informational and intuitive probing are geared towards not only type of person they are (hopefully they have integrity, honesty, and the whole host of other positive entrepreneurial characteristics), but also how far they can take the startup idea they are working on.
For example, every time I meet an entrepreneur, I always bring up the vision discussion. One case that may happen is that I know a lot about the space he is working in and already have some formed opinions about where they should take their business. They ask me what those opinions are and of course I start ranting or spouting ideas. Then I gauge their reaction to my words.
Sometimes they have blank stares on their faces; I can tell they have little idea what I am talking about, or they have some sense but don't have the depth of that knowledge. Sometimes they say they agree with me, but something in their body language or the way they say it tells me it is just talk and I cannot see any depth in understanding.
And the best reaction is when they actually know something about what I say and we have a bromance discussion about how geeky we are in that we both share knowledge and are big fans of this area.
However, if that bromance geek discussion doesn't happen, then I begin to worry. I start to form the limitations of where this team can take a concept. Either they must learn this themselves (first the interest, then the ability to learn it) or they must have the awareness that they must hire the talent to fulfill the bigger vision and not the vision to the limits of their current abilities.
Not many people have the ability to change into new areas of growth, whether it's physical, emotional or intellectual. It is the rare individual that can. Most likely, what we see by the time they are adults, and by the time they are working on this startup, is what we're gonna get.
Believe me, I have tried to get people to do things outside their current areas of interest or strength. But most of the time, it is futile, especially as an outside entity to a startup. If I am not there day to day 24/7, it is really hard to get an initiative going that is not familiar to the personnel there already. This is why I try to be as creative as possible in providing a multitude of ideas and see which stick and which do not, and also try to be as creative as possible within the constraints of the team's abilities and skills. But I have given up trying to make them someone other than who they are today unless they are willing or able to make the change in themselves.
The trick therefore, is to get a sense of these people through information gathering and through intuition, form a picture of their capabilities into the future, and then make the call. Building your sensitivity to determining who people are is an important part of investing; at early stage, however, we need to be able to make that determination as fast as possible since we don't have the luxury of getting to know them over time before we invest.