So, I was reading Guy Kawasaki's questions to ask a startup. One of them is to ask if you can speak with one of the investors on the Board of Directors. A startup that offered me a job asked me if I wanted to speak with one of them. It seems like Kawasaki's advice is mostly predicated on whether they'll let you speak with them or not. There's no indication of what I should actually talk to them about. What on earth should I ask them?
You'd have an interesting conversation around topics like:
What attracted them to the company as an investor. What they feel are the key challenges / risks / opportunities / priorities. How the team is coming together. What's important to be achieved to support the next funding round. What factors they would be weighing up, if they were in your shoes.
This is all a bit generic. I'd certainly want to read up on the person I was going to meet - invest in the relationship from the outset. And with care, if there are big questions you have based on the people you've already met, this is one of your best chances to ask them.
Guy's point is that if you are going to take a really important job in that startup, company will want you to meet the investors hence if you ask and get negative answer that means they don't care about you that much and if you get positive answer, all good.
This certainly doesn't apply to any new hires, if I'm going to hire another programmer to the team and she asks me to meet one of the investors, I assume I'd say "Why the f***?".
However if I'm going to hire someone who's going to take the our flag line product's project lead, then answer would be "of course".
And assuming you meet one of the investors, I'd just chat about the business instead of a particular question.