Very quick follow-up post to my article on Techcrunch.

There was a discussion between @joshelman and @pingupceo who brought up a question that he was recently asked that goes:

“What have I not asked that I should be asking?”

Josh mentioned that this is something that he asks often, and my partner Dave asks this question occasionally as well.

The question can seem a bit tricky because it’s so open ended.  You don’t want to say the wrong thing, nor do you want to evade the question.  How does one handle this?

The question becomes much easier when you think of it as an opportunity, not a trick. The opportunity is to do one of the following:

1. Show off something great about your team or your business that hasn’t come up yet. Usually, something that isn’t obvious, but is totally to your advantage.

2. Bring up an obvious challenge that hasn’t come up yet but almost certainly will with any level of due diligence. It’s better to get in front of the obvious difficulties than shy away.

As Josh put it in one of his tweets, the way he is thinking about the question is: “we are getting to know each other – what have I failed to ask that is awesome to know?”

Finding an investor that is the right fit is hard to do. People are complex, and many times, both the founder and investor have far too little time to really get to know each other. So use these sorts of questions as an opportunity to do this.