At the risk of making life too easy for early-stage companies I’m talking to, here are three of my favorite questions to ask the team — which is usually only 2-3 people at this stage — in one of the first meetings. I usually select a different person for each distinct question
- I’m a star prospective employee (I usually alternate between salesperson and engineer) you’d like to hire. Recruit me.
- I’m a nervous prospective customer. Gently size the opportunity, and then sell me.
- I’m an angel investor you’ve just met. You have one minute, so get me interested in taking you seriously.
These questions may or may not sound trite, but you would be amazed at how effective they can be at figuring out how clearly the team understands what it’s trying to do, what it’s not trying to do, where the value is, why the timing’s right (or wrong), and whether they can communicate with passion in a crowded market why they’re great.