I love asking entrepreneurs questions as it helps me better understand their business as well as how they process information. I also like it when entrepreneurs ask me good questions. There are good and bad questions, but I really enjoy questions that make you think and don’t have a clear answer.

Questions with a clear answer

Some questions have clear answers and you can prepare for them. While this may confirm something you are thinking or already know, rarely is there a new insight from these questions.

Examples from entrepreneurs:

• What stage do you invest at?

• What is the size of your fund?

• What is your average check size?

Examples from investors:

• How many customers do you have?

• What is your runway?

• What are your pricing plans?

Questions that make you think

Other questions do not have clear answers and make the other person think. I love asking and getting these questions because it pushes your ability to think on your feet. Even better is when this is a follow-up question to a certain part of the discussion that shows your ability to listen and connect different threads.

Examples from entrepreneurs:

• Why did you take this meeting?

• What gives you pause about making an investment?

• You mentioned XYZ, how do you feel that impacts ABC?

Examples from investors:

• What did you learn from your last startup that you are applying to this one?

• If this doesn’t work out, what is going to be the reason why?

• How do you think the market will evolve over the next 5-10 years?

Use questions as a way to listen and learn more about the people you are meeting with. I often walk away from a meeting impressed (or unimpressed) by the questions the entrepreneur does (or does not) ask.