25 Hard Questions Every Founder Should Ask Themselves

Here are some of my favorite provocative questions: What's next? What don't we know? What are we going to do? When did you last create something? What's relevant? What questions should we be asking? What's the most important thing? What would make you a little more uncomfortable? What would be your first move as CEO? What is the world telling you?

I’m going to take you through the four most important questions I ask all founders. The goal of asking these questions is not just for you to understand the business but also so you yourself can answer four critical investor questions: Why has this founder chosen this business? How committed is this founder? What are this founder’s chances of succe

There are personal questions you can ask founders to get a sense of what they’re about. The one I care about most is, “What did your parents do?” I used to ask, “Tell me about your mom and dad,” but that’s a bit of a biased question since some folks grow up with two moms or two dads or a single parent, so the best way to do this is to ask about the

Here are seven questions you can ask yourself (and your team) before building a new feature.