Ask them about their journey from pain-point and idea to where they are today. Listen carefully and somewhat skeptically to this story. Ask yourself, where do

Ask them about their journey from pain-point and idea to where they are today. Listen carefully and somewhat skeptically to this story. Ask yourself, where do you get the sense that they are exaggerating or glossing over something. Ask about pivots in product and strategy. Ask about financial near-death experiences. As you probe this story try to get a sense of how the founders handle tough circumstances. Ask about false starts with co-founders or employees that just didn't work out. Try to get a sense of how the founder makes tough choices and deals with interpersonal conflict. Do I think the company will get traction and grow? If I am employee #7 and I can credibly see how this becomes a company with 100 employees then there is room for me to grow and succeed with the company. When the pressure is on, how does the founder treat employees? Is he quick to sacrifice their interests for his own? Does he take responsibility or is he quick to shift blame? Is there a good fit for my skills such that I can make a noticeable difference in technology and business outcomes for the company over the next couple of years?