A few questions that may seem innocuous but are usually much harder to answer

• who is the boss?
• what is your function?
• What makes you qualified for it?
• what is your strength? and weaknesses?
• what is your experience?
• what are your hard skills?
• what are your soft skills?

• what do you really want to do in life?
• what do you want to learn?
• What is your mission?

• what problem do you solve?
• is that a problem people need a solution for?
• why would your solution be good?
• why would anyone pay for your solution ? 

• who and where are your competitors?

• can you make money with your solution ?

• is your growth pace sustainable ?
• is your growth pace quick enough to outcompete the market?

• when are you running out of cash?