- How is the company doing against its goals for the year?
- What does our runway look like?
- What signs of product success are we expecting? What are we seeing?
Note that in any company, and especially in a startup, all of these questions are rife with uncertainty and stress. You should expect these to touch a nerve, and request brutally honest answers. Leaders experience existential fear on these topics frequently, even in great companies.In the responses, be wary of blithe positivity more than bad news. Bad news is normal; a healthy organization learns from it and improves. Optimism disconnected from reality is either an attempt to mislead you or a sign of blindness to results.