There are no stupid questions.

By asking questions people are starting to create awerness about particular topic. 
By creating awerness topic can be adressed in a correct way. 

Our biggest strength is being ignorant and asking as many questions is needed to create awerness.

How many times did you have to postpone Go Live or launch of a new product?
When did you become aware you have to reschedule?
Were you aware of consequences?

How often have risks realized?
Did you have budget for mitigations?
Did you have mitigations for realized risks?

Are your projects exciding your budgets, resources or timeline?
How often are you reported on Project statuses?
What actions can you take based on those Project statuses?

Do you have Account plan?
Do you have Account reporting?
Do you have Account revenue plan?

How is Proposal / Contract managed and signed off?
How is Sales handing over new Account?

Are your employees achieving KPIs?
Are their KPIs aligned with strategy?
Are subjective or mesaurable?