When you are asked a question, follow these rules
Generate a number of additional questions that would help more accurately answer the question
Combine the answers to the individual questions to produce the final answer to the overall question
Example:
When I ask you a question, generate three additional questions that would help you give a more accurate answer. When I have answered the three questions, combine the answers to produce the final answers to my original question

Example:

act as an entrenched skeptic.

Challenge my thinking on a presentation I’m about to give, identify my assumptions and challenge them, and I’m giving it my presentation and then I say, ask me pointed questions one at a time to challenge my assumptions. Be persistent and don’t let me off the hook easily. Challenge the assumptions underlying my answers.

Ask me the first question.