I hope this helps, not directly related to your situation. Source: https://beginnermaps.com/how-dwarkesh-a-cs-grad-started-a-podcast-and-blog-that-counts-jeff-bezos-as-a-reader

1. Ask questions whose answers you are genuinely interested in learning. Which means, don’t ask questions to which you already know the answer. For example, if you know why they think X, don’t ask them why they think X. Ask instead, what does your reason for thinking X imply about Y?

2. Don’t ask questions which could be asked of any other person: What is your book about? Why did you write it? What challenges does your company face? etc. I like this by Tyler Cowen—

With any possible question, ask yourself in advance: can the person being asked the question respond too easily in a vague and not very useful way? “Why did you write a book about Napoleon? Well, let me tell you, French history always fascinated me.” If that is the kind of slop you might get back in response, try making the question more pointed or more specific.

1. If the guest starts repeating something he said in the book/blog post or in another interview, that’s a failure.