The one question list is "what's the biggest risk of your business". This sounds innocent (and definitely under-specified), but it requires known all the big risks and picking the most important one, thinking about timelines, micro- and macro trends, etc.
And then of course the answer itself is kind of irrelevant as long as you get the feeling that it gives you information, it's honest, it's not trying to cover up something, etc.
The most important part(s) of doing due diligence is that it has to be done and diligently by someone you trust. Outsourcing it to the subject of the whole process, and reducing it to checklists makes it 10/10 easy to game. It has to be done to the depth, detail, understanding necessary to have confidence.
That said checklists are very important to establish the possible areas for drilling down. But since time is always a premium it doesn't make sense to do everything just because it's on the list. (Hence your question of getting a shorter list.) But that list has to be tailored to the situation - as other comments noted.
And, obviously, this is why many people try to invest in things they know, and/or focus on areas they know. (And then fail if they ignore the tough questions that stresses them out, or forgot to diversify, or forgot to do reference class estimation and then class appropriate risk weighting. In other words the planning fallacy.)
And then of course the answer itself is kind of irrelevant as long as you get the feeling that it gives you information, it's honest, it's not trying to cover up something, etc.
The most important part(s) of doing due diligence is that it has to be done and diligently by someone you trust. Outsourcing it to the subject of the whole process, and reducing it to checklists makes it 10/10 easy to game. It has to be done to the depth, detail, understanding necessary to have confidence.
That said checklists are very important to establish the possible areas for drilling down. But since time is always a premium it doesn't make sense to do everything just because it's on the list. (Hence your question of getting a shorter list.) But that list has to be tailored to the situation - as other comments noted.
And, obviously, this is why many people try to invest in things they know, and/or focus on areas they know. (And then fail if they ignore the tough questions that stresses them out, or forgot to diversify, or forgot to do reference class estimation and then class appropriate risk weighting. In other words the planning fallacy.)