I know making questions is a a good start, but I am looking something more elaborated.
When I went to interrogation school for the army, the first half of the class is based entirely on those. The second half is classified. If you are under 31 and reasonably smart, highly recommend getting a two year Army contract and going through the training. Even if you are not a US citizen, you can still do it by going through your local embassy IIRC.
The first half of the class is really hard and if you wash out, you can end up being a cook. So, it’s not for the faint of heart…
Beyond that, we had a book list. There’s one that stands out in my memory, but I don’t remember the name of it or the author. The book was written by a German defector in WWII or Cold War that explores how interrogation is more successful using certain approaches and which modern interrogation is built on. It explores building a spy network in the second half, in a foreign country, etc as well.
If I can remember the name of the book, I’ll comment or update here. Sadly, I know exactly where this book list is, but it’s literally an ocean away in a storage unit.
All those skills come in quite handy in the real world to build rapport with people and build up an information network inside your workplace so you have a good idea of what is going on around the company. You can also get those same skills by reading sales self-help books, they just use a different vocabulary and don’t talk about the “dark side” (making people angry, sad, guilt trips, gas lighting, etc) while interrogation makes use of them in some cases.
Blurb from amazon: The Psychology of Intelligence Analysis has been required reading for intelligence officers studying the art and science of intelligence analysis for decades. Richards Heuer, Jr. discusses in the book how fundamental limitations in human mental processes can prompt people to jump to conclusions and employ other simplifying strategies that lead to predictably faulty judgments known as cognitive biases. These analytic mindsets cannot be avoided, but they can be overcome through the application of more structured and rigorous analytic techniques including the Analysis of Competing Hypotheses.
For physical tradecraft, there's lots of reading: old declassified manuals, certainly read non-fiction spy novels (though you have to be able to read between the lines in a lot of places). Billion Dollar Spy is a good one for tradecraft.
I would generally avoid movies -- I can't recall one where I've seen good tradecraft.