I love asking questions, and I love figuring out the context!
And since I love doing both of those things, I have a handful of go-to questions that I use repeatedly. They have become part of my testing habit, and I recommend them to anyone and everyone.
Here are my favourite questions to understand the context of my work:
What problem are we trying to solve? Do we know what we're doing and why?
What's the risk? Are we mitigating the most important thing(s)?
Who cares? Is there anyone we're forgetting?
If you end up using these questions, let me know what you think!