One way I can tell that someone is ready to dive deeper into a problem they’re having is when they open the door with a question.
Often times, that question will be slightly misdirected; it will be pointing at something tangential to the real, underlying problem – but not asking about the root cause of the problem directly.
This, often, is a signal from the person that they’re ready, at least in part, to discuss the real problem.
And that they are aware, on some level, what the real problem is.
If you see an opening like this, step through it with compassion, and go as far as they’re willing to let you in.
Matt Fried 