Talking touchy topics with touchy friends

Hmmm. How do I say this without being too obvious?
Things have happened and are happening and even better thing's will happen. There is a lot of uncertainty around all of those happenings and ideally all the risks associated with such situations can be anticipated and dealt with. And less-Ideal circumstances are prevented or avoided. Considering there is limited experience in dealing with avoidable situations of various natures, ones who have formerly found themselves dealing 'with unfortunate situations must be consulted, to ask what happened, how it might have been avoided, and if they could redo, what they would do differently to set themselves up in more favorable positions. To cut thing's short, I'm asking friend P. K-on how one might do things the less-wrong way to avoid various not-great outcomes in the future. That is all, no big deal.