My Favourite Question to ask Mentors

One of my favorite questions to ask older friends and colleagues whom I admire is, “Knowing what you know, what would you do if you were in my position?” I find this question especially useful when someone has high context of my situation like my manager, skip, or older friend.

Most people refrain from being overly prescriptive. Yet, sometimes this is exactly what I want. In order to reach a certain level of insight, the right questions need to be asked. But if they already have a context of my situation then I can gain this insight by giving them permission to be prescriptive.