Learning to Ask the Right Questions

The Answer to How Is Yes is a fine book by Peter Block.  (The subtitle is: "Acting on What Matters.")  Block believes that real change comes more from pursuing profound questions than seeking practical answers.

 
At the beginning of the Introduction, Peter Block quotes from his book Stewardship (p. 234).  He writes:

There is depth in the question "How do I do this?"  that is worth exploring.  The question is a defense against the action.  It is a leap past the question of purpose, past the question of intentions, and past the drama of responsibility.  The question "How?" — more than any other question outside of us.  It is an indirect expression of our doubts. 

So I am curious.  What are some of the most important questions that you have wrestled with?  What are some questions that we all would do well to wrestle with?