10 of Bobb Biehl’s all-time, favorite questions:
#1 Why?  This gets to the bottom of an issue quickly, addressing purpose, reason and foundation. To get even deeper, ask, “Why is that important.”
#2 What is the long-term ideal?  This moves you past temporary fixes toward solutions for the deep future.
#3 To gain the big picture quickly: “If we could only do 3 measurable things in the next 90 days which would make a 50% difference, what would we do?”
Steve Douglass’ question immediately addresses priority, time and result.
#4 If I could only accomplish 1 measurable thing in the next year, what would I do?  In seconds you get past day-to-day detail into the largest picture possible.
#5 What was your life like in 4th grade?  Age 9 is our most formulative year in life. What you were comfortable doing then is what you’re comfortable doing today. 
#6 How do you plan to make the most significant difference in your life?
This gives deep insight into who you really are and your lifelong values.
#7 What 3 changes in your life would be most pleasing to God?  This identifies where you really need to grow personally and spiritually.
#8 Of all things you do well, what is your single greatest strength, what you do the very best?  This is the most effective way to reach your full potential.
#9 Is there something heavy on your shoulders today?  This non-threatening question leads to many deep and very personal discussions.
#10:  If you could do anything you wanted, had all the time, money, staff and education you needed, and knew for certain that you couldn’t fail, what would you do?  This quickly opens discussions of your ideal direction in life.  

Bobb Biehl is an Executive Mentor.   In 1976 he founded Masterplanning Group International. As its President, he has consulted personally with more than 500 clients. He has met one-to-one with more than 5,000 executives.  Based on thousands of hours of practical experience, he has created 35 leadership / management tools (books, tapes, notebooks) for personal and organizational development – available at BobbBiehl.com