Great questions open up conversations and get below the surface. Below is my collection of the top questions I like use professionally and personally. Feel free to send me some of your favorites to add along.
What was your high and low for the past _______ (week, month, year)?
What are you really excited about right now?
What does success and failure look like in your job?
Have you ever thought if you were not in your current career what would you do?
What do you hope will be different in a year? What can you do to make that happen?
When was the last time you failed at something? What did you learn?
If you could do anything you wanted, money was no object and success was guaranteed what would you do?
How can I be a better friend, coworker, family member…?
What will look like the best decision five years from now?
If no one had trained you for your current job how would you be doing it?
If you could live anywhere in the world with all of your favorite people where would it be and why?
If you could have dinner with anyone who has ever lived who would it be and why?
Who has been the greatest influence in your life? How?
Who do you want to be in ten years? How are you going to get there?
If you could take one burden or responsibility off your plate what would it be?
What three things are keeping you from reaching your potential right now?
What do I most need to stop doing and start doing right now to move forward?
What do you like to do for fun?
How satisfied are you with all areas of your life right now?
How easily satisfied are you?
Are you satisfied with a little money, a little accomplishment, a little knowledge, a little growth, a little weight loss, a little charity work, a little meaningful conversation, a little challenge, a little romance, a little better, a little effort…?
What in your life is worth your supreme effort right now?
How easily distracted are you? What are you doing to combat this?
Imagine you looking back at your life as a mountain range. There are some distinct peaks. What were the top three? Also, there are some valleys there as well. What were three of the deepest ones?
What has shaped you into the person you are today? The people, experiences, failures, successes…
Where does 80% of your frustration come from and 80% of your pleasure?
What do you love about your life right now?
Is there anyone you need to go back and thank for helping you get to where you are today?
Who are three people you admire most and why?
What is the key to understanding the real you that most people miss?
In an ideal world how would you change your life right now?
If money was not an issue what would change in your life?
What are three things you can do in the next 90 days to make a 50% difference?
If you could only accomplish three measurable things professionally before you die what would they be? In the next five years?
Do you prefer setting goals and reaching them or defining problems and solving them?