1.  How are your kids?  

2.  How is your wife?  

3.  Was it worth it?  

I wouldn't

1. Think of your work/home balancing act. Are you happy?

2. What does success look like to you?

3. What does a typical work week look like for you?

4. What business book inspires you the most?

5. What about your business would you change right now?

Bonus: Are you debt-free?

I've listened a lot of interviews with top agents and successful professionals and the most interesting part for me: how they started and what was the WOW moment for each. 

What would you do different if you could start over?

At what point in your career did you know you had made it?

What one thing/practice can you attribute the lion's share of your success?

Were you born into a real estate family or a real estate dynasty?

Do you have a business degree or other college degree?

Can you tell me about your average day?

Do you work 24/7/365 or do you schedule regular time off?

To what or Who do you attribute your success?

Much like Wayne Martin's questions.  

How do you feel about crowd funding to purchase real estate projects? Do you participate or create limited partnerships for private purchases?  If you look back at your career in real estate, what would you tell someone just starting out on how to be successful in the business?  

What time of the day do you go to the gym?

Do you have a trainer?

Do you eat grain?

We all think best when we're in good physical condition....development of the mind and body go hand in hand....

Wanna buy some property?

One of the questions would be if they have family and freids in my area. I would ask for referrals.

1. Tips for time management?

2. What are your biggest time wasters?

3. How do you cope with stress?

Hmmm...this is very thought provoking. I think one question I would ask is...what one thing do you believe propeled you to the top?

I have to think about what else I would ask. 

Jared nailed it...

I like Amanda and Jared Christiansen's answer.

Probably more that 5 questions

What is your priority in your life?

Who is your coach?

What percentage of your business is from PAID advertising?

1.  What would you do different from year one?

2.  Did you get good sound advice from your first broker

3.  Would you hire a coach now after looking back on your start in the business.

I don't think they would talk to me.

1. What is your best lead source?
2. What is your best marketing strategy?
3. What would you do differently if you had a "do over?"
4. Do you have a good life outside of work and would your family agree with that answer?
5. What one thing would you do to change the world if you had unlimited power?

That is not something I aspire to do ... therefore I would not spend 1 minute asking anything. 

I do not engage or envious of these folks. 

I will have to think about this for 30 minutes and get back to you.

I have to review this tomorrow for the input

I do not have any specific questions in mind.

Amanda and Jared Christiansen nailed this one!

If you were a tree what kind of tree would you be?

Ask...then listen...carefully...very carefully....

I would need to know who the agents are so I could research their background and market and customize each set of 5 questions to each situation.