Here are the questions I'm currently asking:

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• What gadgets/apps/software do you rely on?
  
  

• Do you subscribe to any particular productivity system?
  
  

• How do you keep track of what you have to do?
  
  

• How do you make sure nothing falls through the cracks?
  
  

• How do you process email?
  
  

• How do you use your calendar?
  
  

• How do you communicate with your team(s)?
  
  

• What’s the best process or system (rule, tradition) you’ve set up for yourself or your department/office?
  
  

• How do you decide what to delegate?
  
  

• How do you choose what work you’re going to bring home or stay late for?
  
  

• What is the best productivity or time management trick you’ve learned?
  
  

• What tips would offer to a new manager? Hard skills? Soft skills?
  
  

• How do you keep yourself from burning out?
  
  

• What do you do to get yourself back on track when things are overwhelming or tough? Do you have a Mantra?
  
  

• What's the most valuable lesson you’ve learned the hard way in this job?
  
  

• What did you think the job and the role were before you got the job?
  
  

• What do you think the job and the role are now?
  
  

• How does it feel doing the job now versus how it felt when you started?
  
  

• What seemed important in the beginning that doesn’t now? And vice-versa? 
  
  

• Book, podcast, website recommendations that help with work life?
  
  

• What's one question you'd like to hear the answer to?