Questions to Ask Someone You Advise

Learning About and Supporting the Whole Person – take your conversations with those you advise to the next level with these questions.

Future Vision 

  • Your 80th birthday – Write down 5 bullet points you’d want people to say about you.
  • Work backwards from there to determine what’s important to build into your life today. Your answers will evolve over the next 50 years. 
  • What are you reading and/or learning that’s helping you envision a great future for yourself? 

Immediate & Near-Term Issues 

  • Your ideal near-term priorities?
  • Rank how you want to prioritize your time and efforts from 1 to 5.
  • Now rank what your spouse or best friend(s) say are your actual priorities from 1 to 5.
  • How are they different? Are your actual priorities aligned with your 80th birthday bullet points? 
  • What keeps you up at night? 

Self-Awareness 

  • What are your top aptitudes and talents? How are you gifted? What’s your superpower?
  • Energizers – Name them in any part of your life (job, role, hobbies, sports, children, giving back). What areas of your life are most draining? Burdensome?
  • Environments – Where do you thrive most? (Small vs. large, creative, competitive, collaborative, process-oriented, common-good focus, etc.)
  • Assessment Tools – Enneagram, Myers-Briggs, StrengthsFinder, Johnson-O’Connor, YouScience (online version), Strong Interest Inventory, Career Leader, Kiersey (temperament, personality traits, roles), FourSight (entrepreneurial assessment), Love Languages, Spiritual Gifts
  • Time Bomb – If you were to have a fall (publicly or privately) what would be the reason (your weakness/blind spot/Achilles Heel)? 

Relationships

  • Tell me about the key relationships in your family eco-system. With your father and mother? 
  • How would you rate your marriage right now on a 1–10 scale?
  • How do you think about dating and your path towards a long-term relationship?
  • Who has been the most influential person in your life and why? 
  • How would you rate your friendships on a 1–10 scale? 

Career 

  • What is the biggest issue you face in your work life?
  • Do you sense you are well suited for your current work? Can you see yourself being stimulated and fulfilled on your current career path the next five years?
  • If you could “white board” an organization and your role that would be exciting assuming no financial, geographic or other constraints, what might that look like? 

Values & Spiritual Life 

  • Were you raised in a family with a particular worldview? A spiritual or religious tradition? 
  • How is your worldview or spiritual life reflected in the different components of your life? 

Other Questions 

  • What approach or framework do you use to manage your finances? How is it working? Is your spending on lifestyle expenses allowing you to save and be a generous giver? (Example: 75% spending, 15% saving, 10% giving model)
  • If your parents had a physical piece of paper with a script for your life, what would be written on it? What are you most proud of? Your three greatest achievements? 
  • Where is your hometown? How did it impact you? What are you most afraid of?