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?