Leadership-life Fit: Rearview and Windshield

Posted By: Dana Schon, Ed.D. Mentoring Matters, Asst/Assoc Principals, Elementary Principals, ML/Sec Principals, Superintendents,

Reframe, refocus, and refuel. Set aside time to look in the rearview to reflect on 2025, and then peer through the windshield--What’s your vision for 2026? This series of questions can help you surface what you’ve learned in 2025 and apply it to your leadership and life in 2026.

Feel free to reflect on all the following questions or only those questions that really resonate. 
  
Looking in the Rearview

  1. If I had to sum up the past year in one word, that word would be…
  2. My favorite memory from this year…
  3. How am I different now as compared to this time last year? (personally and professionally)
  4. Of what from this year am I most proud?
  5. What is the most awesome thing that happened this year?
  6. What is the most difficult thing that happened this year?
  7. Did these things happen TO me or FOR me?
  8. How did I live my values in my daily work?
  9. What are the three most essential things I learned OVERALL that I want to make sure I “take with me" into 2026?
  10. Who were my greatest champions and advocates (who helped me most?)
  11. Whom did I help the most?  Who needed my help most? Is there a difference?
  12. Who or what got too much of my time and energy in 2025?
  13. How did I contribute to others' success?
  14. What’s something I changed my mind about this year? (I used to think… now I think…)
  15. Where can I give myself more grace moving into 2026?
  16. What time management strategy served me best this year?
  17. Where did I step out of my comfort zone?  
  18. For what am I most grateful this year?

Looking through the Windshield

  1. What story do I want to “write” in 2026? What role do I play?  
  2. What skills do I want to learn and strengthen?  
  3. How do I want to show up for myself and others this year?
  4. What new habit would I love to own? What routine/s might I create to support that?  
  5. What is one positive belief (affirmation) I am going to reinforce?
  6. With whom do I need to build relationships this year and why? What’s my first step?
  7. What are the 2-3 most important things I want to create this next year?  
  8. How do I want to contribute this year?
  9. What kind of leadership-life fit am I claiming for 2026? What is my plan for making that happen?
  10. What will I say NO to?  
  11. What criteria will cause me to say YES?
  12. What do I see is possible for me this year?
  13. What do I see is possible for our team / the people I lead / my family / etc.? (Anyone you love and/or lead.)  
  14. Who needs my help most?
  15. What is the impact I want to have this year?  
  16. What barriers do I anticipate? How might I remove them?  
  17. What have I learned from 2025 that will inform my leadership in 2026?
  18. Next year at this time, what do I want to be celebrating? What’s my first step toward that in January?