Leadership Reflection Questions Every Leader Should Ask Before the New Year

Before leaders plan the year ahead, there’s a more important step they often skip: reflection.

Using intentional leadership reflection questions helps leaders extract wisdom from experience instead of carrying the same stress, habits, and patterns into another year.

This isn’t about self-criticism. It’s about clarity.

How to Use These Leadership Reflection Questions

Set aside 20–30 minutes. Write if that helps. Think if it doesn’t. You’re not looking for perfect answers—just honest ones.

Emotional Leadership Questions

●       What emotions showed up most often for me as a leader this year?

●       When did I feel grounded and confident?

●       When did I feel reactive or overwhelmed?

●       How did I handle pressure?

Boundary and Burnout Questions

●       Where did I overextend myself?

●       What did I say yes to that cost me more than expected?

●       What boundaries actually protected my energy?

●       What signs of burnout did I ignore?

Authenticity Questions

●       Where did my leadership feel most like me?

●       Where did I shrink or avoid conflict?

●       What values guided my decisions?

●       When was I proud of how I showed up?

Problem-Solving Questions

●       What problems drained the most energy?

●       Which challenges were systemic, not personal?

●       What decision would I handle differently now?

Empowerment Questions

●       Who grew under my leadership this year?

●       Where did I delegate well?

●       Where did I hold on too tightly?

Turning Reflection Into Action

Choose:

●       One insight to carry forward

●       One habit to release

●       One support to commit to

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