10 Questions to Raise the Bar on your Leadership Next Year

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.”  – Margaret J. Wheatley

As the year comes to a close, it’s natural to look forward to a bit of a break and the promise of a fresh start in January. But too often we proceed without looking back to appreciate where we’ve been and to reflect on the weakest links in our leadership.

This process doesn’t cost a penny and only takes a couple of hours to thoughtfully complete.

The psychological benefits of reflecting on past events are well-documented. For example, A University of Zurich study found that reflecting on past challenges aids in processing future negative experiences, boosting both self-efficacy and resilience.

Indeed, there’s a tremendous value to pausing, reflecting, and taking stock of what worked and what didn’t work for you, your team, and your organization over the past year.

Before you rush into 2024, use the waning weeks of 2023 wisely to look back and assess. This reflection will help you derive meaning, value, and actionable next steps from both accomplishments and shortcomings of the past year.

To guide you in this important process, here are 10 key questions to ask yourself that set the stage for a thoughtful and productive assessment.

  1. Where did I miss the mark as a leader this past year? (Be brutally honest with yourself here.) Based on this reflection, what behaviors do I need to change in the coming year?
  2. What is one behavior that I will stop tolerating in others next year?
  3. What is one behavior that I will stop tolerating in myself next year?
  4. How clearly have I defined and communicated the direction, strategy, and priorities of the business to employees?
  5. Who in my personal and/or professional life do I need to deliberately distance myself from?
  6. Who in my personal and/or professional life do I need to move closer to?
  7. Which members of my external professional team (accountant, financial adviser, legal counsel, coach, etc.) are no longer the right fit, given where I am in my personal and professional life right now?
  8. Where in my life am I creating an unhealthy codependency? What must change?
  9. Where do I need to define or strengthen a boundary to help me achieve something important?
  10. Which client, supplier, and/or partner relationships should I upgrade / replace to accelerate the business?


“Self-reflection is a humbling process. It’s essential to find out why you think, say, and do certain things…then better yourself.” —Sonya Teclai

Although there are certainly additional questions you can ask to plumb the depths of your leadership, I’ve purposefully kept the list short to encourage you to think deeply rather than broadly.

As you contemplate these with the level of thought and sincerity they require, you’ll uncover answers that make you uncomfortable. Lean into that discomfort, because it’s the indicator of the way toward a better future.

If you’re feeling brave and open to feedback, engage others who you respect and trust. They’ll provide input and feedback to overcome blind spots in your own thinking, helping you answer the questions more rigorously.

While each new year brings the excitement of a fresh start, reflecting on the prior year’s challenges and accomplishments yields valuable insights to help you improve as a leader. May your reflection on this past year help you set the stage for accelerated growth in 2024.

All the best for a healthy, fulfilling, and prosperous new year!


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