A Self-Reflection Guide When Leaving A Role

When we are seeking new opportunities, our focus is forward. We are excited and anxious for what’s to come and we often shed our previous roles like a bad clothing trend. However, it can be helpful to take what we’ve learned from our past, so we can apply it to our future.

Looking back and reflecting doesn’t mean we set up camp in our past. It means taking a moment to recognize where we’ve been. Many of our roles can be a blur – they are fast-paced, demanding, and varied. By reflecting on where we’ve been and what we’ve gained, we step into our next role with a better sense of self, what we want in our career, and what we hope to still achieve.

Take the time to ask yourself the self-reflection questions below when departing your role. They can better equip you for the road ahead.


  • What did you enjoy the most about your role? The least?

  • What impact did you have? What successes can you share, either quantitative or qualitative?

  • What challenges did you face in your role? What did you learn from them?

  • What did you like and dislike about the organization’s culture?

  • What did you like and dislike about your principal?

  • What did you learn about your leadership style?

  • What would you have changed about your role?

  • What barriers did you encounter in your role? What can you do to mitigate those barriers in the future?

  • Did you feel recognized or rewarded in your role? Why or why not?

  • What is one thing you wish you did in your role, but didn’t?

  • What mistakes did you learn from?

  • Are there any personal behaviors you want to change going forward?

  • What skills do you have, and what do you need or want to develop?

  • What do you value in yourself? In your career?

  • How do you define work and life? Did you make an effort to maintain the right mix of both in your life?

  • What are you most proud so far in your career?

  • What type of work engages and energizes you the most?

  • What type of work frustrates you the most?

  • What are three tangible career goals you can make for the year?

  • What do you want to do moving forward?