10 Questions for Leadership Reflection and Upskilling


10 Questions for Leadership Reflection and Upskilling

You say you are a leader… but. When you are a leader, it is important to not only work “in” the business but “on” the business … not only “in” your skills but “on” your skills as a leader.  It is often upskilling, the way we show up through who we are, that makes the greatest difference. When we are deliberate to grow ourselves, Leadership Inside Out, we are continually honing our leadership emotional intelligence and positive impact. In contrast, while it often feels like we do not have time to stop and think about such things, when we do not, we continue to have the same blind spots and shadows that impact our leadership, team, and work.

Reflect on your leadership and upskilling with these questions:

  1. What do you enjoy most about your role as a leader? What is your unique ability and superpower?
  2. What has been the most rewarding experience in your career so far? What is the most frustrating and what is your role in that happening?
  3. What motivates you to continue learning and growing as a leader? What are you learning right now?
  4. How do you approach challenges and setbacks in your leadership role? What skills or team members do you need to move through this?
  5. What advice would you give to someone aspiring to be a leader in their field? What advice would your mentor give you for your next level?
  6. What are your passions outside of work, and how do they influence your leadership style?
  7. What do you consider to be the most important qualities of a successful leader? How are you doing that or not doing that right now?
  8. What are some of the most influential books or resources that have shaped your leadership philosophy? How are you applying them, or could you apply them more?
  9. Can you share a memorable experience that taught you an important lesson about leadership? What lessons are you learning today and what adjustments do you need to make?
  10. How do you prioritize your time and manage your responsibilities as a leader? Where are you breaking your own rules or working against yourself that you want to upgrade?

Pick one or two insights that might have come up and decide how you will act on them. Leadership is a journey and a process. We learn, we forget. We design; we get distracted. We implement, we drift. Leadership sharpening is about taking time to stop, reflect, design, and take a step forward. It matters and has exponential impact as you lead better and those around you lead better resulting in the impact and the results you are working so hard to achieve.