Learning from Setbacks

Leadership Insights

You took some time on Monday to reflect on what went well for you this year. Before you start reading today’s issue of Leadership Insights, pull up your notes! Today we’re going to focus on your low points of the year.  

Reflecting on what didn’t go well serves a fundamentally different purpose than celebrating successes—it’s about learning and prevention rather than replication and momentum. 
 
This type of reflection helps you to: 

• Identify gaps in leadership and patterns you might miss otherwise. When things go smoothly, we often don’t examine the process closely, but challenges force us to look deeper at what contributed to the outcome and what we might have overlooked. 
• Build resilience and problem-solving capacity. By analyzing setbacks, you develop a more nuanced understanding of how to navigate similar situations in the future. You’re essentially building your professional toolkit for handling complexity. 
• Separate controllable factors from external circumstances. Not everything that goes wrong is within your influence, but reflection helps you to distinguish between what you can learn from and what was simply context. This prevents both over-responsibility and learned helplessness. 

The key difference in this reflection is the mindset—you’re not dwelling on failure or assigning blame, but rather extracting wisdom. The most productive approach focuses on specific situations and asks questions like: “What information did I lack?” “What assumptions proved incorrect?” “Where could I have sought input earlier?” 

What Didn’t Serve You Well  

Now take a few minutes with a notebook to reflect on the following prompt (or come up with a different prompt with Sophia):  

Think about moments this year when you were disappointed in your work or in the outcomes of something you worked on. You could also reflect on times when you felt frustrated with your work. Try to write down 2-3 instances when you felt this way.  

What stands out to you about these moments? What feelings or emotions came up for you? What skills or behaviors do you wish you had possessed in those moments?  

What do you think you have ultimately learned from those moments?  

The goal is not to dwell on blame or shame but to move toward the lessons you can pick up! Remember that everyone makes mistakes and faces consequences they didn’t expect or couldn’t plan for. Practicing the Sage means using those times as a learning opportunity rather than as a reason to withdraw from leadership.  

It might be tempting now to try to immediately focus on moving forward, but stop yourself! Taking time to practice reflection is a valuable part of leadership, and we’ll get to how you can apply what you’ve learned about your work this year on Friday!