Learning Through Reflection: Drawing Insights from a Complex Year

Future-focused leaders are skilled at learning through reflection. Meaningful learning through reflection has three steps: reflection, choice, and change.

Learning Through Reflection: Drawing Insights from a Complex Year

Future-focused leaders are skilled at learning through reflection. Meaningful learning through reflection has three steps: reflection, choice, and change.
November 29, 2023

In complex and challenging economic times, it can feel like there’s no time or money to invest in company learning. However, these times inherently have the most learning to offer. A key trait of future-focused leaders is their ability to learn through their day-to-day work; you don’t need to make more time to learn, you need to learn from the work you are already doing.

The amount of learning to gain from both setbacks and successes is completely contingent on the reflection that accompanies these experiences. Times of difficulty tend to offer great amounts of learning, so it’s crucial that you take the time to reflect on the past year as you prepare to lead your organization into 2024.

Leaders tend to be constantly reflecting on their actions and outcomes, but pausing to reflect with intention allows you to maximize your learning and subsequent growth. Meaningful learning through reflection has three key steps: reflection, choice, and change. This framework will help you look back on the past year and draw forward the lessons and knowledge that will help guide your future decisions.



First, identify your key learning moments from the past year. What is a key learning moment? These are moments when you either made a decision without knowing what the outcome would be, or made a decision that resulted in a different outcome than you expected.

We call these key learning moments because they represent times when you encountered a new piece of information that your brain then needed to reconcile with your previously held assumptions and/or beliefs. Since you either didn’t have an expectation about the result of your action, or your expectation was incorrect, your brain will have saved this experience as new evidence of a potential cause-and-effect relationship in the world. Whether or not you internalize this new information and use it to guide your future actions, either consciously or unconsciously, depends on how you engage with it after the experience, i.e., how you reflect on it.

To draw out useful information from these moments, think back to them and consider the following questions:

  • What factors or stakeholders played a bigger role than I expected?

This question helps to identify people or areas that might need more attention in future decisions. For example, if you recognize that a strategic change initiative ended up making slow progress due to a lack of commitment from a specific department, then you may want to involve leaders of that department in change initiatives earlier in the process so they can gain ownership and become change drivers.

  • Did I make any assumptions about the situation that turned out to be incorrect?

This is an important way to recognize where you might have biases or mistaken beliefs that are causing you to misread situations. When making future decisions, it’s helpful to take a moment to think back to these assumptions and see if they could be still influencing your thinking.

  • What was completely unexpected? Did I have any blind spots?

Some events just can’t be predicted or avoided, but reflecting on these unexpected occurrences is still helpful because it can give you ideas of warning signs or forecasting metrics that you could use in the future to better look around the corner and minimize your blind spots.

This type of structured reflection allows you to draw out key learnings from the past year, so you can then decide if they are helpful to move forward with in your next steps.



As all leaders know, sometimes your actions don’t work out because you made the wrong decision. However, sometimes your reasoning and decision were sound, but there were external factors that affected the execution and outcome of the action. The second step, choice, refers to the critical thinking that you must use to identify which lessons you want to bring forward into your next decisions. Not every unexpected outcome means that you made the wrong decision, so it is important to closely consider whether the learnings you identified during your reflection are relevant for the future.

Here are some tips that can help you tell which learnings are most likely to help you see around future corners:

  • Assumptions: If the same mistaken assumption or underestimated stakeholder has come up multiple times when reflecting on the past year, it’s likely an important lesson to address.
  • Blind Spots: When it comes to uncontrollable events that may have blindsided you, instead of focusing on how to prevent them, focus on trying to identify forecasting signals that could help you to see these events coming, so you can better prepare for them even if they are unpreventable.
  • System Dynamics: Consider if you are likely to be in a similar situation again, i.e. making decisions involving similar systems and groups of people. If the answer is yes, then pay close attention to which stakeholders had the greatest impact on the outcome, whether they acted as you assumed they would, and if there are levers in the system that you could pull more effectively. If the situation was relatively unique, then it may have fewer lessons to offer, or they may be more nuanced.
  • Deep Understanding: Retrospectively, do you feel that you have a good understanding of why the outcome was what it was? If not, be careful of applying lessons you have taken from the situation, because there may be more nuance or complexity involved than you recognize, so changing your behaviour in response to an unexpected outcome may have even more unexpected consequences if you don’t fully understand how the system is responding to your actions.

Be mindful in how you choose to let your reflection shape your future actions. Future-focused leaders recognize the importance of learning from their actions, but with meaningful and intentional choice and reflection, not by being reactive to every challenge of the past.



Now that you’ve drawn your lessons from the past year into your future-focused thinking, it’s time to put them into action and make positive changes through your learning. A classic trope of New Years is how easy it is to reflect and make a plan to create some type of improvement in your personal or professional life, only to have that plan fall to the wayside as soon as the busyness and speed of your day-to-day life resumes. To avoid this trap and actually maintain your learning momentum throughout the coming months, try out these three tips:

  • Be Realistic and Concise: Try to condense the lessons you took away from 2023 into a few key points that you can easily keep in the front of your mind, or on a sticky note on your desk. The simpler you can express your main takeaways from the year, the more likely you will be to actually keep them in mind in your day-to-day decision making.
  • Avoid Reactivity: The goal of learning through reflection is not just to change your actions whenever something does not go to plan, it is to notice and understand why unexpected outcomes occur, and if you could or should have done something differently. As you continue reflecting on your future actions, keep this in mind and don’t let one negative outcome shake all of your confidence in your decision making.
  • Ask for Feedback: The people in your life have valuable insights to share, so it’s always a good idea to check in with your colleagues and other people in your life to get a second opinion on your plans and check in throughout the execution. The best way to look around corners and avoid your blind spots is to add another perspective.


This year brought challenges for leaders in almost every industry. To truly draw the most out of the year, look back before you step forward into next year. It may seem counter-intuitive, but future-focused leaders actually need to spend a significant amount of time mining the past. Meaningful reflection is the basis of building a learning culture for yourself and in your team. Spend some time this December reflecting on your key learning moments from the past year, and choosing which lessons you want to bring forward as you make changes and continue growing into next year.

Authored by:
STRAAD intelligence™

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