3x5 Leadership_Leader Reflection Series

Thus far in this reflection series, we’ve addressed what reflection is and why it is important for leaders. If you are new to this series, I encourage you to check out part I and part II of this series first.

Next, we begin to address how to actually engage in reflection. I’ve found these activities to be most effective in the continuous process of “collecting dots and connecting those dots.” The remaining parts to this series aim to materialize this abstract theory and turn it into tangible application.

Reflection Process Framework

Before addressing common reflective activities, I believe it is important to establish a reflection process framework to follow. In order to make reflection as beneficial as possible, the following four things should be met; they can serve as your reflection checklist.

  • A place to think and reflect. Determine your preferred outlet(s) for reflecting. A “place” to think can be a literal location where you do your best thinking (coffee shop, favorite chair, etc.), a certain time of day (early morning, lunch, or evening before bed), or a specific activity.
  • A place or way to record your reflections. Your lessons learned and great ideas only last as long as you can remember them. We need to establish a platform to capture and maintain our reflective thoughts. This can include things like a written journal or an enduring digital document (like a Microsoft Word document or on the Evernote app). When developing this platform, it is critical to make sure it is something that you can maintain and are able to reference in the future. Personally, I don’t like the idea of dozens of journals cluttering my bookshelves because I’ve found that I will not go back and reference them. Instead, I prefer a digital document that I continue to add to and consolidate all of my best thoughts.
  • Method to expand or make sense of your thoughts. Certain thoughts from your reflection may need added attention to fully develop; you may not be able to fully grasp it on your own or by a singular reflective activity. Consider ways that you can expand your thought and better make sense of it. This can include talking about the thought with a trusted peer or mentor, or writing out your myriad of thoughts and emotions related to the idea.
  • A way to enact and/or share your reflections. Finally, reflection is pointless unless it changes and improves the way we think, behave, and lead. So, how do we take our new ideas and integrate them into our daily behavior? Some ways that I’ve found to deliberately integrate reflective lessons into my behaviors and attitudes are by using the “One Big Thing” framework and leveraging SMART goals, which you can learn more about by clicking on the respective links.

Now, with this framework in mind, below are common reflective activities to consider. These activities can support different stages of the reflection process, so I encourage you to consider where and how they can best enable your own reflection process.

Remember, reflection is highly individual; you likely do not naturally reflect in the same ways that I do. Thus, I encourage you to find your best reflective activities through some trial-and-error. I’ve spent years testing and refining how I reflect; it will never be a perfect system and I always find ways to improve how I think, learn, and improve.

Unstructured Time

Do not underestimate the value of allowing time for unstructured thinking. It may feel like wasted time because we may not necessarily be doing anything, but some of my best personal ideas have come from unstructured thinking. In creating space for unstructured thinking, you allow whatever you subconsciously consider important to surface, often as a stream of consciousness. Through this, you can untangle the knot of ideas and emotions and pull out the essential parts that matter.

Personally, my best unstructured thinking time comes while running, walking the dog, completing chores around the house like washing dishes, and similar “mindless” activities. Consider how you can best allow your thoughts go where they naturally want to. Are there certain times of day, places, or events that lead you to naturally think creatively and freely? Ensure you maximize the impact of those times by having a means to record thoughts so they don’t come and go unregistered. Finally, don’t worry about trying to be efficient with this time. There should be no expected return on investment (ROI) for your time dedicated to unstructured thinking.


As I asserted in a previous post about why I write, physically writing out your thoughts helps you clarify, complete, and fully articulate them. It also allows you to archive those thoughts for the future. There are many faces to journaling, though. Below are three different things to consider to determine how you prefer to journal.

  • Structured versus unstructured: similar to unstructured thinking, your journaling can be that as well (or not). Some may prefer to start with a blank page and pour their thoughts onto the paper. Others need a structured system, where their thinking is guided by an established framework.
  • Types of structured journaling: for those that rely on structured journaling, it can follow different paths. First, many invest in formatted journals such as the Best Self’s SELF journal or Michael Hyatt’s Full Focus Journal. Others may prefer custom systems where they answer journaling prompts that they find relevant. You can create your own journal prompt system by answering a series of questions that you choose. You can rotate journal prompts daily (where you answer different questions each day of the week), answer a set of questions at the end of each week, or maybe answer questions for a particular season (change every month or quarter) and then rotate to a different set of questions. If journaling through prompts interests you, feel free to check out my list of recommended journal prompts here.
  • Analog versus digital: Finally, some may like to build their collection of journals on their bookshelf where others may prefer a digital platform. I am in the digital camp, using a series of Microsoft Word documents that I maintain on my Dropbox App; that is what works best for me right now. Other digital solutions include Evernote or Day One Journal.

To investigate journaling as a means for reflection, I recommend you check out popular entrepreneur, Ryan Holiday’s article on the 14 ways to make journaling the best thing you do in 2018.

Reviewing Notes or Personal Notebook

Where I find many leaders fall short in their reflective notetaking or journaling is in actually doing something with their notes. A bookshelf of decade’s worth of journals or green notebooks may look impressive, but how are those copious notes remaining relevant and acted out? Leaders need to incorporate an avenue for consolidating and routinely reviewing their written reflective thoughts as part of their overall reflective process, which best enables a method to expand and makes sense of your thoughts within the framework I offered above.

How are you extrapolating key thoughts and lessons from the books, blogs, and articles you read? What about things from podcasts or professional development sessions that you attend? If you write notes from all of these things, how are they remaining relevant and enacted, not just more papers stashed away in a drawer or bookshelf? To maximize reflective impact, I believe leaders need to define how they record lessons, consolidate them, and ultimately review them to keep them relevant even years later. Though I expand on my personal system to do this in the next part of this series, there are two blog posts to help you consider how to do this:

Mentorship or a Peer Coach

One of the best outlets to help you expand and make sense of our personal reflections is by talking about them with trusted peers or mentors. Similar to writing out your thoughts, discussing them with someone else forces you to complete your ideas and articulate them for that person to understand. By talking them out, you also gain another point of view on the matter that you may not naturally consider, which allows you to further connect more dots.

Trusted mentors and professional peers can serve as valuable sounding boards for your new ideas. These relationships should be naturally founded on mutual trust, so should be a safe space to introduce ideas that you are wrestling with and need help making sense of. The concept of a peer coach may be a new one for many, so I encourage readers to learn more about how to engage in peer coaching here.


First, I recognize that there is a considerable volume of ideas that I recommend enacting in this post. Do not get overwhelmed in thinking that you need to start all of these ideas now! It took me years to learn these reflection outlets, implement them, and ultimately refine them to what they are today.

I recommend that you start small. Test out one new reflective activity first. Spend a short time, maybe 15 minutes a day or once a week, engaging in this new reflective activity. Focus on this one new activity over an appropriate amount of time (maybe several weeks) in order to make it a habit. Then, you can work to expand that activity or add a new one.

In the next part of this reflection series, part IV, I outline my personal reflection system to offer an example for others to consider. As I stated in the beginning of this post, everyone reflects differently, but I hope by sharing how I reflect, I can inspire you to continue to develop and refine your methods of reflection in order to maximize its impact on your leader learning and growth. In that post, I’ll expand on how I create space for unstructured thinking; how I consolidate, organize, and review my notes; and how I leverage journaling and peer coaches.

These thoughts on reflection are based on my singular experiences, preferences, and education. I would love to hear others’ views on how they best reflect in order to add to the arsenal of ideas for other readers to learn from. Feel free to comment below or to share on the Facebook or Twitter pages (links below).

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  1. Been thoroughly enjoying this series. I’m starting to write more to be able to capture thoughts and experiences that I find could be useful at work and home, but reflection is something I need to get much better at doing. I feel like I lose a lot of great insight in my mind by not writing it down or sharing it with someone.

  2. This series is timely as we (my company, Trimetis) are just about to run a study of behalf of the UK MOD exploring alternative structured methods for self-reflection, particularly in support of developing our mental models and action schema that support decision making, assessments and judgments. We’d be happy to share the results and the self-reflection structures with the readership if you are interested. We won’t have data until the summer next year, but hope that we will have a coherent narrative that will at the very least start another conversation about productive ways to think/reflect. We will be referencing your own thoughts on this as part of our background research, so thanks for sharing.

  3. P.S. to provide something a bit more meaty to the conversation… here is a link to some work by Peter Fadde & Gary Klein which provides a way to structure reflection activities… however their solution requires you to “prime” the learning *before* you do the experience. I think that this might be a critical piece of the learning/development puzzle that is often neglected in conversations about reflection where the focus is always on “after the fact”… http://crashingpatient.com/wp-content/uploads/2011/07/deliberate-performance-by-Fadde-and-Klein.pdf

    1. Rob, thanks for sharing your thoughts and the resource! I always enjoy when we can expand the conversation. Ref your resource, I just listened to a lecture by Dr. Angela Duckworth today at work on all of her research and findings on “grit.” Large part of the presentation was about deliberate practice, which I see in the document. I look forward to checking it out!

      1. indeed… however the Fadde/Klein focus is on deliberate performance as so many people don’t have the ‘luxury’ of lots of time to practice, but are always ‘doing’… so the question is, how do we develop more effectively from our on-the-job experiences during performance as opposed to practice; where arguably we learn about the realities of friction, uncertainty etc and not the sometimes (by necessity) ‘sterile’ environments of practice.

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