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Five Questions to Aid in Deep Reflection

Updated: Nov 30, 2021

While going through the editing process for Divergent EDU my editor left me a comment in an area where I alluded to divergent thinkers using deep reflection to develop their core beliefs. She told me to give readers examples of questions that they could ask themselves to drive deep reflection. My first thought was that deep reflection is so personal, how could I give anyone directions on how to do it? But I started to pay attention to my own line of thinking while I reflect, and I think there are some questions that can be used to guide deep reflection in a variety of situations, even though the path of the reflection is very personal to the one doing it. It took me until I was an adult to figure out how to deeply reflect. Nobody taught me how to do it and the only reason I know now is that I made it a mission to discover what deep reflection could do for me. Deep reflection is also one of the five characteristics of a divergent teacher that Elisabeth Bostwick and I laid out in this blog post.

Deeply Reflective – Divergent teachers recognize that significant growth cannot happen without taking time for deep reflection. They know how they reflect best, whether it’s through writing, meditating, or driving quietly in their car on the way home. They have strategies in place to allow them to take the time and hold reflection in high regards as one of the reasons they are who they are professionally. Deep reflection goes beyond what could go differently in a recent lesson. It also leads an educator down the path of discovering how their own beliefs and assumptions affect what they do in the classroom or how they perceive and communicate with others. Understanding the difference between surface-level reflection and deep reflection is an integral part of divergent thought. Once you understand what you believe, how it affects what you do and how you are perceived, it is easier to change your behavior and push yourself forward.

So often we regard the question, “How could things have gone differently/better?” as the be-all and end-all of reflective thought. It’s a fine place to start but does not necessarily lead us down a path of reflection that will end with how our involvement affected the ending. It still gives us the room to blame other people or things for anything that may have gone wrong. Deep reflection begins with questions that force us to think deeper about a situation. We may use just one of these questions or a few, but the result will be our discovery of adjustments or changes we can make within ourselves to change the trajectory of similar situations moving forward.


Is there something in my own personal or professional journey that is creating an assumption or bias? Lately, there has been special attention brought to how our journeys and personal stories affect the way we act, believe, and teach. I am 100% in support of that being the case (as proven by my book The Fire Within). After all, it’s our differences that make us stronger together. However, it’s also our journeys that have embedded certain assumptions and biases into our thinking. It is nearly impossible to operate completely without them, but it is important that we recognize if there are internal drivers for decisions we make and the interactions we have that may be affecting them in a negative way. Recognizing assumptions and biases and opening ourselves up to testing them in favor of finding alternative ways of handling situations will move us to more effective decision-making and divergent thought.


Are my expectations appropriate? This reflection path will most likely be followed up with additional questions that can range from logistical (Have I provided them with the professional learning opportunities they need to do what I’m asking them to do?) to spiritual (Is there something in their past/current situation that makes this change/decision/action difficult and they may need more emotional support?). In order to answer this question completely, you may need to gather additional information and return to the reflection. Another question that would fit into this category: Do I have the right to have my expectation of this person, or should it be up to them to set their own expectations upon themselves?


What could I have adjusted to create a possible alternative ending? In Wisconsin, if you are in a motor vehicle accident and you have gotten rear-ended, you are still partially at fault. Why? How could this be when you were just sitting there waiting for the light or parked legally minding your own business? Because you were there. Because had you not been in that spot, the accident wouldn’t have happened. Every situation that we reflect on is similar to this concept. We have had a part in the outcome. Sometimes, it’s something major that affects relationships, breaks trust, or perpetuates a negative feeling. Sometimes it’s as little as an unintended initial reaction or facial expression. There is always something that we can adjust in order to adapt to any situation and possibly change the ending. Deep reflection allows to see these things and create an alternative ending when it happens again in the future.


Do I have something to apologize for? A friend once told me, “I don’t like to apologize because it’s hard.” But I feel like if it’s really that difficult, that usually means it’s the right thing to do. Something being hard should never stop us from doing the right thing and sometimes that means swallowing our pride and apologizing. An important follow-up question is: Am I really sorry or am I just saying it to move on? Also, just saying I’m sorry really isn’t enough. When the apology isn’t specific, it loses some of its power. It needs to be truly authentic and the added specificity will help the person know that you’ve given it thought and you know where you went wrong. If you just apologize just to satisfy someone or move past a bad situation, people will know. I have actually said these words: “I’m sorry that I made a decision that didn’t make sense to you at the time. Not only did I allow other situations around me influence the decision that affected you, but I didn’t give you the information you needed to see why I was making the decision. For all that, I am sorry.” Also, just because you reflect and process and decide an apology is necessary, don’t forget that the person you’re apologizing to may need additional time to reflect and process the apology depending on the severity of the situation. Be reflective enough to understand that just because you’ve decided to say you’re sorry doesn’t mean that the other person is ready to accept it.


What did I do that went really right? Deep reflection doesn’t always mean we are looking for ways we have screwed up. It’s just as important to remember and celebrate what went well so we can replicate it if similar situations would come up in the future. If we never celebrate the great things we do we will live with the anxiety that nothing we ever do is right and that’s certainly not true of anyone. The trick is to find the balance between recognizing what went right and what could be adjusted in order to find our areas for growth while still remaining positive about what we accomplish.

True, deep reflection is a skill that needs to be practiced. Some people do it during quiet, alone time and some need to write it down to work through it. It’s not always a fun process as we are looking for ways we can improve or situations we may have negatively impacted, but the amount of personal and professional growth that can be experienced is exceedingly rewarding. There are few other activities that can have such a lasting impact on how our relationships function and our decision-making process.

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