End of the Year Reflection: Are you doing it correctly?

Olga Skipper
6 min readDec 15, 2020
Photo by Christian L on Unsplash

My client and I spoke the other day, and she told me that she has 7 reflection questioners and feedback surveys to fill in till the end of this year (2 weeks to go). And of course, she procrastinates on them because the time investment is huge and the value is not clear. It feels forced, and it feels like a time waste.

At the same time, here am I. Only a couple of years ago, seeing focus and Olga in one sentence was close to a miracle. As I might have told you in my previous posts, as a child, I was diagnosed with ADD, and I am pretty much interested in everything in this life. And my own reflection practice became the most important tool of my leadership practice to achieve incredible focus.

Two sides of the same coin.

Through studying adult learning, developmental psychology, neuroscience, and the science of human performance, I know how crucial it is to reflect, yet what makes startup leaders shiver when they hear the word “reflection”? Here are only a couple of common reasons “not to reflect”:

  • Reflection feels like a waste of time without a clear ROI: in my client's example, she calculated that she needs approximately 7 hours to complete all the forms. It is one work day within two weeks of a leader's time. As conscious of her time as she is, she wants to make sure she is spending her time with purpose.
  • Reflection is perceived as an external demand: the first time young leaders face reflection is when they are asked to conduct one. This initiative comes very rarely from the inside; it comes from the outside in the form of bosses, books that tell them to do so, HR managers, etc. If those people have time and skills, the value of reflection might be explained, but most commonly, it is not.
  • It feels like you need to take a lot of time to reflect properly: When you start reading self-development books, listen to podcasts and youtube videos, you might get an impression that you need to “do it all” to have a working routine: morning journaling, evening reflection, weekly reflection, monthly reflection, etc., etc.
  • Reflection might feel like a form of self-criticism: and it shouldn’t be.
Reflection as a form of self-criticism

How to fix reflection?

To experience and understand the benefits of the reflection, you don’t need to do it perfectly; you also do not need a lot of time, be “brutally honest with yourself,” etc. I can write the whole blog post on the theoretical proof of the importance of the reflection, but it might not be enough for the doers like us.

We need to try it to believe it. Here are a couple of things that you can do to create a routine that works for you:

  • Start small: take 10 minutes a week, not more, for the next 4 weeks. It doesn’t matter whether you do it in the morning or the evening, beginning of the week or end of the week, pick a time that is the most suitable for the 10-minute reflection.
  • Understand your own Why: Set a goal. What do you want to understand during your reflection exercise? Do you want to know how you spend your time? Do you want to know how well you manage your energy or tasks? And what will it give you if you answer that question? There should be a clear benefit that you can articulate.
  • Attach a metric: For example, I reflect to focus only on those activities that directly impact the speed with which I achieve a goal. My metric is a monetary value (the direct impact) of my actions on my business. Aka, if I invest this hour today, how much will it bring me back in the future. Your metrics can be both Hard and Soft: team satisfaction, employee churn, clarity of your decisions, etc.
  • Celebrate your wins: Write down a list of your wins for this week and celebrate it! Tell your partner, call a friend. Make yourself a gift, and it can be as small as a glass of favorite wine or watching a movie. Make sure you appreciate the good parts of the week.
  • Look for learnings, not mistakes: We loooooove looking for mistakes. Yet, these 4 weeks are 4 sprints, 4 experiments that you are conducting, so see them as such. Self-criticism will hold you back from the gifts of reflection. Be a learner, not a judger. Instead of “whose fault is it?” ask yourself, “what am I learning here that can inform my future planning?”
  • Just do it for a month and at the end of the month, reflect on the value you received from those 10 minutes and how your relationship to the act of reflection has changed.

That’s it: no complicated schemes, templates, groups, no heavy lifting. And the same process can be used for giving feedback to your employees, running 1:1, etc.

Follow effective action with quiet reflection. From the quiet reflection will come even more effective action.

Peter Drucker

I could have finished my post here, yet I know that some of you will ask this question, “Great, but what’s the advanced level?”

Advanced Level

Today I have a whole reflection calendar and both morning and evening routines. The longer you use reflection as a tool for your growth, the more you want to reflect.

On the way to a healthy reflection practice, I found some traps that I would like you to avoid. Here is what I would recommend you think about if you are moving to the advanced level of reflection.

  • There is “Time to do” and “time to reflect.” Keep them separate: This is the biggest trap. The more you feel the value of reflection, the more you reflect and, unfortunately, the less you do. You can only reflect on Doing. So Do! At the same time, we are structured in a way that to reflect, we need to access different parts of our brain than those that we access while doing. As a rule, I do not reflect on my week and my weekly priorities in the middle of the week. I do it only once, on Sunday. And I do not debate with myself whether those priorities were set correctly. I will do it next Sunday. It is a rule that I do not bind. It is like having two coders: one writes the code, the other one reviews it.
  • Have a clear reflection routine, not only a schedule: observe yourself, what are the places that you reflect the best, what are the questions that go deep and make you come up with the best answers? Do you need a tool, a tracking method? Do you want it to be digital, or you prefer paper and pen? Try different approaches and find yours that gets you to the best reflection.
  • Find someone to reflect with you: Unfortunately, humans are notoriously skillful in closing their eyes on their own shortcomings, limiting believes and behaviors, both good and those that need to be corrected. Find a peer, a coach, a mentor, who can mirror you and show you parts of yourself that you do not see.

Don’t hesitate to share your experience with reflection! Please comment and reach out directly via hello@olgaskipper.com

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Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions. http://olgaskipper.com