A Guide to Personal Retrospectives: Reflect, Learn, Grow

You’ve probably heard of a team retrospective before, traditionally used within Agile teams at the end of a sprint to encourage continuous learning while creating cohesion among teams by celebrating wins, accepting failures, and identifying opportunities for growth from these experiences. Side note, if you want to learn more about the team retro check out this article to help you get started. Similar to the team retrospective, a personal retrospective is an incredible tool to supercharge your growth, improve your self-awareness, and make you a better leader and teammate.

But why focus on myself, you ask? For starters, no one really wants to be around the teammate with absolutely no self-awareness. You know the Jerry who microwaves leftover fish in the break room? Don’t let that be you. Spending time reflecting on yourself and making efforts to improve will make you a better teammate, friend, and human. From a professional development perspective, you may be surprised to know that your leaders, colleagues, and employees will have deeper respect and trust for you if you are able to acknowledge your opportunities for growth and plan to achieve these. Again, who wants to work with the Karen who claims to be perfect in every way, refusing the slightest criticism and never changing? The answer is still no one.

This article will provide insight into how to incorporate a personal retrospective into your schedule. We’ll break down the value, processes, tools, and more to give you the confidence to start running your own retros and to inspire your team members to give it a try.

Value of Personal Retrospectives and the Insights it Provides Into Your Personal Growth:

A personal retrospective offers a number of benefits to your personal development, including enhancing self-awareness, improving decision-making abilities, and fostering a mindset of continuous improvement. By committing to a personal retrospective, you are also committing this time to yourself, acknowledging the importance of your development and growth. It’s incredibly easy to get pulled into everyone else’s problems and priorities, but to become your best self, and the best leader you can be, you have to be willing to focus on yourself at times. If you spend too much time in the trees, you will never see the forest. If this sounds like you, incorporating a personal retrospective is a great first step to reconnect with yourself.

Acknowledging Successes and Failures:

The key to a successful retro, whether for a team or yourself, is honesty, sometimes the unfiltered, brutal kind. To achieve growth of any kind, we have to acknowledge our mistakes to be able to learn and grow from these. At the same time, focusing solely on failures can lead to a misrepresentation of your true self, casting self-doubt, which can be crippling to leaders who would otherwise have a bright future. Balancing successes against failures is a delicate balance, and most of lean more heavily towards one or the other. By systematically creating a process that encourages reflection on each of these points independently, we can break some of our engrained patterns to become better rounded, deepening our self-compassion and understanding.

Celebrating Success

Acknowledge and celebrate your successes, big and small. At some point between childhood and adulthood the participation trophies stop, the corporate world is not warm and fuzzy, there are no pats on the back and “good effort!” pizza parties after a loss. I’m not suggesting you start expecting trophies for showing up to work and doing your job, but part of a healthy retrospective is being able to acknowledge your own efforts, to thank yourself for the wins that you’ve worked hard to achieve, regardless of whether others recognize them. There is always room for judgment, for improvement, for opportunity to do things differently, but this is not the time or nitpick. Practice acknowledging and celebrating your wins, without the caveats.

Acknowledging Failure

We’re trained to be failure averse. Just typing the word failure gives me a small twitch. But without failure, there is no growth, no learning, no challenge to become better. Why is it so hard to accept and acknowledge our failures when in reality, we have all failed, at lots of things, over the course of our lives. If you take magnitude out of the equation, the reality is, we experience many small failures over the course of our week, sometimes even a single day. If you don’t like the “F” word, call it something less painful, the key to an effective retrospective is to acknowledge the opportunity to have taken a different path, to improve, to choose differently in the future. Failure is a learning opportunity, and by being brutally honest with ourselves for our part in failures, we develop a deeper understanding of ourselves and continue our personal growth.

The Retro Process - Where to Start:

Just like a team retro, you can tailor the personal retrospective to your particular needs, challenges, and schedule. My coaching on which of these to choose, is the same I would give a team who is looking to adopt these principles: start with more than you think you need, not less. Once you have built the habit of doing your retrospective and developed better self-awareness, you can experiment with changes to frequency, as you will have a baseline to measure against to determine whether the change has impacted effectiveness. Not once in my career in consulting, have I worked with a team that started with the “less is more” approach and ultimately found success. I’ve also never seen a team that started with less, choose to increase the frequency of their series and acknowledge their mistake. Most often, I’m brought in when the team is failing, and blaming their issues on the current process, never acknowledging that their changes could have had a negative impact on its effectiveness. See how I brought us full circle there? Listen to your coach, acknowledge your mistakes, and don’t blame the process or tools when you choose to take the easy out.

The Newbie - Weekly Retrospective Format:

If you’re new to the personal retrospective, start with a weekly reflection, ideally at the end of your week, while the information is still fresh. The weekly retrospective is a great opportunity to track and measure progress against short-term goals, develop deeper insight into common challenges you face, and better identify your most observable strengths. A key benefit of the weekly retrospective is to identify quick, actionable insights which you can start to implement right away, seeing immediate growth. Longer term, the weekly retro will show you trends, common behaviors, and pitfalls that can then be acted upon as part of your long-term development plan.

If your week is all over the place, and you find that you struggle to remember yesterday’s outcomes, let alone 4 days ago, I’d suggest incorporating a super quick, 5-minute exercise to mark the end of your day. After you’ve finished your last meeting, and shot off the final email of the day, set a timer for 2 minutes to jot down (on stickies, paper, or on a digital notepad) your accomplishments of the day, big or small. Shoot for 3 if you’re able! Once your time is up, reset the timer for 2 minutes and jot down your failures, missed opportunities, or mistakes. Do your best to hit 1-3. If you chose pen and paper over a digital notepad, snap a photo, or quickly transcribe this information into digital format for your end of week review. You’re done!

Your weekly retrospective will look very similar to the daily retrospective, with a little more time incorporated to allow you to reflect more deeply on findings. Expect your weekly retro to take as long as 30 minutes without the daily retro, or 15 minutes with the daily.

Weekly Retro:

Identification: Just like the daily retrospective, your weekly retro will start with a review of your accomplishments and opportunities. Start by setting a timer for 5 minutes to brainstorm and jot down all of your wins for the week, regardless of big or small! Once time is up, reset that timer to 5 minutes and this time, brainstorm and jot down all of the failures, mistakes, or missed opportunities over the past week. Try to hit at least 5 items in each category! If you struggle with this, you may be trying too hard to find the "worthy" items and not giving yourself credit for the small wins or holding yourself accountable for missed opportunities. If you find that your list is reflective of the most recent few days rather than the whole week, consider revisiting the daily retro concept or even a midweek retro to capture the information while it's fresh.

Prioritization: Once you have your two lists, I want you to give yourself 2-3 minutes to prioritize the wins, followed by a quick prioritization of failures or opportunities. Once you have your two prioritized lists, let's start by addressing the wins.

Reflection: Take a few minutes to reflect on each win on the list, consider the impact you made, and how this win might contribute to your long term goals and personal growth. Capture these two points in a journal of your choosing - I like digital because it's easy to sort and return to later, but you do you. Just remember, you'll be reflecting on this information at the end of the quarter, so make sure it's easy to reference!

Finally, we are going to focus on the list of prioritized failures. Reflect on what happened in each of these situations. What could you have done differently? Do you see any common themes here? Be gentle on yourself but also realistic about how you might have taken a different path to achieve a better outcome. Capture in your journal any themes you've identified. From the highest priority items choose 1-3 to focus on improving over the course of the next week. For highly complicated issues, set a small, realistic target of what can be achieved in such a short period of time. Set yourself up for success by keeping this goal small, specific, and achievable. Monday morning, this should be plastered in your mind and maybe even on your desk as a reminder of how you hope to grow over the coming week.

Daily & Weekly Retro:

If you chose to start with the daily retrospective, kudos to you for your commitment, here is how to incorporate your notes into the weekly retro:

Follow your typical Daily Retro process to capture achievements and failures for the day.
Give yourself 1-2 minutes to review your achievements and failures captured earlier in the week.
Perform the steps of the "Weekly Retro" as laid out in the section above starting at the "Prioritization" step.

Your weekly retrospectives are a great balance between short-term and long-term goals. Over time, you'll see trends appear that tie into your long-term goals or that you may want to incorporate into these. In the short-term, you will find small, meaningful ways to improve while taking the time to celebrate your achievements.

The Experienced - Quarterly Retrospective Format:

A quarterly retrospective is a powerful way of assessing your progress against long-term goals. I strongly suggest discussing the outputs of your quarterly retrospective with your manager or a mentor to validate your progress, and obtain potential insights that you may have overlooked. You'll find that if you pick up the habit of a quarterly retrospective, you'll be better prepared for performance review cycles, and have deep insight into your strengths and opportunity areas.

For the quarterly retrospective, I like to follow a very similar approach to the weekly retrospective outlined above, leveraging your professional development plan and associated development goals. The order of activities will change slightly, as follows:

Give yourself 15 minutes to review the key wins, impact, growth opportunities and common themes identified over the course of the quarter - capture these in digital or physical stickies, color coding the "wins" as one color and "opportunities" as another.
Now that you have two columns, do you have any past opportunity areas that were transformed into "wins" over the course of the quarter? Excellent! Cross out the opportunity sticky and mark the associated "win" with a star. Keep these near one another as you'll be capturing this information shortly.
Perform a quick exercise to bundle like wins, and like opportunities or themes - choose the best sticky for each bundle that reflects the group or write a new sticky if needed.
In your journal for the quarter, I want you to capture your top 10 distilled wins, top 10 distilled opportunities, and the complete list of "opportunities turned into wins".
Write a brief 2-3 sentence summary of each of these items to guide a discussion with your manager or mentor.

Part of the review process should entail a comparison against your professional development plan and/or development goals. If you don't have a plan or goals for the year, utilize these findings as your North Star, setting goals for yourself that align to your professional ambitions, strengths, and opportunity areas.

The Advanced – Annual Retrospective Format:

The annual retrospective should be a fairly simple activity if you've performed your weekly and quarterly retro's consistently.

Start by performing the quarterly retro outlined above so you have a complete view of the past year.
Give yourself 15 minutes to review the distilled wins, distilled opportunities and list of opportunities turned into wins for each of the last 4 quarters. Recreate these same categories for the full year, identifying your most significant wins, remaining opportunities, and a list of all opportunities that have become wins.
Identify whether any like wins or like opportunities exist that should be bundled, group these and choose the sticky which best summarizes these.
In your journal for the year, capture your top 10 distilled wins, top 10 distilled opportunities, and the complete list of "opportunities turned into wins".
Write a brief 2-3 sentence summary of each of these items, with a focus on how these align to your professional goals, and development plan.

By the time you perform the annual retro, you should have a solid grasp of your strengths, weaknesses, and opportunity areas. Your annual retro is a great way to summarize your year and provide your manager with the information to support any calibration or rating discussions your organization conducts. Most of us already perform this activity every year and often struggle to provide a meaningful representation of all of our efforts and growth given how much time has passed. By leveraging the personal retrospective process above your year end review should be smooth, structured, and highly impactful.

Building a Habit of Reflection in 2024 and Beyond:

With the start of the new year is an opportunity to start fresh, test new ideas, and push yourself to new heights. Why not focus on yourself for a change and see what an impact it can make on your personal development and overall well-being? With our guide, you have the framework to kick start your personal retrospective journey. Remember that the process is meant to evolve with you and should flex as your circumstances, goals, and life changes. Don't be afraid to test and iterate if you find that elements of the process don't work for you. We'd love to hear your feedback on what you try and how you evolve the process, drop us a comment below to share your experiences.