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Four Work Reflection Exercises and How to Weave Them into Daily Practice

Updated: Aug 16, 2023

I cannot - CANNOT - believe we’re officially halfway through 2023.

Somehow I blinked and here we are.

That said, I am all about learning from the past to springboard into the future. And what better time than smack dab in the middle of the year to look at how we got here and at where we’re going?

Reflect on this

Think about a milestone or goal you reached in the last six months (could be big or small!) and then ask yourself these questions:

  • Was there a key learning from that success that still informs your work today?

  • Did you pause to debrief and assess what went well and what went wrong?

  • Did you pause to celebrate your progress en route to the final achievement?

Small, but mighty work reflection practices

When it comes to reflection, I think a lot of us fall into the “great intentions” camp. We know there is value in looking back at what went and not-so-well upon completing a project, but the truth is... another project awaits and everything's on fire. “Let’s just skip it this time and do it over Slack.” You’re not alone. I know I’ve fallen into that pattern more times than I’d like to admit. The reality is that most of us are stretched beyond capacity and things like project reflections become a “nice to do” in a world overflowing with “need to do” tasks. Like all great backburner-ed intentions though, it eventually catches up to us. Suddenly, the thing you skipped to save yourself time is actually costing you that exact resource. And that’s only if you’re lucky and it doesn’t spill into revenue lost or employee resignations. The great news is that little actions can help your team reflect without requiring you to put a cumbersome new process into place!

Four ways you can build reflection into your workflow

1. Designate the first 5-10 minutes of team meetings for open reflection.

Use some of the questions from the reflection section above if you don’t know where to start. Be sure to define some ground rules and have a hard cutoff time or this can easily take over the rest of the meeting.

2. Incorporate reflection-focused questions into your 1:1s.

Of course, you’ll only want to incorporate these once you’ve built psychological safety with the team member you’re managing. One that exists, some of my favorite questions include:

  1. If you had a magic wand, what one thing would you change about how we approached our last project?

  2. If you were leading the project, what would you do differently?

  3. What is a potential risk you see that could impact our next project if we don't address it

  4. What's a mistake you've make recently? What did you learn from it?

3. Start a weekly reflection-focused Slack thread.

This allows everyone to respond when they have time. Make sure leadership understands why you’re kicking off this initiative and goes out of their way to include their own learnings, making it safer for everyone else to chime in.

4. Build reflection into your All-Hands meeting.

Reiterate the importance of regular reflection to the whole company by instituting a “Reflection Section” in your regular All-Hands agenda. Invite different teammates to share what they’ve learned in the last few weeks on their own team, then celebrate the willingness to reflect and share honestly, whether learnings were positive and exciting or uncomfortable and difficult.

A woman sits and reflects on the 2023 work year so far. She's wearing a gray sweater and clasping her hands in front of her face while she thinks.

Your Turn

If you’re ready to dive head-first into the reflection pool, I’ve got just the exercise to get you started: it’s a traditional project retrospective, with a WTWT twist. Pick a recently closed, launched, or delivered project or milestone. Identify the key players, stakeholders, and decision-makers who contributed.

Circulate the following set of questions to each individual

  • What do you consider the greatest success of this project? At what stage in the project did you start feeling confident about this outcome?

  • What do you consider the biggest challenge, failure, or opportunity to this project? At what stage in the project did you start feeling concerned about this?

  • Was there ever a time you wanted to raise a concern about this project? If so, what stopped you?

  • Has anything about the outcome of this project changed how you aim to approach your next project kickoff?

Review the responses and determine how to discuss, distill, and disseminate the learnings. You know your culture here; your team may be ready to discuss this openly in a meeting, or it may be up to you or a project lead to distill these learnings anonymously.

As a group, commit to using at least two learnings to augment your next project plan

  • Say all your teammates shared that they had concerns early on but didn’t feel empowered to raise them. Perhaps you’ll add an open forum discussion to address growing concerns earlier on in the next project cycle.

  • Say most of your teammates reported that a change to reporting cadence mid-project helped them feel more aligned and informed. Perhaps you’ll consider starting your next project with this reporting cadence in mind.

  • Say your teammates all identified a need for clearer decision-making ownership and cited a lack of this as a project staller. Perhaps you’ll document your project team’s decision-making process for ease of reference next time.


The goal here isn’t just to allow teammates to identify which outcomes were or weren’t achieved, but to give them the time, space, and safety to understand how they got there. Continuously practicing this level of intentional reflection – and reaffirming its value by allowing it to influence the process – can help your whole team balance past learnings with future outcomes to create a more harmonious here and now.

Need help operationalizing reflection? Let's talk.

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