Free Sample Chapter
Gain the Confidence and Knowledge You Need to Lead
Stop waiting for the right opportunity, and learn from a circle of inspiring mentors from our upcoming book, The Engineering Leader Within.
1-Day Leadership Experience
Break through team friction, get on the same page, and create a high-trust and high-performance team.
Design Your Work Relationships as Alliances
Start investing in the infrastructure of your relationships with Co Leadership's Guide to Designing Powerful Alliances.
At the end of every month, we run a retrospective.
It's the single most important recurring conversation that we have. We always leave them feeling re-energized and re-motivated for our work, and that continuous rebuilding of energy is critical for any long-term endeavor. We have the retrospective even when there are other urgent things to get done.
The goal of our retrospectives is to create the space to reflect on and celebrate how we're doing, so that we can increase our success and performance for what's ahead.
After months of tuning, we've designed our retrospectives to now consist of five parts: happiest moments, big wins, assessments of progress, lessons learned, and gratitudes.
In this post, we'll explain why we've designed our retrospectives this way as well as how you might adopt this format for your team.
Isn't this retrospective structure overly positive?
If you're an engineer like us, an initial skepticism toward this structure might be that it seems to skew positive. Many teams often view retrospectives almost as post-mortems. They value excellence and quality and believe that the best use of a retrospective is to spend the vast majority of time pointing out what went wrong and what could be improved.
We might have felt similarly many years ago. However, one thing we've learned is that people in general, and engineers in particular, tend to focus on mistakes and areas of improvement, rather than celebrating what's going right.
Think about how much positive feedback you give or receive relative to negative feedback. For most people, it skews negative. And think about how tragic it would be if people stopped doing the activities that you valued because those activities weren't explicitly being celebrated and known to be good.
Moreover, our bias actually leads us to underestimate the impact that leaving a retrospective feeling positive and excited can actually have on team performance and motivation.
Decades of research in positive psychology have shown what author Shawn Achor calls the “happiness advantage.” Retraining our brains to capitalize on positivity can actually improve our productivity and performance. 
In one study, students told to think about the happiest day of their lives outperformed their peers on a standardized math test. 
In another study, doctors who were primed with happy thoughts were able to come to correct diagnoses twice as fast as a control group. They were also more creative — they made half as many “anchoring” errors where they inflexibly stuck to an initial diagnosis. 
In a third study, students primed for positivity were able to see everything in the background in a series of images, whereas students put into a negative mood missed substantial parts. 
These benefits show the value of designing a retrospective structure that actually leaves the team feeling happier, re-energized, and re-motivated about what things are going well.
If say, 80% of the time, things are actually going really well, spending less than 80% of the retrospective celebrating what went right can actually create an inaccurate reflection of reality. Without taking the time to celebrate, it's easy for a team to feel like they're never good enough and constantly falling short.
At worst, that can have a negative impact on the team. At best, it leads to a missed opportunity to boost team motivation and productivity.
How to Adopt this Retrospective Format for Your Team
To adopt this format, schedule a recurring time for your team — it could be weekly, bi-weekly, or monthly.
Here are the five parts, the prompts we use, and the goal of each part:
Happiest Moments. What were your happiest moments at work this month?
Happiest Moments is our favorite part of the retrospective. We celebrate and share the most delightful parts from our last month. They could be conversations, activities, or things we shipped.
Big Wins. What wins and accomplishments do we want to celebrate this month?
The goal is to review and celebrate what we've done. We always leave this part amazed at how productive we've been (even if one of us has been traveling or on vacation). The fact that we're amazed only points to how easy to just focus on the day-to-day and lose sight of the bigger picture.
Assessment of Progress. How did we do relative to what we scoped out for the month? What are we doing relative to the goals that we set out to do at the beginning of the year?
The goal is to perform an honest assessment of where are, based on our top priorities. For us, those priorities include growth, revenue, and content. In reviewing progress, it helps to have defined the metrics that you care about for each.
Lessons Learned. What could we have done better on? What do we want to do differently going forward?
We believe strongly in real-time feedback and bias toward that during our normal work. But sometimes, it takes a retrospective to provide the breathing room to zoom out to the bigger picture. The goal is to identify the broader trends that we've identified and articulate how we want to shift our behavior going forward.
Gratitudes. What are we grateful for?
Gratitude is a core driver of well-being, and countless studies show that gratitude leads to higher energy, more emotional intelligence, and more happiness.  The goal is to take the time to appreciate what we have and share what people have done for us, knowing that the gratitude will actually lead to higher team performance. Gratitude can also help build a culture of positive feedback.
Doing all five parts lasts us anywhere from an hour to a few hours. For larger teams who want to do it in less time, we'd recommend:
- Focus on three segments: happiest moments (which can include big wins), lessons learned, and gratitudes.
- For each segment, go around the room and have each person share one thing.
We used to not do our retrospectives initially. But we found that it was too easy to fall into the trap of being heads-down on getting things done and not making time to talk about important things.
Now we're committed to doing them. And it leaves us feeling great about doing the work we're doing. We want the same for your team.
Get effective leadership frameworks & tools in your inbox
Learn the most valuable frameworks and tools for effective leadership that we're teaching hundreds of tech leads, managers, directors, engineering VPs, and CTOs in our coaching and leadership experiences.