I’m a big fan of team reflection. The opportunity for team members at different levels and functions to collectively share what they have seen and learned is refreshing.

It also delivers four benefits to company culture.

First, it’s a great leveller. Founders need to depart from the hand-waving sales narrative and talk straight with their teams. And team members need to organise their thoughts and communicate in ways that contribute to the discussion. In both cases, this can feel uncomfortable, but it does break down perceived hierarchies and remind the team that you’re all in it together.

Second, hearing and analysing the reflections from team members can help founders identify blind spots in how they have interacted with their teams over the last year. If the founders and management team are open to it, these blind spots present opportunities to improve planning and communications in the year to come.

Third, reflection provides perspective. On how much the team has achieved and how many fires have been fought and extinguished along the way. The force multiplier is that perspective, like humour, is free, infectious and a great circuit breaker.

Finally, team reflection can be cathartic. And this is particularly important after a big year when the team is running on fumes and doing everything possible to close our pre-holiday milestones.

Before I share the process that I find useful, I want to be clear that an annual reflection habit complements existing reflection practices. In other words, teams shouldn’t only find time to reflect once each year. It should be happening as part of regular rituals, including 1:1’s and all-hands meetings.

Annual reflection timing 

I start this process in early December, and it usually happens in two steps. The first step is a prelude to a team conversation. It involves, often in a weekly standup, providing the team with a structure for how the reflection should work. I also describe what I will be looking for in judging whether the reflection has been successful or not. I ask the team to think about my criteria for success and encourage them to form their own too. This step helps them internalise what success might look like and also helps them prepare for the conversation.

I have two success criteria for the annual reflection.

Hearing thoughtful reflections from each team member is the first. This demonstrates that they have taken the time to identify critical events. They may have been surprised, confused, frightened or elated by those events. But if they have identified them, there is a good chance they have learned from each situation, and that is critical.

Second, I see that by sharing their insights, each team member feels a sense of satisfaction and to some extent, relief. I think this catharsis and perspective provides the team with a kind of permission to enjoy their upcoming holiday.

It’s important to realise that this exercise is not an after-action review (AAR). The role of an AAR’s is to take immediate action after project or mission execution to capitalise on what went well and what can be improved. The annual reflection is a less formal and less structured event and designed to help the team reflect on a broader timeframe.

Preparation is simple

Ask your team to review their diaries and look for two standout meetings, events or milestones for each month of the calendar year. It should take 15-20 minutes. As part of this review, ask them to note down why the meeting, event or milestone was important to them.

When it comes to the annual reflection conversation, divide the year into quarters. Then ask each team member to raise one meeting, event or milestone from each quarter.

In addition to presenting my reflections, I actively listen out for observations that surprise me. I consider these my blindspots.

If I can ask a clarifying question to dive deeper into the topic without disrupting the flow of the session I do, otherwise, I followup separately.

In any case, my experience is that these sessions yield a rich cross-section of events and lessons.

One last thing…

As I’ve written about before, routines and rituals are the keys to establishing and maintaining a companies drumbeat. This reflection process is an essential ritual because it provides a platform for conversation and lesson-sharing as a means to create perspective after a busy year.

New comers benefit from annual reflection as much as team members who have worked the entire year. It’s also an essential exercise for solo entrepreneurs who should be doing an annual reflection with mentors and advisors.

This is an exercise I wished I had known about a decade ago and I hope it helps you too.