It’s the most wonderful time of the year! It’s the annual look back and learn time of year!
We notice that between December and January every year, our clients ask us to help them design and facilitate meaningful staff retreats and off-sites.
One of our top rated activities and most meaningful exercises is always making space for teams to reflect on the year, consider their best learned lessons and make plans for the near-term future based on those shared learnings. Some call these Annual Team Retrospectives (or Retros), Team Debriefs or Annual Look Backs.
Whatever you call it — the act of making space for team reflection exercises help pull out new shared learnings and often lead to more meaningful future actions. So here is a quick reference guide of tips and tricks for how to build in meaningful “thinking time” for your organization or team.
First, The Why
Permission to Pause: Why do we need to pause and reflect? Research shows that when we slow down and focus on fewer things at one time, we are better problem solvers and come up with more creative ideas. Not to mention, slowing down can be great for business!
Research shows that employee engagement, empathy building, exhibiting kindness, and reducing a negativity bias are all things that can happen when work cultures create time to slow down and focus sometimes.
Science of Reflection: Ever heard the term “Metacognition”? Here’s a great re-cap of Metacognition, how it came to be researched as a concept and how we think about it now. But in short, Metacognition is thinking about thinking — and for adult learners, it can help people figure out how to take learning from one context and task and apply it to another.
In my master’s work I studied the concept of “transfer of training” — how someone learns something in one context and what it takes for them to apply it in another. In short, when you make space for meaningful reflection to happen (called ‘critical reflection’ in academic literature), people have the potential to learn how to get better at something.
Start With Individual Reflection, Then Share Together
Individual Reflection: Before the group gathers to share reflections together, everyone needs to spend some solo time thinking on their own. When individuals come up with ideas first and then share them, we can avoid group-think and gain value from a diversity of ideas and perspectives.
Not comfortable doing individual reflective work yet? Here are some tips to support you in developing this valuable skill set. Your group reflection outcomes get better when you learn how to pause and think critically first.
Why Group Reflection: Research suggests that when people reflect and collaborate together it leads to influencing each other’s ideas for change and ways of operating at work. Work-based reflection plays a critical role in on-the-job learning. So let this be a case for why you shouldn’t only run asynchronous reflective activities, but rather push for in-person gatherings or virtual sessions that can lead to more overall engaged employees.
A Case for Organizational Learning! And heck, maybe you’ve been trying to build a “culture of feedback” (what I might argue is the jackpot at the end of the rainbow of happy and engaged humans at work). Practicing reflection is a very healthy way to build organizational learning. It helps a workplace be more human when organizations are willing to build on learning lessons and normalize the idea that things don’t always work. No one workplace is perfect. And even if you had a “perfect quarter,” the likelihood of you repeating “perfection” is a waste of time. Instead, make space to learn together and prioritize what can be focused on next.
What Is a Reflective Learning Activity? A Retrospective? A Debrief?
My Current Definition: A set of questions that compel people to think about past experiences and draw out possible new “insights” from the act of reflecting. New insights might also lead to future actions.
Slight tangent, but stay with me:
As a professional facilitator, the concept of ‘debriefing’ how I experienced a group’s progress is one of my favorite parts of the job. A good debrief with clever co-facilitators and aware clients will always result in us all learning how to design better, more meaningful gathering experiences and how to better show up to help move a group of people forward.
I’ve been facilitating groups since high school and I likely put my 10,000 hours into group facilitation somewhere in my late 20s…but in the last decade or so I’ve been hearing the term “retro” to refer to group reflective practices more and more often. It comes from the word Retrospective (to look back) and has been popularized from software development agile practices.
My understanding is that the design-thinking-mvp-digitial-mindset-lean-start-sprint-inspired-agile-infused-software-development-innovation…ness of the way digital start-up organizations work have become more mainstream.
By mainstream, I mean that I’m seeing more non-profits, government and educational institutions using the language of “retros” for group reflective learning sessions. Huzzah! We have done it! We have found trendy ways to promote and influence organizations of all shapes and sizes to learn together! Who cares what we call it!
This experiential educator, group facilitator and trained professional is thrilled organizations are building their reflection + learning muscles! Call it whatever lands for your teams and cultures, or don’t call it anything and just DO the actual reflective work.
Ok, tangent over and back to what a group reflective activity, a retro or a debrief experience can look like.
So, What Does This Look Like?
Answer: Questions. Context. Scope of Time.
Questions:
So first things first — in our experience, there are 4 categories of questions that are most commonly used in a group reflective activity. These days I’m calling these the “Golden 4” in reflective activities. Consider these questions as foundational and a place to start from (you can always get more creative than this, but let’s start here).
The Golden 4 Questions
What’s been working?
What’s not been working?
What am I / what are we learning?
What ideas do I / do we have to improve or change things in the (near-term) future?
Context:
Consider what is the right work context lens you want your team to be thinking about the questions through. You want the questions to provoke and intrigue people to think about right focus areas and topics that will render the best new insights.
For example, perhaps you want your group to reflect on WHAT type of work activities they deliver on. So, maybe you want the group to think about the services you offer, the products you build or the outcomes you strive for. Then you take your context (what we work on) and map your reflection to the 4 questions above (what’s working, what’s not, what’s being learned and what’s next in light of our reflections?).
Another example, say you want your group to reflect on HOW they are working together in order to deliver on WHAT they are trying to do at work. So, maybe you want the group to think about how they work together in terms of team norms, role clarity, effective meeting practices, accountability or decision making practices. In this case, you’d take your context (how we work together) and map your reflection to the 4 questions above (what’s working, what’s not, what’s being learned and what’s next in light of our reflections?).
And yes, you could absolutely ask a group to reflect on both WHAT they work on and HOW they work together in the same retro (we design for this with client staff retreats all the time). You’ll just need more time to uncover people’s perspectives and ideas since the more thinking you ask them to do, the more time you need to unpack it and make meaning of it all together. Thinking about thinking can be magical! But it deserves space and time to do it well.
Scope of Time:
How far back do you want your group to think back on and reflect about? There’s no right answer on how to do this, but if you’re asking people to reflect on longer scopes of time (say a full year or more) you’ll likely need to consider how recency effect will weigh in the reflective insights people share. It’s not a big deal, but generally it helps when you pause to reflect at a natural point in your work-life-cycle or cadence of work activities.
Most Common Examples of Scopes of Time For Reflections:
Annual Reflection Activities or Retrospectives on the year — we see this most often at the end of the calendar or fiscal year for an organization.
Quarterly - you bring your team together to reflect every 3 months to help you do better planning for the next 3 months.
When an organization is kicking off some kind of strategy work, be it a strategic or adaptive planning process, they’ll often pick a scope relevant to previous plans, visions and activities.
At the end of a time-bound project, program or event where you can run a reflective learning activity with the people involved to pull out key learnings + ideas for the next type of initiative like this.
How to Run a Reflective Session/Retro/Debrief With Your Team
Make a case for why reflective learning as a group is valuable
What will matter to your group? Craft your argument around what they need to hear to buy-into your reflective activity ask. Science? Research? Data-driven results? Personal or influential stories?
Share how it will work before it happens
We call this front-loading in experiential education or managing expectations in client services work. Bring people into the process by sharing what you think it’s going to look like and feel like. How long will it take? What do individuals need to do before, during and after the experience? What can they expect during the experience? How should they show up? What mindset do people need to enter into the experience with? What will happen with the ideas the group comes up with? What happens after the reflective activity?
Schedule the Reflective Learning Activity and assign pre-Work for individuals to reflect on the questions before your team gathers
Schedule a time that you’ll gather to share reflections, look for themes, build new insights, and identify next steps together.
If you are new to this — we’d recommend at least a 2-hour block of time. Teams who do have a practice of group reflection might only need 60-90 minutes together. Meet in-person when you can, virtually if you can’t. Never asynchronously. If you don’t use the 2 hours, you’ll give people time back and they’ll appreciate it. They will, however, be annoyed if you don’t schedule enough time and leave the reflective exercise unfinished so better to block more time than less to start. This is where “permission to pause” comes into play.
Individual reflection pre-work — at least 15 minutes. When you schedule the reflective session, give everyone a pre-work or the homework assignment of reflecting on the questions individually before they walk into the session. They should see their individual reflection work as their “ticket” to get into the group reflection. Personally, I’m a fan of printing out worksheets to write on with a pen, but others will be fine to type out their ideas and bring them into the session. Here’s a simple sample worksheet you can use for inspiration and adjust accordingly for your context, scope of time, and specific questions to get your team thinking.
Facilitate the Group Reflection Activity [or hire an outside facilitator to help you do this part better]. The basic steps that will help you use your time effectively and draw out new nights and future actions are the following:
Kick-Off + Housekeeping: Review the goal of your reflection learning activity. Outline the behavior guidelines for the session and review the agenda (how you’ll use your time together), roles, and expectations for the session.
Step 1: Solo Reflection Review: Give everyone 3 minutes to read over their individual reflections they completed before walking into the session. Ask them to highlight the ideas they reflected on that feel the most important to share with colleagues today. [This step gives anyone who didn’t do their homework a few minutes to jump into the head space we wished they took for themselves before the session began.]
Step 2: Small Group Share-Outs + Key Themes to Share Back: Break your team into smaller groups for everyone to share their individual reflections. Tell the smaller groups that they have x time to share their reflections. Then get the group to transition from sharing to looking for common themes between reflections and to pick the top x # of themes they will surface to the full group. [Example, let’s say you have 30 people on a team, I’d recommend that each team share back their top 3 key insights from each question category. If you had a team of 10, maye you could do 5 key insights from each quest category. The more ideas folks share back, the more time you need to unpack the ideas in a full group format]. Get the group to write their top ideas onto something so they can show and share back in the next step.
Step 3: Large/Full Group Share-Back, One Question at a Time: Each smaller team is invited to share their top key insights per question category. For example, you start with “What’s working” and one team shares their ideas for the entire group. All other teams are listening if any of their ideas are similar they can put them together with what has already been shared to build a quick cluster of ideas. A cluster of ideas shows us a theme or pattern is emerging. Move through each question category until all the ideas have been shared.
Step 4: Large Group Reflection + Learning: Once all ideas have been shared as the group a few full group reflective questions to get them to consider the themes and patterns that have emerged so far. This step leads to new insights and new ways of thinking. Questions like: What themes are the most obvious? What are you surprised to see? When looking at all of this, what’s worrying you? When looking at all of this, where are you most engaged and excited? What clearly needs to be a priority in our work next?
Step 5: Now What: Based on What We Learned, What Will We Do Next? Based on the answers form Step 4, there are likely topics that the group identified as what needs to be worked on “next.” Consider breaking your team into smaller groups to start making plans for how to improve and change things for your near-term future. This might be a start to what will be another planning session following the reflective session. Reflection and action planning are allowed to be different sessions and mindsets. Sometimes you’ll have time to do both. Sometimes you won’t.
Wrap-Up + Next Steps for Follow-up: The most skipped, yet critical step for what happens after a team reflection exercise is…YOU NEED TO TELL OTHER PEOPLE WHAT YOUR TEAM LEARNED! Share your learnings! Socialize the new insights and ideas your team has. Socialize the challenges. Socialize the successes. Socialize that your team is learning! Socialize your ideas for improvement and change. Make a plan for how you’ll share your reflective activities.
Sample Agenda Might Look Like This:
0:00 - 0:07 Kick-Off + Housekeeping Review
0:07 - 0:10 Step 1: Solo Reflection Review
0:10 - 0:50 Step 2: In Small Group Share-Out (20 minutes)
In Small Groups pull out Key Themes to Share Back (20 minutes)
0:50 - 1:20 Step 3: Large/Full Group Share-Back, One question at a time
1:20 - 1:40 Step 4: Large Group Reflection + Learning
1:40 - 1:55 Step 5: Now What: Based on what we learned, what will we do next?
1:55 - 2:00 Wrap-Up + Next Steps for follow-up
Excited and ready to follow these steps and get started? Or do you feel like you need a little bit more coaching? Should it help, read this to learn about 11 skills of an effective facilitator and bring these tips into your reflective learning activity with your team.
Pro Tips for Running Reflective Activities With Your Team or Organization
Don’t rush a retro! Caution: A rushed retrospective is like paying for a 60 minute massage and only getting 30 minutes. How would you feel if this happened to you? Cheated? Frustrated? Half relaxed? If you’re going to ask your group to reflect, you need to leave enough time for everyone to share their perspectives, find common ground, build shared understanding and create new insights together.
New to reflective learning in groups? It takes some time to get good at this. But you will get better, faster, more efficient and more self-aware about your team strengths and weaknesses the more you do it. If your organization is new to running team reflective activities like this and you are new(er) to facilitating these types of group conversations, I’d highly recommend 2 hours to start.
I know what you’re thinking — but Hannah, we don’t have that kind of time! Here’s my argument for why you can give your team permission to pause. I find that the more organizations flex their “reflection” muscle in some kind of regular cadence (be it quarterly, 2-week sprints, at the end of a project/initiative/experiment/etc.) the faster they are able to truly pause, to think, to build new insights and to identify next steps together.
These teams tend to move into a ‘high performing’ category in team dynamics and are able to move through these types of activities faster because they do them so often and learning is the goal.
If you’re new(er) to this, I’d recommend you give yourself extra time to make a case for WHY these reflective activities can be so powerful. It is just straight up hard to slow (the f*%k) down and make space to think individually and then together.
Running a Reflective Activity Virtually: If you are running the session virtually, use a collaborative white boarding software like Miro (personal fav), Mural or Google JamBoard. People can write in their reflections before gathering, but you’d need to give explicit instructions about what people should do, where they should write their reflections, if you want them anonymous or not, etc. If people are new to these tools, you’ll need to factor in “on-boarding” / “demo” time — but that’s an investment I’m always happy we leaned into for the opportunity cost of a meaningful participatory experience for the group.
To wrap-up, though I tried to write a blog post that could be put to use instantly for folks, know that a skilled facilitator’s job is to figure out how to design exactly the right process your team needs to reach your desired goals for the group.
Hopefully, you see the value in making space and time for group reflection and shared learning. That said, know that you can always hire a facilitator to help you craft and customize the right conversations you know your team needs to have. Hiring a facilitator means you can let someone else focus on the right processes while the team in the room gets to focus on the right content.
Oh and we love it, like we really love it. Hopefully our passion and excitement for nerdy processes jump off the screen for you today…so put us to work to help your teams with reflective learning activities!
