When we’re in person, we can wander the room and get a sense of whether a team is stuck, whether someone’s dominating a conversation, or whether they’ve gone off track from the instructions. In Zoom, we have no practical way of doing that. So the primary tool I’m using here is timeboxing.
Get an inside look at how professional facilitators design and run high-stakes remote meetings. Follow along as we dissect a real 50-person marketing team retrospective, from initial planning through execution and lessons learned. Perfect for anyone looking to level up their meeting facilitation skills or manage large-scale remote collaboration.
Additional Resources
Fix Your Meetings with DAVID
The Art of Focused Conversation
Why Scrum works when it works
How to Get Useful Feedback on a Work-In-Progress
Contact Us
📧 Share a challenge or episode idea: mailbag@humanizingwork.com
Connect with Humanizing Work:
Episode transcription
Richard Lawrence
Welcome to the Humanizing Work show!
In addition to teaching facilitation skills, our clients often bring us in to design and facilitate large or high-stakes meetings and events for them. For example, this week, Peter is going to be facilitating a multi-team year-end retrospective for the marketing group at one of our clients. In this episode, I’m going to chat with Peter about how he designed and how he plans to facilitate this event. And we’ll look at how he did the collaborative visual space in Miro because it’s distributed. We’ll describe it for you if you’re listening, but definitely check out the YouTube version to see how the Miro board looks and to get inspired for your distributed meetings.
This is a specific event with specific goals for a specific client, but our goal with this episode is to give you two big things:
- How to think about and shape a retrospective to be more effective than the popular “what worked? what didn’t? what should we try?” approach
- How to approach designing big meetings, in general, so that they achieve your desired outcomes
Peter Green
As of this recording, the meeting hasn’t happened yet, so in the first part, we’re going to talk about the design and the plan for the meeting, and then we’ll come back and record a postscript on how it played out. So, stay tuned until the end to get the whole picture.
Richard
When we design meetings, we use the DAVID approach that we’ve described in previous episodes. Real quick, DAVID stands for: Define, Arrange, Visualize, Insulate, and Decide. Define is about having a clear purpose. Arrange means planning a structure that’ll achieve that purpose. Visualize is about including shared visuals in your meeting. Insulate means keeping the meeting focused and flowing by actively facilitating. And Decide is about having a clear outcome at the end.
So, let’s start off with Define—what’s the purpose. Peter, without sharing too much about the client, tell us a bit about the context and the goals for this event.
Peter
This retrospective is part of a yearend review that John, who is the Chief Revenue Officer in this organization, is leading. The Marketing Org reports into him. So he is collecting data from the broader organization separately from this retrospective on what they’re seeing from the Go To Market teams. This retro is intended to gather data from the teams themselves. And then John will get his whole leadership team together in a retrospective next week where we take the input from the broader org, the input from this team level retro, and other info that the leadership team is aware of and then they’ll make plans for how to improve going into 2025.
So for this team level retro, there are two big purposes. The first is exactly what you’d expect from this kind of retrospective–to see how things are going and pick some improvements. John is curious about a few aspects of how things are working, like if the teams are using agile practices, how decisions are being made, how the current team structure is working for the teams. Things like that. The second purpose, though, is to model and teach how to do retrospectives. So I’ve designed this particular retrospective to accomplish those two big goals, and I’ll frame it that way when I kick off the meeting.
Richard
Peter, I know you’re a visual thinker, so Arrange and Visualize are pretty coupled together for you in your meeting design approach. Tell us about the overall structure you use for a meeting like a retrospective, and then let’s dive into the specific activities and visuals you have for each part of that structure here.
Peter
That’s right, when I’m designing something like this, I almost always draw it rather than describe it in words. Like any retrospective we design, we’re using the four step pattern from The Art of Focused Conversation, Observe, Reflect, Interpret, and Decide, which we often abbreviate as ORID.
This is a pretty large retrospective, there are almost 50 participants across 7 different teams. So I decided to lay out the Miro board with the ORID steps going from top to bottom, and then each team having sort of a column that goes through the four steps.
So, starting at the Observe step, I ended up with three frames to gather objective data. In the top frame, we ask each team to add sticky notes indicating any events in the past year that had a big impact on them.. So, this will allow teams to capture things like membership changes, or things that were going on outside of the company, even, or outside of their Go To Market part of the org. There have been a couple of reorganizations. One of the teams that’s participating in this, for example, has moved into a different part of the organization. Any big process changes they’ve made—things like that.
The next frame down in the Observe category is specifically about how the teams are using Scrum or not. It’s an infographic of the Scrum framework. Some of these teams have had some training a while back on how to use an agile approach to marketing, and John is curious what practices the teams are using and why. And, this really isn’t intended to be like a check up;“Hey, are you actually doing what we trained you on—” He’s just curious. What are you using? So there are four sets of icons that teams will drag over the Scrum infographic to indicate different things, like “we do this pretty close to ‘by the book’,” has a specific icon. “We do something sort of like this,” has an icon. “We’ve never really done this,” has its own icon, and finally, “We used to do this but we stopped.” Which has its own icon as well. Then there are sticky notes to add a little context, like why they choose to use a practice or not to use it, why they started or stopped, and any variations in how they’re using that part of Scrum.
The final frame in Observe is about how work flows into the team, where interrupts come from, where there are dependencies, and the results for the team. In this frame, the teams are going to be doing a lot of sketching of their workflow. And they’ll be identifying things like key stakeholders that influence their work, who they coordinate with, or stakeholders that are impacted by their work.
So that’s a lot of data, three different frames, kind of three different lenses on it, but it should provide a really good basis for the next three steps in the ORID process.
So let’s move on to Reflect.
For Reflect, I chose to start with a visual reflection and then three text questions. For the visual, I’ve laid out what we call “visual explorer cards,” this is several diverse images we’ve either licensed or created. Each team member will pick the card that they think best summarizes the year. So, this move really helps people get out of their heads and into their emotions. That’s what the Reflect step is intended to do, once they’ve picked the card that they think best summarizes the year, then there are three prompts that each person will reflect on and respond to: the biggest surprise of the year, the time we were most frustrated during the year, and an event that changed how we thought or felt. Participants will answer individually in this section, since you really only can only reflect on your own emotions to start, then they’ll take a few minutes to read through other team members’ answers to get a sense of the range.
Next, we have the interpretive step, and we’re getting to the sort of “so what” of all the data. What are the patterns that matter? What are the big themes that stand out? I’ve laid out a series of interpretive questions here, and unlike the reflect step, teams will need to align on group answers to those questions. In this step, we’re not going for “What is your interpretation and my interpretation?” it’s “What is our collective interpretation of the data?”
Finally, in Decide, the groups have a frame that’s split in half. On the left side, we’re asking them to come up with a change the team plans to make on their own. They can own this change. On the right, we’re asking them to give advice—sort of a proposal– for what the Go to Market Leadership Team should change going into 2025.
Richard
That sounds like a good structure. So, moving on, thinking about Insulate from DAVID… What do you think are some of the key points where the meeting could go off track, and how do you plan to facilitate so it stays focused on the goal?
Peter
One of the challenges of this style of remote meeting is that the large majority of the work is going to be done in Zoom breakouts. Now, when we’re in person, we can sort of wander the room and get a sense of whether a team is stuck, whether someone’s dominating the conversation, or whether they’ve gone off track from the instructions. In Zoom, we have no practical way of doing that. So, the primary tool I’m using here is timeboxing. I’ll do one small piece at a time with a clear timebox. I’ve found that (and I’m sure you’ve seen this too, Richard), that often, a few teams will sort of terribly fail on that first timebox– they don’t even get close to accomplishing the goal by the time of the first timebox. Then they realize that we’re serious about it and they need to pay attention to it; and it gets better as the meeting goes on.
Then, I’m going to be really clear in how I frame each instruction to make sure the goal of the exercise is clear.
Another thing I’ve done to help here, and really that John did, is that he reached out to some of the team members who have more positional authority, who have been around longer, and invited them to act more as facilitators in their team’s breakouts, and to be sure they aren’t taking up too much of the air space.
Finally, there aren’t going to be a lot of cross-team debriefs. It will be mostly the teams working through the content within their team. If there’s time at the end, I may invite teams to share what they’re proposing for the leadership team, but there won’t be a lot of opportunity, when we’re all together, for people to take the larger meeting off track.
Richard
OK, so the final D in David is “Decide. It’s about having some sort of decision or output that the whole meeting moves toward. And it sounds like in this case, it’s those two proposed changes: the one for the team to do, and one for the leadership team.
Peter
That’s right. And one other thing I’ll say about that, is that I’ll make it clear when I’m framing the proposal to the leadership team that this isn’t like a demand. This isn’t like a “Leadership team, go do this.” I’m really going to have them frame it as advice: “Here’s what we would advise the leadership team to consider going into that broader meeting.”
Richard
That’s good, because not every team has the complete picture, but they have a useful view that they can contribute to.
Peter
Exactly.
Richard
Right. That sounds like a solid facilitation design to me. Of course, this kind of design is a little risky—you don’t really know how it’s all going to work until you actually get into the room. How did you build iteration and feedback loops into your design process to mitigate that risk?
Peter
Ya, anytime I’m designing something large like this, A) sometimes it’s easy to get stuck, or you feel like “Alright, I got here and now I don’t know what to do next; but B) I’m always concerned that I’ve missed something or overlooked something or even that I’ve misspelled something or misinterpreted something. So, I’ve used the Humanizing Work feedback process which we’ve described in previous episodes, both with you, Richard, as you know, and with John. You probably noticed several improvements and changes based on your advice, that you gave me over the last week, and the same is true with John’s input. It’s a much better design as a result of those two rounds of reviews.
Richard
That’s great, and we’ve mentioned a lot of resources like that in past episodes, and we’ll link to all those in the show notes.
I think this is going to be a great experience for the client. So, good luck with it! We’ll stop here and resume the episode after the event to talk more about how it went.
Ok, we’re back, and Peter has facilitated the big retro for our client. So, Peter, how’d it go?
Peter
Every team ended up making some strong recommendations for the leadership team, which was our big goal.
Richard
Nice.
What were some bright spots in the meeting from your perspective as a facilitator?
Peter
Two bright spots for me: First, this was a pretty big meeting with seven teams, lots of people, and overall we had really strong turnout with people staying actively engaged in the different stages of the retro.
Second, like I mentioned before, we got what we wanted, which is really good data and themes from those teams, some of which turned out to be new data for John, our executive sponsor for this. That’s really the big goal here, so it was nice to see that emerge.
Richard
What was challenging about facilitating it?
Peter
This retro was another reminder that any prediction of timing we make will be optimistic for something that we haven’t done before. For activities we’ve done a whole bunch of times we usually have a good sense of what timeboxes to pick and how long a section will take. But this was pretty much all new content, or at least new versions of content we’ve used in other ways before, custom designed for this group. As an example, for framing the meeting, I had allocated in my schedule, 5 minutes. But Zoom sessions rarely start on time since people are getting logged into the session. And this particular client has a practice of starting meetings at 5 after the hour, to give people a moment to get from one Zoom session to the other, but we forgot about that when we scheduled it. We scheduled it on the hour. So, as I was starting to frame the meeting and getting ready, even at 2 past the hour, half the group had joined. So I was sort of like framing things, but knowing that not everybody was there, So people were still joining the Zoom as I framed the meeting, and that chime of new participants joining kept repeating in my ears, and I think I subconsciously took longer to explain the ORID structure than I’d planned, just sort of hoping everyone would get on the call before I launched that first breakout.
Richard
Probably lower energy as a result too, in your frame, right?
Peter
Ya. It’s so tricky to do. Right? With 90 minutes you have to be very economical with the time.
Then even opening the first breakout we had a technical issue, with how the breakouts were set up. I’d checked a box earlier, when I created the session, that didn’t persist, and so people weren’t able to join the breakout; so I had to close them and reopen them. So, diagnosing that and fixing it took another couple of minutes of unexpected time. Things like that add up in that 90 minute session. So, by 17 minutes into the hour, I was 10 minutes behind. Which is not a fun place to be as a facilitator.
So, I always design with that optimism bias in mind, so there were places I could go a little faster to make room for that initial lag behind, But this one felt like it was treading the boundary a bit between “we’re focused” and “we’re rushed.” So I had to be really mindful about that.
In fact, as we wrapped up and we were debriefing the retro, one participant shared that they wished they had more time to just talk, versus filling in sticky notes and going in and out of the time boxed breakouts. I mentioned earlier that the Insulate goal in DAVID is a little tricky for remote meetings of this size. The increased structure is an attempt to meet that goal. But it can feel to some participants like too much structure and not enough talking!
Richard
I think that’s a downside or trade-off of multi-team retros in general, even if you’re in person. Because you’re optimizing for some of the larger themes, and you necessarily trade off the opportunity to follow a thread of conversation that might make sense for any particular team. So, in that case, it’s probably valuable to frame around that at the top and just let people know you’re not going to go as deep on your particular team things, because that’s not what we’re doing here, but you can always come back to that later.
Peter
Right, at this size there are lots of things we’re trading off like that. The time management is important, and the structure makes trade-offs to get lots of data and cross-team themes to emerge. And the really strong outcome from the retrospective is that both of those things happened. I did a quick review of the results with John after the retro, and there were some really useful surprises in there for him, both in the data, sort of in the observe step, as well as some of the other steps including the Decision step with team level changes, where he said “Oh, I wouldn’t have thought about that,” and proposals for the leadership team; where he said “Ooh. I want to learn more about that.” This is going to give us some strong data to bring into the leadership team’s retro which is happening next week, and I’m excited to see how that team takes that data, combines it with the other data they have, and makes some big improvements going into the new year.
Richard
Facilitation at this scale is always challenging, but it sounds like you did the thing that we think of as the core of the facilitation role of creating a space for people to have better outcomes than they would have on their own, and this was probably a much better outcome for a group of this size than a less structured conversation in that same 90 minute timebox.
Thanks, everyone, for tuning in to this week’s Humanizing Work Show. If you find this real-life case study format valuable, share the episode with someone else who’d benefit, like it on YouTube, give us a review in your podcast platform, and let us know in the comments or by emailing us at mailbag@humanizingwork.com. And if you’d like some help designing or facilitating a high stakes meeting of your own, visit the contact page on humanizingwork.com and reach out.
Last updated