I recently had the pleasure of organizing and executing a risk brainstorming session for my department. I don’t often get to facilitate larger things like this, so it was exciting to pull out Liberating Structures and comb through to find the right structure. I was also excited that this session was to be primarily IN-PERSON, which meant dusting off my beloved sticky notes.

Overall, it was a good session. But there were definitely some learnings from it that I wanted to share as I think them over. First, I’ll start with an overview of our context, then I’ll talk about the structure of the activity, then I’ll enumerate the learnings.

So, our context: I work in the Platform Engineering department within a rapidly growing B2B SaaS start-up (scale-up? When do you stop being a start-up?). Our department includes teams like Site-Reliability Engineering, Identity and Access Management, Service Infrastructure, etc. In addition to “keeping the lights on,” we are striving to evolve our technical platform and pull the rest of the engineers (sometimes, kicking and screaming) into the future. Cool. But, we’re understaffed and suffering from turnover. Less cool. We decided to gather in one of our offices so that people could actually meet and hang out in person and get some of that magic “connection” that is so much easier in-person.

So we’ve got our gathering. We have our purpose: social connection. But you can’t get budget to fly 20 people to NYC and put them up for 3-5 nights just to hang out. We designed a fairly light-weight agenda of activities to get people thinking and talking. Enter: my brainstorming activity.

We wanted people to think proactively about risks we may face in the next year. We’d already submitted ourselves to the excruciating annual planning exercise imposed on us and shared the plans internally, so there was no point in rehashing that. The challenge put to me was: in 90 mins, let’s get people thinking about the risks we may face in the next year, without feeling defeated by it all.

Next up, structure. My constraints: 90 mins. Mix of ~⅔ people in-person and ~⅓ of them joining remotely (this was a trend even before COVID, but I expect entirely in-person meetings/gatherings are a relic of the past). My room was large but had only a single large table in it rather than an amalgamation of small ones. I decided ahead of time to divide people into a total of 5 groups (2 online and 3 in-person), and picked a few different themes for the groups to focus their thoughts on so that we could be assured to get different ideas from each group. In-person groups worked with sticky notes and notepads, and I set up a Mural board for the online folks. Time breakdown for the activity was planned like this:

1. 20 mins: Welcome, introduce activity, walk through an example, break out into groups.
2. 2 mins silent brainstorm: what are some ‘worst case scenarios’ for your group’s theme?
3. 10 mins: share with your group. Together, pick one you think is likely but can be mitigated.
4. 2 mins silent brainstorm: what are some things we could do to ensure that your chosen worst case scenario DOES happen?
5. 5 mins: share with group.
6. 10 mins: Discuss: What are we doing right now that resembles some of your list?
7. 10 mins: how can we change our practices to stop moving towards these worst case scenarios?
8. 8 mins: Check out, in groups – what is something you learned or noticed?

You’ll note the times don’t add up to 90. Because we hadn’t put actual breaks into the schedule (rookie mistake!), I decided to sacrifice 15 mins so that people could use the washroom, grab coffee, etc. before the next session.

Overall, great activity, people seemed energized and excited, but there are also things I can improve for next time. Here are my top 3 learnings:

1. Always converge at the end. Because I decided to sacrifice time for a break (necessary, but should have been built into the schedule so that I could have my full time), I opted to not do a phase at the end where all the groups came together to share their learnings, figuring that I’d just collect the notes and share them after the fact for async convergence. Not to be dramatic, but this choice basically undermined the entire activity and made it useless. 

What I realized upon gathering everybody’s notes is…people don’t take notes in the way I expect them to. From the notes, it was hard for me to determine where each phase of the activity started and ended, so summarizing that was not really possible. Plus, I was hoping to go over these notes together with leadership so that we could say “here’s what we’ve learned and where we think we should go,” but due to schedules being difficult in December, that still hasn’t happened and it’s been almost a month since the activity. Everybody’s lost context and the energy is gone.

Next time, the group convergence part will be my top priority, and I’ll plan the time for the rest of the activity around that.

2. Make an effort to bridge the remote/in-person gap. I decided to go with 2 remote groups and 3 in-person groups with no mixing so that the tech and set-up would be easier. While I did set up the Mural board for the remote folks to work on, this split of experiences was, frankly, lazy, and ended up with the remote people having a “second-class” experience. 

I was also too enamored with the idea of doing sticky-note brainstorming again. It wouldn’t have been too difficult to set up the Mural board so that EVERY team was working online, which could have led to a single artifact as output. This could have partly mitigated the lack of group convergence.

For similar activities I run in the future, everybody will be working in a shared Mural board, and I’ll set up the rooms such that there can be a mix of remote & in-person folks working together (this just requires booking several extra Zoom-enabled rooms and sending groups there).

3. Have a dedicated Zoom facilitator in addition to the in-room facilitator. This was something we DID do, and it worked beautifully and I will be doing it every time for future activities like this. One of the people joining remotely was a leader who was also involved in the planning, so he was assigned the task of facilitating all the Zoom activities. This made it so that I didn’t have to worry about the technical management of breakout rooms or answering technical questions, and could focus on the in-room facilitation. I had a side chat open with him so that we could coordinate and keep everything running smoothly. I gave him the list of instructions of when to form the breakout rooms and what instructions to give and when. This worked very smoothly, and I totally recommend it for anyone doing something similar.

My biggest takeaway from planning this activity is that you have to think hybrid-first, which is not the natural way I usually think about activities and really is evident in how the activity ran. This takes a lot of extra planning and preparation, but is worth it to unlock the potential of every single attendee and not just those in the room with you.