Tips on planning a virtual design thinking workshop

I was unfamiliar with the inner workings of virtual workshops until recently, when work calendar had a sudden spike in the number of online workshop invitations. In June, my team and I participated in 12 hours worth of workshops and facilitated another 4. I’ve enjoyed the planning aspect; here are six things we’ve observed and documented. It’s not exhaustive, of course, neither is it linear — things can happen in parallel or non-sequentially. If you’re looking to lead a workshop, hopefully this helps unveil the planning process a little bit.

1. Align on goals and evaluate expected outcomes
2. Create an agenda, assign tasks, and write a script
3. Choose participants collectively
4. Schedule event and send calendar invitations
5. Set up, check access permissions, and pilot
6. Send reminders and get an updated headcount

Before continuing, I’d like to respectfully note that workshops aren’t the magic key to the problem-solving kingdom. Specifically, in the context of design research, it doesn’t quite replace the value of methodical research. Nevertheless, it’s a good way to get started, run exploratory sessions, and do collaborative work.

Step 1. Align on goals and evaluate expected outcomes.

With the team, define the concrete things we want to get out of the workshop. These can be questions we want answered, quotes or reactions to an artifact, etc. These concrete items serve as an anchor for planning the agenda and subsequent activities. An offering manager encouraged us to think about it this way: doing [activity] gives you [result] — how does [result] address our objectives? Identifying and evaluating expected outcomes can be worthwhile: if it’s difficult to relate the results back to the objectives, consider modifying or even changing the activity.

Goals guide activities. Activities lead to results. Results ideally fulfill the objectives.

As an example, we ran two workshops with professional analysts to understand how they work, who they work with, what their concerns are throughout the project lifecycle, and what technologies they use. Generally speaking, creating an as-is scenario map would be a solid activity choice, since the resulting artifact visualizes what happens along the journey. However, the team had already established a broad understanding of that journey and would like more nitty-gritty details. Thus, we modified the probes from doing, thinking, and feeling to tasks, concerns, people, and tools to be more explicit and more aligned with our objectives. This isn’t to say that the original version wouldn’t have applied, just that for our purpose then, we decided it was more fitting to change the probes.

On the left: textbook as-is scenario map (prompts: phases, doing, thinking, feeling). On the right: our modified version (prompts: phases, tasks, concerns, people, tools).

Step 2. Create an agenda, assign tasks, and write a script.

2.1) Create a detailed agenda and allocate enough time for each activity. Factor in time for instructions, discussions, and breaks. Also, consider adding extra cushion period — so many things can happen: technical difficulties, late arrivals, or perhaps a particularly engaging discussion that you don’t want to cut short.

Moreover, when setting the order of the activities, think about the expected energy level. Starting off with lower effort activities can help the participants ease in, warm up, and build rapport. Here’s an example activity order based on the expected energy level:

Example agenda based on expected participant energy level. Start with warm-up (introduction, expectations, etc.), continue with the main activities, and conclude with cool-down (Q&A, next steps, etc.)

2.2) Assign tasks to teammates. There are quite a few moving parts that go behind delivering a smooth workshop experience. Therefore, it can be tricky to run solo while keeping track of all these moving parts. Assigning roles or tasks to teammates helps distributing the workload. Some common responsibilities include: facilitating, note-taking, and time-keeping.

2.3) Write a script and have it handy. The script doesn’t have to be fully written out, word-for-word, but at least write out the bullet points — they serve as a “hey, don’t forget to mention me” reminder. Personally, I tend to speed through things when nervous; having a script is grounding so I don’t accidentally miss something I should show or explain to the participants. Here are some bullet points we use and reuse:

• Introduction (team + participants)
• Objectives (why we’re here, what we’ll be doing)
• Recording consent (audio, video, photos)
• Rules of engagement
• Q&A before the official start

Step 3. Choose participants collectively.

Depending on our roles and the context, we may or may not need to decide who to invite to the workshop. This step is probably more relevant for when we do have a say on the participant list, for example, running workshops with external folks for user research purposes.

After gathering an initial pool of participants and creating a shortlist, I’ve found it helpful to get input from teammates on who to finally invite. This keeps the team engaged, ensures that the participant profiles really do fit who we’re looking for, and keeps my own bias in check.

From an operational standpoint, I’ve done this two ways. One way is to do a spreadsheet: create a spreadsheet, organize participant qualifications or attributes into columns, then add columns for teammates to cast their votes. When sharing, don’t forget to remove sensitive and/or irrelevant information as well as personally identifiable information (PII).

One way to select participants with teammates: create a spreadsheet, organize participant qualifications or attributes into columns, and add columns for casting votes. This is our Airtable base with artificial data.

Another approach mimics the way we print documents and lay them all out on a table: create participant flash cards (include their relevant attributes on each card), copy these cards onto a digital canvas, and have teammates dot vote. This is arguably more effortful but can be more fun.

Another way to select participants with teammates: create participant flash cards, copy the flash cards onto a digital canvas, and dot vote. This is our Mural board; content is hidden.

Step 4. Schedule event and send calendar invitations.

Secure time slots with stakeholders and send calendar invitations. Make sure all relevant parties — stakeholders, teammates, participants — know when and where the workshop is going to happen. Include agenda if appropriate.

In terms of how much we should schedule in advance, I think it depends on a few factors. I’ve had invitations that came in as early on as 3 weeks and as late as 2 days beforehand. Some factors to consider include:

• Priority. How urgent is this workshop? Is it more serious, or more casual? If the workshop isn’t a high priority and the invitation comes in too late, people might not clear their calendar conflicts for it, justifiably so.
• Size. How many attendees are we expecting? The larger the party, the sooner we may have to schedule it, since it’s often trickier to coordinate schedules among larger parties.
• Duration. How long is the workshop? The longer it is, the sooner we should set a time and send out invitations, since it’s a larger commitment to block out, say, 4 hours, compared to 1 hour.

Step 5. Set up, check access permissions, and pilot.

5.1) Set up the tools and create collaterals that will be used during the workshop. If the activity involves answering questions in a Google Doc, set up those Google Doc templates and have the questions ready to go. If the activity involves putting sticky in a Mural board, create the board structure and lock it to prevent unintentional or accidental edits. Additionally, consider adding instructions directly in the tool that the participants will be using, so that they can refer to it any time during the activity.

5.2) Check on logins and access permissions. Double check on how participants can access the materials. Some tools require a license or company email for access; in these cases, external participants might not have access and there needs to be a workaround. Some tools require a personal account to log in; in these cases, it would be productive to ask the participants to sign up for an account beforehand, so that this additional step doesn’t cut into the actual workshop time.

5.3) Pilot, pilot, pilot. Walk through the workshop flow with a colleague or a friend to identify potential bugs and make changes. More preparation beforehand minimizes the oh-no moments during the session.

Step 6. Send reminders and get an updated headcount.

Send a reminder email to participants with instructions on when/how to log onto the web conferencing tool. The reminder may need to go out hours, a day, or even a few days beforehand, depending on the audience and the nature of the workshop.

Confirm RSVPs to update the expected headcount. Knowing a (more or less) accurate headcount helps me feel more prepared. It also allows us to make last-minute changes in case we had planned for a 10-person attendance when the actual turnout is 3. Knowing this in advance gives us time to make changes prior to the workshop, instead of being surprised and needing to improvise on the spot.

I love a good planning process. It’s rewarding to see how managing all these moving parts culminates in a smooth, pleasant, and professional experience for attendees. To recap, here is the (non-exhaustive) list of items:

1. Align on goals and evaluate expected outcomes
2. Create an agenda, assign tasks, and write a script
3. Choose participants collectively
4. Schedule event and send calendar invitations
5. Set up, check access permissions, and pilot
6. Send reminders and get an updated headcount

For further reading, here are some materials on how to guide and facilitate workshops:

Design thinking activities and tools - Enterprise Design Thinking

What I've learned from facilitating over 100 remote collaborative workshops

Best practices: How to facilitate a virtual workshop?

How to do your workshop right – 11 tips & tricks

Disclaimers: some images in this post have been modified to hide potentially sensitive information. Views are my own and do not represent those of IBM.