How to run a successful remote ideation session — Part II

Dyl Cook
Purplebricks Digital
8 min readMay 12, 2021

Dylan Cook | UX Designer at Purplebricks

In How to plan a successful remote ideation session — Part I, we covered all the elements needed to successfully prepare for your ideation before getting started. To re-cap;

  1. Invites sorted — ✅ check!
  2. Teams organised — ✅ check!
  3. Agenda set — ✅ check!
  4. White board area created — ✅ check!

Time to get started

So, the day for your ideation session has arrived and you’re ready with your plan of action! We’ve talked about the importance of planning the agenda for your session, but not gone into what it consists of. There are a wealth of activities at your disposal, and I’m going to go over some of the ones I used in my most recent ideation session. These are tools that have served me well in the past, and that can produce some valuable outcomes.

Let’s break some ice

For these sessions I always start with an icebreaker. It’s a neat way of getting people relaxed while hopefully having a bit of a laugh while they are doing it. It’s also helps people in the session who have never met before or might not interact very often to get to know one another better, which can ultimately foster better discussions. If they’re going to be working together for the next three hours, it’s a good idea to make sure they are comfortable with each other before you get started.

If you go online and search for icebreaker examples, you are going to be spoilt for choice. A favourite that I use for smaller groups is ‘Two truths, one lie’. If you’ve never done this one before, each member of the team reads out two truths about themselves and one lie, leaving the rest of the team to try and guess which is the lie. This option is great as it allows the team to get to know each other a bit better, but also lends itself to a bit of fun social deduction.

I always find you should pick an icebreaker that works well for the tasks ahead. In this case, and because I had a much larger group, I went with ‘Lost at Sea’. The task is for each team to imagine they are lost out at sea (the Atlantic Ocean to be more specific) on a life-boat, after a fire destroys their yacht. They manage to save 15 items, which they must rank in order of importance to keep them alive until help comes.

On the face of it, it sounds a bit dry. However, once the task begins, it encourages a lot of discussion and problem-solving style thinking amongst the team, which can end in a lot of laughs as they try and decide how much more important a sextant is over shark repellent, for example. Plus, there is the added competition to make sure the teams gets the right order and survive over the other teams. It’s a really good icebreaker that encourages team building and problem solving, which was important for the tasks ahead.

For this introduction, I assigned 30mins. This included time at the end to read through and mark the answers to see which team managed to get saved. It was also useful for making sure that the breakout rooms and Mural board were working as expected before we began the main bulk of the session.

It’s play time

At this point your team should be relaxed, and you’ll know that your Mural boards and breakout rooms are working, so it’s time to get on with the session.

Start with an introduction about what your team is trying to do in this session and why. In our case it was Trying to improve the property search experience based on user feedback. You can let the team know what activities you are going to do, briefly, in order to try and solve this problem.

How might we?

To begin, use a technique called How Might We’s, or HMW (you don’t want to write it out in full each time), which will form the backbone of this session. If you’ve never done them before (and chances are your team might not have either), they are a great way of reframing problems in a more positive light, which also helps to keep the meeting more upbeat. AJ & Smart have a great tutorial and explanation for How Might We’s, but to put it in context:

How might we make search better?

This is way too broad.

How might we make the perfect search form with these exact filters?

This is way too specific and does not invite much discussion.

How might we make “no results” a helpful experience?

This is a great way to reframe a user problem such as “I keep getting no results and it’s frustrating me!”, as it allows more scope for discussion while pinpointing an area of the search experience to focus on.

It might take time during the session to get used to it, but you should get some great questions posed from this exercise.

In this task, I used my pre-prepared Mural board, which had all the user feedback organised into 6 areas. I then asked each team to spend 5 mins on each area, writing as many How Might We’s as they could. This task is about quantity not quality, getting as many ideas out as possible in the short time provided. It’s always good to remind people that no idea is bad, crazy or stupid, especially if some members of the team lack some confidence. It’s good to have every voice contribute to these tasks.

Once the time is up, assign each team to an area, (or two if you have more areas than teams) and ask them to read through the How Might We’s and see if these can be arranged into their own sub-groups. This should take no more than five minutes.

Once the time is up, ask each team to run through their assigned area and what sub-groups they organised their How Might We’s into, and why. This can lead to insightful discussion, and is an opportunity to discuss why they feel a certain sub-group could be more important than another.

Testing, testing…

Next, it’s time to do the dot test. Each member of the team gets three dots. They can choose three sub-groups which they believe are worth expanding upon, or they can place all three on a single sub-group if they feel particularly passionate about it. The aim is to see which sub-groups have the most value to take to the next stage of the session. Mural has this functionality built in, which really helps rather than having to create your dots manually.

Time to draw

Sub-groups narrowed down, it’s time for your teams to pick one each and enter my favourite part of the session, the world of Crazy-8’s! Crazy-8’s involves the teams drawing 8 sketches in 8 minutes based on their chosen sub-group.

This is usually the point where some members of the session will get a bit nervous, as it involves them having to draw or sketch out their ideas. It’s important to let them know it’s not about the artistic flair, but more so the ideas, and communication of those. At this stage it’s about getting their ideas out of their head and on to paper/a screen.

If you’re lucky, some of the team could have iPad Pros and may be able to sketch their ideas digitally. However, it’s more likely they will sketch on paper. In these instances, simply instruct the participants to take a photo, share it to their machine via email or Slack, and add it to the Mural board so everyone can discuss and add notes. It can be a little bit of a convoluted process, but it’s better than holding up the sketches to a webcam and everyone squinting trying to make out what the ideas are.

Once the 8 minutes are up, the groups can discuss their ideas amongst themselves. The aim is to settle on a maximum of two ideas that they then want to sketch up to a high fidelity and expound upon.

Show and tell

This is it, the final showdown — The elevator pitch.

Each team should upload their two designs to Mural, discuss why they chose them, what problems they solved, and what value they could bring to our users. It shouldn’t be too long either. It’s an elevator pitch, so a couple of minutes with some time for any questions before moving on to the next team. Once all ideas have been showcased, it’s time for the last dot test to see which ideas should have further progression.

End your session with an outro, explaining what will happen next. The collective ideas will be reviewed, progressed and user tested as prototypes. Let them know how and where they can keep track of this. Don’t forget to thank them for their time, and your first remote ideation session is complete!

So what now?

I’m going to finish with three key takeaways:

1) Remember, your role during all of this is to facilitate and provide context and answers to any questions your team may have during the session. Your goal is not to provide ideas, but to make sure everything runs on time and doesn’t go off course. Float around the break-out rooms as best you can and enjoy listening to the discussions and thought processes.

2) It sounds foolish, but don’t forget to remember to add comfort breaks. It’s amazing how involved you can be when planning these and forget basic human needs. Factor in this time when you plan out your session. Around 10mins for each break will give people time to do what they do and maybe grab a coffee. The last thing you want are people uncomfortable and disengaged.

3) This might sound negative, but things may not go to plan on the day. There may be poor wi-fi effecting yourself or another team member. Or perhaps someone can’t make it. These things happen so don’t panic, just roll with it. Make sure everyone knows the agenda, and things can stay on track.

I hope this helps for your next ideation session. If you have any feedback or suggestions from your own experience, let me know, as it’s always good to keep evolving. Good luck!

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Dyl Cook
Purplebricks Digital

UX Designer, Researcher, Illustrator, film buff, one-time podcast host and general weirdo!