Design | 17 min read

Designing workshops that work: getting better at brainstorming

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As a product designer creating digital experiences, it’s equally important to obsess over the physical ones too.

Design and collaboration go hand in hand. When we want to discuss problems, imagine new ideas and brainstorm solutions, it’s best to bring people together. But beware: that alone doesn’t automatically guarantee creative outputs and ideas. Too often, a discussion can go unfocused, brainstormed solutions end up scattered and lacking direction, or the session dissolves into a competition of who can assert their ideas louder.

Collaboration comes in many flavors, from small informal working sessions and group critiques to full-blown workshops. Workshops are an opportunity for a team to untangle a problem together by going through a series of exercises designed to get to a specific outcome. They’re about getting stuff done, and are often used as milestones to start things or make decisions. At Intercom for example, we like to run workshops to kick off big projects with the broader team. Most recently, I ran a multipart workshop about the vision of our support products that we repeated across design, product management, engineering, and marketing in both Dublin and San Francisco.

There’s nothing scarier than giving someone a blank piece of paper and saying, ‘Go, give me all your ideas.’

It takes clear and deliberate planning to run a kickass workshop. As the organizer, it’s your responsibility to ensure everyone’s time is spent wisely and you uncover the insights needed to move the project forward. When done well though, workshops are invaluable to jumpstarting your team’s progress on any project by uniting diverse opinions and getting people on the same page.

Here are my tips for running a successful design workshop (though this advice can be applied to problem-solving workshops more generally).

Start with an overview

Get the bare-bones, high-level plan of your workshop in place by answering these basic questions. I like to do this in a Google doc that I can share with key stakeholders and get feedback on as I’m planning.

What is goal of the workshop?

In a few sentences, write out why you’re holding this session as if you’re sending out a calendar invite for it. Then, try to articulate concrete goals in the form of actions. For example, these were the goals of the workshop I ran:

Every creative workshop should have clear goals

Who needs to come?

Everyone in your workshop should actively contribute, so it’s best to keep numbers relatively low. I’ve found that a group of 5-8 people tends to be big enough to amass varying ideas, but small enough for everyone to still participate fully. Optimize for in-person participation since there’s a certain effect that physicality can bring to working through problems, but there are ways of making remote participation work if needed. It’s also helpful at this stage to bring in folks with different perspectives, especially if the session is around communication or generating solutions, so keep that in mind as you comb through your invite list.

What do you want to take out of the room?

List the tangible outcomes from your workshop that you want to share or report on afterward. Similar to your goals, this will help you clarify how to structure your workshop later. As an example, the deliverables for my workshop were:

  • At least one concept/screen from each designer at reasonably high fidelity
  • A list of generated ideas and a summary of the session to send out to the product team
  • A doc of draft product principles to send to the product team for feedback and review

What date will it be? How long will it run?

Based on your goals and the number of people you’ve invited, find a date and roughly estimate how long the workshop will take. Know that this estimate will likely change, but having a ballpark number will help you plan later details, like where the workshop will be or what exercises to run with the group.

Where will the workshop be held?

Think about what kind of space your session needs, considering its length, goals and number of people. For example, you may decide that a 4-5 hour session is better held offsite to make it feel special and draw more focus. The workshop environment should feel fluid and open to encourage dialogue among the team. My favorite tip is to find a larger room with a tall table in the center surrounded by high stools, so everyone can either sit or stand. This way, people sitting and standing are roughly at the same height – giving folks a sense of equality and flexibility at the same time. Make sure there’s plenty of wall space and whiteboards too.

Work backwards and think in chunks to make a plan

With a rough overview in place, it’s time to create a workshop outline. Take a look back at the goals you listed, and think about what activities you need to do in your workshop to achieve them. Try to organize these activities into distinct chunks of your workshop. Assign a rough time estimate to each section, and as you plan out more of the details, you can go back and adjust the length of your workshop as needed.

For example, for my workshop on the vision of our support products, here’s what I had come up with at this stage:

Background (~1 hour)

  • Intro (5 min)
    • Goal of workshop
    • Agenda
    • Warm-up exercise
  • Building understanding (20 min)
    • Background info on domain
    • Looking at competitors
    • Analogous examples
    • Internal research
  • Framing the problem (5 min)
  • Talking about the future of support (20 min)
    • Interviews from other stakeholders

— Break (5 min) —

Pre-brainstorm activities (30 min)

  • Exercises (30 min)
    • Love letter, break up letter (10-15 min)
    • Drawing the present vs. future (10-15 min)

— Lunch (1 hour) —

Brainstorm (35 min)

  • Warm-up exercise (3-5 min)
  • Brainstorm (30 min)

Sketching (40 min)

  • Mind map (10 min)
  • Sketching on paper (30 min)

Share out (30 min)

  • Share out (20 min)
  • Wrap up (5-10 min)

Brainstorm principles (1 hour)

Next steps (5 min)

  • Plan for next step
  • Feedback on how session went

 

Detail the activities in each section

Now your workshop is taking shape. You’re at the point where you should go back and hammer out the details so you’re crystal clear about what you’re going to discuss with the group and what exercises you’ll do together to help you accomplish your goals.

I’ll share some advice on how to facilitate common aspects of a design workshop – getting the group acquainted, brainstorming, sketching and sharing ideas.

Use improv games to warm up

People are coming to your workshop from a variety of other meetings, so while they might be physically present in the room, their mind might still be wandering from a previous discussion. In one workshop I participated in, even though the organizer had stated the goal of the session up front people were confused about what we were trying to do when we jumped into brainstorming cold, simply because they had been distracted at the start of the session. We had to spend an extra five minutes backtracking to catch everyone up, and from there it took some more time gearing up to brainstorm out-of-the-box future concepts. We ended up losing time and momentum because people merely weren’t focused.

It’s worth taking the time at the beginning to set the tone for your workshop and get everyone thinking as a team in sync. Improv games are a great way to do this by energizing people and setting them up to be productive in your session. For instance, if one of your goals is to brainstorm future solutions to a problem, everyone in the room needs to be free of previous distractions and get to a place where they actually can do this – where they feel uninhibited and able to let their minds play.

Here are some of my favorite improv games to help everyone become present. If you’re worried about the skeptic in the room, I’ve found that taking a few minutes to explain the goal of these funky exercises can assuage any concerns long enough for people to get into the game and the benefits to start kicking in.

    • Alphabet
      • Everyone stands in a circle. The goal is to recite the alphabet one person at a time, in no particular order. If more than one person says the same letter at the same time, you have to start over from “A”.
      • Good for: Energizing the group, building group focus.
    • Sound ball
      • Everyone stands in a circle. One person throws an invisible “ball” to another, accompanied by a sound. As the person catches the “ball”, they must repeat the sound that was thrown, and throw the “ball” to someone else with a new sound.
      • Good for: Energizing the group.
    • What you see is not what you get
      • Put random objects in an opaque bag. Have each participant pick something out of the bag without looking, and as fast as they can, use the object in a way it was not intended.
      • Good for: Thinking outside the box.
    • Three things
      • Everyone stands in a circle. One person turns to the next and names three random things as fast as possible. That person then has to say how the three things are related as fast as possible.
      • Good for: Thinking outside the box.
    • Word-at-a-time proverb
      • Everyone stands in a circle and each person in order says one word at a time. When the group feels an idea or sentence is complete, they put their hands together and say “yes yes yes.”
      • Good for: Energizing the group, building group focus.

For more on bringing improv into the design process, check out Liz Gerber’s paper on this subject. A quick Google search will also bring up plenty more improv activities you can try.

Be mindful about brainstorming

There’s nothing scarier than giving someone a blank piece of paper and saying, “Go, give me all your ideas about our product’s future vision in five minutes.” Even scarier sometimes is when there are six other people in the room, and you’re expected to talk about this together.

Running a good brainstorm is all about making people feel comfortable enough to toss around ideas. But this isn’t always easy. Common problems I’ve heard are folks talking over one another, one person sharing all the ideas, or someone’s ideas getting discounted for some reason. And so, no matter how experienced a group is, I always like to take a minute to go over some ground rules for brainstorming before we begin. Even a quick run-through will get everyone on the same page and in the mood for a productive session together.

Rules for brainstorming

IDEO’s rules for brainstorming

  • Defer judgment
  • Encourage wild ideas
  • Build on the ideas of others
  • Stay focused on the topic
  • One conversation at a time
  • Be visual
  • Go for quantity

As an illustrator and one who enjoys hand-drawn slides in the workplace, I’ve sketched out these rules into reusable assets so they’re handy anytime I do a workshop. From feedback I’ve gotten, people seem to respond well to their informal and inherently creative nature – a good way to ease into brainstorming and sketching. Feel free to try these out for yourself in your next workshop.

To help get people’s creative juices flowing, it’s also good practice as the facilitator to have a couple of example ideas up your sleeve, so you can start the conversation and spark ideas in other people. Ask questions and introduce constraints if people are stuck brainstorming; for example, what if we had a million dollars to solve this problem? What if we had to deliver it in two weeks?

Depending on the group dynamics, sometimes I also find it helpful to split the brainstorming into two sections. First, spend a few minutes getting everyone to write down their own ideas on Post-its, and then have them get up and share on a whiteboard. Continue to build on top of ideas standing around the whiteboard after everyone has a chance to share their initial thoughts.

Shek, one of our designers, sharing an idea about automation in our brainstorm.
Shek, one of our designers, sharing an idea in our brainstorm.

How to sketch more ideas

Sketches are often the most tangible output from a design workshop, allowing everyone to explore concepts on their own. It’s critical here to strike a balance between freedom and constraints – give people enough time and space to sketch out ideas, but constrain them to encourage creativity.

With many groups, I’ve found that when we have too much time to explore ideas, we tend to go deep on a few concepts and get attached to them quickly. The goal of sketching out ideas in a workshop though is to go for quantity, not quality. We want the “bad” ideas, the technically unfeasible ones and the “north-star” concepts, just as much as we want near-term fixes and predictable solutions. Anything goes. This is the time to let your ideas flow, unfettered, and get a braindump of all possibilities. There will be plenty of time later to think rationally and cut back, but the more you get out all your ideas now, the more confident you’ll be of your ultimate solution.

As a rule of thumb, 10-15 minutes of sketching time for an hour workshop is more than enough. Again, as the facilitator, encourage quantity over quality.

Pro tips:

  • Putting on some calm background music can help people focus (but ask first, since this depends on the group’s preferences).
  • Crazy 8s” is a helpful technique for groups that might feel stuck or intimidated by sketching ideas. Have everyone fold a sheet of paper in half, and in half again, until you have 8 sections. Encourage folks to draw one idea in each box and try to fill all 8 before time runs out. I’ve found that having a tangible numerical goal to shoot for can help push some people to think of more ideas.

Sharing ideas productively

It’s not enough to just individually sketch ideas – sharing them around the table is where the interesting discussions take place. Have everyone put up their sketches on the wall, so the group can see all the ideas equally. Give a few minutes to each person to walk through what they came up with, and build in extra buffer time if possible to allow for conversation.

If one of the goals of the workshop is to assess these ideas, dot-voting is a great way to help the group narrow thing down while giving everyone an equal voice.

Lastly, before wrapping up, make sure people jot down names on their sketches to help with follow-up questions after the workshop.

Delegate when needed

At this point, you’re doing a lot. If you’re the one running the workshop it can feel totally overwhelming to not only plan and run the whole thing, but also to prepare all the content needed for it.

Don’t be afraid to ask for help. Consider pulling in teammates to flesh out sections of the workshop. Your PM might be the most knowledgeable about the product domain, or a researcher might be the best at explaining use cases. In my workshop for example, I asked a few other designers to prepare a few slides on competitors and analogous examples. Sharing this responsibility helps everyone feel involved and invested in the process. Changing up who’s presenting has the added benefit of keeping the session feeling fresh, so folks aren’t bored by the monotony of just one person talking for hours.

Make slides

With all the details planned out now, it’s time to bake your hard work into slides. Yes, put in a slide for that five minute break, a slide to recap what you’ve done and what else is left in the workshop, a slide to illustrate the activities you’ll do. The goal here is to offload the plan entirely from your head so that you’ll feel in control and relaxed during the actual workshop. It can feel like a lot of work but it will create a smooth schedule that can elevate the workshop experience for everyone.

Offload your workshop plan onto slides so you feel in control and relaxed.

Fun fact: the slide count for this workshop was 135! It’s all about mapping those small details 😃

Keep track of time

Timing activities accurately is an art. You should always have an estimate for how long something will take, but expect this to be fluid in reality and be prepared to roll with the punches on the day of.

Keep an eye on the clock to stay on track, but do this subtly. I’ve timed activities before by projecting a countdown timer on a screen for convenience sake, but have found that it’s hard to brainstorm and be creative under that kind of pressured environment. The best experiences for me have always been the ones that have felt most natural and lightweight for those participating. As a facilitator, simply announcing 10 minutes for an exercise and then keeping one eye on the clock will put your attendees at ease. It may be a little more effort for you – but it will be a better experience for everyone else.

Extra jazz

For bonus points, here are more tips to make your workshop even more seamless, natural and thoughtful:

  • Show up 10 minutes early to prep, make sure technology works, and even set the mood with upbeat music to energize folks as they arrive.
  • Stop periodically to check for bio breaks. Water and snacks are a nice touch to keep energy levels high.
  • Set ground rules around using devices so everyone has common expectations and won’t be distracted throughout your session.
  • If the group starts to get derailed by off-topic questions or comments, push for progress on your original plan by capturing these points on the whiteboard and coming back to them later if you can. Make an effort to address these questions after the workshop if you run out of time.
  • Nominate someone beforehand to be a documenter for the workshop.
  • It’s nice to have someone taking pictures of people in action during the workshop. This kind of documentation is not only a good momento, it can also be a valuable inclusion to a workshop recap you might send out afterward.
  • If you have remote participants, try to use a moveable webcam to make it easier for folks on the line to see sketches, post-its, and whiteboards up close. Encourage them to share out their ideas first to make sure they feel included.
  • Spend the last 5 minutes wrapping up to discuss next steps and action items. Thank everyone for their time. This can also be a great chance to ask for feedback on how the session went.
  • Send out a recap to all participants and stakeholders to summarize what you did in your workshop.
  • Add in some photos and artifacts from the session – this keeps the momentum going and helps communicate next steps to the team.

Try it out

Organizing and facilitating a workshop can be challenging. But by stringing together the right people and plan, design workshops will become an important part of your team’s process to kick-off projects, discuss problems and cook up new solutions. As the facilitator, being deliberate and thoughtful in how you structure these sessions will pay off in spades as your team generates momentum in solving hard problems. And don’t worry, you’ll always have another chance to iterate on the experience 😃

Are there any other workshop tips and tricks you swear by? Give these ones a try, and let us know what you find works well in your next design workshop.

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