How to Run a Successful Design Thinking Workshop

Collaboration is at the heart of design thinking. Every project benefits from an in-person workshop. Here’s how to design and run one well.

Chris Conley

July 25, 2016

In a world dominated by email and one-hour meetings, in-person workshops can seem like a significant commitment of time. But workshops, with their social energy, engaging dynamic, and intense focus, can ignite a team’s progress on a project.

We have been running workshops with our clients for almost 20 years. They are a part of every project. And they never fail to produce a ton of value.

But I often hear about the risk people feel in planning and running a workshop: “I don’t want to waste everyone’s time for two days,” “What if we don’t get anywhere in the end?” “I’m concerned people won’t participate.”

Does this sound like you? Are you hesitant to make workshops part of your project? Or have you run workshops that failed to produce the kind of excitement and value you were hoping? Do you fear failure when putting on an important client workshop?

Fear no longer. Running successful workshops is not rocket science. But you do need to let go of some long-held assumptions and adopt a number of principles that are guaranteed to make your workshop a success.

Here is my best advice for accelerating your projects with an awesome design thinking workshop.

Get in the right mindset.

Workshops are not about you or your work on the project to date. If you’re going into the workshop worried about whether the client will like what you are going to present, you’re already in trouble.

Workshops are about a broader group engaging with the project in a deeply meaningful way.

You are hosting the workshop to allow others to apply their expertise to the challenge. You’re inviting them into the project to help you. You’re giving their ideas a chance to surface and improve the project.

So set the conditions that will engage the attendees.

Don’t overstuff the burrito.

OK, let’s talk agenda.

You know what happens when the burrito is stuffed too full. Yep, it’s a blowout. A total mess. There’s no way to finish the burrito gracefully.

Don’t let your agenda be the overstuffed burrito.

The worry and angst about running a workshop often leads us to pack it too full of activities. “There is no way we’ll need a full 90 minutes for that.”

Yes, you will.

When you have interesting content and an engaged client team, any activity requires about 90 minutes or so. Here’s how that breaks down:

  • 10 min. Clear setup for the activity.
  • 10 min. Teams understand the task and get started.
  • 30 min. Do the core of the activity.
  • 15 min. Reflect as a team on what was accomplished.
  • 15 min. Share out and discuss the content created.
  • 10 min. Break and reassemble.

Designing your workshop in rough 90-minute chunks will save you a lot of pain. You won’t need to rush, delete activities on the fly, or otherwise cause confusion.

Of course, 90 minutes isn’t a hard-and-fast rule. Make sure to sprinkle in a shorter or longer activity here or there to keep the dynamic interesting.

A one-day workshop has room for three to four activities. A two-day workshop, six to eight. That’s not counting breakfast, lunch, and dinner.

Design the activities.

Too many people design workshops around PowerPoint presentations. Ugh, no wonder they fail to inspire!

While you will definitely have content to share, keep presentations to less than 25% of the workshop time. Spend the rest of the time in well-designed breakout activities, sharing results and reflecting on the ideas and directions offered.

Well-designed breakout activities engage the attendees in real work on the content of the project. Here are some examples. You could have participants:

  • Review customer video and create a journey map.
  • Play a “board game” that embodies the content of the work.
  • Tear down one or more competitive products or services, and present on how they create unique value.
  • Go on a field trip in the city to experience a unique business.
  • Run an “obstacle course” that is set up to represent the activities a customer must go through.
  • Brainstorm ways of solving a particular problem.
  • Build prototypes of possible solutions.

We’ve done all of these and more in our workshops. The key is to pair an easy-to-follow activity with content relevant to the project. Reflection and discussion of the activity afterward provides tons of new value and perspective on the project.

Embrace the unexpected.

Too often people running workshops seek to control the conversation and input of the attendees. This is a bad goal to shoot for.

Respect the intelligence and agency of the attendees. Embrace the unexpected questions, answers, and topics that come up. If you don’t know the answer to a question, say so.

Great workshops embrace the surprising content, ideas, and tough questions that come up when you actually give people a chance to work on a project for real. Sometimes the unexpected is a great idea or new angle on the project. Sometimes it is the elephant in the room that starts to appear but nobody is talking about it.

You should talk about it. The project’s success may depend on it.

When criticism is shared, embrace it, too. Don’t get defensive. Just reply, “Interesting, say more about that.” Often attendees will share what’s behind their concern. They will be impressed that their voice is being heard and that you are being fair and open to real feedback.

Plan plenty of reflection time.

Reflective conversations are an essential and powerful part of every one of our workshops.

After every activity, we open up the floor for a ten to fifteen minute conversation. While we may use some specific prompts, the best conversations are when the attendees are itching to contribute and talk about what they just experienced.

We discuss what was surprising about the content we just covered — what it might mean for the project or the company overall, what is challenging about the ideas, or suggestions the attendees have for how to move the work forward beyond this day.

Each of these reflective conversations helps us understand the viewpoint of the attendees. It also helps them build understanding and alignment among each other. This adds the momentum necessary to sustain the project internally at the client organization.

Make things.

Ensure that your attendees bring their ideas to life through simple mock-ups and prototypes. We always have a prototyping session in our workshops. We spend time building ideas together.

After about two hours, you will have an inspiring show of tangible possibilities.

Take the time to clear tables and set up the mock-ups nicely. Have the attendees share their mock-up, showing what ideas are embodied in it. Imagine the pride and sense of accomplishment you have when creating an idea you believe in. The attendees experience the same.

This is not about fun and games. On numerous occasions, we’ve had clients file patent disclosures after an afternoon of prototyping. Even when no intellectual property is created, conversations that result from a discussion of the prototypes is richer than we would ever have had just talking about ideas.

Design the edges of the experience.

There is the core of the workshop, but don’t miss the opportunity to inspire, provoke, or delight on the edges of the event.

A quick example: We were working on a project with a hospitality client. The morning they arrived on a shuttle bus, our whole staff ran out to greet them. We took their luggage and allowed them an unburdened stroll right into breakfast.

In anticipation of their departure, we then secretly put luggage tags on their bags with insights from the project, thanked them for their time, and bid them a safe journey home. Surprised and delighted is a great way to leave a workshop.

There are lots of ways to delight on the edges. Put something interesting in the adjacent rooms where attendees will step out to make private calls. Have an interesting technology demonstration set up during breaks. Invite representative customers to hang around during breaks for informal conversations.

Focus on what matters to create amazing workshops.

Workshops are an opportunity to engage others in your project. Stop worrying about yourself and design a workshop that provides an amazing experience for the attendees.

Design the workshop from the attendees point of view. Don’t spend more than 25% of the time presenting. Design specific activities that are engaging and relevant to the content. Look for opportunities to delight them on the periphery of activities.

Above all, don’t try to control the conversation. You worked hard to create the context for great work to happen. Engage fully and be prepared to listen.


About Chris Conley

Chris was a founding partner of Gravitytank, an innovation firm that joined Salesforce in 2016.  A former tenured professor at IIT's Institute of Design in Chicago, he is now an innovator-at-large.

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