How to Design a Successful Workshop

Workshops are a great way to get your team aligned and moving quickly. I design workshops to meet my client where they are and get them to their destination. I never want to be part of a workshop that doesn’t help teams achieve results.

At the same time, a workshop needs to be something repeatable, reliable, and teachable for our business. The approach I’ve developed for our team is modular. We use different exercises to achieve the client’s needs and slot them in.

We start by asking three simple questions and then answer them through interviews, observation, and our own research. The three questions are as follows:

Where do we want to go?

  • What are we trying to achieve in the workshop?
  • What needs to be accomplished so we can move this idea, project, initiative, or strategy forward?

Where are we?

  • Where does the sponsor/client think the group is? Where does the team think they are?
  • What are the blockers?
  • What major roadblocks lie ahead?
  • Does the team have a clear picture of the path ahead or is it constantly changing?

How do we get there?

Imagine a creek crossing with rocks of different shapes, sizes, and degrees of slipperiness. There are many paths to get across, but you have to focus on picking one rock at a time.

  • What do you need to achieve with each step, since you only get a few of them?
  • What exercise will help achieve that step?
  • How do you tailor it?

Putting it Together


To bring this all together, I gather my team and draw something like this on a white board. The number of boxes represent the steps that will best fit in the chosen time period (usually a day). I aim for an hour per activity, because after that people lose focus.

We talk about what needs to be accomplished in each step and which activity will work best. Having different activities is important because it provides a variety of interaction and allows for both extraverts and introverts to participate in their own ways.

The last step is to create an action plan. We never want a client to walk away without knowing how to go forward.

Having a plan is critical, even if you throw it out in the first hour (which I have done). Going through this process ensures you are solving for the right things and gets you to plan B in a hurry.


Jessica Hall

Jessica Hall

VP, Product Strategy & Design

Jessica Hall is the VP of Product Strategy and Design at 3Pillar Global. She is the co-author of ‘The Product Mindset: Succeed in the Digital Economy By Changing the Way Your Organization Thinks.’ Her teams help startup, midsize and enterprise clients invest in products that customers want and drive business forward. Jessica has done everything from user experience design, strategy, product management, video production, to multi-channel marketing. Previously, she built the UX team at CEB and led the creation of the Newseum’s interactive exhibits and websites. Her work has been recognized by the Web Marketing Association, American Association of Museums, The Webby Awards, Time, Graphic Design USA, Forbes, and The Washington Post. She holds a Masters in Design and Digital Media from the University of Edinburgh and a BA in Journalism from American University.

One Response to “How to Design a Successful Workshop”
  1. Chester Martin on

    I’m interested in learning more about your workshops. I am potentially interested in having a team-building event where my team of about 12 gets an intro to design thinking while also working on something non work related. We’re familiar with agile software development and work in Washington DC.

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