How to design a winning workshop: Step 1 of 5

How to design a winning workshop: Step 1 of 5 as written by a facilitator of strategic workshops with text over background with team using sticky notes

If you’re a workshop leader or meeting facilitator, at some point you’ve probably observed the not-so-fun energies of resistance and aversion among your participants.

It’s an unfortunate reality that mostly likely happens because people have been burned in the past by inefficient, unproductive, and boring sessions that feel like a waste of time.

The truth is, the workshop experience is going to be a waste of time if it isn’t grounded in a well-thought-out design. Structure and purpose are key to unlocking team potential, inspiring innovation, and driving outcomes. 

In real time, this looks like a group of participants that are set up for success and show up:

  • Ready and willing to collaborate

  • Aligned or working toward alignment in session

  • Primed to explore new possibilities 

  • Respectful of one another and of the time being spent

In this five-part series, I’ll break down the arc of a winning workshop from beginning to end, with guidance around how the session might flow and sample activities you can copy/paste into your own plans. 

By the time we finish, you should have a good understanding of the structure and methods that will support a positive experience for all and help your groups reach their desired outcomes.

So, where does a winning workshop design begin?

The first step of strategic workshop design is grounding and expectation setting

Part 1 of this series and today’s focus is all about grounding and expectation setting. 

The foundation of any good workshop is the prep work (whether the session is an hour long or a week long). Always make it your first order of business to get the group oriented around the work ahead.

Some things to try before the workshop to ground people and set expectations:

  • Define who is participating and what, specifically, each person will contribute to the session (remember, the sweet spot for collaborative design is typically 5-7 participants).

  • If there are people who want to contribute but aren’t able to join the full session, gather information from them in advance through an interview or survey, then share it with the team. You can also invite people – like key stakeholders – to weigh in during a dedicated, structured “Ask The Experts” session.

  • Once you’ve identified your core team, send an email to participants in advance to help level-set, share the purpose of the workshop, and tell them what to expect during the session. I like to include a high-level agenda but don’t include every detail that I need to run the session. 

  • It’s also helpful to include things like: remote vs virtual etiquette; expectations around official breaks in the agenda, or technology (like if you’ll be using a virtual meeting room like Zoom, or a digital tool like Mural, and what they need to know about it); and requirements around availability and clearing calendars (to deter multitasking). Last, let participants know what supplies they’ll need in order to prevent a scramble when you’re ready to start an exercise.

The easiest way to align on the above is by using this worksheet. I use it to plan for my own workshops and outline the who, what, when, where, and why.

Getting organized around these elements helps eliminate surprises and takes some of the uncertainty out of the mix (in my experience, humans generally don’t like surprises, especially at work). When people arrive at a session with an idea of what’s expected of them, they’re more apt to show up with positive attitudes.

Another part of Step 1 is planning a few activities during the workshop to make sure the group is on the same page.

Some activities you might want to try include:

  • Playback information that has been agreed upon prior to the workshop, like what the team wants to accomplish together. This is a good way to orient everyone around shared meaning before diving into the work.

  • If you’re starting from scratch and need to move the team into alignment, I recommend starting with this Playing Field exercise to define success in terms of good, better and best. Those milestones can refer to interim goals that happen en route to a bigger goal, or different versions of success that range from most realistic to most ambitious. I break down how to run this exercise at the link.

  • Maybe you want to help the group understand what’s working for and against them. This Assets and Liabilities activity is an excellent way to capture inputs from everyone to get a better understanding of the current climate.

Any one of these activities can take a little or a lot of time, so consider a few things to help assign timeframes to your agenda, like:

  • How much information you have going into the workshop. Is it just a quick review of previously-reviewed materials to confirm alignment? If so, you may only need an hour.

  • Are you coming in with almost no intel and need to do a lot of work together in the room? If so, budget more time. I spend as much time as it takes to do this work because it’s the most important step (in my opinion). Sometimes it takes an hour, sometimes it takes a half day: whatever it takes, don’t rush it!

Doing this level of prep work can sometimes feel cumbersome, but it’s truly the foundation for a productive session and the best way to ensure you are setting your team up for success.  

From there, you can dive into the next piece of workshop design: activities for understanding the customer and their needs which I cover in Part 2 of this series .

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