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102: How to Facilitate a Great Workshop

A few weeks ago, I ran a workshop with the marketing team at at top 20 U.S. college. The focus was on developing team resilience in era of hybrid and remote work and got a ton of great feedback.

Jason Shen
Jason Shen
6 min read
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Cultivating Resilience is a newsletter that helps innovators navigate change and bring new product and ideas into world. It's published by Jason Shen, a resilience coach, product manager, 1st gen immigrant, ex-gymnast, and 3x startup founder.

As an organizational leader, you will be called upon to facilitate or direct an offsite, where a team gets together away from the normal business operations to learn, plan, connect, and imagine. If you'd like to get better at facilitating those discussions in an engaging way, you'll enjoy this writeup.

A few weeks ago, I ran a workshop with the marketing team at at top 20 U.S. college. The focus was on developing team resilience in era of hybrid and remote work. The ~20 person staff had previously been all in office, but during the pandemic they hired several fully remote employees and had been running into some friction as the moved to a partially in-office model.

IRL facilitation FTW!

The organizer gave me three hours to make magic happen as part of their semi-annual onsite activities where new hires got a tour of the campus, everyone got trained on a new project management tool, and think about how they work better.  

I had a blast facilitating the workshop and I think they got a lot out of the event as well. One attendee, a reserved woman in her late 30, told me that it was "the best workshop I've ever done in my life. By far". (I'll take it!)

So what made it so good?

Pacing and Activities

The first step is making sure you've allocated time appropriately. I broke the three hours into 3 sections: 45 min, 60 min, 45 min, with two 15 min breaks. I would switch teaching modalities every 10-20 mins, keeping the work interesting.

Breaks are important!

The exercises themselves spanned the gamut from group conversations, individual reflection, paired conversations, three way or four-way converations, a guided meditation, and even a segment where I made half the team debate the other half on the merits of work from office versus work from home. (The trick with that one was that everyone had to debate the opposite of what they were themselves doing).

The variation in activities ensured folks paid attention, stayed high energy, and didn't get bored.

Talking pillow > talking stick

Did my homework

I did a lot of prep for this workshop—starting with 2 calls with the Associate Director who had brought me on. He explained the background of the team’s growing pains with fully remote employees (thye had recently lost a fully remote employee to another team). The director also set up calls at my request with a more senior in-office team member, and a more junior fully remote person for different perspectives.

These conversations gave a lay of the land and a taste of the toojcs and issues that would come up in discussions. It allowed me to follow later discussions without needing to interject and ask basic questions, and I think it made my takeaways more impactful because I framed them with their unique situation in mind.

Active facilitation

A good facilitator knows when to talk, when to ask questions, and when to cut off someone who is going on too long (this happened during the intro where I asked everyone to find a partner to introduce with a "fun fact", and one fact turned into four or five before I really started enforcing the rule).

But going long isn't always bad, there was a really productive conversation later in the session that ran over another activity and I decided to cut the whole thing out rather than try to rush things. This requires having a general time estimate for every part of your workshop--I had mine tracked by 5 min increments

Because there are always some folks who can dominate a discussion, a good facilitator also needs to gently call on quieter folks to make sure all voices were heard. At one point I was tossing a pillow around to call on folks who hadn't spoken up. I also moved around the room to listen in when people were in small groups, which gave me context for facilitating

Capturing ideas in real-time

Included authentic personal anecdotes.

While a good facilitator probably talks about 30% of the time and let’s the group talk about 70% of the time, that 30% really has to count. Because this was a workshop about navigating hybrid work and building greater resilience, I started by telling a version of my own journey in realizing the importance of becoming skilled in resilience--from my first company's failure to my later entrepreneurial success.

I then talked about my sister who went to this same school, was female rookie of the year across all sports, then hurt her knee sophomore, and didn’t get to compete for the rest of her NCAA career.  Since hybrid work and only first emerged thanks the pandemic, it was a good reminder that a lot of things have been lost or totally transformed in the last few years, but that adaptation was possible.

If you enjoyed this article and you want to learn more about facilitating workshops or other interactive group discussions, then I highly recommend you check out this book by Rob Fitzpatrick and Devin Hunt called The Workshop Survival Guide: How to design and teach educational workshops that work every time.  It is an extremely readable and practical book that goes into much more detail about many these topics and if you troubleshooting strategies in case things go wrong. Fitzpatrick also wrote The Mom Test which is a highly readable and practical book about customer development for entrepreneurs and this is a great follow up.

The Workshop Survival Guide: How to design and teach educational workshops that work every time: Fitzpatrick, Rob, Hunt, Devin, Rosen, Adam: 9781071344378: Books
The Workshop Survival Guide: How to design and teach educational workshops that work every time [Fitzpatrick, Rob, Hunt, Devin, Rosen, Adam] on Amazon.com. *FREE* shipping on qualifying offers. The Workshop Survival Guide: How to design and teach educational workshops that work every time

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Writer, executive coach, and resilience expert helping founders & product leaders move through adversity and ship things that matter.