Best.
Workshop.
Ever.
DocuSign is in the midst of a multi-year effort to modernize its stack and experience.
My work for this in-person meeting galvanized almost 200 people to commit to moving towards that goal in a more serious way than I’d seen in almost four years.
I designed two days of activities, recruited and trained facilitators, organized the space and got the gear together, facilitated my own group of participants and led the entire group.
Read on below.
Why this? Why now? Why me?
About 3 months after running an effective priority- and roadmap-combining workshop for two European teams, word got around, and I was asked to do another workshop for our Growth team.
At first it sounded rote and normal: a workshop about alignment and priority setting, with roadmap items emerging, but then... I learned there would be over 100 people, it would be in person, and the goals were ambitious for a DocuSign get-together.
What did I do?
So… I’m gonna need a bigger boat. I got to work on:
Designing eight hours of in-person ideation workshops spanning 2 days for 170 employees across all major functions — marketing, design, content, engineering, growth, and their leadership
Recruiting and prepping nine facilitators and a photographer to facilitate 30-person breakouts
Supporting the selection and organization of a venue that would hold all of these people, work for the activities I designed, and purchase all the supplies (have you ever bought and transported 200 Sharpies at once?)
How did it go?
The space was extremely… hotel beige. People started out ambivalent, not knowing what to expect. Pretty soon they were shoulder deep in (compostable) Post-its, making new connections, and building partnerships that wouldn’t have otherwise existed.
What did I learn?
That I am really, really good at structured conversations and workshop design, at scale.
Sounds fun, but what were the outcomes?
Most importantly for where DocuSign was at, I was able to
Facilitate conversations that built unified momentum for relevant business change that will continue for at least two years
Galvanize our product-led growth teams to action, exploring shared ideas for reaching ambitious goals that went into their OKRs
Help Growth executives build a successful case for the CEO to include the ideas we developed in the product roadmaps
Make the Product Experience team look great at a moment when the products were under a lot of (warranted) experiential scrutiny
The best outcome for me personally was what people said afterward.
I was approached by multiple people, including sponsoring execs, who told me that was the most effective, engaging gathering they’d ever attended for work.
My workshop results were presented multiple times to executives and I was asked to run a shorter version of the same workshop for those VPs. That was pretty cool.
