The Art of Risk-Taking: 3 Things We Learned at this Year’s Collaboratory

By Emily Winograd

Vulnerability. Honesty. Risk-Taking.

If you’re like many of us, these words more likely describe your improv class than the last professional conference you attended. With a full agenda of speakers, breakouts, and networking, professional gatherings often hit the mark on delivering high-quality, dynamic content, but don’t always create the space to wrestle with challenging questions or to explore new directions for a field.

The Collaboratory is an annual gathering which aims to serve as that space for the hundreds of Jewish innovators that attend. When we designed this year’s Collaboratory, we wanted to make sure the event’s theme – The Art of Risk-Taking – was more than just a tagline. Our goal was to empower participants to “try on” risk-taking, to open up, and to gain new competencies that would inspire bold action in the future.

Yet running a conference about risk-taking is a risk in itself: you have to walk the walk. So, with excitement and mild trepidation, we explored content, speakers, and formats that pushed the boundaries of past convenings. Here are three things we learned in the process:

Vulnerability and honesty are the greatest risks of all but theyre worth it

On opening night, after dinner plates were cleared and the din of small talk had died down, we dimmed the lights for our evening program, which began with an interactive keynote from Pamela Schuller of Stand Up Inclusion. Pam’s talk, titled Face Your Fears: What Barking and Stand-Up Comedy Taught Me About Risk-Taking, focused on bringing people together through interactive improv games, but she didn’t start there – she first shared stories from her personal experience with Tourette Syndrome, modeling the kind of honesty, vulnerability, and risk-taking she hoped her audience would embrace.

To bring that theme closer to home, the next speakers to take the stage were five outstanding members of The Collaboratory network, who headlined our first-ever story slam event: CollaboraSTORY. Expertly prepared by ELI Talks, and emceed by Aaron Henne of theatre dybbuk, these storytellers stood bravely before their peers to reveal key moments on their journeys to becoming Jewish innovators. Their stories were personal, touching on themes of race, gender, and sexuality. Capping off the evening with CollaboraSTORY was a gamble, but it served as an early example of how bold vulnerability can set the stage – literally and figuratively – for more intimacy, honesty, and connection at a large convening.

Our keynote speaker, Vu Le, author of the popular blog Nonprofit AF, took a different approach. While Vu shared stories of growing up in an immigrant community, he focused more on straight talk – the kind of brutally honest analysis that’s needed to move a tough conversation forward. Easing us in with quippy banter and photos of baby animals, Vu raised topics often considered taboo, focusing on the tensions and structural issues that inhibit nonprofits and funders from really moving the needle. At the same time, Vu spoke optimistically about the power and potential of creating “epic” cross-sector collaborations in the nonprofit world. His comments were sometimes provocative, but his directness opened up the space for dialogue and inspired new ways of thinking. Early survey results show that Vu’s talk was actually among the most beloved keynotes in The Collaboratory’s six-year history.

Dont forget the scaffolding

Vu’s keynote introduced one of the riskiest topics we unpacked this year – the relationship between nonprofits and funders – but we didn’t want to just leave people hanging. We needed to provide scaffolding – opportunities to dive deeper, engage in dialogue, and explore the potential for taking risks together. We tackled the rest of the day 2 agenda with this in mind.

Immediately following the keynote, Vu Le and Jane Leu (one of his co-authors on the new book Unicorns Unite: How Nonprofits & Foundations Can Build EPIC Partnerships) led 75+ participants through a jam-packed optional session, our most popular breakout of the convening. Through a series of activities and discussions, session participants – both funders and nonprofit leaders – forged and strengthened relationships by sharing their deepest frustrations, gaining insight into each other’s realities, and then crafting practical ways to pursue their shared goals together. We also created space for each group to dive more deeply into their own needs, including the breakout session “Nonprofit Insomnia: What’s Keeping You Up at Night?” and a community of practice gathering for funders. These follow-up sessions not only provided space for processing, but also brought the lessons of the keynote home by creating an environment for immediate practice and integration.

Later that evening, attendees had the option of continuing the conversation at the RiskTaker’s Collaborative, an LA community event co-hosted by UpStart and Slingshot in partnership with ROI Community and the Jewish Funders Network. Featuring the 26 organizations in the Los Angeles Slingshot Guide, the program combined the vulnerability of the previous evening’s storytelling with the honest dialogue encouraged by our keynote. Each featured organization shared a story of a risk they took, such as launching a new program, testing a new video marketing campaign, or even upending their entire staffing structure. Many of them presented in partnership with a funder, who provided their perspective on the case.

As capacity-builders, we recognized the vulnerability involved in openly sharing risk, and, in some cases, owning up to a “fail forward” moment. To mitigate stress and enable these innovators to put their best foot forward, we developed a framework for outlining their stories (inspired by the Design Thinking framework of “immerse, frame, imagine, and prototype”), provided a sample video case study, and held a webinar to help structure their presentations. At the event itself, we assigned a facilitator to each table, responsible for bridging the case study into a broader discussion, which served to unearth best practices and generate ideas about how to apply them to future risks and partnerships. These preparatory measures, combined with support on the ground, enabled the featured risk-takers to feel confident in sharing their risks with the community.

Risk is an ongoing process, best practiced in partnership with stakeholders

Reflecting on the last six years of running The Collaboratory, if we’ve learned anything, it’s the importance of continually iterating, learning, and improving on our model. Risk-taking is deeply embedded in this process, as each year’s new elements present opportunities to succeed or fail in the eyes of our most dedicated stakeholders. Yet for a gathering focused on serving innovators in a rapidly changing world, the greater risk is to remain stagnant, failing to respond to evolving needs.

We relied heavily on The Collaboratory network itself – through our Participant Committee, Los Angeles Host Committee, sponsors, and more – to help us identify and creatively address those needs. We designed interactive art installations in partnership with LA Jewish design firm Custom & Craft. We expanded our 1:1 coaching opportunity to serve around 70 participants, a 100% increase from last year’s pilot, and contracted with session leaders to provide specialty coaching in their areas of expertise. With the wisdom and support of dynamic local organizations like the Jewish Federation of Greater Los Angeles, Tzedek America, and many others, we were able to expand our offsite offerings from one tour to three, recognizing the importance of getting people out in the community (and out of their seats!).

As UpStart moves to deliver on our bold strategic plan, we face the thrilling, yet daunting task of growing The Collaboratory network and program offerings. The network that has supported and found value in The Collaboratory for the past six years will be critical to informing our path toward this ambitious vision. As we grow, we will continue to focus on fueling their fire, and on encouraging them to take risks to design a bright future for Jewish life. We look forward to the “risk” and opportunity of building the next iteration of The Collaboratory.

Emily Winograd is the Design Services Innovation Lead at UpStart, which fuels and connects the ideas, leaders, and organizations that reimagine how – and why – people engage with Jewish life.