Creating a Safe Space for Failure

Author: David McMillin       

A presenter at Fail Festival Slush Impact 2015 in Finland — described as ‘the crash and burn party for positive social and environmental impact initiatives’ by startup innovators.

Most conference programs focus on success stories and examples of leaders who have taken the right path to get positive results. Those kinds of case studies make sense. After all, attendees want to recreate those positive outcomes for themselves and their organizations. “Everyone enjoys talking about successes and how great they are,” Wayan Vota, a failure festival consultant, told Convene. “That’s good marketing fluff, but it’s hard to learn from successes. The presenters are so focused on making it sound like a success that they gloss over the issues and the stumbling blocks they faced,” he said. But “real learning comes when you talk about what didn’t go right.”

Vota organized Fail Festival, an annual event held in Washington, D.C., from 2011 to 2017, to celebrate stories of mishaps and missteps. The idea came from Vota’s experience working in international development. “When you’re working with a donor, you don’t want to let them down,” he said. “You want to say how beautiful everything was thanks to their grant money or their assistance.”

International development isn’t the only field where professionals gloss over mistakes that have been made — that tendency stretches across every industry. There are some audience segments, however, that make particularly ideal candidates for failure-focused conversations. The American Society of Association Executives (ASAE) first incorporated a session on failure at the 2016 edition of its annual Technology Conference & Expo.

Michelle Kudrin, ASAE’s learning director, conferences, told Convene that the breakout session was so successful that it now serves as the closing general session for the program. “I think perhaps the session works well with technology professionals as they are used to troubleshooting and solving such varied problems in their everyday work and can relate to the stories told,” Kudrin said, “and the people telling them.”

While technology professionals may be more comfortable with mistakes, many workplace cultures are risk-averse and punish human error. And feeling shame for being responsible for something that didn’t turn out well is not only a natural human trait but somewhat of a societal norm. Then, there are others whose egos may be too fragile to admit they made a mistake. Since failure stirs up negative feelings, Vota’s aim with his annual Fail Festival was to help everyone embrace “the idea that failure is a normal, everyday aspect of what we do.”

‘Fail Tales’

The ASAE session features formal presentations that Kudrin calls “fail tales,” but the format is designed to turn attendees in their seats into storytellers, too. The audience tosses a chatbox (throwable microphone) around the room to share their own failures and offer suggestions on how they would have approached the situations that presenters document.

“During the 2018 session, presenters shared their fail tale from the stage, and then, the facilitators asked the audience how they would have resolved it,” Kudrin said. “The presenters did not reveal the conclusion of the fail tale or how they resolved it until the end, after audience feedback. It kept the audience in suspense, but it was very interesting to hear how the audience would have handled the failure, and then compare that feedback to the actual resolution.”

Steps are taken to keep things light, even if the failures discussed are something of a big deal. “At the beginning of the session, the audience is asked to take an ‘oath’ based on the Fail Fest rules of etiquette that are fun and humorous, but also encourage attendees to not tweet any fails shared by audience members,” Kudrin said. “Our hope was to lighten the mood and make people feel as though this was a safe space. Last year, the audience took a vote on the most ‘epic’ fail tale told, and the winner was given a fail fest trophy. The tone of the session encourages participants to be open to sharing and learning from failures.”

It turns out that failing can sometimes feel like winning.

Laying a Foundation to Talk About Failure

Besides Wayan Vota’s Fail Festivals, he also has worked with a range of organizations to launch similar initiatives at their own events. After consulting for such organizations as the Bill and Melinda Gates Foundation, International Finance Corporation, and United Methodist Church, Vota has a few suggestions for organizers looking to include a session about failure in their program.

  • Lighten things up. Vota has found that conversations about failure work best when people can raise their glasses and toast to their mistakes. “Talking about failure can be painful, so it’s best to have a drink in hand,” he said. “You should always keep it fun. If you’re not laughing, you’re crying.”

Of course, an open bar isn’t appropriate for most conference breakout sessions. ASAE’s Michelle Kudrin said that the association’s fail sessions set the right tone by kicking things off with a humorous exercise to create a safe space for people to share.

  • Start at the top. Vota pointed out that the person who takes the stage at the beginning of a failure session or workshop can help put the room at ease. “I like to have the highest-paid person in the room go first,” he said. “If the most important person sets the tone for being candid about what they did wrong, it creates a kind of psychological safety that encourages everyone else to feel comfortable.”
  • Storytelling is key. In Vota’s Fail Festivals, each presenter — there are typically no more than eight — gave a five-minute lightning talk that he compared to a roller-coaster ride. “You know what’s about to happen,” Vota said. “So the aim is to build up the excitement that leads to the failure.”
  • Redefine failure. “Failure is relative,” Vota said. “I think we need to stop thinking about the world ‘failure’ to only be catastrophic failure. Failure comes in many levels — from the mundane of ‘Honey, I forgot to get milk’ to serious, but not life-altering failures like many sports teams’ [losses] to planned failures like the alpha or beta versions of any software program. Once you understand the nuance around failure, you can then see how it’s normal in everything we do.”

Switching the Narrative

Of course, a failure-focused session would be only half-baked if no time was spent on how to avoid the same kind of mistakes next time. “I usually coach presenters to think of the failure that moved them to change the way they work or live,” Wayan Vota said.

Not following through is a common failure story and teachable moment. One presenter shared how he neglected to reach out to a contact a friend recommended to discuss a possible career move. “Now, he follows up on nearly all leads and is conscious of what the failure to follow up means to himself and the person who was expecting the call,” Vota said.

“Another presenter gave out grants at a foundation, and for their $5,000 grants, they didn’t do much follow up,” he said. “Then, they discovered that one of their grants caused a person to over-invest in their idea and lose $20,000 — and many of their friends.”

Knowing that the money instilled a level of over-confidence that created a bigger failure for the recipient made the organization reconsider its grant-review approach. “From now on, the report from that grant is required reading for every employee,” Vota said. “It made the foundation realize that every grant, regardless of amount, impacts people’s lives.”

David McMillin is an associate editor at Convene.

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