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By: Debbie Madden

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October 18th, 2017

Stride's Toast to Failure

Teams

At Stride, “Learning from Failure” is one of our core values. We consider learning from failure to be ‘required’ by all Striders. It runs a thread through everything we do, from hiring, to partnering with clients and vendors, to running our internal communications.

One of the ways we celebrate learning from failure is with our quarterly Toast to Failure.  Here’s a peek under the hood inside one of my most cherished Stride ceremonies:

It’s Friday. All of Stride is together for our quarterly Open Space. Once a quarter, we gather the entire team for a full day of learning and open space sessions. It’s a day filled with team bonding, learning and collaboration.

At 11am, we all gather in a circle and being our Toast to Failures.

Someone on our sales team goes first. He raises his hand, “I’ve got one. On my second day as a Strider, I deleted Stride’s entire Dropbox. Not only that, I couldn’t figure out what I did to cause all of the files to be deleted, and I couldn’t figure out how to restore the files. I spent the better part of the day working with another Strider to figure out what went wrong. In the end, we were able to restore the files. I learned that it’s ok to make mistakes at Stride, even big ones, as long as you own problem solving the solution.”

All of Stride raised our water glasses, clapped and shouted “Hooray”, “Congrats!”

Next, a Stride developer raises his hand. “I’ve got one.  Last week, I was working a hairy feature with my team. I was stuck. I felt immediate imposter syndrome. I didn’t know what to do. I stepped away from the keyboard, got some coffee. When I came back, I realized I needed to step back and think through the problem with the team. I called for an impromptu whiteboarding brainstorm. Four of us talked for 15 minutes. As it turns out, we had all been going down the wrong path. We figured out what we were stuck on, and the team was grateful I spoke up. I learned that when I’m afraid I don’t have the answer, it’s ok to ask for help and that it will sometimes even benefit the entire codebase and the project.”

Again, we raised a toast, cheered wildly, and supported our co-worker in this moment.

Over the years, we’ve had many Toasts to Failures. Some mistakes are small, some are big. Some learnings come immediately. Some take months to materialize.

No failure it too big or small to learn from. Celebrating the bumps in the road, the moments of uncertainty, the failures, is one of the things I love most about Stride. We have created a safe space for honesty, for humility. And it makes us all better.

No one at Stride, from our newest, most junior employee all the way up to me, is afraid of failure. We embrace it. As a result, the innovation, the experimentation, the breakthroughs, are outstanding. It is only by letting go of that fear of failure that teams are able to truly break through to greater learnings and outcomes.

About Debbie Madden

Debbie has over 20 years of experience in NYC tech. She is passionate about helping businesses improve through software. As CEO, Debbie has unparalleled leadership experience in the technology space - she built 4 companies from the ground up prior to co-founding Stride.

With a reputation as a passionate woman executive in technology, Debbie is a sought after writer and speaker. She has appeared in popular media outlets such as Harvard Business Review, Huffington Post, Forbes and The Wall Street Journal.

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