Last week, I shared the importance of an accepting culture where workers are encouraged to be humans who mess up.

A while ago, I shared a similar mistake-normalizing practice with a client and he named a common worry: “It feels like all we do is make mistakes. If we start talking about it, we risk an all-out fight.”

Remember the caveat from the celebration practice? The mistakes shared should not be so big that it’s a complicated story or so heated that it’s an active conflict. This client had an organization whose structural gaps were so deep that tensions had been building for a while.

The Sunlit Strategies team sees all the work we do as systems-tending. Even if we’re coaching one leader, we do our best to understand the organizational environment. I asked this client, let’s call him “Forest,” to tell me the story of his work.

He and two friends created a startup with an incredible idea. When the small group launched their business, they were eager to get the product out and capably handled the administration between the three of them.

Their product did better than expected and production quickly outpaced the business infrastructure. While this success made it feel like there could be no problems, unspoken expectations about who would do the underestimated administrative work boiled in the distance.

The ideas were solid, the leaders had rich expertise. But the process of creating a system wasn’t there -- they hadn’t seen themselves as parts that needed to be organized. Of course, conflicts arose as we’re likely to individualize and personalize mistakes instead of seeing a bigger picture. Without organizational structures like feedback practices, the problem compounded, and resentment built.

So when Forest heard of a kind attitude towards mistakes, he was terrified it’d be the pin that would burst the bubble.

Eventually, they budgeted to hire operations staff but the trust and dynamic between the leaders had changed. Luckily, having been hired to lead struggling organizations (more on glass cliffs later) before, I reassured them we wouldn’t parachute in for a simple celebration practice and leave.

First, we tapped in with the admin team to support in creating a system that worked for their module of work and allowed for clear responsibilities, workload transparency, and compassionate acknowledgment of mistakes.

Next, we spoke with each of the leaders to process their disappointment and reflect on the stories they had about what happened. When my teammate and I felt they were ready -- after they’d had some aha moments of self-reflection and started having more questions than judgments -- we sat down to have a difficult conversation. Forest had the great courage to get the dominos going: he led with his mistake. As they spoke to each other and named what each other already knew but needed acknowledged, they started naming gaps in performance they’d all been tiptoeing around.

Communication is that contradictory tool of immense power. The simple, daunting process of clearing a buildup of judgment, shame, and hurt started with accepting the reality of mistakes. With support, Forest’s team more easily accessed the humility, grace, and sense of humor needed to keep their dream business successful.

We bring all our old experiences to every new, experimental thing we try. Most of us expect mistakes to be shamed and excised from the working experience as weaknesses. But being able to sit with the inevitably of missteps long enough to see something in them worth celebrating takes deep strength and humility.

More next week about the structural supports that lessen the likelihood of mistakes and accountability practices that help in their aftermath.

Til then, happy mess-ups to you & yours.