7 days ago
I Created a Meeting to Call Out My Team's Mistakes. What Happened Next Surprised Me.
This story appears in the May 2025 issue of Entrepreneur. Subscribe »
There's an idea rooted in startup culture: You've got to fail to win. People love to throw that around, but we still aren't very good at actually admitting or discussing those failures. We'd rather brush them under the rug — and as a result, we never really learn from them.
I decided to fix that at Biller Genie, the company I cofounded with Thomas Aronica. It's a platform that automates billing and invoicing to get people paid faster. I wanted to know every screwup my team was making in real time and face them head-on. So I created a "Fuckup of the Month" meeting, where all of our employees gather to share their mistakes.
The point isn't to be dramatic. It's to learn together to solve our problems faster. And you know what? It works.
At our first meeting, people were hesitant, so I led by example. I started by telling them my own screwups. I emphasized that everyone's going to make a mistake, but the important part is: Will you own it or cover it up? How will you fix it? What will you learn? How do you put up safeguards so it won't happen again? And how do we all move forward?
Related: Why Failure Is Crucial in Finding Your True Purpose
Over time, the meetings have become livelier and more open. I start by asking for volunteers, and it often begins with something lame, like, Oh man, I locked my keys in my car. But once people get warmed up, they'll share maybe 10 or 15 fuckups — and some are big. I'm usually already aware of those, because I've had to deal with the fallout. But the rest of the team might be hearing about them for the first time. And when they do, the whole room stops — and it's like, we're going to fix this together.
Take this example: A few years ago, a team member was on a training call with a customer. When the customer started speaking negatively about one of our partners, the team member agreed and also spoke badly about the partner. Then, to add insult to injury, a manager inadvertently sent that Zoom recording to — yup! — the very partner in question! No one told me that this had happened. Eventually, I got a call from that partner saying, "This is defamation."
I confronted the manager, and he brought it up at our next Fuckup of the Month meeting. He admitted that he hadn't fully understood the repercussions, which was useful: It made me realize that I needed to train the entire company on defamation, libel, and slander, and reinforce that our partners are our most important assets — we need to protect them at all costs. I also made a new rule: If you do anything that could put us in jeopardy with our partners, immediately race to my office.
When employees share their screwups and see me reacting constructively, it sends an important message: "I won't punish you for failing." However, I do expect people to be open about their mistakes and learn from them.
Related: 6 Things You Gain By Embracing Failure and Learning From Mistakes
Image Credit: Evana Vazquez
Here's another doozy: An employee accidentally did something that caused a customer's invoices to be sent to the wrong company. In this case, he told us as soon as it happened.
We discussed this at the next Fuckup of the Month meeting, and the team drew many lessons from it. The first is to get help quickly. Because the employee told us about his mistake immediately, we were able to fix it without any serious repercussions. Additionally, I realized that I needed to emphasize to the team the importance of double-and triple-checking their work. I reminded them that handling people's finances was a big responsibility and that doing it correctly was a major priority. "As a company, we do move fast," I acknowledged, "but not at the expense of accuracy. Take a few extra minutes if you need to."
Sometimes, our Fuckup meetings teach us lessons about our technology. This happened when a junior employee was training someone on our system and accidentally changed the billing settings for 3,500 of our customers. Major problem. But again, this employee came straight to find me and even interrupted a meeting we were having with one of our largest partners. She was shaking and said, "I need to speak with you right now."
That moment took guts, and I think the culture we built with our Fuckup meetings gave her the courage to do it. Had she not told us, things could have gone very wrong. Instead, with her help, we were able to take care of the problem that day. Plus, her mistake exposed a vulnerability in our system, and we ended up making our technology better. I was so impressed by the way she handled it all that we gave her the "Fuckup of the Year Award" — which we truly consider a badge of honor!
What I've learned is this: When you build a culture of owning your failures, you become better at creating solutions. And by talking about your fuckups, you ensure that they don't happen again.
Related: Want to Be a Successful Entrepreneur? Fail.
