Bad News

This was one of the toughest things to teach my team.

Things are going to go wrong. Some of it is going to be your fault, and some of it is going to be out of your control. Don’t hide it, don’t worry about having all of the answers before you surface it, and don’t wait to share the bad news.

First, I need to give context for why it matters. People naturally are excited to talk about the wins and, in business (and life), shy from the negative. But when people don’t bring the bad news, it delays decisions and makes organizations political. Remember, everyone is human. We all know people will make mistakes and have issues they are working through. Knowing that the managers and leaders are aware of the problems is a big component. We can’t have confidence they’ll solve them if they aren’t even aware of them. And the inverse is true; when a manager is aware of everything happening, it gives leadership and their peers a lot of confidence that the issues will be handled.

In 2018, we had a problem at Goat with a fairly expensive shoe that caused a big issue with a customer. The customer contacted customer service, and they informed their manager. Luckily, as part of that thread, they copied someone in operations who started to spread the news so we could all be aware of it and solve it. Literally, less than ten minutes had gone by from when the inquiry had come when it had made it through the layers of my department to me. While my head of fulfillment was giving me the thirty-second rundown, I got a call from the CEO wondering what happened and, more importantly, wanting to know if I was aware. Not only was I already aware, but my team was already in the act of resolving the acute issue and working through the root cause.

Building on the notion from earlier about trust, my team knew that alerting the team of problems was the right thing to do. Nothing was to be gained — and plenty was to be lost — if they tried to bury things under the rug or solve it themselves.

But this didn’t come quickly. People don’t want to look bad in front of their bosses. And team members are on all different levels of the spectrum. Some come from cultures or families or had previous jobs where the slightest sign of weakness was a massive failure. But that’s not how you build a cohesive team built on trust.

In an unrelated event in 2018, I identified a massive issue affecting us during the holiday season. It was one of those events where I was turning over stones, making sure there was nothing hiding, and I found a systemic bug. By the time we assessed the issue, it was as many as 1,000 orders that could have been affected. I called our CTO and got him up to speed so we could close the issue, and then I called our CEO and let him know about it. From identification through assessment to alert, only fifteen minutes had passed. The CEO didn’t need to do anything, but he needed to be aware. A large reason for that is it builds trust. He can know that if an issue does occur, we’re never going to “hope no one finds out.”

One takeaway:

Be fast with bad news.