Sometimes Your Job is to Get in the Way

The Head of Product, Customer Service, and the CTO of Slack were sitting in the front row at an important conference. This was peak Slack; we were all the buzz, the fastest-growing enterprise software company in history. The conference speakers were singing out praises, and at that precise moment, Slack was down. Again.

I wish I had kept the message the CTO sent me. It approximately read, “Stop all releases immediately. If we can’t keep the service up, we shouldn’t be checking in any code.”

Game on.

A Necessary Line in the Sand

Elmore Leonard wrote the book Get Shorty in 1990. Chances are, you know the movie starring John Travolta better than the book. In the movie, Travolta plays Chili Palmer, a small-time loan shark from Miami. He’s part of a New York-based crime family, and he ends up traveling to Hollywood, where he inserts himself into the movie-making process.

Chili Palmer loves movies. He has deep knowledge of the history of movies and of Hollywood. The moment he shows up, he’s educating insiders about the history of Orson Welles’s Touch of Evil. It’s never explained where Chili’s love of movies came from, but it is clear from the beginning that he wants to make movies.

It turns out the skills of a loan shark apply nicely to film production:

Find money,

Convincing skeptical people that you have a movie,

Charming humans to help you make a movie, and

Clearly drawing a line in the sand when necessary.

Chili Palmer’s defining characteristic is conveyed by the line he speaks when he draws a clear line in the sand. When asked, “Who are you?” Chili replies, “I’m the one telling you how it is.” Reading this line does not do its delivery justice. Spoken just once, it defines his no-nonsense leadership style for the rest of the film.

Keep Slack Up

I was the VP of Engineering, so I took the message from the CTO and sent it to the Operations VP, “Shut down pushes to production.” I grabbed my Chief of Staff, and we quickly built a list of names we needed in a conference room right now. A combination of VPs and senior leaders who collectively had the best picture of how Slack worked.

“We’re meeting here now. Come immediately.”

Thirty minutes later, with everyone in the room, I stood up and stated, “Starting today, we are rebuilding our development pipeline to prevent outages. Who wants to start?”

What started as an eight-hour meeting turned into five different working groups defined by that initial crew, each task a different investigation into how to fix our development process. Those working groups turned into a series of tools and practices that — three months later — completely changed how software was developed, tested, and pushed to production. Downtime didn’t vanish, but became an anomaly. In hindsight, it’s obvious that we needed to take drastic action in order to change the engineering culture of the company. Of course, we didn’t want Slack to go down, so why didn’t we act sooner?

In the moment when you are running as fast as you can, and everyone is cheering, it’s hard to see imminent disaster. More importantly, it’s unclear who is responsible for taking action. Someone, I’m sure, will say something when it’s actually really bad. I’m sure. Right?

I recently argued sometimes it’s your job to stay the hell out of the way. Just use small nudges, a quiet word here and there, but demonstrate trust by staying out of the way. You know what’s harder? Standing in front of the team and telling them, “I’m the one telling you how it is.”

Chili Palmer’s line sticks with me because it’s equal parts charisma and competence. As a leader, you have a burden to tell them how it is. It’s often a last resort move. It’s a get-their-attention move. And it’s not without risk.

A Cadillac of Minivans

Early in the movie, Chili arrives at LAX and is driven by a bus to his rental car. It’s pouring rain, and the lot is empty save for a single minivan. As Chili gets out of the rental bus, he sees the minivan and tells the driver, “Wait, I ordered a Cadillac.” To which the bus driver confidently responds, “That’s the Oldsmobile Silhouette. It’s the Cadillac of minivans!” Chili reluctantly gets in the car.

Later in the movie, Chili introduces Danny Devito’s character, a famous vain method actor, to the minivan. Devito sees the minivan, “Hey Chili, is this your ride?”

“Yeah, I like to sit up high and check everything out. I mean, it is the Cadillac of minivans,” as he clicks the key and the side door automatically slides open. He delivers the line with the same charisma and competence.

By the end of the movie, much later when Chili has become a movie producer, the closing overhead shot shows the parking lot at a studio… full of Oldsmobile Silhouettes.

That’s the choice. That’s the risk.

Stay the hell out of the way? Or tell them how it is? The discipline isn’t picking a stance — it’s knowing which moment you’re in. Stay out of the way at the wrong moment, and Slack stays down. Step in at the wrong moment and you’ve sold the team a Cadillac of minivans.