Let the developers carry your message

Matt Stauffer
6 minute read

Tighten loves the Cubs. Dan's a lifetime Cubs fan and he finally got me on the bandwagon this summer, and even folks in the company who weren't previously fans became fans temporarily when Dan promised the whole company a day off in the case of a Cubs World Series victory.

A little bit of back story

Before Wednesday, it had been 108 years since the Cubs last won the World Series. To put this in context, that means there are Cubs fans who are 100 years old who've never seen them win before. There may not be a single Cubs fan alive who's ever seen them win before. This is a huge deal.

At one point during the Series the Cubs were down 3-1 (they'd lost three games and won one). In a best-of-seven series, a team only needs four wins to take the Series, which means every game from then on could have been their last: the Indians only had to win a single game and they'd win the Series. Nevertheless, the Cubs made it the whole way to Game seven, and they even started the game off with a huge lead—but by the end of the game they'd lost the lead.

I'm not a lifelong baseball fan, so I've tried to tell this in a way that'll make sense to you even if you aren't a big sports fan either. The important thing for you to understand here is that there may never be a more important or more tense moment in the history of the Cubs—maybe in the history of baseball.

How Maddon managed

What does this have to do with business? Why am I writing about the Cubs here? Well, first, I may have only become a fan this summer, but I've since lived through the most exciting time in Cubs history, so I'm a bit excited about everything Cubs. If I could sleep in my Cubs hat I would.

But there's another piece here. There was a turning point in the game that led to the Cubs' final win. The game was temporarily paused (a "rain delay") while the grounds crew rolled out huge tarps over the field. Each team huddled up in their clubhouse.

This is the time that I, as a manager of developers, expect the team's manager to be taking the responsibility on himself to drum up the excitement and the plans to finish off right. Scenes from sports movies where the coach draws wildly on a chalkboard were running through my mind. When things get tight (ha!) at Tighten, that's when I buckle down, down a few coffees, and get ready to micromanage code.

But interviews with the manager (Joe Maddon) and the players show that's exactly the opposite of what Maddon did. It's best summed up in this article: The rain-delay meeting that changed Cubs history. In essence, Maddon spent the most important moment of the game checking a weather report, watching from a distance as the players gathered themselves together and met without him.

How on earth do you find yourself in the tensest, most important moment in the history of your franchise and not jump in front of your players and try to motivate them to do good work? How do you not dance and gyrate and yell and plead to try to get them to do what you want?

"Let the peers carry your message"

The answer, as I've learned in trying to hunt down his reasoning, is that Maddon has spent his entire time with the Cubs training them to lead themselves. It seems he commonly says "I'd rather the peers carry my message," which I interpret to mean this: all the motivational speeches in the world only mean so much when they come from the people who are in charge, or the people who are paid to be motivational. The best, and the most powerful, come from the people on the ground.

Bradford Doolittle, the author of the ESPN article I linked above, made the connection for me: "It's a little like parenting," he writes; "you teach your children well, and then trust they will follow the lessons they've learned."

It seems they did. We now know that Cubs veteran Jason Heyward brought the team together without being asked or prompted and gave them the inspirational speech I expected from Maddon. He told them what they needed to hear, it seems, because from that delay forward the Cubs owned the game.

Maddon trusted his people on the ground—his players—to lead each other in the moment. He trusted that he had led them well enough up to that point that they now knew how to lead each other, and he stepped back and let it happen.

Bring it home

My people on my ground? They're developers. I don't fancy myself Joe Maddon. We're not in the World Series. But I am a manager, and I do find myself in stressful and high-pressure situations at times. And my default response is to manage more in those moments, not less.

I want to cultivate a culture in hiring, leadership structures, and employee development that lets me be Maddon in our next rain-delay moment. I want to empower my developers so that the next time things get tight, it's better for me to go check the weather and watch my developers gather the team around and motivate each other.

As an added bonus, we've heard reports about what Heyward told the other Cubbies when he gathered them around. "He just wanted to get everyone together and remind us that we've been picking each other up since Day 1," said Addison Russell. Heyward himself said: "Just needed to let these guys know they're awesome. Don't get down. [..] We've been doing this all year, so continue to be us."

Here's the best part. Maddon trusted his team. He knew they were the best and he knew they could lead themselves. And what did Heyward say to his teammates as he helped lead them to victory? He reminded them of who they are. He spoke the truth to them that Maddon already knew: You are the best. You just need to keep being who you are. We got this.

I want Tighten to be a place where I know my team is the best—and they know it so well that, when things get tight, I can sit back and watch them remind each other. This is who we are. Just keep being the best. We got this.