Would You Teach Your Boss to Swim?

If your boss came into your office and asked you for swim lessons, what would you say?

That’s the conundrum Tim Stamm found himself in last year, when his superior quietly sidled up to Stamm and said, “Will you teach me how to swim?”

“I’ll be honest,” Stamm chuckles as he tells the story, “It was one of those moments where I knew that if something went wrong, it could go really wrong.”

Had I been conducting this interview via Skype or e-mail, I probably would have chalked that up to hyperbole – after all, who isn’t a little intimidated by their boss? But this conversation was happening in the most surreal of places – on a New York City Police Department boat in the waters lapping at the foot of the Statue of Liberty. Stamm’s boss is James Waters – correction, Chief James Waters, Chief of Counterterrorism for the NYPD. In other words, the boss is one of the most powerful people in New York City and respected around the world.

I actually had interviewed Waters remotely earlier this year, for an article appearing in the August 2019 issue of Triathlete magazine. On the “Make it Work” page, I profiled Waters in the context of his busy days – a real-life superhero who fights bad guys 24/7, yet somehow finds time to train and race. I knew he was a higher-up on the NYPD, but it wasn’t until last week that I fully understood what kind of power the Chief of Counterterrorism wields. It started with an e-mail from Waters, who heard I was in New York City for a stop on my book tour: “Want to join me on boat patrol tomorrow morning?”

I said yes, of course, because who in their right mind would turn down that opportunity? Within five minutes of accepting the invitation, my phone pinged with notifications of all the details from his office, from pickup time to questions about my coffee order. It was clear that Waters – excuse me, Chief Waters – could snap his fingers and make it so.

Which makes it all the more endearing to watch Stamm and Waters interact. They are quite far apart on the hierarchy of the NYPD – Waters is a three-star bureau chief, only one of 12 in the entire 30,000-plus force with such a designation, second only to the singular four-star chief of the NYPD; Stamm, as a police officer, is much lower (“I have way less than zero stars,” he laughs. “I’m a grunt.”). Still, there is a clear mutual respect between the two. Their friendship started when Waters, inspired by what he saw from the sidelines of a local race, decided he wanted to give this multisport thing a shot. The only problem? He had no idea how to swim, bike, or run, much less put all three together. “Take swimming, for example,” says Waters. “I could stay afloat, but I didn’t really know how to swim. When I went from one end of the pool to the other, I was so out of breath.”

Waters sought out the help of the NYPD Triathlon team, helmed by Stamm. “I went up to Tim and very quietly, very discreetly, said ‘Look, I’m 58 years old. I want to do a triathlon, but do you think I even can?”

Such humility is in stark contrast to where the conversation was five minutes ago, when Waters was answering my questions about what it takes to keep the millions of people in New York City safe from acts of domestic and international terrorism. When Waters gives a command, people carry it out without question. But in the pool, one of the most powerful people in New York City was – well, just another guy in the pool. The members of the NYPD triathlon team were suddenly in the position of telling Waters what to do – a dynamic that was jarring at first.

“I think a real turning point for us was when we invited him to watch us race,” says Stamm. “When I showed up, he was already there, carrying coolers and setting up tents. I said, ‘Sir, we have people who can do that for you.”

“Nonsense,” scoffed the boss. He wasn’t Chief Waters in that moment, but a fellow triathlete.

As our boat sailed under the Brooklyn Bridge, Waters and Stamm talked about how triathlon really is the great equalizer: You can be someone’s boss, but in the pool, you’re the protégé. You can have a 10 thousand dollar bike and get passed mid-race by someone on a 50-dollar garage sale find. You teach and you’re taught. You cheer for others, and they cheer for you. Sometimes, you’re the victor being hoisted up on the shoulders of the team, and sometimes, you carry the coolers and set up the tent.

It’s a lesson Waters applies to his work on the NYPD. When Waters steps away for a moment to talk with a captain, one of the officers on the boat, a boots-on-the-ground guy for the counterterrorism bureau, shows me a photo of Chief Waters from last December. While patrolling an event at Rockefeller Center, Waters appeared alongside him, fully suited in heavy bulletproof gear and walking the beat like a one-star officer. He stayed for the entirety of the shift.

“That means a lot to us,” says the officer. “He could say in his office all day, but he doesn’t.”

“Why would I stay in my office?” says Waters when I ask him about the photo later. “I ask a lot of the men and women in the counterterrorism bureau, but it’s important to me that they know I would never ask anything of them I wouldn’t do myself.”

As our boat pulls in to the harbor, I realize that Stamm’s original assessment was right – if something went wrong in bringing Waters into the fold at the NYPD Triathlon team, it could have gone really wrong. Mixing work and pleasure can backfire spectacularly. So can coaching your boss, especially when your boss can snap his fingers and put you in a crappy assignment as payback for almost drowning him at swim lessons.

But when things go right, they can go so wonderfully right. That’s the coolest part about our sport – it can foster some of the most unlikely friendships and teach us the most profound lessons about humanity. All we have to do is be willing to put aside our initial hesitation – whether it means to supplicate or to step up – and take the risk.

“It’s changed my life,” says Waters.

Stamm smiles and gives a respectful nod. “Happy to help, Chief.”

Read more about Chief James Waters in the August 2019 issue of Triathlete magazine.