Stay Out of the Wind and Away From the Back

How should PMs pick projects at big tech companies?

Many of you might remember that I used to race road bikes competitively. After about a decade racing all over California—and one too many trips to the ER—I retired from the peloton to the safety of a Peloton. I learned a lot about product management from bike racing though.

One lesson: how much your “position in the field” matters, and how that might apply to PM’ing at a big tech company.1 You probably know that cyclists cluster together in tight packs—called pelotons or echelons—to save energy. Depending on the wind speed, direction, and road conditions, drafting behind someone else requires up to 30% less energy than a cyclist sitting in the wind. After 50 or 100 miles, that extra energy you’ve conserved comes in handy for the bunch sprint or the final climb, where the least gassed rider still in contention can win. In other words, patience and cleverness are rewarded in bike races.

Much of bike racing is spending several hours working to find and maintain the right position in the pack so you can survive until the finish. What’s the ideal position? Well, if you’ve been following along, you know it’s not right at the front. Those riders are using the most energy of anyone. You don’t want to be there for long unless you’re a masochist looking to break away and win solo (that seldom works). Because nobody can last very long in the wind, riders cooperate to rotate and take turns at the front, called “pulls.” Spending too long at the front is a bad idea.

Naturally, you also don’t want to be at or near the back. The back of a fast-moving peloton is a sketchy, terrifying place. You’re constantly at risk of being dropped as the field expands and contracts like an accordion around every turn. Exhausted riders are sitting up and quitting all around you. People are understandably keen to get off the back, which means making risky and unpredictable moves that can lead to crashes. And if you fall off the back, you’re cooked. It’s almost impossible for a single rider to catch up with a peloton going 25-30 mph without the benefit of drafting off others. Ugh, the back. So the back is out if you want to survive to the finish.

It turns out the best place to be is near the front, but not at the front. In a field of 60-80 riders headed toward a final climb or a bunch sprint, I always wanted to be in about the 10th position. That’s far enough from the front that I was sheltered from the wind but close enough to see what’s happening if I had to make a move. There’s another reason to be around the 10th spot: the riders ahead of you are mostly strung out in a thin line safely controlling the race, whereas the riders behind you are all jockeying and shuffling for a better position. Your position. That means if a crash happens, it’s likely to happen behind you, not in front of you. (See the photo above for why you don’t want a crash to happen in front of you.)

If you watch world-class riders in an event like the Tour de France, that’s exactly what you’ll see: teammates in identically colored jerseys maneuvering around and attempting to control the race so their designated rider can get into a solid position about 10th from the front, in order to survive to the finish with the most energy reserves. Hours and hours of this, day after day.

I write this because it offers lessons for how product managers in big companies should choose projects for the long-term benefit of their careers. This tweet from Lenny Rachitsky describes what I mean:

When I saw Lenny’s tweet, it reminded me why I enjoyed PM’ing Google Docs and Google Calendar so much (2006-08, then 2008-10). It was the perfect balance of important but not in the line of fire. Docs and Calendar were never the projects execs at Google were most interested in and worried about. I would experience that later, and it wasn’t fun. But nobody senior (at that time) ever questioned their importance to the company's future, which meant I never lacked people or resources,2 and nobody really messed with me. I would also experience that, and it was even less fun.

If you bring it back to cycling, working on the #1 project at the company might seem tempting. It’s the most important thing, and you’re right in the spotlight! I talk to many PMs who have declined offers from Instagram or Microsoft because they wouldn’t get to work on the highest-profile project. But that’s like the cyclist at the front of the field: you’re in a lot of pain while shielding the riders behind you from the wind. You might end up a hero, but you might also end up a broken, exhausted shell of a person. More likely, you’ll tucker out before you reach the finish line if you try to do it for too long. On the other hand, working on relatively unimportant projects that don’t drive the business is like sitting at the back. You’re gasping for air, constantly at risk of being dropped, and hardly anybody knows you’re there. It sucks.

If you think of your PM career like a really long bike race, neither of those are good strategies for staying in one piece and surviving to the finish. To me, a project like Google Docs circa 2006 or Google Calendar circa 2008 was like being comfortably settled into the 10th position in a peloton. We had visibility with execs, our success was by no means guaranteed, and we still had to work really hard. Our achievements were recognized and celebrated. (Both projects got me promotions, and the Calendar team won Google’s OC Award, which, while no longer given, was a big deal.)

Docs and Calendar were never the first thing Eric, Larry, and Sergey asked about when they walked into the office in the morning, and we didn’t have scores of execs and middle managers breathing down our necks or sticking their noses in our work. It was always, “great job, the work you’re doing is super important to Google.” Rarely, “we urgently need an update first thing tomorrow morning.” Not bad.

This post might come across as cynical, but I don’t mean it that way. Good PMs pick projects that maximize team and product success. You’re not sandbagging if you turn down The Most Important Project™ at your company for something a little farther down the list where you feel more likely to succeed on your own terms and have fun. Of course, there might be times in your career when you do want to take a big pull at the front of the field and lead that #1 project. Make sure the timing is right for you, and be clear-eyed about what you’re getting into. I also recommend putting a time limit around it if you want to have a long and happy career. Sitting on the front isn’t sustainable for more than a year, two tops.

It turns out there is a sweet spot at big tech companies between the Eye of Sauron and retiring to The Shire. I reckon it’s somewhere around the tenth most important project at the company.

Photo of a bike race crash. A water bottle floats in the air.
This photo was taken a split-second before the one above, just as the crash is starting and before everything hits the fan. You can only see the top of my helmet because, again, I’m in the wrong position. Note the flying water bottle.

Reminder: I’m looking to interview PMs about their company’s product culture. If you’ve worked for a company with an outstanding product culture, now or in the past, I’d love to interview you. I’ve already done a handful and they’ve been a lot of fun. I’ll be highlighting individual companies in future newsletters, keeping names anonymous.

If you’re interested in participating, please fill out the following form. Even if I don’t reach out to you for an interview, I’ll try to include your submission in some way in a future newsletter.

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1

"Big company” here doesn’t just mean FAANG: it’s probably good advice for anyone at a company with more than 1,000 employees.

2

People aren’t resources. Please, stop calling people “resources.” Join me in this fight.