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Hiring At Startups: the Tom Brady Problem

Kwindla Hultman Kramer
Don't Panic, Just Hire
8 min readFeb 14, 2017


Last week Tom Brady won his fifth Super Bowl. Lots of people think he’s the best quarterback ever to play football. But he was drafted in 199th position when he graduated from Michigan seventeen years ago. Six quarterbacks were picked in that draft before Brady.

It’s hard to tell which high school athletes will stand out in college. And it’s even harder to tell which college athletes will be star professionals. The greatest basketball player ever, Michael Jordan, was picked third in the 1984 NBA draft. In fact, 11 of the 40 NBA number one draft picks between 1970 and 2010 never made the All Star team!

I’m not an athlete, or a coach, or a scout, or a general manager. But I’ve often thought about the parallels between hiring people to work at startups, and picking athletes for teams. I’ve directly participated in hiring a couple of hundred people over the years (which means I’ve interviewed or considered probably ten times that number). And I’ve had plenty of surprises in both directions.

I’m an optimist, so I get surprised more often when people don’t succeed in a job than when they do. And tempering my optimism has been one of the most important things I’ve learned about hiring. A hire that doesn’t work out is extremely costly (in money, of course, but in time and team morale, even more so). So I’ve learned that I do much better when I try hard to focus on red flags and reasons why we shouldn’t make someone a job offer, than when I follow my natural instinct to think about how someone might grow, or evolve, or change to be a perfect fit for a job.

Which brings us back to the Tom Brady problem. One of the biggest mistakes you can make, hiring for a startup, is to think you’re hiring people who will grow into a bigger role as the company grows.

This is a completely natural mistake that, like many mistakes in life, stems from good intentions and understandable concerns.

Startups grow fast. Everything changes as a company grows. Living through the 5 people to 100 people growth phase feels a little like jumping from high school sports to college. And 100 people to 1000 feels, maybe, like going from college to the pros. In a high growth startup, 5 people to 1000 people can happen in just a few years. And of course it makes sense to hire people expecting that they will be key contributors to the company for several years.

But it turns out that it’s exactly backward to focus on the idea of hiring people who will be able to grow into “next level” managers in the future. Instead, you should be focusing on hiring people who will excel at the job you need done right now. You should think of your hiring process not as the NFL draft (a guess about someone’s future prospects), but as the free agent market (an evidence-based filling of a specific role).

It turns out that the skill-set gap is large between, say, being a good individual programmer and being a really good systems architect. The same goes for being a product manager on a small team versus managing 50 people and having responsibility for reporting upward to other executives. Like Tom Brady, some people make the jump look surprisingly easy. Most people — even most very talented, impressive, and delightful people — do not.

And it’s especially hard to predict whether someone will make the jump to the “next level” because — in a startup — you never know in advance exactly what that level will look like. Startups are by definition experimenting, iterating towards product market fit, searching for a business model. Even if you do succeed in identifying your Tom Brady and offering him a job, if it turns out you are a basketball team rather than a football team, your Tom Brady hire doesn’t help you.

On the other hand, it’s much easier to interview a person for a job if your primary goal is to figure out whether they’ve successfully done something pretty similar to what your company needs them to do right now.

A percentage — but, empirically, a fairly small percentage — of the people you hire will definitely grow as your company grows. Watch for that, seize on it, and make the most of it. But don’t organize your hiring process around the hope that someone you bring on board today will go from writing code themselves to managing a Facebook-sized engineering organization.

Hiring startup executives is hard

If you’ve read this far, you’ve read all the advice I have to give. Everything that follows is just discursive speculation, since I’ve been thinking about this topic (specifically, the analogy between how hard it is to hire executives for high-growth startups and how hard it is to draft professional athletes) for about a decade.

Brad Feld told me a story, once, about a CEO who called to tell him she had bad news and good news. The bad news was that she had just fired her 9th VP of marketing in three years. The good news was that she had decided not to try any more to fill the position.

Brad told the story to illustrate the difficulty of finding the right marketing executive at a startup. But my experience is that the pain is more general than that, especially as you shift into high-growth mode: all executive positions are tough. Product/market fit is hard. But executive/company fit is pretty hard, too, at a company that’s doubling in size every year.

It’s tempting to think there could be a Moneyball — a data-driven — approach to assessing executive/company fit. Maybe so. But “data-driven” implies having a lot of data, and I don’t. (Nobody I know does, either.) So without data to work with, a Moneyball toolkit for executive hiring is mostly just an interesting thought experiment.

I do find working with “anecdata” is useful, though. And, of course, I think using analogies as tools to think with is useful, or I wouldn’t have written this post.

Still, our pro sports draft analogy breaks down in a pretty fundamental way if we push it too far. Going from high school to college to the pros is tough because the competition gets massively better at each level. The rules, while not exactly the same, are similar enough that “the game” is a constant. That’s not true in a startup. A team lead at a 20-person company needs an almost completely different skill set than a senior manager at a 200-person company. Making the jump to the “next level” isn’t about competition. It’s about being able to do a completely different job well,.

On the other hand, the analogy holds because excelling at the “next level” as a startup grows is, fundamentally, about a really mysterious combination of natural strengths, situation, psychology, and an ability to adjust and evolve.

Natural Athletes

When I was in high school I played a lot of basketball on courts on the Duke University campus. This was in the Grant Hill and Christian Laettner era. Duke won back-to-back national titles in 1991 and 1992. Because there were rules limiting off-season “official practice”, the members of those national championship teams played a lot of pickup basketball.

There’s no question that the best natural athlete I saw play in those years was Grant Hill. There’s also no question in my mind that the next best was Marty Clark, who started a total of 9 games in his Duke career. But on the pickup courts it was clear why Clark had been recruited so highly.

He usually arrived with one of his boys, who spent the whole afternoon throwing him half-court alley-oops. And when he wasn’t dunking on people, he was draining shot after shot from 30 feet.

So why wasn’t Clark a star at Duke? Why didn’t he make the NBA? If you’d asked me, based only on the evidence of the outdoor courts, who would have an NBA career, I would have definitely thought Marty Clark was a lock. Context, psychology, mystery. Who knows for sure. But the experience of watching Marty Clark play transcendent pickup basketball has always stayed with me.

Which brings us back to Tom Brady, who struggled in his first two years at Michigan before winning the starting quarterback position, and who was so unbelievably underrated coming out of college. I once traded stories in an airport lounge with a woman who went to Michigan, and who had a ro0m-mate there who dated Tom Brady when he was 7th on the depth chart. We thought it was so cute, the wannabe quarterback thing, she said. Hope he’s going to class, we always said.

With the benefit of hindsight, is it possible to second-guess with any precision why the scouts and GMs who let Brady fall so far in the 2001 draft shouldn’t have? Not really. Ask five people what makes Brady so good, and you get six answers. Context, psychology, mystery.

Tick tock

I have a pet theory, though. I think that there are many, many people with the physical tools to be a great NFL quarterback. But there are far fewer with one relatively small, very strange, mental quirk that is the difference between decent and great. NFL quarterbacks — loosely speaking — succeed when they throw the ball quickly, and fail when they don’t. Tom Brady gets rid of the ball faster than any other quarterback. His mental clock machinery is wired up to the rest of his brain better, and differently, than anyone else’s.

There’s a great, great New Yorker piece by Berkhard Bilger from 2005 titled “The Egg Men.” It’s about restaurant kitchens, and it starts out “Las Vegas is a city built by breakfast specials.” Bilger is interested in the curious and surprisingly difficult job of cooking traditional American breakfast food, in a very busy environment, in parallel, and fast, and well. He quotes, at length, a neuroscientist named Warren Meck who studies the circuitry “that allows the brain to time several events at once.”

Meck has yet to put a short-order cook in a brain scanner, as he has done with musicians, but he suspects that the results would be similar: their oscillatory neurons will have grown far more synapses than those in the average person’s brain. If they are asked to time certain events, more of their brain will light up.

Tom Brady happens to be the best short order cook in the world, but he accidentally missed his calling and instead became a quarterback.

One thing that does work — investing in junior hires

Oh, I do have one last piece of advice. If you have the bandwidth and budget, hiring very junior people is a terrific investment in the future. If you know that you have a lot of work to do across the board and you can give junior folks good stuff to learn on, and you’re willing to commit the time and energy needed to mentor junior hires and give them valuable on the job training, it’s both very rewarding and comes with a lot of upside.

Maybe the sports analogy is that you’re running your own in-house farm team system. And that can be a very good thing. Some of those junior people will turn out to be great.

And if you’re thinking about doing this, first go read Marc Hedlund’s wonderful “What do you Make as a Manager?” essay. Seeing a junior hire grow into someone you’d enjoy working for is one of the best things about doing a startup.



Kwindla Hultman Kramer
Don't Panic, Just Hire (formerly Pluot), Oblong, Media Matters for America, AllAfrica -