Sam Seely

Two quotes and the product paradox

“The fox knows many things, but the hedgehog knows one big thing.” — Archilochus

“The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” — F. Scott Fitzgerald

The life of a product manager is one of pattern recognition. You look at problems and try to remember whether you’ve seen them before.

I like quotes as a pattern recognition tool. They’re pithy and memorable, and yet, despite their simplicity, they can provide a lens into deeper, more complex ideas and problems.

Take the two quotes above. They stand strong enough on their own—the first a classifier for idealists and pragmatists, the second a reminder on the role of contradiction and self-doubt in great thinking—but when taken together, these two quotes provide an important lesson to the aspiring product manager, a pattern to recognize.

This lesson is simple. To be a great product manager, you must be both the hedgehog and the fox.

Foxes and hedgehogs

Let’s start with the first quote. “The fox knows many things, but the hedgehog knows one big thing.” I found this a few years ago in Isaiah Berlin’s essay The Hedgehog and the Fox.

In the essay, Berlin classifies the great writers of literature into two categories. On one hand are the hedgehogs, those minds who know one big thing, who forge their worldview with monastic belief into a single, fervent truth. Dante, Proust, Dostoyevsky: these are the cheery titans of camp hedgehog. In the other corner are the foxes. They fashion their pen not around a philosophy, but around the world itself. They write of the reality around them in all of its details and complexities, but without the unifying principle that embodies the work of a hedgehog. Shakespeare, Chekhov, Austen. All foxes.

In his book On Grand Strategy, John Lewis Gaddis’s takes Berlin’s idea out of the world of literature and into the world of war and diplomacy. Here, the hedgehogs represent those leaders with an ultimate purpose or mission, the foxes those leaders with a more tactical, pragmatic bent.

The book looks at these hedgehogs and foxes of history and asks, which is it better to be?

Gaddis starts with the hedgehogs. History is littered with stories of “too much hedgehog, not enough fox.” Napoleon is a good example. Hot off a winning streak through continental Europe, Napoleon set his sights on a trip into Russia. A true hedgehog, he was completely indebted to his vision. He dreamed of a French flag soaring over Moscow. He did not, regrettably, dream of Russian winters or of overextended supply chains. The result speaks for itself: one of the great military fiascos of history. Napoleon marched into Russia with 685,000 men. He marched out with 22,000.

Napoleon's march

Menard’s map of the French invasion. The brown line marks Napoleon’s path to Moscow. The black line marks his retreat. The line’s width marks the army’s size.

The foxes, too, have their faults. Where hedgehogs (such as Napoleon) err in overcommitting themselves, foxes err in not committing themselves enough. Take General George McClellan, the fastidious Union general who, after weeks of careful planning, preparation, and fortification, always found a reason to call off his latest impending engagement with the Confederate army. These delays, always carefully justified in tidy correspondence, enabled the escape of the Confederate army on multiple occasions, leading to the extension of the Civil War and a massive loss of American life.

It’s here, with the faults of hedgehogs and foxes strewn across history, that Gaddis asks, if a leader can’t find success as a hedgehog or a fox, where can good leadership be found?

His answer: in the middle. To be both hedgehog and fox. To lead others towards a vision with drive and purpose, while spotting the logistical potholes that pock the road leading towards it.

No leader better exemplifies this balance than Abraham Lincoln. Throughout the Civil War, he had but one goal: the preservation of the Union. Everything he did, he did with that goal in mind. Despite his steadfast commitment to that end, Lincoln realized better than anyone the immediate concessions that were needed to ensure the Union’s survival. This meant stomaching his own support of the Fugitive Slave Act in his inaugural (a hugely unpopular decision in the North that allowed Lincoln to keep crucial border-state allies) so that two years later he could be in a position to announce the Emancipation Proclamation. He made short-term concessions in support of a long-term vision.

It’s in this contrast—the short-term and the long-term, the fox and the hedgehog—that we can see what made Lincoln such a great leader: his ability to hold two ideas in opposition.

Ideas in opposition

This brings us to the second quote at the top of this post, Fitzgerald’s famous aphorism: “The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”

I love this quote. On the surface, it’s so academic, so perfunctory. If you only ever read the quote, it would stay that way forever. But when you read the larger piece it comes from—Fitzgerald’s 1936 essay The Crack-Up—you realize that those words, with their definition of a “first-rate intelligence”, are not coming from a man who has retained the ability to function. Fitzgerald is writing in the waning years of his life. In a few years he’ll be dead at the age of forty four. In this quote, he’s lamenting something he’s lost: the ability to hold two ideas in opposition. For Fitzgerald these ideas were (i) the supreme confidence that he could produce something great and (ii) the complete self-doubt that actually drove him to that greatness. It was faith in the long-term coupled with an almost maniacal attention to detail in the short-term. It was the hedgehog and the fox.

For Fitzgerald, it was a paradox he could only hold on to for so long. He wrote his great novel and then fell into relative obscurity.

I drift into the backstory of The Crack-Up not to mourn Fitzgerald, but to underline that being both fox and hedgehog is hard. To drive towards a vision while embracing the complexities that keep you from achieving it; it’s an ability beyond most of the great figures of history.

The paradox of product

What these quotes are really about is our ability to deal with paradox. To me, there’s no place where that’s more true than the seat of a product leader or founder. A product leader is responsible for contributing to the strategy and vision of the product they help to build. To make that vision a compelling one—not just as something users want to use, but as something that team members wants to build. The only way to do that is by believing, with every ounce of one’s being, that the vision they promote is the right one.

But if the lessons of history tell us anything, it’s that we can’t just set a blind course and expect to find success. Like Napoleon, we, too, might find ourselves walking back the way we came with half the team that started with us. Instead, we have to constantly test that vision and strategy. We have to constantly poke and prod to see whether it’s still relevant, to see whether the landscape has shifted around us. Even when we do arrive at a sound conclusion, we need to doubt whether we’re executing well enough against it, whether the team we’re a part of has the discipline to stay focused against that plan.

So where does that leave us? As product managers, we need to be both believer and doubter. To continue driving forward while always checking to make sure we’re moving in the right direction. This comes forward in a few ways when you’re in product.

The first is in vision and strategy. In tech, where “the platform [sic] for all of your x needs” value props abound, any vision needs to be looked at from an objective distance. Do we want to be the platform of x because we can offer differentiated, defensible value in all of the specific functions that roll up into x; or are we oversimplifying the complexity of our market in pursuit of the grandest vision imaginable? To choose the latter is to look back at three years of product decisions and see a litany of unfocused, unforced errors. It’s the path of too much hedgehog, not enough fox.

On the other end of that spectrum are the aptly named “feature factories” of the product world. The feature factory looks at the immediate short-term wins and tacks them into the product one after another, not stopping to think of the single cohesive vision that those features should work towards. These small fixes make pockets of customers happy, but they rarely build the sort of long-term sustainable value that comes from a continued focus on a single goal or strategy. Herein lies the path of too much fox, not enough hedgehog.

So how do we stay both fox and hedgehog when we work in product?

One way is to look to the other product leaders who have done it. I’ve pointed to Stewart Butterfield’s We Don’t Build Saddles Here on this blog before, but I’ll bring it up again as a careful balance between end vision and the short-term details that get you there. The essay is a bugle blast for Slack employees to rally behind the company’s mission, but its final call to action is actually one about doing all the little things right. That’s not the easiest message to communicate in an inspiring way, but whenever I come back to this essay, it still gets me just as excited to go out and build something great as the first time I read it.

The other way to maintain this balance between the short and long-term is to recognize when you’re drifting too far in either direction. It’s in those moments that you have to remember to constantly redirect yourself back towards the middle, back to an uncomfortable position of paradox. The two quotes above have helped me to strive towards that position, and I hope they can do the same for you.