Those Who Teach, Can Do

In Silicon Valley, intelligence is both abundant and coveted. Because of this fact, Silicon Valley job interview questions have gotten tougher — and weirder — as interviewers devise queries designed to identify the best of the brightest. Consider, these brainteasers that various companies have asked job candidates in recent years:

• How many golf balls can you fit in a school bus?
• If you had to paint all the buildings in New York, how much paint would it take?
• How do you weigh an elephant without using a weigh machine?
• How could you solve humankind’s biggest crisis given $1 billion and a spacecraft?

If you can quickly come up with plausible good answers to these — especially the last one — then I predict you will have a set of very successful interviews!

Compared to the questions above, the interview question I pose most often to entrepreneurs and job candidates is fairly straightforward — but also more reliably revealing:

• Thinking back to a significant project you worked on in the past, what’s the most important thing you’d tell your then-self to do differently?

In asking this question, I’m hoping to find out a number of things about a person. What do they see as the most relevant variables in a given job objective? How do they characterize risk and opportunity? How do they measure improvement?

In other words, I’m not just looking for insights into what they learned. I’m interested in understanding how they learn. How do they conceptualize their takeaways from the experience? How do they communicate them to others? Are they what I call an “explicit learner”?

Along with sheer intelligence, grit and creativity are other key characteristics employers and recruiters seek out in Silicon Valley. These are highly valuable traits to have. But what I’ve found in my experience is that truly breakout performers also tend to place an unusually high emphasis on improving their capabilities and performance over time. They’re infinitely curious individuals who always want to read one more book on a subject, conduct one more experiment or test, and ask one more question. Coupled with this facet of their personality, they also have an extremely well-developed ability to share the knowledge they acquire with others. They’re explicit learners.

Our capacity to learn is a foundational characteristic of humanity. Other species possess this capacity to some extent as well — but there’s no such thing as dolphin kindergarten. Humans are such devoted learners we organize the first 18 years of our lives around immersive obligatory learning in many countries. And many people make systematic learning — aka formal education — their primary pursuit for even longer than that.

But formal education is just one kind of human learning, and not always the most important one. When I think of learning, I think of it as the acquisition of skills or knowledge with a deliberate orientation toward improvement. It starts with experience or study, but also demands reflection, subsequent action, and assessment. The goal is not just to know more things, or enjoy a variety of different pastimes. The goal is to systematically prepare yourself for future opportunities; to increase your ability to successfully adapt to both anticipated and unforeseen challenges; to better understand when to make decisions and what variables you should consider before making them.

Obviously, people learn in many different ways. You can learn formally or informally. In groups or alone. Intentionally or intuitively. In work settings, I’m most apt to look for people who incorporate learning into their lives in a 

 deliberate, persistent, and explicit way simply because I believe that individuals who’ve developed habits that make learning central to how they interact with the world are more likely to learn more than those who don’t embrace learning so intentionally.

Airbnb’s co-founder and CEO Brian Chesky is a good example of this kind of explicit learner. I remember the first time we did a radio appearance together, he immediately turned to me after we had finished and said, “What could I have done better?”

Any time I ask Brian similar question about some aspect of his career or past performance, he always has a well-considered answer to share — because thinking about the world in this way is a habit to him.

Like all explicit learners, Brian understands that while consciously asking questions and gathering data is one aspect of explicit learning, another key part of it involves reflecting on whatever information and feedback you’ve collected, and then synthesizing it into some illuminating way.

And this is ultimately what I’m looking for when I ask people what they’d tell their former selves to do differently if they had a chance to re-do some past project. Can they present their learning as a compelling story or anecdote, or a memorable aphorism?

The process of doing so is useful for two reasons. First, it turns a private observation or revelation into a shareable asset, which has obvious value in a business setting. The more explicit learners you have on your team, the more you all learn from each other; the value of each individual insight compounds across the organization. Second, the attempt to express what may be a vague or somewhat intuitive notion or revelation into a more explicit aphorism or principle encourages you to think more analytically and discerningly about what you’ve learned. What are the most crucial aspects of the insight? Are there ways to broaden it?

For example, many years ago I invested in a company started by someone I knew in a social context. Let’s call him Bob. While the investment was significant enough that I would have done a reference if the entrepreneur had been someone I was unfamiliar with, I didn’t with Bob — because I assumed I knew him given our interactions in a social context.

But it turns out I knew Bob less well than I thought I did. In reality, he had substance abuse issues and often went completely AWOL for days at a time. This is not a quality you want in a CEO, and especially not in the CEO of a newly launched start-up that needs a steady and vigilant hand steering the ship.

As you might expect, my instinctive takeaway in the wake of this experience was an obvious one: “Don’t do any more business with Bob!”

But that’s not actually a very useful learning because it’s only narrowly applicable. And in thinking about it some more, and trying to formulate a better learning, I arrived at a more broadly useful conclusion. Namely: “Knowing a person in one context doesn’t mean you know them in every context. So if a project or investment would typically require a reference check, and you don’t actually know the person in the relevant context, do a reference check!”

In this way, I learned more than just how to deal with Bob in the future. I learned how to avoid going into business with other potential Bobs.

Inevitably, the reflection and assessment that occurs as you think about how best to express or concretize an insight increases your understanding of it: It’s the old saw about not truly understanding something yourself until you can successfully explain it to someone else.

This, I believe, is why Mark Zuckerberg doesn’t just choose a new learning goal each year, but also publicly shares his efforts to do so and reports on how it turned out. It’s why Bill Gates doesn’t just voraciously read books, but also regularly publishes reviews of them. Through this process, the student becomes the master.

Or to put it in another way, in a contrarian twist on George Bernard Shaw’s well-known aphorism, “Those who teach, can do.”

Which, you may have noticed, is the title of this essay. Or at least it is now.

When I started writing this essay, I called it “My Favorite Interview Question.” But when, in the process of wrapping things up, I decided to challenge Shaw’s famous quote, I also realized I’d learned a punchier way to title it.

And because this is essay-writing, I actually could go back in time, in a manner of speaking, and tell my first-draft self what to do differently!