“Don’t boil the ocean,” Terry said as he slapped a tall stack of
papers on my desk. “Just tell us what we need to know.”
I was staring at a serious problem. To help our firm win a multimillion-dollar consulting contract, I had five days to tell my new boss everything there was to know about airline bankruptcies. Problem was, I didn’t know the first thing about airline bankruptcies.
I barely knew the first thing about anything. It was my first month of my first job out of college, and I had no idea how I — a 23-year-old with zero existing insights on the industry — was going to tell a senior partner anything that wasn’t going to get me fired.
“Feel free to use the Internet,” Terry said as he shut the door to my office. I didn’t know whether to laugh or cry.
No one warns us that adulthood is full of such sweat-inducing dilemmas, where the stakes are your reputation, your career, and (rightly or wrongly) even your sense of self-worth. When you’re in over your head, how do you quickly figure out what’s important? Is there a way to go from incompetent to in control — really, really fast?
As I’ve since discovered, there is. Here’s how it works.
Ted Greenwald knows all about deadlines. As a news editor at the Wall Street Journal with almost 35 years of experience in journalism, Greenwald’s job depends on delivering stories on time and on point.
Greenwald recalls having to get up to speed for a story on network security, a particularly gnarly topic for an outsider. “I really could not make sense of the article,” Greenwald tells me. To make things worse, Greenwald confesses he is “a very slow reader” who doesn’t have time to consume huge piles of research or take multiple passes through material. To survive in the newsroom, he developed two routines.
First, Greenwald says he always “Googles once.” Whenever he starts working on a new story, “instead of reading anything, I do some searches. I just open up a bunch of tabs that look promising; I might very quickly have 20 tabs open.” This doesn’t strike you as all that revolutionary; you probably do the same thing when you’re trying to understand something unfamiliar to you. But you probably also find yourself falling down an infinite digital rabbit hole, right? The key, according to Greenwald, is to build a quick overview of what other people have said — and then stop Googling.
To prevent getting sucked into a time-wasting vortex of endless searching, Greenwald says it’s important to move on after the initial search. You’ve got to do it in one sitting. “Whatever I get there, that’s it — I’m done at that point,” he says. “It’s a limited view, but it skims the cream.”
And the best cream, according to Greenwald, is something you wouldn’t expect a business journalist to search for: pictures. Particularly when the information he’d like to understand involves data, Greenwald suggests looking for images, which convey dense information better than text or raw numbers. “I just imagine what graph I would like to see and type in some words that describe that in Google Images. You may not get the graph you want, but you’ll get something that’s related to it.”
But sometimes, Greenwald admits, image searches come up empty. Even then, he still has to put the pieces of the story together on his own. And that’s when he goes to the drawing board — literally.
“If I’m trying to understand a process, often I will sketch it out as a diagram. It helps me understand the gaps in my knowledge.” Just by using a pen and paper, Greenwald can get to the root of the problem, which is how his story on network security came together. “I probably went through 20 pieces of paper,” Greenwald says, but in the end he finally grasped the complex topic and was ready to write.
Jules Maltz gives away hundreds of millions of dollars for a living. The 36-year-old partner at Institutional Venture Partners has helped make bets on some of the hottest tech companies of the past decade, including Twitter, Snapchat, Slack, and Dropbox.
But writing big checks isn’t as easy as it sounds. If he takes too long, a hot startup will find other investors. If he rushes in, he risks getting caught in a bad deal. “I see all sorts of companies in different industries,” Maltz tells me. “If I don’t make the right call quickly, I risk missing out on the next big deal.”
When the pressure is on, how does he decide which companies to back and which to let go? Maltz’s secret isn’t just talking to smart people. It’s “talking to the right smart people.”
When Maltz led his firm’s investment in Oportun, a financial services company primarily serving Hispanic communities, he had to figure out what mattered most in retail banking — not his professional forte. “I picked up the phone,” Maltz says. “We talk to 10 to 20 people before we make any investment.
That’s more than just a venture capitalist doing his due diligence — it’s a way of efficiently circumventing a lot of bad (or just superficial) information and getting straight to the heart of the matter. Maltz believes there’s never a shortage of Googleable experts and industry analysts willing to share their knowledge. Once you find a few, Maltz recommends “letting people ramble a bit” before asking the most important question of all: “The best thing you can ask is, ‘What questions should I be asking?’”
When Maltz posed that question about Oportun, he learned that, above all else, success in retail banking hinged largely on customer enthusiasm. And, as smart as the industry analysts might be, there was no way they could tell him how much Oportun’s customers loved the bank; it was time for Maltz to get outside his office and inside customers’ heads.
“I had to learn about a customer who wasn’t me,” the red-headed, Jewish, native Oregonian told me. Maltz stalked retail locations to find customers willing to talk about their experience. Call it old-school market research if you like, but it was also the most efficient and reliable way for Maltz to brush up. Only by collecting insights straight from customers’ mouths could he understand if the bank was a company people would stick with over the long term.
Guided by questions from industry experts, the insights Maltz collected helped him make the case for a $47 million investment. However, without the firsthand information Maltz heard from Oportun’s customers, the deal would never have happened.
As Maltz sees it, a hotline to experts is one shortcut to getting up to speed. But there are key insights experts can’t reveal. The most valuable insights often come from people who are are closest to a product, policy, or service but outside your sphere.
“Many people only look at a problem from their point of view — that’s a terrible way to do things,” Maltz says. Knowledge often comes not only from asking the right questions, but meeting with the right people.
If anyone knows how to digest new information quickly, it’s author Shane Parrish. His blog has over 80,000 subscribers hungry for his weekly insights on a wide range of topics, from business tips to creativity advice.
“When I used to learn new subjects, I would explain them with complicated vocabulary and jargon,” Parrish wrote in a post. “The problem with this approach is that I was fooling myself. I didn’t know that I didn’t understand.”
Sometimes insider terminology can make a project appear more intimidating than it is. Unfamiliar words, acronyms, and shorthand can seem like gibberish to someone just getting started. But not knowing jargon can be an advantage.
The famed Nobel Prize-winning physicist Richard Feynman (whom Parrish has written about) believed in two kinds of knowledge: the shallow kind, which only reveals the names of things, and real knowledge, which comes from truly understanding how they work.
Your more experienced colleagues might be able to spout familiar terms, but that doesn’t mean they know what they’re talking about. As Feynman once wrote, “If you ask a child what makes [a] toy dog move . . . the answer is that you wound up the spring.” But “spring” is just the word used to describe what’s visible outside the toy. What happens inside is the object of real knowledge. “Take apart the toy; see how it works. See the cleverness of the gears; see the ratchets. Learn something about the toy, the way the toy is put together, the ingenuity of people devising the ratchets and other things.”
In my case, the “ratchets and gears” were the mechanisms of airline finances and bankruptcies, and to take them apart and put them back together again, I did what Parrish recommends:
“Write out everything you know about the subject as if you were teaching it to someone else. Not your smart friend but rather a toddler. This may sound silly, but this part is incredibly important and has worked wonders for me learning new things.”
If you try this and find your explanation depends on a convoluted vocabulary, you likely don’t understand the subject well enough and it’s time to go back and simplify.
Today, I’m an author, speaker, and consultant, and I use these techniques to brush up on practically any topic while I’m under the gun. At my first professional job, with a multimillion-dollar deal at stake, I couldn’t fake it — I had to get up to speed. I started by getting a lay of the land on what’s already known. Next, I synthesized what I’d learned with a few rough sketches and then got on the phone with industry experts who could help me spot the gaps. Finally, I broke down the problem and practiced explaining what I’d learned in simple language that anyone could follow.
I hustled, but five days proved plenty of time, even for a 23-year-old starting from zero.