Although I watch a lot of instructional videos and attend group classes, the biggest gains I’ve made in technique or understanding have come from directly asking someone.

There’s an article called “Learn from People, Not Classes”:

Granted, it’s usually easier to build a learning network if you’re employed by a well-known firm, have a broad existing network, or have something in your background that will incline people to respond to your request. But it’s worth the effort, given the potential of learning via one-on-one conversation. In that setting people often offer observations they might not share in a large group, online, or in writing. And because learning via conversation is driven by your questions, the lessons are delivered at your level. It also requires that you do your homework—there’s no lurking passively in the (literal or virtual) back row.

Here’s another instance of the power of one-on-one learning. When Brian Chesky, a true infinite learner, was scaling up Airbnb, he sought advice from people such as Warren Buffett. “If you find the right source, you don’t have to read everything,” Chesky told the class we teach at Stanford. “I’ve had to learn to seek out the experts. I wanted to learn about safety, so I went to George Tenet, the ex-head of the CIA.”

Still, the world is full of experts who lack boldface names. “Talk with other entrepreneurs, not just famous entrepreneurs,” the Dropbox cofounder Drew Houston told Reid on the Masters of Scale podcast. “Look for people who are one year, two years, five years ahead of you. You [will] learn very different and important things.”

I still take private lessons, and we go over both new and old problems. But I’m also asking questions to nearly everyone I train with, because many will be good at something that I’m not good at.