a cheat code for learning faster

When I got to Ohio State as an undergrad, I didn’t know what I wanted to do. I joined the undecided program (which is so aptly called “Exploration” at Ohio State) and started taking my Gen Eds.

Years later, I spoke at events to prospective students on behalf of the Exploration program. My message was this: Exploration is not a magic bean. It buys you time, but it does not give you answers – you have to try things out.

For me, that meant finding a way I could apply my interest in writing. So my freshman year, I started hanging out in the Newsroom for the student newspaper, The Lantern.

Given that I was there all the time, it wasn’t long until I started getting noticed and asked to take on stories that we were getting tipped.

This led to some cool coverage, including tracking down Terrelle Pryor’s lawyer during Tattoo-gate, and the fallout following the death of Bin Laden.

After cutting my teeth on these stories, I was given the opportunity to cover the Ohio State football team as an underclassman during the fall quarter of my sophomore year.

That quarter was a revelation for me.

Every Tuesday, reporters were permitted to attend a media lunch. We were fed an amazing spread at the Fawcett Center and given access to players and coaches at a short press conference prior to that week’s matchup.

As a reporter, we were expected to then write a unique piece to run in the following Wednesday edition in anticipation of the game.

The man who really stood out in this room was Tim May. Tim has been a sports reporter for the Columbus Dispatch since 1976. And the thing about Tim was that he snuck in the first question to a player or coach every single time.

These rooms aren’t really a meritocracy and there isn’t a true pecking order. The way questions are often fielded are by order that they are first heard, and they must be heard clearly. You’ve probably seen the videos of reporter’s swarming someone with microphones and yelling for attention.

Essentially, Tim’s timing and vocal authority was incredible.

The implications of not being the first to ask a question meant you were trying to be the second. Or the third. Or the fourth.

As a reporter, you form a concept of a story in your mind so that you can ask questions that add to the narrative of that story. But that means getting your questions out, heard, and answered.

Furthermore, you wanted your story to be unique. If someone else asks a similar question and is taking your angle, you may pivot your direction.

That quarter, I learned two incredible lessons:

  1. The people I saw on TV were just people, and could be talked to as people
  2. One of the most valuable skills I could gain was the ability to ask good questions.

In recent years, I’ve had people tell me that I “just ask great questions.” As a product manager, this lets me ask non-leading questions to potential users. It also helps me form relationships faster.

By asking thoughtful, unique, and open-ended questions (i.e. not “yes” or “no” questions) you really can learn a lot very quickly from someone who knows the information. Recently, I spent an hour on the phone speaking to a friend about his process for buying and selling on Amazon. After that hour-long discussion, I felt completely equipped to begin importing and exporting on my own.

And like many other things, this skill has a compounding effect. The more questions you ask with intention, the better you get at forming your questions.

Why is the Tim Ferriss podcast popular? Yes, he has access to amazing people to interview, but more so, he asks questions that get interesting and insightful responses from those subjects.

To really learn quickly, find someone who already knows the subject and ask them thoughtful, open-ended questions.


Want to get better at asking questions? Listen to interviews. Some of my favorites are You Made It Weird (podcast), WTF (podcast), the Tim Ferriss Show (podcast), and Howard Stern (YouTube).


Hey, can I have your email address? I will only send you more articles like this one.