Interviewing experts to learn

I recently appeared at Rich Armstrong’s Twitter Spaces, and the topic of meeting other people (“networking”) came up (1:06:35). It reminded me of a draft for career advice that I pitched Forge (it was just sitting around, and this was an opening to unstick it). 

When I was a junior in college, I was at a loss for how I was going to get a job. I’d failed to get into the business school of my choice, and I was experiencing confusion about how I was going to get my first job. 

I got busy, picked up some freelance writing jobs, and came across an opportunity to write for a national technology publication called Techvibes. Through this, I started getting invited to conferences. Conference organizers would also offer to set me up with entrepreneurs and business leaders for interviews, in the hopes that I’d publish their words. 

That was a “Eureka!” moment for me. 

Ordinarily, I wouldn’t have been able to connect with these leaders. I didn’t have much to brag about, I wasn’t perceived as someone special for them to have my eye on or a desire to recruit. But, with Techvibes, I was able to offer them some value: brand association, a channel for them to discuss their industry, and an opportunity to share an article to their social networks.

I used this to proactively reach out to business leaders I wanted to learn from. For example, I emailed Gary Vaynerchuk and had a conversation

I still interview people I want to learn from. (Here’s a recent one with Marshall Goldsmith.) The immediate main benefit is in meeting new people that I wouldn’t have met otherwise, and finding a way to add value to their work. I also have an excuse to ask them a lot of questions and learn what I want to learn. And I’ve learned a lot. It’s way more effective than talking to people at networking events, or even writing a blog post on your own, because you get to learn with someone else—there are two brains working together. 

This is why authors like Tyler Cowen still do Conversations with Tyler, and why Mark Zuckerberg does his own podcast. Ryan Holiday met one of his initial mentors Tucker Max through a book review, ran an interview series at the New York Observer, and still runs one at The Daily Stoic. Maurice Brown talks to Black designers at Revision Path. My old boss Tommy Walker talks to content marketing experts at The Cutting Room. Debbie Millman talks to designers at Design Matters. My former colleague Zeno Rocha talks to developers at ByteTalk. (These are just the ones off the top of my head!)

While I borrowed Techvibes’s credibility, I could have just as easily started my own podcast or blog and used that as an occasion to reach these leaders. You don’t need to be prominent or influential to start interviewing people. 

Here’s how you can talk to busy people in any industry, from any place:

  • Figure out what you want to explore and learn. For example, if you’ve signed up for a class on origami, maybe you want to learn how origami entrepreneurs work, or how artisans fold.
  • Set up a blog. (Medium is a great place to start.)
  • Set up a podcasting tool to record interviews reliably (I like Zencastr). 
  • Find 5 people you want to talk to. Ideally, you can either ask for an intro, or talk to someone you already know who does this. (For example, when I started my series on editing business blogs, my first email was to my friend Sean.) You might need to cold email people (see template below!).
  • Figure out the interview subject’s email address with Norbert. Write a short email introducing yourself, what you’re working on, why you wanted to talk to them. 
  • Figure out what you specifically want to learn from them! Do your research, and elaborate on questions/answers you’ve already seen. Try not to ask them stuff they’ve already answered.
  • If you hear back, set up a time to do it. Let them know you’ll be recording the interview for transcription.
  • During the session, before you start recording the interview, introduce yourself and the series again. Start asking questions, and focus on listening and following up to explore questions further. Don’t worry too much about taking notes, because you’re recording.
  • After the conversation’s done, get ready to publish it as a Q&A at Medium, or as a recording at a podcast.
  • That’s it — rinse and repeat!

Here’s a simple, rough, version of a template:

Hi [person’s name—this could be the interview subject, or their publicist],

My name is [name] and I’m a contributor for [publication name], [describe the publication’s mission and/or target audience in a sentence]. [Write a sentence or two on your familiarity with the subject’s work, and what particularly resonates with you.] It’d be great to interview you [or subject’s name if addressing their publicist] for a piece [list the topics you’d want to discuss].

Would you [or subject’s name if addressing their publicist] have 30 minutes to conduct this interview this week or the next?

Thanks for your consideration!


[Your name]

Eventually, as you start doing more interviews, you can link to them to demonstrate what the final piece might look like and present an idea of who else has participated.

If you’re really in the season for meeting new people, I highly recommend this. It can take a lot of time, so you’ll want to make a few hours per week to research and produce. Still, worth every minute! 

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