Informational Interviews Work for Freelancing. Here’s How to Make Them Less Painful.

Keeping up a steady flow of these casual conversations throughout the year can help you in all sorts of ways — connecting you to interesting people, exposing you to potential new work opportunities, and helping you define the work you’re doing or want to do.

When I was in college at a D.C. university full of students who were always chasing elite internships, I often equated networking with schmoozing. It was disingenuous, it was draining, it was the embodiment of D.C.’s often-smarmy media scene.

Now I think differently. Sure, sometimes networking is awkward. But as journalists, getting to know more people is critical. It’s how you find story ideas, develop empathy for people with experiences unlike your own, and learn about new things. And, for better or worse, success in journalism is often all about who you know.

The idea of endless networking is intimidating and exhausting. But there’s a simple way to bring some structure to the effort: the informational interview. I know, the phrase might invoke unpleasant memories — of college career counselors, awkward coffee shop encounters, or the dreaded cold email — but these conversations don’t have to be painful. For me, they’ve been a source of inspiration and industry intel, and I believe they can serve the same purpose for other freelancers.

But before you can get to your interview, you’ve got to find someone to talk to. My approach varies here. Meeting with alumni of my university helped me get my first reporting job right out of college. I’ve also leaned on the networks of former colleagues and friends, direct-messaged journalists on Twitter, sent InMail with my LinkedIn Premium membership, scheduled calls with Digital Women Leaders, and written dozens of emails to people I’ve never met.

Embracing these conversations required a bit of reframing. I view them as casual catch-ups with new people, rather than a formal networking exercise. Lately, I’ve been having them to learn more about potential work opportunities in different states, and in different industries (like academic publishing).

Over the years I’ve developed strategies to make this practice manageable.

Keep conversations short

I like to keep nearly all informational interviews to 20 minutes. I learned this tip from the book The 20-Minute Networking Meeting by Nathan A. Perez and Marcia Ballinger.

Perez and Ballinger make the case that a longer meeting isn’t necessarily a better meeting. If anything, they say that the fear of a long meeting is what holds people back from either setting up or agreeing to the conversation.

Of course, a conversation may end up going a little longer — you don’t need to cut people off to race off the phone. But generally, I ask for a conversation of about 20 minutes, and block 30 on my calendar. I use the remaining time following up on leads or writing a thank-you email.

Phoebe Gavin, a career coach, recommends keeping the conversation even tighter. Ask for 15 minutes, and prepare between one and three specific questions, Gavin says.

“Let them dominate the conversation (everyone likes hearing themselves talk), but listen for an action item to enhance your follow-up. Your primary goal should be to start a relationship, not to get information. If the conversation goes well, they’ll be interested in having more,” Gavin told me in an email.

Stay consistent

As a freelancer, it’s easy to get tunnel vision — but if you’re solely focused on your next writing assignment or potential client, you’ll lose out on the chance to get to know people without an end-goal in mind.

Instead of relying on informational interviews just when you’re on the hunt for work, use them all year long. I’ve found this especially important as a freelancer. When I’m lighter on work, I schedule more of these conversations.

Keeping up a steady flow of these casual conversations throughout the year can help you in all sorts of ways — connecting you to interesting people, exposing you to potential new work opportunities, and helping you define the work you’re doing or want to do.

Follow a structure

With some practice, you’ll find the conversation format that’s right for you. Here’s my general approach:

Prepare in advance. Before you send an email asking for someone’s time, be sure to have a concrete idea of what you want to get out of the conversation.

Are you hoping to learn more about future roles on their team? Are you trying to understand what to expect from a new editor you’re working with? Setting a big-picture goal for the call and telling the person upfront can help them decide if they’d like to make time for you.

Show your work. In my messages requesting a meeting, I make clear why I am reaching out to the person. This is also a chance to show I did some research before contacting them.

“Showing that you’ve done your background research plants the idea of credibility in the other person’s mind,” John Lees, a UK.-based career strategist told the Harvard Business Review in 2018.

I then give a brief summary — a minute or two max — of my experience and what I am hoping to get out of the conversation. And, if someone else recommended the conversation, I always name them (with their permission, of course).

Write your questions down. I keep a Google Doc for each conversation (which I store in one folder on my Google Drive for easy future access). I typically prepare about five questions — even though I don’t ask that many, the research helps me feel confident going into the conversation.

My questions depend on my end goal. Lately I’ve been trying to learn more about what the journalism industry looks like in another region of the country. Some of the questions I’ve asked people with this goal in mind include: What is the atmosphere like for freelance work? What media outlets or companies are really exciting you? What do you think this space will look like a year from now?

When I was preparing to quit my full-time job, I had conversations centered on what a transition into freelance work could look like, and how to shape my schedule and offerings.

My last question is always the same — Who else should I be talking to?

Stay organized

I use a few tools to keep informational interviews from taking up too much time.

I use the scheduling platform Calendly to avoid clogging up email inboxes with scheduling attempts. (I learned about Calendly from Gabrielle Ione Hickmon, a writer, artist and strategist who spoke at a Study Hall-sponsored event last year.)

I keep my notes from calls in Google Drive, and this year I’ve started using a spreadsheet to track my conversations — including whether I’ve sent my post-conversation thank-you email. (Always send a thank you!)

Don’t be afraid

If I feel intimidated to reach out to someone, I think about the reverse scenario — I’d be flattered if someone reached out to me. It’s all about approaching people with curiosity and genuine interest in who they are and the work they’re doing.

When the conversation is framed as just a chance to get some behind-the-scenes details, it feels less awkward. And in every conversation, I’ve encountered people who are eager to help me and generous with their time and expertise.

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