How to Level Up Your (Interview) Pitches: A Breakdown

What is essential in a strong pitch, how to prep for emailing strangers and how to advance yourself even when pitches don’t go

Writer Roadmaps: “How To” Guides For Launching A Writing Career (Part 7 of 8) 

NAVIGATION UPDATE: Both this and the next lesson are strictly how-to focused, so we’ll be making a style pivot. Alexandra will provide you with the core principles and Steve will provide his thoughts in italics. Together they’ll leave ya pitch perfect.

By now it should be clear that while we’re working on craft, we’re also working on community, career, and cash flow. And a literary life involves constantly pitching ourselves and our work, whether we’re querying agents, applying for fellowships, or drumming up attention for our forthcoming books with juicy essays in The Cut or whatever.

Is it annoying to have to do this? Maybe! But this is the life we chose. So why not get comfortable with all that pitching and self-presentation?

(And don’t forget: paid subscribers will be invited to pitch us their own Roadmap interview ideas at the end of this course. If we like what we hear, you’ll get $100 to make it happen. For an audience of over 30,000 writers.)

To help us get started, let’s hear about pitching interviews from Guggenheim and MacDowell Fellow and gold star human Alexandra Kleeman.

Photo by Fred Tangerman at Djerassi

Alexandra Kleeman is the author of the novel Something New Under the Sun, Intimations, a short story collection, and the novel You Too Can Have A Body Like Mine, which was awarded the 2016 Bard Fiction Prize and was a New York Times Editor’s Choice. In 2020, she was awarded the Rome Prize and the Berlin Prize, and was awarded a Guggenheim Fellowship in Fiction in 2022. She is an Associate Professor at Cornell University and a Contributing Writer at the New York Times Magazine. Something New Under the Sun was named one of the New York Times’ Notable Books of 2021.

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Yes, she’s the author of a story collection and two novels but her reporting, book reviews, and essays and criticism also appear in the glossiest mags, and have you seen these profiles in New York Times Magazine? Singer-songwriter Angel Olsen, writer Yiyun Li, filmmaker Yorgos Lanthimos, and actors Rachel Weisz and Michelle Yeoh. Oh my!

Needless to say, Alexandra knows what she’s talking about.

We’ll touch on:

• Why pitching can feel like leaving home

• How to pitch toward your own growth

• How to prep for emailing strangers

• What is essential in a strong pitch

• How to advance yourself even when pitches don’t go

Pitching an interview, article, or book review involves a different set of writerly muscles than your core writing practice. It can sometimes feel overwhelming, strange, or alienating for that reason: the intimate and esoteric landscape of your interior writing life can be a place of comfort or at least familiarity, and when you're asked to leave it and begin interacting with a broader industry—publishing, media, publicity—things can feel very strange indeed. Here are some tips that have been helpful for me as I've navigated this more outward-facing part of a writer's life: