Hiring Writers at Your Startup? Scrap Your Usual Approach

The best writer I ever hired at a startup wasn’t a former journalist. He wasn’t a former marketer or a former teacher or even a former liberal arts major.

The best writer I ever hired at a startup didn’t have a resume. He didn’t have a LinkedIn profile or Google+ account or even a Twitter handle.

The best writer I ever hired at a startup is trying to work at your startup all the time, but 99 out of 100 times, you pass. I should know — I almost did. And that’s why we need to collectively scrap the usual hiring process if we want to bring in great writers to run our blogs, our PR, or our content marketing in general.

Seemingly every startup today buys into the idea of content marketing (so much so that we created a blueprint for executing your strategy). Naturally, this leads to more open jobs for in-house writers at startups, instead of your more traditional media outlets, PR firms, and advertising agencies. But the usual hiring process isn’t built to source, select, and hire great writers and, in fact, it’s practically set up to eliminate them.

To understand just how strange it can be to hire a great writer compared to a more traditional marketer, let’s go back to the story of the best writer I ever hired. His name is Jeff, and it was nothing short of a miracle that I didn’t screw it up…


It took several years for him to admit this (which is odd because he admits everything bluntly enough to make Louis C.K. blush), but Jeff actively avoided sharing his resume with me during his interview process. This was back when I was director of content at Dailybreak Media, and I was hiring several creatives to build a new team that would grow our audience and work with our brand partners to launch native or sponsored content campaigns.

After he was hired, Jeff revealed that my boss at the time, our chief product officer, had actively advised Jeff against sharing his resume with me. That’s because I’d just come from a big corporation (Google) and had a “process” behind reviewing and interviewing candidates, and Jeff’s resume basically read two things: high school diploma and bartender, 10 years. My boss knew, and rightly so, that I’d have latched onto those two facts during my process and immediately tossed the resume, along with an excellent and qualified candidate. So instead, my boss shared only Jeff’s (utterly great) writing samples and suggested that I meet with him the next day when, oh by the way, he was already scheduled to come talk “career stuff” with us.

It was instantly apparent that his writing talent and personality were perfect for our team, so all that was left to do was complete my process by assigning him a relevant project as a final test. Thus, he’d managed to skip the two steps (resume screen and phone screen) that would have undoubtedly eliminated his candidacy. He went on to absolutely crush the assigned project and even submitted a second piece voluntarily, cementing him as far and away the best candidate.

His resume literally never mattered. But in most cases, it would have been the only thing that mattered — and not in a good way.

Why We All Usually Botch This Hire

As the demand for writers and content creators increases, more and more companies turn their one-size-fits-all hiring process onto the writer community for the first time. They package job descriptions that sound like any other job. They review resumes like they would for any other function. And the checks and balances designed to pull the best candidates through the pipeline ultimately fail, leading to the hiring of moderately qualified but ultimately not great candidates.

Here’s the thing: Most great writers don’t look or feel like the typical candidate. Their resumes aren’t the best representation of their skills or experiences. Their day jobs are rarely focused on showcasing their writing and creativity, as with Jeff’s 10-year stint as a bartender or another ex-Dailybreaker’s previous role stocking shelves for a retail company. In addition, a writer’s personal projects can often seem too quirky, too “artsy,” or too irrelevant to a hiring manager’s industry, despite these projects representing a huge source of personal and professional growth and skill development, thus preparing them to be better contributors for your company.

So no, great writers don’t often smell like great marketers, and unfortunately, this means most companies are easily thrown off the scent when it’s time to hire them.

(By the way, it’s important to note that by “great writers,” I don’t mean a marketer who is now required to write more in 2014 thanks to this style of marketing. I also don’t mean a copywriter more adept at slogans or banner ads. Sure, they can be good contributors, but when everyone else is hiring good contributors, give me a truly great writer — someone who’s honestly content writing just for fun, just because, whether fiction or nonfiction, book or blog. These are the kinds of writers who can cut through the insane clutter out there and be constantly and uniquely creative. When everyone else tries to make dud missiles fly by over-marketing bland, boring pieces, you want the upper hand by being great both creatively and in terms of marketing tactics. And I don’t know about you, but I can train someone in marketing much more easily than I can train someone to write well.)

Scrapping the Standard Playbook

Hiring Jeff required a warm intro and a few deft moves by my then-boss to circumnavigate my big, corporate-y process. It was a huge learning experience for me personally, and between that moment and my time vetting writers as head of content for HubSpot (I reviewed over 100 candidates in a year), there are a few changes to your hiring approach I’d recommend:

1. Write Unique Job Descriptions, Emphasizing Creativity

This can’t be overstated: DO NOT use the typical template for job descriptions. Ditch the standard “blurb + bulleted responsibilities + bulleted requirements” format.

Instead, remove all needless requirements that don’t relate to being a great writer (like BA degrees or loads of experience working in your industry, though those might be listed as “preferred”). Then, to really attract the right candidates, focus the job description on the actual process of writing and being creative rather than the marketing function and desired results.

Lest you do a spit-take on that last part about neglecting to talk about results, hear me out. This is all about understanding what motivates a great writer to actually produce results for you.

So many roles in business can be extrinsically motivated decently well. You put a carrot or a goal ahead, and that’s enough — they want to go get it. Sales is the obvious example. They want to hit numbers and perform a task not necessarily because they adore performing the task but because there’s a payout somewhere down the road that gets them excited.

Writers, however, must be intrinsically motivated, just like any production-oriented job role (design, video, etc.). Anyone who loves to write and create in general will tell you that they do so just … because. I write a personal blog not because I want a massive email list but because I like to write and need a place to put it. I design stupid cartoons not to sell them or grow Twitter followers but because I like the act of sketching. Creatives are found creating all the time and just because they enjoy it. How often do you find marketers voluntarily marketing other businesses at night or salespeople picking up a random object in their homes and trying to sell it on the street for fun?

(Note: I’d argue anyone is better off when they’re intrinsically motivated regardless of job function, but my point is that writers are rarely if ever motivated by hitting an end result. They admire and want to experience and improve their craft. This can be harnessed for your benefit at a startup, but you need to broadcast the job appropriately to find the right candidates.)

So instead of writing “publish X pieces per week to grow audience” in your job description, you could say “brainstorm weekly pieces and maintain a daily editorial calendar.” Instead of “develop buyer personas to focus our content strategy” you should say “research and understand our readers and be their internal champion.” Instead of “repackage long form pieces into smaller projects to be distributed around the web,” you should say “find creative ways to produce related pieces across many mediums and channels.”

These subtle differences focus on the process itself, rather than the end result. Though it’s counterintuitive for many in business to think this way, I promise you that one begets the other — better content builds bigger audiences and drives more results.

2. Review the Right Things About Your Candidates

The first thing you look at shouldn’t be the resume.

Their portfolio trumps their past jobs, and it’s not even close. Who cares if they’re currently working at Costco? What does that say about their writing? Nothing at all. The first thing you start with needs to be their writing samples, plain and simple.

And by the way, if they’ve written about your industry in the past, that’s a huge bonus. But it’s still just a bonus, not a requirement. Great writers understand how to research well enough to learn various subjects, and interviewing experts always makes for a great approach regardless of a writer’s knowledge.

If you’re skeptical about that point, just think about the world of journalism and how many different topics exist to be covered, from sports to tech startups to international politics to the education system and much, much more. Media outlets constantly hire writers who are great at the nuts and bolts of writing, interviewing, and so on, and they then learn to become subject matter experts. To hire candidates who are experts, great writers, and seeking employment at the right time is to hire a bunch of unicorns.

The second thing you look at shouldn’t be the resume.

The second thing should be their online presence. Google them! See what side projects they’ve done, or read their tweets or blog posts. This is all evidence of their skill set. Reading a blog post about sales written by a sales rep isn’t proof that he or she can actually sell. But a blog post written by someone who claims to be a writer? Those are actual examples of their work.

As for side projects, don’t be scared off by wildly quirky and irrelevant pieces. Making is a muscle, and fun or random side projects help creatives get stronger. (Think of it this way: A basketball coach who wants a shooter understands that, even though the motion of a pushup looks nothing like a jumpshot, the former leads to a better, stronger version of the latter.)

The third thing you look at shouldn’t be the resume.

Nope, no resume yet! The third step is to look at their cover letter. Always keep in mind that a cover letter is a work sample when it comes to hiring writers.

The only reason I listed this third and not second is that most of us are improperly educated by career centers and online templates/resources for cover letters. It’s unfortunate and sad. They always propose those outdated, formulaic, block-text approaches to cover letters, where being “unique” means changing “I’m interested in your job” to “I’m very interested.”

Top-notch writers can and should use their cover letter to stand out, but it’s still rare. Out of the 100+ I reviewed with HubSpot, only two stood out: a video someone created as a substitute for a text email, and an impassioned note about the state of our industry which started, “I’m afraid.” Wow! Two simple words that stood way out compared to a sea of “Dear Hiring Manager.” That great cover belonged to Erik Devaney, who still works at HubSpot today.

3. Assign Projects — And Do So As Early As You Can

If I didn’t think that most candidates want to talk to a company and gauge interest before creating an original piece for them, I’d ditch the phone and in-person screens entirely and just ask people to submit a project. (I might actually try this someday just to find out if it works.)

But if and when you like a candidate, assign them a relevant project. Give them a loose framework and loose instructions, as well as a deadline that feels a little aggressive to see how they perform under pressure.

For example, give them a couple working headlines for blog posts and ask them to choose one and write a draft by the next day. Or give them a half-baked draft of something you’re already creating and ask for rigorous edits, both for copy and concept. You can also use editing as a way to further test candidates who are too close to call — if two writers absolutely nail their assignments and you’re stuck, ask for them to self-edit and explain everything in detail.

Make sure the assignment is something you’d actually use day to day too. It’s like putting them on the job before you actually make a decision, just to test the waters — a luxury available when hiring writers and other production-oriented jobs. (It’s much tougher to put a marketer or sales rep to work before hiring them, for example.)

Of course, the resulting idea and written piece is the writer’s property. After all, even with the same headline assigned, no two writers will produce the exact same paragraphs. As such, I don’t believe their assignments are yours, so if I ever published a candidate’s piece, I’d pay them regardless of whether they got hired. I’d highly suggest doing the same — it’s just the right thing to do.

Just to Recap

  1. Ditch the standard playbook and mentality. Great writers don’t often smell like great candidates for other roles.
  2. Write a great job description by appealing to creativity, rather than marketing tactics and business results.
  3. Spend your time looking at the RIGHT things submitted by the writer. Resumes and past job functions often fall way down the list compared to other roles.
  4. Assign relevant project work under a strict deadline.

Fast-forward from our time together at Dailybreak, and Jeff now finds himself with an amazing job as the first content manager at another startup with tens of millions in revenue, where he’s responsible for their entire content strategy (congrats, Jeff!). It feels like a lifetime ago that he was a bartender that I almost made the huge mistake of not hiring.

Today, if you ran his resume through the standard hiring process, Jeff would come out the other side looking like a great candidate. But to get there, he was initially an exception to the “usual” rules.

Here’s hoping you make room for yours.