I’ve hired dozens of freelance writers through working at CXL and now HubSpot and with my content agency. I’ve also done some freelance writing myself.

If you don’t know what you’re doing, hiring freelancers can be frustrating, sometimes downright catastrophic. Here are the lessons I’ve learned through the years:

  • If possible, work first with your personal network
  • Next, look for referrals in your network
  • After that, try to poach good freelancers from other sites you admire
  • On job ads, filter candidates with a Brown M&M’s clause
  • Filter further by being very obvious that this isn’t a bullshit gig and bad work won’t be accepted (show high standards)
  • Create an entertaining and super comprehensive editorial guide
  • When you find a writer you like, keep them around and pay them more than they ask
  • Build a system that works for you and the writers
  • Be fast (don’t be the bottleneck)
  • In most situations, choose domain expertise over beautiful writing

I’ll walk through each point below.

If possible, work first with your personal network

This is true in any case of hiring, but if you know writers, and you know they’re good, try to work with them.

You’ve already established a relationship, you presumably know their writing style, quality, and areas of expertise.

This is the lowest hanging fruit in hiring freelancers. It’s why I would hire Shanelle Mullin, Kaleigh Moore, and others in my network for everything if only I could afford them.

Next, look for referrals in your network

Unless you’ve been in the game for a while, you probably won’t have a big personal network of good freelance writers. I can also ascertain that from the fact that you’re reading an article on how to hire freelancers.

Anyway, what everyone can do, whether they do or don’t have a network of good freelance writers, is ask your network for referrals.

Think of any business owners, marketers, content managers, etc., you know and respect – reach out with a canned email and ask if they know any good writers for your topic.

You’ll probably end up with at least a handful, probably a couple dozen referrals depending on the industry.

Better yet, some names will come up over and over again, so you can pre-filter for those with the best reputation. The greater the frequency of recommendations and the greater the reputations of the recommender, the better.

If you have a decent Twitter following, you can also send out feelers there:

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After that, try to poach good freelancers from other sites you admire

Maybe you don’t know any great freelancers, and for some reason neither does your network (or maybe you have virtually no network for some odd case). Well you certainly have blogs and publications you enjoy reading, yeah?

If not, question why you’re in the content marketing/editing space at all.

If so, try to poach ‘em. If they’re freelance writers and they have bandwidth, all it takes it matching on price. Even if they’re an employee, they can probably be convinced (yours truly has taken money for words on a blog post in the past).

Additionally, if they’re an employee of a complementary company, they may be interested in guest writing, provided that your blog is decently well known and you have a good domain authority. I used to email any author of a piece I liked that I found through GrowthHackers, Hacker News, or whatever, and see if they wanted to spin up a piece for CXL (and met some of the best writers that way).

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The only caveat here is that just because someone has published on a high-quality site doesn’t mean they themselves are good. A good editor can turn garbage into gold (more on editors later).

I’ve certainly made this mistake in the past and it’s really fucking awkward. You then either have to re-write the article (loss of time) or you have to have an uncomfortable conversation and reject their work outright (even though you reached out to them in the first place).

I’ve definitely had to re-write almost all of an article and put it under the guest author’s name (though of course I’ve never paid for a piece under those circumstances – only guest posts)

A good heuristic here is to look for the quantity and diversity of the writer’s work. If they publish a lot and have done so on different sites, you can assume they are the primary engine beneath the quality.

Unless they have ghost writers, which many of your favorite marketing influencers do (side note: stop trusting marketing influencers and thought leaders).

On job ads, filter candidates with a Brown M&M’s clause

If you do put up a job ad on something like ProBlogger (I’ve had the most luck on this job board), you’re going to get a lot of bad candidates.

You’ll get some good ones, too.

But some will be irrelevant to your line of work (“I’m a biostatistics Ph.D, here’s my thesis as a writing sample.” “Sir, this is a Wendy’s”), and many will just be lazy and blasting out pitches.

To filter for the latter, I like to put a line or two in the job ad that selects for attention to detail (aka a Brown M&Ms clause to show they’ve read the description thoroughly).

It could be something simple like telling people to email a specific address with a very specific subject line. It could be something more creative like heading to a specific landing page, filling out a form with a particular entry, and sending their favorite 90s band. I don’t know. You just gotta make it something to filter out the mass pitches and blasts.

Whatever the case, this is a good way to filter out the bottom 10-20% of candidates.

Filter further by being very obvious that this isn’t a bullshit gig and bad work won’t be accepted

This is clearly dependent on the type of blog you’re hiring for, but when I was at CXL, basic BS was our arch nemesis. Peep Laja told me that the first time we met up. It was genuinely hard to get published in CXL (which I think also helped us filter in for good writers who liked the challenge).

It’s likely that, even if you’re not trying to produce that level of content, you don’t want some re-hashed garbage that took the writer an hour to write. That’d be a really ineffective content strategy, right?

So in my job descriptions, I like to make it painfully obvious what the writing, editing, and publication process will actually be like. Actually, I make it sound more grandiose and difficult than it will be, in the hopes that it will scare away lazy writers looking to make a quick buck.

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I wanted artisans, people who cared about the craft. My job description reflected that and I ended up finding phenomenal writers. If you find working with cynics and mediocre people acceptable, you’ll soon find yourself among that crowd. Demand excellence and pay well for it.

Create an entertaining and super comprehensive editorial guide

You can use this as part of the job application/description, but no matter what, you should create an editorial guide document that explains who you are, what you’re trying to do, what you expect, and if possible (though less important in my opinion), tactical stylistic and grammatical rules to follow.

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I actually don’t care if someone uses an oxford comma as long as their writing is holistically excellent and the material is substantive. Style won’t save bad substance.

A good editorial guide can make the writer excited to work with you. Done well, it can serve as a piece of PR or word of mouth (see: Tommy Walker and “The Code”)

Plus, you, as an editor or content marketing manager, have to hold up your side of the working arrangement as well. Throwing a freelance writer in the deep end is negligent and lazy and will produce a varying level of work quality (and more cleanup for you later, silly).

Just put in a few hours and write one. It will also help you clarify your own goals and stylistic strategy.

I even write up content templates at HubSpot if we’re going to be putting together a predictably formatted piece of content (like a listicle). If writers continuously make mistakes, it’s obvious that it’s my fault for not clearly communicating expectations. So I write a template and answer those there, which saves all of us time and energy.

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When you find a writer you like, keep them around and pay them more than they ask

At this point, you may have noticed it’s hard to find excellent writers. Again, you wouldn’t be reading this article if it were easy, and I wouldn’t be writing it.

Couple that with being in a niche industry (CRO, analytics, etc. – even digital marketing is somewhat niche in the grand scheme of things) and you’ve got a limited number of writers who will even be a possible fit, ever.

When you find them, treat them super well and pay them a lot.

They’ll inevitably raise their prices as they pick up steam in their careers. Pay them. Don’t be penny wise, pound foolish.

If you have a proper content marketing strategy, you should be getting massive returns on each piece of content, or at least in your program in aggregate (if you’re not, it’s probably not the writers’ fault).

I like to send Christmas gifts and shit sometimes, too. And I give referrals and testimonials to writers I love working with. People like working with people they like. Be cool.

Build a system that works for you and the writers

When you’ve got a few writers locked in and in a good workflow, build a system that introduces the least amount of friction possible – for both you and the writers.

Tommy Walker built a great system while at Shopify. I pretty much stole it and adapted it when I came into CXL. All you need is a few tools:

  • Trello
  • Google Drive
  • Email

That’s it.

We built out a Trello board complete with content ideas, our workflow kanban (ideation, working, draft, second draft, published, promoted, etc.). All freelancers were invited to the board and attached their drafts and comments to the card they worked on, ensuring transparency and clarity. We all worked through Google Drive for easy sharing and editing. We emailed to communicate. Easy.

CXL board

Now that I’m growing a content marketing agency, I’m constantly tweaking this system. The tool I like the best is actually Airtable now, just due to its combinatory effects of being basically a spreadsheet and a project management tool combined (it’s got great UX as well).

We’ve built a board that includes, first, all of our company principles and documents. It’s a good checkpoint. We also include our clients and their content roadmaps as well as our board of freelance writers. We can assign each writer to a given client and map out the particular topics they are writing for them. This allows cross-pollination of ideas from all our writers and gives us a high-level management view of what everyone is working on and when it is due.

We still work through Google Drive because of the collaboration abilities, but we’re curious to try other tools built for big content teams such as Airstory. We attached a Google Docs draft on each writing assignment on our Airtable. After all this, we have a nice single source of truth for our full client workflow. Plus the writers get to see it all as well (and can, of course, filter for their own workflows and assignments so as not to get overwhelmed with data).

And of course, we use Wordable on any site that uses WordPress. It’s a no-brainer.

Be fast (don’t be the bottleneck)

When someone emails you, finishes a draft, or asks a question, respond right away. Be quick, clear, and as brief as possible in your response. As Marky Mark Lindquist (content marketer at Mailshake) said in a Wordable interview (quoting his boss Sujan), “never be the bottleneck.”

It’s not cool to wait around 4 days to respond and hold up the whole workflow because of your editorial ineptitude.

This will also train writers and other people you work with to expect slow work from you, and it will train them to be slow in their responses back to you. It’s a domino effect that results in a sludgy, shitty system bent on mediocrity.

In most situations, choose domain expertise over beautiful writing

Ryan Holiday wrote a great article on those wanting to be writers. In it, he said:

“No one ever reads something and says, “Well, I got absolutely nothing out of this and have no idea what any of this means but it sure is technically beautiful!” But they say the opposite all the time, they say “Goddamn, that’s good” to things with typos, poor grammar and simple diction.

Good writing saves nothing. On the other hand, a deep, compelling or stunning message can float writers who struggle to even complete a sentence.”

I genuinely don’t care if someone messed up a comma or has plain language (actually, I much prefer plain language). I don’t care if you can’t write an introduction to save your life. Most blog post introductions should be cut anyway. We don’t need to hear a quirky intro to a how to article on SEO tips. Just give the tips.

All I care is that you have something interesting and useful to say and that you can transmit that message in a unique way. That’s how good content gets ranked and shared. That’s why people bookmark articles. Not because it’s beautiful writing.

The only exception is if you’re in an industry, like poetry or fiction, where beauty and style is a core component of the message you transmit.

In all other cases, find good content marketers who can write an article that isn’t just re-hashed garbage (pulling from the same 3 sources as the hundred other bloggers), and get an editor who can smooth out the stylistic kinks so it reads well.

Style should never get in the way of the message, but it should never be the message either.

Work with a great editor to fit everything else into place

The real value here would be to give you 11 tips to finding and hiring great editors.

Unfortunately, I haven’t figured that out yet (at least systematically). If you’re a great editor looking for part time work, email me as soon as you can.

I’ve met a few dozen amazing editors and have worked with a handful, and I can tell you that they are both rare and invaluable. Particularly if you work with a lot of domain experts (for example, Intercom’s blog), it’s important you have someone filtering things in at the top who can make things readable, interesting, and consistent.

Good editors can not only bring consistency, clarity, and quality to an individual blog post, but to an entire blog or content program as well. They’re the reason you know Intercom’s blog is good. They’re the reason you know Unbounce, Shopify, and HubSpot’s blogs are worth reading. They bring a level of order to the chaos.

Conclusion

Hiring freelance writings is really difficult, but possible and necessary if you want to build out and scale a content program.

I’m sure you have some of your own tricks up your sleeve, and I’d love to hear them (comment, email, whatever). But these are mine, and I hope they help you hire better writers.

  1. Some good points about hiring freelance writers. I did a similar post as well.

    I think, if you can get a writer who has the ability to deliver a strategy, that’s a plus. I’ve watched a few of the content agencies pop up over the past few years like AudiencOps and Grow and Convert. I like so many of the things they have done.

    So many companies decide to hire a writer without any idea of the strategy they need to employ. I think that causes problems for their content strategy.

    Thanks for sharing your experience Alex!


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