Hiring Content Writers: Part Four - Working with Writers

You can’t judge a writer’s skill accurately until they produce content for you. The paid trial is where the evaluation process truly begins. Use this time to observe how well the two of you communicate and how much coaching or editing they need before their writing matches what you want.

Send a kickoff email

Once I decide to hire a writer, I send them a kickoff email. Below, I’ve included an actual kickoff email I sent to one of my writers:

I’ve just sent over the contract for you to sign. Let me know if you have any questions.

Once you sign, you can begin working. The first article I’d like you to write is Green Beans. You can put the text in this shared document:


Here is the site style guide:


Please bill for the time that it takes you to learn the style guide and research the basics of the keto diet. I know there’s a lot in the style guide, so I’m not expecting you to get it perfect on your first try, but do your best to adhere to it.

You can enter your hours in this spreadsheet:


Limit your time on this first assignment to 5 hours. If you’re approaching 4.5 hours, and you’re not finished, take the last half hour to organize the work you have so far, and share your progress with me. There’s not a ton of urgency on this, but if you could let me know what day to expect the work, that would be helpful.

Can you also send me a mailing address where I should send your checks? I’ll mail the first one on Saturday, September 7th for any hours you’ve worked through 9/6.

Several critical things are happening in this email:

  • It clarifies that the writer’s work must be under contract.
  • It provides a style guide and lays out my expectations around it.
  • It timeboxes the assignment to prevent billing surprises.
  • It instructs how to bill me for their hours.
  • It explains how I will pay them.

I describe each of these elements in detail below.

Create a contract

When you hire a writer, you need a contract to eliminate any ambiguity about the relationship. Can the writer resell their content to other sites, or do you require full rights to their work? A clear contract minimizes misunderstandings and legal disputes later on.

Creating a contract is easier than it sounds. There are plenty of free, example contracts online for freelance writing. Obviously, the best contract is one that your lawyer creates for you, but if you can’t afford a lawyer, an online template is infinitely better than no contract at all.

I used this template with some modifications and then used Docracy to collect e-signatures from my writers.

Sidenote: I find the Docracy interface buggy and unintuitive. I only mention it because it’s the service I used, but if you find a better service, choose that (and tell me about it).

If you hire through a freelancing marketplace, they likely have a default contract that does what you want. For example, Upwork’s default contract assigns all intellectual property rights to the client, so you probably don’t need an additional contract.

Keep your first assignment small and easy

No matter how good your writer is, there’s always a learning curve as they figure out how to write content that matches what you want. You can accelerate their learning by keeping a tight feedback loop. Start them out with small, simple assignments. As they master the easy stuff, gradually progress to more complicated and substantial projects.

Timebox early assignments

If you’re paying by the hour, it’s critical to timebox your freelancer’s work. Otherwise, you might assign them what you think is a 30-minute task only to be gobsmacked by a 15-hour invoice. Unexpectedly high hours are not necessarily an indicator that the writer’s trying to rip you off. Writing assignments vary widely in thoroughness, so it’s crucial to align everyone’s expectations.

Here’s the instruction I give to my new writers:

Limit your time on this first assignment to 5 hours. If you’re approaching 4.5 hours, and you’re not finished, take the last half hour to organize the work you have so far, and share your progress with me.

As you work together more, give the writer more autonomy by increasing these hours caps or eliminating them entirely.

Use a style guide to enforce consistency

Do you want the content on your site to be formal and serious? Or do you want it to be irreverent and a little bit silly? Your writers won’t know what type of writing you want unless you tell them. This is even more important if you’re working with multiple writers. Otherwise, you end up with one article on your site that’s sterile and highly scientific, while another is filled with teen slang and animated gifs.

Your style guide tells your writers what kind of writing you want and what conventions to follow. Here’s the style guide for Is It Keto:

Screenshot of Is It Keto's style guide

Is It Keto’s style guide

Resist the temptation to create rules for every imaginable scenario. Limit the style guide to issues that come up frequently for your site. For example, Is It Keto focuses on the keto diet, so its style guide explains how to format food measurements and how to abbreviate words like “carbohydrates” and “ketogenic.”

Make it a Google Doc or a wiki so that there’s a single, authoritative version that’s easy to update. If the style guide is trapped in an email or PDF, it’s difficult to ensure that everyone’s working from the latest version.

Your style guide is a living document, and you should continue updating it as you work with your writers. For example, if you see a writer omitting the Oxford comma, but you’re an ardent supporter, it’s short-sighted to simply correct the mistake. Instead, update your style guide to mention that writers should use the Oxford comma, and point the writer to this new section.

Add to your style guide judiciously. The longer the guide, the harder it is for people to learn it.

I pay my writers to learn the style guide. It’s helpful for the relationship because it shows them right out of the gate that I respect their time. It distinguishes me from clients who disrespect the business relationship by demanding unpaid work.

Agree on an editing workflow

Your writer’s first draft will likely require editing, guidance, and feedback. A clearly defined workflow for revisions minimizes pain and wasted effort during this process.

Here’s the editing workflow I use for Is It Keto:

  1. I create a Google Doc with an article template.
  2. I share the Google Doc with the writer and ask them to fill in the template.
  3. The writer emails me to let me know when they have a draft ready for me to review.
  4. I add margin comments to the Google Doc and make inline edits in “Suggesting” mode.
  5. I email the writer to let them know that my edits are complete.
  6. Repeat steps 3-5 until the article is ready to publish.

As you continue working together, focus on minimizing the rounds of review. Look for patterns of error, and think about whether changes in your style guide could prevent them.

Give tactful feedback

Good freelancers take pride in their work, so keep that in mind as you provide feedback. If your feedback is rude or insulting, you make the freelancer’s job less pleasant and shorten the lifespan of your working relationship. This is not to say that you should withhold criticism, but you should provide it in a way that’s tactful and helpful.

When you give feedback:

  • Be specific
  • Focus on the writing, not the writer
  • Consider whether your instructions are the problem

Freelancers consistently tell me that clear, empathetic feedback is the key factor that separates the good clients from the bad. Surprisingly, rude feedback seems to be the norm rather than the exception. This means that you stand out as an exceptionally pleasant client merely by providing a basic level of courtesy on par with a face to face interaction.

Bad: You did a terrible job on the first paragraph. Rewrite it.

This is poor feedback because it’s vague and pushy. It also frames the criticism as a personal attack instead of focusing on the work itself.

Good: I had difficulty following the first paragraph. The sentence structure is repetitive, and it uses the passive voice too heavily.

This is a more tactful rewrite of the feedback above. It calls out specific problems with the writing, and it avoids the word “you” so that the writer doesn’t feel that this is a personal attack.

Decide whether to terminate a writer

As you review the writer’s first few drafts, look out for signs that you should terminate the relationship:

  • Their writing includes careless errors such as grammar or spelling mistakes.
  • They repeatedly violate your style guide.
  • They miss deadlines.
  • They bill a higher number of hours than you can afford long-term (if you’re paying hourly).

It’s a bit of an art to decide when to bail on a writer. My own process is to be fairly accepting on a first draft — it’s okay if they’re still struggling to learn my style guide, but I’ll end the relationship over egregious spelling or grammatical errors. By draft two or three, I expect the writing to be close to publication-quality, but they’re usually still learning the nuances of my desired style.

Remember that it’s hopeless to fix an unskilled writer. If their writing is illogical, boring, difficult to understand, or syntactically incorrect, it’ll stay that way for years.

If a writer fails to meet your standards, see the section on terminating writers.

Pay promptly

Who Pays Writers is a crowdsourced collection of freelancers’ working experiences. Promptness of payment is one of the strongest factors in these reviews. Writers value clients who pay the freelancer in full soon after the work completes.

To maintain a healthy relationship with your freelancers, define when they should expect payment, and meet those expectations. On freelancing platforms like Upwork, this is straightforward, as you simply need to approve hours when prompted. If you’re working with a writer directly, you’ll have to apply more diligence.

When I pay writers directly (rather than through a freelancing platform), I ask them to enter their hours in a shared Google Sheets spreadsheet.

On alternating Mondays, I mail them a check for the hours they’ve accrued in the pay period.

Tip: See if your bank offers check mailing as a free service. I use Chase Business Checking, which allows me to use their Bill Payment service to send anyone a physical check for free.

Meet regularly in person or on video chat

If the writer seems like someone you’d stick with beyond a paid trial, start scheduling regular meetings in person or via video chat.

It’s tough to maintain a healthy working relationship with someone exclusively through email. I’m personally more liable to grow frustrated with my teammates if we only ever communicate in writing.

I remember a specific instance with Morgan, one of Is It Keto’s early writers. She often submitted work that used the passive voice, even though it violated the site’s style guide. Annoyed, I’d often ask myself, “Why doesn’t she care enough to catch these errors herself?”

When Morgan and I began meeting over video chat, it immediately became apparent that she cared deeply about the quality of her work. Passive voice was just her blind spot. And we all have blind spots for errors in our writing. My editor always criticizes my comma usage but I, have no, idea what she’s talking, about.

Use these meetings as an opportunity to grow as a manager. Be open. Ask if there’s anything about the workflow that makes it harder for them to do their best work. Is there anything you can do, as the client, to make the job more pleasant or efficient? Your freelancer might be doing unnecessary work because they mistakenly thought you wanted it that way.

Recognize that meeting with you is work for your freelancer, so let them know that you’ll pay them for their time.

When you find a good writer, invest in the relationship

It probably took a long time to find a writer that matches your needs. Now, it’s time to nurture the relationship so that it lasts as long as possible.

Allow them to share in your mission. If the business is growing thanks to their writing, share those victories with your writer. It’s motivating for them to see the impact of their work instead of feeling like they’re cranking out thousands of words for a paycheck every few weeks.

With one of my freelancers, I found that many of my suggestions parroted lessons I learned from The Elements of Style (aka Strunk and White). I asked her if it would be okay if I sent her a copy, and she happily agreed. Later on, she specifically mentioned that gift as something that made her value the job — it demonstrated that I was interested in and supportive of her long-term growth as a writer.

Terminating writers

If you’ve found a good writer, congratulations, you’re done!

More commonly with writers you’ve hired on a trial basis, you have to face the unpleasant business of terminating the relationship. The next section explains how to do this cordially and professionally.

Thanks to my writer, Morgan Province, for offering insight to help me create this guide. Special thanks to Alexis Grant of The Write Life for volunteering her time to provide me with feedback.