How to Hire & Manage UpWork Writers Without Pulling Your Hair Out

This post may contain affiliate links so I earn a commission. Please read my disclosure for more info.

Doug’s Intro: Christy is a marketing professional with serious skills in hiring freelancers. It’s a perfect example of taking existing skills and using them for internet marketing. 

She’s also a student in Multi Profit Site, making $9,000+ per month as of Nov 2021.

You’ll be able to hire a team of writers and publish dozens of posts (without writing it yourself) after you read this post. 

Check out more results…

Consistent upward traffic



Download the templates, including Upwork Job Posting, Creative Brief, Onboarding Guide for Writers, & Article Status Tracking.


For many of us, part of the appeal of affiliate marketing is the notion of being able to do everything yourself. Goodbye team meetings, bureaucracy, and approval chains. You’re in control of every aspect of your site, your content, and your schedule.

  • Except, what if you have a day job?
  • Or, you aren’t a confident (or quick) writer?
  • Or, you just want to sit down after a long day and watch an episode of The Great British Baking Show without feeling convicted that your affiliate to-do list isn’t getting done?

Yes, you can do everything yourself. But, you don’t have to.

Content Creation Virtual Assistant – Help Isn’t a Bad Thing

If you’re willing to invest some time and money to find, train, and manage quality freelance writers, you’ll be able to offload articles on your wishlist and feel confident that work is getting done — even when you’re not the one doing it.

As a first-time affiliate marketer, and someone who writes for a living, I resisted the idea of hiring writers for several months. I didn’t think I’d be able to find Upwork talent knowledgeable about my niche for less than an arm and a leg.

On the other hand, I wanted to pump a ton of content into my new site fast so it’d have more time to “bake” on Google. Time was my biggest scarcity, and I had a giant article list I’d never be able to write myself.

So, I read Doug’s Upwork advice (yet again) and finally decided to give it a try.

In this article, I’ll share the 5-phase process I used to:

  • Hire 12 writers on Upwork.
  • Assign a round of trial articles.
  • Execute a content “sprint” of 84 blog posts.
  • And, finally, land on the 3 writers I plan to keep using in the future.

Let’s Get a Few Things Straight First

Aside from my affiliate site, I run a business that uses 100% freelancers. I’m also a writer and creative, so I have a deep understanding of the kind of people I do (and don’t) want to work within a freelance capacity. I also understand that writing for other people is darn hard work, and writers rarely feel appreciated.

As you consider hiring writers, remember:

  • Freelancers are PEOPLE. Do not treat them like nameless cogs in your blog machine. They’re skilled professionals, and they deserve to be treated as such. This is especially true if you want to develop long-term relationships with talented writers.
  • You’re a manager, so act like it. Even if your Amazon affiliate income site is a small side project, that doesn’t mean you can half-ass your management duties. It’s up to you to hire (and sometimes fire), manage deadlines, pay on time, and behave in a way that makes freelance writers want to work with you.
  • The Golden Rule applies. The way you communicate with freelancers online matters. They’re under no obligation to work with you, so make sure you’re professional, organized, and appreciative.

Phase One: Preparation

Take 5 minutes to copy and paste Doug’s Upwork job description, post your job, and wait for awesome bids to roll in… right?

Not so fast. Setting yourself (and your writers) up for success takes preparation.

1. Set Your Budget

Before you begin, set your overall budget and per article budget. In my case, I weighed the amount of time an average blog post was taking my Type-A self vs. how quickly I wanted to get 100 blogs on the site.

I decided to hire 10 writers to do a trial post for $50 each ($500 total trial budget).

$50 per article?!

Yes, you can hire cheaper writers for as little as $10-15 per post. As a writer myself and someone who supports freelancers for a living, I personally wasn’t comfortable offering less than $50 for 1,000 words.

2. Create Your Job Description

I’ve attached the exact Upwork job post I created, except I changed it to be about dogs.

Download the templates here.

Make sure you proof (and re-proof) for typos, and be really detailed if there are any deal-breakers.

For me, I only wanted to hire writers with significant experience with my niche topic. I feel an authority site needs to project exactly that — authentic authority on the subject matter.

3. Get Organized

How hard can it be to keep track of a couple of writers and articles? Answer: Things snowball… fast. Set yourself up for success by getting organized before you hire a single writer.

I’ve included a template based on the tracking Google Spreadsheet I use to manage my writers. (Tab 1 shows how I began.)

4. Do the Math

If you follow Doug’s school of thought, you should already have a pretty good list of Keyword Golden Ratio compliant keywords you want to target. (Read more about KGR here.)

You want to have more than enough article ideas before you hire writers so they aren’t sitting around waiting on you later.

5. Create a Style Guide

If you’re hiring several writers, you want everyone to follow the same basic tone, style preferences, etc. I created a detailed onboarding document for my Upwork writers, and I’ve attached a version of what I use.

Use it as a starting point — you don’t need to copy it exactly.

Phase Two: Screening & Hiring

Now you’re ready to post your job description on Upwork and start hiring!

Here’s what to do next:

  1. Create Your Account: If you’re new to Upwork, you’ll need to create an account and set up your billing info through a credit card or PayPal.
  2. Post Your Job: Take your shiny new job posting and put it out there! Be sure to double-check you’ve set up any parameters you want (e.g. US freelancers only) and put if it’s a fixed price or variable price project. Be sure to note if it’s a trial job or ongoing.
  3. Screen Applicants: You’ll be automatically notified by email whenever a writer is interested in your job. You can click on his or her profile to learn more, see work samples, and check reviews. If you required answers to any questions in your application, read those responses carefully. Look at how they write and whether they actually answered your question in a compelling way.
  4. Hire Writers: I was amazed at how quickly — and how many — writers responded to my job within 48 hours. Most of all, I was shocked there were actually people knowledgeable about my niche on Upwork! Even better: many had expertise on sub-niche topics that I did not. I ended up accepting 12 trial writers instead of 10.
  5. Make Notes: Now that you’ve made your initial selections, go back and record key info about each writer in your tracking spreadsheet. Make notes about their background, areas of expertise, and any other interesting bio information. (I’ll share why in Phase Three.)

Phase Three: Trial Assignments

Congrats! You’ve hired your first freelance writers, and help is on the way.

Next, I recommend doing a trial ghost blog post with each writer. This allows you to see how they communicate, whether they hit deadlines and the quality of content they produce.

1. Do Some Matchmaking

Go back to your tracking spreadsheet and start making notes about which articles on your to-do list align well with the background of each writer. For example, if you hired a writer who mentioned she has a Border Collie, she might be a great person to write your article about Training Tips for Border Collies.

2. Give People Options

I offered each writer a choice of three topics for the trial blog post. Not only was I curious about what they would choose, but this also showed the writers I paid attention to them as people and wanted them to enjoy the work. Happy writers write better content.

3. Write Creative Briefs

Once the writers chose their trial topics, it’s time to put together creative briefs. Here’s where many readers may roll their eyes (it takes more time), but it was one of the keys to my success.“Trash in, trash out” comes to mind.

If you spend a little extra time setting writers up for success, you’re far more likely to get content that hits the mark in return. (Evidence: I maybe had to ask for light revisions twice across 84 freelancer posts.)

I created a thorough creative brief for EVERY blog post, and I’ve attached a sample here. This way, the writer knew the purpose of the piece, target audience, and the type of information/sections I wanted.

I also wrote the title and subtitle, as well as section sub-titles ahead of time myself so they were SEO-centric. If you want to include a few FAQs at the end based on your SEO research, add those to your brief.

4. Make Yourself Available

Each time I delivered an assignment and creative brief, I made sure the writer knew I was available to answer any questions that might arise.

5. Review and Record

When you get articles back, the fun really begins! Read each piece carefully and assess how well the writer adhered to your creative brief and style guide. Is the writing engaging and informative? While it’s fresh in your mind, go back to your tracker and input notes about each writer’s work. You’ll reference these again when it’s time to pick the best writers in Phase Four.

Phase Four: Content Sprint

Once you’ve gathered your trial articles, you’ll have a much better sense of which writers deserve additional work.

In my case, I decided to keep 10 out of 12 writers for my content “sprint” and do 45 more articles. (The 2 people I didn’t keep missed deadlines and turned in sub-par writing.)

  1. Do MORE Matchmaking: Depending upon how many writers you decide to keep working with, this phase can be as easy or as complex as you like. I went back to my tracking spreadsheet and article hit-list and slotted article topics for each writer. Again, I tried to ensure at least a couple of topics aligned with each writer’s unique interests and skill sets. In a few cases, I wanted to target bigger keywords and requested “double posts” for those at twice the word count and twice the pay. On average, each writer got 3-5 additional article assignments.
  2. Vet Your Ideas: I then went back to each writer and shared my list of topic ideas and deadlines for the next sprint. It’s better to double-check that they feel comfortable with your topics before you write all your creative briefs.
  3. Repeat Steps #3-5: You know the drill! Creative briefs, stay available and review and record your feedback in the tracking document. Check out my sample tracker to see the kind of notes I made during the sprint. These made it really quick to choose my “winning” writers at the end whom I’ll work with long term. Note: I like to put positive feedback in green and negative comments in red. This helps me remember which writers are doing the best at a glance.

Phase Five: Pick Your Winners

My content sprint lasted about 90 days, and it was a lot to manage. Again, my goal was to fill my new site with a ton of SEO-rich content up front and then let it “bake” on Google for 8-10 months.

Review Your Feedback

My tracking document was critical throughout the process. Keeping detailed notes along the way reminded me how each writer did on their blogs, what types of articles they did best (e.g. product comparisons vs. informational topics), and which freelancers’ work required the most editing time.

Watch for Patterns

My tendency is to want to give everyone another chance. But, once you’re through a content sprint, you’ll have all the information you need to see patterns. Some writers went above and beyond every time — in quality and word count.

Others turned in average work that took hours of editing and formatting. In other cases, you may have a writer that knocks it out of the park on a certain type of post (e.g. product comparisons) but doesn’t wow you on anything else.

That person may still be worth keeping and only assigning topics in their sweet spot going forward.

Wrap Up Contracts

When you reach the end of your sprint, it’s time to close out all your Upwork contracts.

This lets you give feedback through Upwork’s system for everyone, then you can create new contracts for only those writers who made the final cut. Leaving freelancer feedback is a common courtesy, so you should always do it.

Out of my group of 10 content sprint writers, I’m going to offer ongoing work to 3-4 of them. These were the freelancers who never missed a deadline, turned in super clean writing, followed creative briefs well, and were delightful to work with.

Room for Improvement

Overall, I’m really pleased with how my process worked and the results it produced. Sure, not every article is as polished as I’d like it to be yet.

Part of delegating is coming to terms with the fact other people don’t do things “your way.”

Things I could improve next time:

  • Spread Out Deadlines: I set deadlines for batches of 5-10 articles about every 10 days. That turned out to be a LOT of work on my end to keep up with creative briefs, reviewing articles, and getting everything into WordPress. When I do my next sprint, I’m going to leave 2-3 weeks between deadlines.
  • Get WordPress Help: During the trial period, I was able to keep up with getting new articles into WordPress, formatting them, adding pictures and links, and publishing them myself. But, with my other full-time job, the content sprint soon got to be too much. I ended up hiring a virtual assistant to take draft posts and put them in WordPress, along with basic proofing. Then, I hopped in to edit, insert links, and find photos.I’m not in a place where I want to invest in a real content manager (yet), but I absolutely see the value now. See Doug’s article about Content Managers here.
  • Press Pause: Some articles need more polishing and editing before they’re ready for prime time. Next time, instead of rushing to get everything published, I’ll pump the brakes on the posts that need a lot of TLC and come back to them when I have more time.

Onward and Upwork!

Here are a few results I’ve seen since hiring Upwork writers. Keep in mind the site is only ~6 months old and has ~115 articles. The vast majority of articles have been added in the past 2 months and are quite young in Google terms.

This quarter, the site has begun making $400+ per month.

Note: I’ve also continued to write blogs myself and have featured a few guest contributors. Guest posts usually account for the traffic spikes below.

February 9 – April 24 // Consistent upward traffic

Upwork posts started February 9 // Momentum!

Look Out For These Mistakes

[Editor Note] I’m made some silly mistakes!

Mistakes I Made With Hiring Writers

I started hiring writers within the first 45 days of my online journey.

I knew it’d be a great way to leverage my time — and remember, I have a fear of writing. So I welcomed the ability to not work on things I don’t enjoy.

Here were the best/worst mistakes:

Hiring writers from Fiverr.

I paid $5 for content and expected it to be reasonable. It wasn’t.

One of two things happened:

  1. It was broken English and made no sense.
  2. It was rewritten content from a software based “content spinner” that works by replacing words with synonyms.

I believe you can get better content if you upgrade the gig and pay more money.

Not leaving much feedback on Upwork after the gig.

Freelancers want and need to get more feedback, hopefully positive feedback. So if you leave detailed feedback and make it positive, you’ll be able to hire them for another job. That’s ideal once you go through the trouble to hire someone.

Bad job postings on Upwork.

If you look at job postings on Upwork, you’ll see a lot of really bad ones. They’ll say, “I need 5,000 words on Mongolian Throat Singing tomorrow. But I don’t have much budget.”

And that’s literally it! So, I beefed up my job listing and made it thorough, clear, and professional. The quality of applicants went up dramatically.

Excepting Excuses.

Someone will be late in submitting work. It happens.

“The plague is going around my neighborhood, but I’m better now…”

They’ll have an excuse like…

  • “My brother got sick…I’ll have it done tonight.”
  • “The power went out for 18 hours and our food went bad. I’ll write it immediately.”
  • “The plague is going around my neighborhood, but I’m better now…”

In each case, nothing happens and you get another even MORE impressive excuse.

I have a TWO Strike system to deal with this. Look, I know life gets in the way sometimes.

A freelancer gets one excuse and that’s it. If the deliverable is late or another excuse is given, I’ll end the contract.

What should I do if I’m not a native English speaker?

Here is what I would do:

If you’re on a tighter budget, I’d hire writers from Upwork. Then, I’d hire an editor to take care of the technical part of content: Grammar.

You’ll notice that this is exactly what I do:

  1. Hire a writer.
  2. Hire an editor.

So if you need content in a language you don’t speak, it shouldn’t be an issue. You’ll be following the same process as me.

[end editor note]

Bottom Line

Put in the effort to hire good writers and manage them well. In return, you’ll be able to grow your site content without pulling all-nighters or emptying your bank account.

Treat freelancers well, say thank you, and watch your affiliate site grow organically.

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Comments on this entry are closed.

  • Subham

    This is something I related to one of my site. The site I was build almost year before and had only 12 post on it but I didn’t touch it for year because was busy working with other projects.

    One day I noticed site getting really nice traffic and income not so much but compared to 12 post only it was making $200 per month. So I decided to start working on this site so I sell one of my old site on flippa for $7500 and invest all the money to this new project I start finding nice related writers from upwork and verious industry forum and manage to hire 4 writers who know my topic really well.

    After that I make a list of topic I will gonna target first ( I was target very specific questions and low competition kw) within 6 months I publish around 80 new post and most of them are around 2000 to 4000 words.

    Alongside publishing new content I also focus more on grow my Pinterest account.

    After 8 months letter the site is now making around $2600 from affiliate and ads combine.

    • adam

      very nice brother, I also have an amazon niche site ( 20 posts ) mix of informational and affiliate articles, it has only 2 months and I only get a little bit referral traffic from forums, but not organic traffic, I haven’t built any links, I keywords I target are KGR compliant, I waiting from the six months mark to see what’s gonna happen. I’m glad you made it

  • Omar

    I am curious…

    Question. What have you done for link building?

    Because this niche is fairly competitive and I would imagine the site would need some form of links if it is to rank for any of the commercial keywords..

    • Omar – the niche was just an example. But Christy has worked on a lot of things for link building – blog commenting and guest posting primarily. Plus, she’s done a lot of networking so she’s been able to get natural links and social interactions.

  • hecz

    Don’t load all images…

  • Chibuzor

    Hi Doug,

    Thanks for the article. I crossed $100/mo last two months using KGR and I’ve got less than 15 review pieces on the site.

    Thanks so very much. I’m aiming for $200 this month.

    • Nice work! I took out your URL to protect your site. 🙂 You shouldn’t be telling people your site, Chibuzor. You’ll get negative SEO & copycats.

  • Trevor

    “Part of delegating is coming to terms with the fact other people don’t do things “your way.”

    This is a barrier I have yet to overcome. I guess you have to bite the bullet and give it a go.

    I”m surprised by the “Press Pause” action. Even if the quality is not to your standard, isn’t it better to publish and let it “bake” until you have time to revisit and amend?

    • Trevor, It took me a while to let go too, but that’s when things took off.

      I”m surprised by the “Press Pause” action. Even if the quality is not to your standard, isn’t it better to publish and let it “bake” until you have time to revisit and amend?

      Sure, I could go with your suggestion. It’s a personal choice.

  • Ronak

    Hey Doug I tried contacting to you but seems you are little buzy to answer everyone 🙂
    No problem
    BTW thanks for KGR method after few website i have created a Niche based website but i have few doubts which i didn’t find answer of.

    1. Suppose you search for ALLINTITLE:XYZ
    on first page google results shows 300 results but then when you try looking for last result it says google have only 42 results till page 5 only. so in this case what should we consider 300 results number or actual number 42.

    2. Suppose you have a 1 DA website a new website you looking for a new keyword and find a keyword with 170 searches using Ubersuggest but when you alltitle it show ACUTAL results 60.
    which is higher than .25

    but when you look at the results all are bogus results only title are same but content is totally irrelevant sometimes some scammy websites open and on first website it shows 3 videos first then few pinterest then a 9 DA ecom website(SHOPIFY DROPSHIPPING WEBSITE) then again few reddit results and at 10th position a alibaba link
    so will you consider that as all the results are irrelevant but KGR is also saying to skip it.

    I guess I should use as it does not have competition but waiting for what you think about it.

    Sorry For Super long comment with poor english.

    • Ronak, I don’t remember an email from you…but if you tried on Facebook, then I never saw it. I stay away from FB and only answer my parents there. 🙂

      1. I suggest you ask a question like that on the relevant post. This isn’t related to hiring writers.
      2. Go watch the KGR Masterclass on YouTube. If you don’t have your answer after that, then email me and I’ll do a whole video answering your questions.

  • Mark

    Hey Doug,

    My name is Mark, and I am freelance writer. Seeing that you hire on Upwork, I was hoping I can work with you.

    I would love to send you a sample, but I do not want to leave a link to my blog here owing as I do t want to get negative SEO.

    If you can, reach out and hopefully we can work together.


  • Earl

    It’s taken me a loooooong time to wrap my head and wallet around ordering content, primarily because of my circumstances with a new job.

    I just hired a young that I know personally to do some writing for me and I’m glad I did. I’m paying a little more but he’s an English major, takes direction well and does a good job of mimicking my writing style.
    It leaves me to focus on and write the kind of blog posts I wanted write when started the site and delegate the more tedious stuff to someone else.
    It’s taken me a loooooong time to wrap my head and wallet around ordering content.

  • Stephen

    Great post. Lots to digest. I think I will try to do a (much) scaled down version of this.
    1 takeaway – there are lots, but one thing I thought was interesting was that she pays $50 per article, for quality but also for ‘ethical’ reasons. I’ve also felt uncomfortable with what I’ve offered US based writers (typically $15-20) so I will change that.

  • Dan

    Hey Doug,
    the images on this page are not loading at all, tried w 2 browsers.
    Must be lazy loading related.
    Have a look at it, please!

    • Dan, thanks for the heads up. No clue what’s going on…and it seems to be intermittent. It is lazy load related, but I’m not sure whats up.

  • Carl Broadbent

    I have launched a new site after 3 months of researching over 150 KRG article for the site. I recruited a team of 2 writers and a content manager. The site is now 4 months old and has 60+ articles all KGR. Early signs are good and already have 2 Google no1 snippets. I look forward to adding the other 100 articles and seeing their results in the next 3-4 months. Great case study and thanks for sharing Doug.

  • Ronald NTB

    Hi, thank you so much for sharing!

    Can I ask something? It will be so happy if I can receive the answer from you & Doug Sir!
    I’m Vietnamese. My budget for me to start is so tight. (around $250).

    My English is semi-good enough (it’s mean I can correct the grammar, using words for exact intent). But it’s not pretty good like you & I can’t write an English article in a proper format.

    So I want to ask, can I write in Vietnamese (because I’m so good at content writing in my native language). Then I hire someone (Vietnam) that’s excellent at English level to translate it to English for me?

    It’s just the strategy I want to use for the first time. Then when the site grows up, I will reinvest to hire an English native speaker to write for me.
    Can I do that?

    Thank you so much. I really want to hear from you.

    • Hey Ronald, You can do that, yes. However, I have no clue about how well that will work out. My assumption is that it’ll be expensive, cumbersome, and harder than you expect. I’d advise you to write in English the best you can and hire a good editor to clean it up. That’ll be cheaper and cleaner in the long run.

      I’ve never done this so I’m making some assumptions about the process.

  • Mike Syms

    Great post Christy. I also have a hard time letting go of some of the creation but it is one of the best ways to multiply my efforts. I have had connent written through iwriter and upwork but so far have mostly been disappointed by the quality.
    I am now interviewing through upwork to try to find someone to groom into the position but i hadn’t thought of trying to hire a bunch to test first before focusing in on the best ones to direct my efforts on.
    My first site is still fairly new and is just starting to get sales, however, the biggest thing holding me back is being able to create enough quality content fast enough so i know this is where i really need to focus my attention right now.
    Thanks for the inspiration.