This week, I share the lessons that I’ve learned hiring and working with other freelance writers. As a writer and having worked as a project manager for several other teams over the last five years, I have gained a lot of experience in the area of outsourcing to other freelance writers. Now, while outsourcing comes with its benefits (e.g. an expansion in your skill set and your ability to make more money), there are key elements to your call for writers that you must get right. In this video, I talk about how the questions you ask and the information you give has a direct impact on the quality of responses you get. I also talk about setting expectations around things like communication styles, as well as the value of test projects. 


Hey! Laura here, and I want to talk about some of the lessons that I have learned hiring and working with other freelance writers.

As a writer myself, and having worked as a project manager for a lot of different teams over the past five years, there are certain things that I have learned when it comes to outsourcing to other writers. There are many different reasons you might want to do this. As a freelance writer, you might be wondering whether you’ll ever be in a position to actually hire another freelance writer, or how you could extend the services you’re currently offering. By hiring other freelance writers, you open yourself up to both of those opportunities at the same time.


Outsourcing to other writers

What do I mean by that? First of all, your business might ultimately get to the point where you cannot do every single project on your own. You’ll need to outsource some or all of the content creation to somebody else on your team. I have run my business both ways – handling all of the work myself, and outsourcing almost all of it to a team of writers that are working for me. The second reason you might want to consider doing this is because it expands your skillset and your ability to make money. As an experienced writer yourself, you are uniquely positioned to help train other writers and manage teams of freelancers for other companies. I have done this several different times.

At one point, I was working with a team, managing more than 20 writers who were writing over 400 blogs every single month. As the project manager, I was responsible for tapping those writers, giving them titles, managing the workflow, and taking care of invoicing under that contract. I have also done this for several other companies, including Microsoft and True Car. I’ve learned a lot of lessons and made some key mistakes along the way, and that’s what I want to talk to you about in today’s video.


Put a lot of thought into your postings

First of all, it’s really important how you post the ad. This is true regardless of whether you are hiring one writer to be your backup on your team or a team of writers to carry something out for a particular client. How you post the ad, the questions you ask, and the information you give is going to lead to better candidates. If you just write a really quick two or three sentence job post application on Upwork or Craigslist and just say that you are hiring writers, there is a really good chance that you are not going to get quality responses. Why is that? Because anyone and everyone will apply, and the other problem with that is that the people who really do like to work on specific projects – those who may be your ideal writers on that team – are going to see a generic job post and ignore it; they won’t even apply. You are actually shooting yourself in the foot right out of the gate.

When you post a job application or a call for writers somewhere, be really specific about where these writers might spend their time. Is it in a Facebook group for freelance writers? Is it on Craigslist? Is it on Upwork? Is it somewhere else? You have to find where they are hanging out first. You also want to write a really clear job description. What are the typical topics? Give an example of an approved article or topic. Explain the process briefly so that the writers will know how much work they’d be responsible for and whether this is a retainer or one-off project.


Specify the number and kind of samples

Additionally, be really clear in the way you ask for writing samples. If you leave it up to them, some people will not send a sample at all. I know that’s strange to think about, but I just submitted a call for writers a couple of weeks ago, and I got 150 applications. At least 20 of them included no writing samples. That was an immediate delete from my inbox. If I can’t see your work, I am not going to hire you, and I am not going to recommend you to a client. Make sure that when you post a call for writers, you explain what you are looking for. One sample, two samples, three samples, does it need to be a specific type of writing, like a whitepaper or a blog – ask for that information. That way you’ll have a really good chance to vet the other writers.

When you are outsourcing to someone else, it’s also very important that they understand your communication style and the client that they will be working for. If you are serving as the middleman, like the one landing the contract or the one managing it for somebody else, you are responsible for clarifying all those things. If the client has some particular guidelines, you need to present them to the writers in the test job process as well as during the project itself.


Always test a potential writer

Finally, let’s talk about test jobs. I strongly recommend this, whether you are managing new writers for a client or just doing it in your own business, you need to not only look at their samples, but also give them the opportunity to complete a project. This should be a paid project; however, it should be small in scope. Perhaps one article or an initial project that only takes a couple of hours. You are doing this for a couple of reasons: whether you are hiring someone as your own backup blog writer or looking to add this person to a 12-man team writing for one of your clients where you’re serving as a project manager, you want to see how good they are at following instructions, how strictly they adhere to deadlines, and how they choose to communicate with you.

It is a given that if you hire a lot of writers to do a test project, some of them will drop off and quit the project altogether. It’s just what happens, and sometimes you’ll get applications from people who seem like a great fit for the job, but they can’t handle the other professional aspects of submitting a writing project. They’ll miss deadlines, they won’t follow instructions, or they’ll submit work that’s not up to par or even duplicate content. I just hired about 20 writers for a client of mine, and two of them were cut from the project and pretty much self-selected. They didn’t follow the directions, and when they were doing their paid project, they didn’t like hearing feedback from the editors, which I had made clear from the beginning was going to be part of the project. They never even completed their test job.

This is more relevant when you are hiring larger teams of writers; however, it still applies when you choose to give somebody a test job for a smaller project. If you have somebody who is going to be doing one or a couple of blogs for you per week, I still recommend giving them a really clear test job with a 72-hour turnaround and clear instructions. See if they can meet the bar with that; it’s going to tell you a lot about their potential for working with you in the long term. A star in the freelance writing world will rise to the occasion and probably meet or exceed your expectations, but it’s just as valuable to know who’s simply not going to cut it, so you can end the relationship early on.

These are just a couple of the lessons that I have learned working with other teams of writers. If you are thinking about expanding your freelance writing business, check out some of the advice we have here on this YouTube channel or on my blog at And remember – if you are looking for an opportunity to increase your leads in your freelance writing business, I have plenty of resources all about how I have used Upwork to generate more than $300,000 in leads in the last couple of years alone. Best of luck in your freelance writing career!