Getting Started in Freelance Management: Tips for Outlines and Deadlines

Are you planning to contract freelancers to take on some content tasks? Or are you looking for ways to improve the assigning and working relationships with your current freelancers? This roundup is for you.

We interviewed 26 freelancer managers to learn about:

• The most helpful information to include in freelancer assignment briefs (for the company)
• Tips on sending assignments and setting deadlines
• Ways to streamline the editing process and save valuable time

Without any further ado, let’s dive in.

13 recommended parts in a freelancer brief

What information should you include in a freelancer’s brief to best streamline your process? Here’s what freelancer managers think. Their responses are based on what would most improve company efficiency.

(Be sure to check out what freelancers think in the freelancers’ version of this roundup!)

1. A detailed outline

“I find that outlines are the most helpful element we include for each assignment. By providing outlines, we let the freelancer know exactly what we expect of them. They know if they don’t give us content that matches the outline, then they’re going to have to re-do the job. Before we started using outlines, we had a huge bottleneck where we were waiting for rewrites.” –Pete Danylewycz, US Angler

“We try to include a brief outline for any blog posts or research papers we outsource, with bullet points to provide suggestions for our freelancers regarding the overall theme, tone, and purpose of the content. We also include a small number of sources on the topic to jumpstart their research or illustrate the type of content we would like them to create. Ultimately, we find that including all this useful information in briefs works to reduce the number of future edits and results in a better final product.” –Teresha Aird, Offices.net

“I include a specific article template. All templates break down the article’s structure into shorter sections, each under a subhead. I’ve found that writers of all levels of experience find it easier to both research and write when the content is broken down into smaller chunks.” –Alan Furth, Really Simple Guitar

“Though it depends on the assignment, there are almost always a few key outline elements essential for a smooth collaboration:

• A short description of the task: It may seem obvious, but freelancers may work on a very specific task as part of a wider project, and it makes a great difference having context and understanding the bigger picture
• Clear bullet points with key task requirements: Such as a headline, a concise summary of the topic, the keyword target, word count, other SEO considerations, as well as details of where the content will live or what it’s intended for.
• Timeline and deliverables: It’s important to agree on these from the start, and set clear deadlines and milestones as relevant for your project.” –Bogdan Marinescu, Digital Trails

2. Keyword-related elements from an SEO service

“We use usetopic.com to generate our freelancer outlines for each article. The tool allows us to create suitable headings and know what words or phrases to use based on the top 10 in the SERPs for the keyword phrase we are going for. It also lets us look at those top 10 article’s outlines for a high-level perspective.

“The ability to know what headings our freelancers should use, ancillary words and phrases, and how the competing top 10 are structured helps us rank almost immediately. We have taken over a few number one spots doing this.” –Ben Walker, Transcription Outsourcing

“I do my best to provide as much info as possible for writers. I know what it’s like to be provided with little to no information and getting incredibly large expectations. I use SEO software to provide them with guidelines, in terms of keyword density, the number of images, content length, the number of headings, and keywords to include in the text.” –Marcin Stryjecki, Booksy

3. Required subheadings

“One of the most helpful aspects of freelance assignments is providing subheads for the writer to incorporate into the content. This serves a few different purposes. First, it’s a means for our in-house team to perform some initial keyword research so we know what to expect when it comes to the information in the completed article.

“Second, it provides the freelancer with an outline of what questions to answer in the content. Third, it makes it easier to optimize the freelancer’s content, expediting the posting and scheduling process.” –Adam Rowan, Twelve Three Media

4. A headline and synopsis

“I always include a proposed headline and a two to three sentence synopsis (which also acts as a mini outline). If the topic is involved, I might even find a few resources to include or an example of someone covering a similar topic well. Doing things this way isn’t as fast and easy as just saying, ‘We want an article about X,’ but it sets clear expectations, reduces the back and forth, and makes it more likely you’ll get a deliverable that works for you.” –Elliott Brown, OnPay Payroll

5. Goals and expectations

“I provide context and background information on our company to help the freelancer better understand what the business entails. I also define my expectations, the quality of content I need, and my project goals. These details help the writer understand our goals and come up with solutions that address them.

“Defining the target audience and the customers is important. And stating your competitors will greatly help inform the freelancer’s direction in researching to provide quality content for your audience.” –Harriet Chan, CocoFinder

“We set very clear expectations with our freelancers on the exact job they are to perform, when it is to be completed, how many hours they have to complete the assignment and when they will be paid. We believe that the clearer we are with people regarding what success looks like, the happier they will be when working with us vs. another firm.” –Andrew Gottlieb, No Typical Moments

“Providing in-depth standard operating procedures (SOPs) has been monumental to our efficiency when working with freelancers. The SOPs help communicate exactly what we’re looking for and eliminate many back-and-forth conversations that would usually be required without them.

“To give an example, we send our freelance writers a detailed style guide that directs them on formatting, content structure, content features, and more. Once we made the effort to really flesh out our style guide, we noticed an immediate improvement in the quality of writing we received.” –Thao Tran, Voltcave

6. Branding guidelines

“We include a client rundown for every piece assigned to help our freelancers adopt the best tone and perspectives to reflect the client’s brand. It saves time for everyone involved to have clear directives all in one place, describing who the client is, their brand voice, and why their content needs to be heard.” –Amanda Lutz, Clara Agency

7. Introduction videos

“Create an introduction video where you walk them through the communication process. Making a video at the earliest stage saves tons of time, and reduces the potential for mistakes. Freelancers will obviously have their area of expertise, but it is important for us to track them efficiently so we can analyze the process on a weekly basis.” –Nikita Chen, LegitGrails

“Videos are by far the most effective tool we have found for managing freelancers. Shooting a video brief is fast – really fast if you have the right Chrome extension – and shows the freelancer exactly what they need to do, from initial assignment to follow-up edits. Unlike a Zoom call, they can rewatch the videos as many times as they need to.” –Katie Elzer-Peters, The Garden Of Words

“I like to record a short video using Loom to be clear about timelines and requirements, but also to explain the context and goals. Using a video allows me to directly show some content and examples to use as inspiration. An indirect benefit of using Loom is that you receive a notification when the video is watched, so you know if they saw it and when.” –Pedro Bailadeira, Water Filter Portal

8. A live video call

“For writers, I always do the very first briefing on a Skype or Zoom call. I’ve found writers are thankful for the one-on-one interaction. Some of them have told me it’s the very first time someone goes beyond email to brief them. This helps build up trust and rapport.” –Alan Furth, Really Simple Guitar

9. Clear solutions that anticipate potential problems

“First, I try to predict anxiety before it arises. Next, I provide absurdly detailed solutions. Maybe they don’t know where to source some info. They are not sure how to write a section. Answering their questions before they even arise creates a compelling dynamic and mutual understanding that we’re in this together: ‘Hey, I know what you will struggle with. Let me try and help you out.’

“Second, I ask the freelancer for their input on the outline itself. And I listen! This is not a gimmick. Treat your freelancers like you would a colleague sitting next to you. They have great ideas. Asking them to weigh in and implementing their suggestions builds ownership and leads to professional fulfillment.

“Anticipating fears and alleviating them, followed by asking for actionable input, creates a culture that folks often don’t believe can be created with remote workers. It fosters personal responsibility and enables the best passive efficiency booster – caring about your work.” –Andrey Doichev, Inc And Go

10. Example or model content

“The most useful element I include is examples. Examples come in two forms: One is examples of previous content from our website. This gives the freelancer an idea of how to format the piece, and ideas on wording and positioning, especially when it comes to writing about our own product.

“The second type of example I give is examples from other sites. This usually occurs when the brief is about a new topic we haven’t written yet, but has been written well by another person. It provides a strong idea of the direction we want to take, while also acts as informative resources for the freelancer on a new topic.” –Joy Corkery, Latana

11. Requirements to name the benefits for the audience

“We ask freelancers to tell us why the article is important for the audience and how the audience can benefit from it. It helps us understand the intention of the article and whether the writer actually knows about the target audience.” –Saurabh Wani, Automate.io

12. Clear tone guidelines

“The most important part of the assignment brief that helps our freelance writers avoid heavy editing is clear guidelines for tone. Since we started including writing samples to guide them into the correct tone, we have required much less editing.” –Eulises Quintero, Titoma

13. Information about the audience

“Information about the audience and goal for their task. I like this because it helps freelancers solve small problems by themselves. When stuck at a fork in the road of where to take an assignment, they can ask themselves which path will get them closer to the goal and best serve their audience. Even if this doesn’t work every time, it saves a lot of time and helps them stay in a workflow, which means better results overall.” –Stefan Palios

What’s the best way to assign articles and deadlines to freelancers?

Like most processes, the “right” answer varies depending on the needs of your company and freelancers.

Still, the frameworks offered by our surveyed managers will hopefully help you form your own calendar and assignment process.

Read on to find inspiration for your own freelancer management workflow.

Use organizational tools

“We use a Google sheet and put our articles in order of priority. If something comes up like a guest post opportunity or a new relevant blog post we think needs to be done first, we will email the writer and ask them to move it up the priority list. The expectation is two articles per week.” –Ben Walker, Transcription Outsourcing

“I send out monthly assignments on Trello. Since I don’t have that many articles to assign, I’d rather prepare a monthly schedule so I don’t have to worry about it further down the line.” –Marcin Stryjecki, Booksy

“We use a Google spreadsheet with a list of planned article details, assignees, and deadlines. Every article has a status cell, starting from ‘To Do’ all the way to ‘Published,’ which content creators change depending on the task’s state.” –Roman Vasilenko, Rocket Labs`

“When assigning articles, we usually try to work with freelancers on bulk orders in order to establish a sizable bank of finished articles for posting. Our content calendar is accessible for all freelancers via Basecamp, providing transparency as to when articles are due to go live and the associated deadlines.” –Teresha Aird, Offices.net

Consider letting freelancers choose assignments

“As new assignments are available, we add them to ClickUp and freelancers are able to pick up the new assignments as they complete their current assignment. This works really well for us because it eliminates the bottleneck of freelancers waiting for new assignments. Instead, they get to take ownership and get their own assignment from the available pool of article titles.” –Pete Danylewycz, US Angler

Leave room for flexibility on both ends

“Finding quality freelancers is job one, so I’m happy to work with their schedules. I have a monthly calendar and I ask each freelancer what they think they can complete. Firm deadlines are important to set the right expectations, but flexibility in putting together a plan is important, too.” –Elliott Brown, OnPay Payroll

“Assignments are usually sent by the week. I send assignments where the content is due to be published three to four weeks in the future, so there is plenty of time for any amendments and neither myself nor the freelancer is under any pressure. However, I will give an idea of the workload I have available for the foreseeable future, so the freelancer is able to easily juggle and take on work.” –Joy Corkery, Latana

“We allow writers to select a few topics from a master list to set their calendar for the next week or two. This ensures we can still publish the specific topics we want, while giving the freelancer flexibility. I feel a monthly calendar of assignments is too limiting for a freelancer.” –Thao Tran, Voltcave

“We assign articles for the month after a conversation about the freelancer’s availability, and then do our best to have outlines and topics to them one week ahead of their deadlines. Since freelancers are typically juggling many different projects, we find it’s best practice to give them a bit of flexibility instead of tight turnarounds whenever possible.” –Amanda Lutz, Clara Agency

“We send out a monthly calendar of assignments, but stagger the deadlines over the course of the month. This gives our team room to manage editing and posting more effectively, rather than handling all the pieces at once. It is also important for sending content to our clients for approval, providing them with more time to review and give us feedback.” –Adam Rowan, Twelve Three Media

“I plan content several months in advance with room for changes. This buys us time for any timely stories or other pressing work matters. I assign articles each week rather than in bulk because I know my freelancers are juggling multiple clients and tasks. This way, I get confirmation on if they can take the assignment in real time and it’s top of mind.

“My job is to plan in advance, however I want my freelance writers to focus on what’s in front of them – that’s their job. If they aren’t available that week, I am able to quickly reassign to someone else who is available. I do this with each individual freelancer’s bandwidth in mind and always ask for confirmation.

“By planning ahead, this also allows me to be flexible with my freelancers if they need an extension. I want them to be able to do their best without worrying about meeting an unreasonable deadline or having to rush through their work.” –Laira Martin, Vegamour

Set clear expectations

“We tend to set an overarching timeline when we start working on a project, setting objectives and clear expectations from the get-go. Following this, we assign more detailed weekly or daily tasks to ensure a collaborative approach, and keep both sides on the same wavelength. We make use of project management tools such as ClickUp, which help us stay organized and meet deadlines.” –Bogdan Marinescu, Digital Trails

“We assign freelancers work on a per-project basis, month by month. Our intention is that, at the start of the month, the freelancer has a good grasp of what their monthly (and then, trickling down to weekly) workflow will look like. There could be additional projects introduced throughout the month the freelancer would need to agree to.” –Andrew Gottlieb, No Typical Moments
Consider assigning a series of similar articles to the same freelancer
“We assign content by series. The first article is usually written in-house and serves as a reference. The later articles are outsourced as a series to the same writer. Depending on the writer’s pace, we outsource one set of three to five articles per week. The assignments might stretch out as we want to allow the writers to deliver their best work.” –Peter Thaleikis, RankLetter

Streamlining your editing processes

Several freelancer managers emphasized that clear outlines and processes, as well as freelancers who are well-aligned with your guidelines, will shave time off your editing routine. This leaves you valuable hours for other tasks.

As Elliott Brown of OnPay Payroll told us, “If you brief topics well and work with the right people, it should be more of a proofreading process than an editing process. We usually don’t require a lot of revisions, unless something material is missing from a piece.”

These sentiments were widely echoed:

“My initial editing process takes around an hour, and I budget an additional half-hour for any additional revisions the client requests. I find hiring freelancers who are aligned with our writing standards saves quite a bit of work down the road, so thanks to our hiring process, it’s rare we ask a writer to revise their article.” –Amanda Lutz, Clara Agency

“With our detailed outlines, I’d say it only takes our editor one to two hours to edit each article. If the editor rejects the article, she will leave comments on the Google Doc and the writer can amend it in their own time. For urgent articles, our editor will prompt the writer to finish up ASAP, but this is rare. Even so, our writers all have the initiative to revise their articles in 24 hours.” –Rachel Cassidy, Animalso

“Focusing on detailed article structures and alleviating concerns before pen hits paper creates a unique editing process for us. Most of our articles come back to me with very few edits needed. After I provide feedback on their work, our freelancer spends no more than 30 minutes implementing fixes before forwarding the article for final proofreading and publishing.

“When working on a larger set of articles with the same structure and intent, the editing process practically disappears after the first handful.” –Andrey Doichev, Inc And Go

“On average, I spend around 45 minutes editing an article. Revisions are usually not very substantial, so my writers are almost always able to deliver the revised article the same day. I think putting so much effort on the briefing process helps avoid substantial revisions.

“The initial interview also helps me evaluate whether the writer enjoys music and guitars (our niche). If I can tell this, I know they’ll enjoy writing for my website, and this translates into fewer revisions and higher-quality content overall.” –Alan Furth, Really Simple Guitars

“Our editing process is usually fairly instantaneous due to the writing quality of the freelancers we have developed relationships with over the years. Writers rarely have to revise articles. However, on the off chance we need to send an article back, we give the writer 48 hours to make recommended changes.” –Teresha Aird, Offices.net

Using detailed editing feedback to set even clearer expectations is also invaluable:

As Nicholas Martin of Pest Control Hacks shares, “As soon as one of the writers finishes an article, the editor highlights all the mistakes and preferable stylistic changes in Google Docs, and encourages authors to analyze their mistakes and make corrections based on their observation. This way, we reduce the overall number of mistakes in the long run as authors learn to avoid them.”

In conclusion

We hope this inside look at how other freelancer managers work – from briefing to scheduling to editing – inspires you as you build or refine your own processes. Try some of the tips managers have shared above to save time and improve your relationship with freelancers.

And don’t miss our other roundups on managing freelancers!