From the first briefing to the deadline and beyond, communication is key to successfully managing freelancers.
To help in this process, we surveyed freelancers from across the globe to find out what tips they have on how to best manage them. We also asked about their work styles and preferences, and preferred tools for communication, in an effort to encourage transparency in that area.
But first, let’s start with setting the stage for good communication with freelancers. Specifically, what all freelance managers should include in the initial assignment brief.
What type of information is most helpful for article briefs?
Every freelancer has a different preference when it comes to article briefs, but it’s clear that most prefer to have a detailed outline. Include any and all information you think would help the freelancer write the best article.
Here are tips for what you should include in an article outline, shared straight from the freelancers.
“I want to be sure I’m on the same page as management. I don’t want to question what the desired outcome of the piece is. Any and all clear communication of the overall goal of the piece, who the target audience is, and any supporting facts or data they wish for me to incorporate is what I desire the most.” –Vickie Pierre, Expert Insurance Reviews
“For me, it’s the thrust of the piece and the intention behind it. Who is this article aimed at? How should it help them? And what do you hope to achieve with this piece of content (for example, email signups)?” –Kelly O’Hara, Copy Goals
“I find it most helpful to have a working title (or concept), any major ‘must discuss’ points, approximate length of the piece, and if there’s a contributor I have to interview, who that is and their contact info.” –Rachel Tindall, Capturing Your Confidence
“Including external and internal links and providing me with a keyword brief from an SEO software has always been more than enough for me.” –Marcin Stryjecki, Booksy
“I simply need a one- to two-sentence synopsis of an article topic to draft a minimum of 1,000 words. If they want certain keywords included, I will need those to insert throughout the article.” –Imani Francies
“The intended audience of the content. This helps process the briefs in the context in which the article will later be used. When I don’t receive this information from the manager, I ask for it.” –Jabran Kundi, The Stock Dork
“As much detail as possible, including what kind of tone the company would like, and if there are any subheadings they want to include for SEO purposes. My favorite briefs are ones that include a few example articles for me to take inspiration from.” –Phoebe Gill, Your Green Grass Project
“I love when managers share specific examples in their briefs. Unless they’re writers themselves, I find that many managers have a hard time describing what they’re looking for without an example. In many cases, they haven’t written the type of content that they want, but they do know it when they see it, so having them include examples they like is a huge help. If they don’t have an example of what they do want, the second-best options are examples of what they don’t want!” –Camila Reed
“It’s important for me to have all my information accessible from one place. For example, for each project, I receive a step-by-step guide of the process, including all the formalities. That guide also includes links to writing guides. This keeps me organized and helps me not to forget simple yet important steps.” –Melanie Musson, Clearsurance
Consider a freelancer’s time and work preferences
Freelancers might not communicate their time preferences and work styles without your (the manager’s) prompting. But taking the time to find out how they work best – and striving to balance their preferences with your needs – will make the assignment process run smoothly. Whether it’s IVR software, email, or channels like Slack, make sure to discuss this with your freelancers.
Below, freelancers share their time preferences for certain assignments and explain why they work best with those times.
“I am a big self-editor. For shorter assignments, like blog posts or brief articles, I like at least two days to work. One day to get it done, and one more to revisit for edits and rewrites. After pouring hours into an assignment, it’s easy for my mind to become cluttered. I believe having that extra cushion helps me get the brain-break I need to look at what I’ve written with a fresh set of eyes and a clear mind.” –Vickie Pierre, Expert Insurance Reviews
“For regular articles, depending on their length, I’d have one day to one week to complete them, depending on urgency. I always preferred shorter deadlines, because I’d usually postpone the projects on longer deadlines for the last day.” –Marcin Stryjecki, Booksy
“For shorter pieces, I prefer to have about one to two weeks. For longer pieces, like courses and email sequences, I like a month at least. The deliverables should drive the timeline – the more complex they are, the longer I need to complete them well.” –Rachel Tindall, Capturing Your Confidence
“I am usually given my writing assignments on Mondays and am expected to deliver them by the end of the week. This setup really helps in preventing writer’s block, since I can write when I’m most productive.” –Hazel Santos, Skill Success
“It might take two to three days to complete a well-researched, long-form blog post, in my niche at least (B2B, SaaS, marketing). But I’m always grateful when I receive an assignment at least a week or two in advance so I can schedule it at the right time for me. Freelancers love our flexibility.” –Kelly O’Hara, Copy Goals
“I have assignments (usually 2,000–6,000 words each) coming in almost daily, and usually finish them within one week. Unless they are high priority, in which case I do them within a couple of hours. However, I prefer having as much flexibility as possible (one of the main reasons I chose freelancing).” –Denise Mai, Digital Nomad Soul
“I’ve found good quality content takes a lot longer to develop than clients anticipate. If they want content that will truly stand the test of time, they need to be patient. At the same time, it’s important to ship projects and keep moving forward. It’s a balance.” –Karen Miller, KMW Content
“If it’s the first time I’m working with a specific client, I prefer extra time. For a typical blog-style article, I like to have as much as a week for the first piece so I have time to ask questions without missing the deadline. An online conversation can be dragged out for several hours or an entire day as both people answer questions when they have time. I don’t want the question and answer process to cut into my writing time and put me into a time crunch.
“When it comes to clients I’ve already worked with, I’m happy to work on a shorter timetable. Because I already know what they’re looking for, I don’t need as much lead time and can complete most blog-style articles in just a few days. I do like having some room to breathe, though, since I’m managing several clients with a variety of deadlines.” –Camila Reed
“For most short-form articles, having at least three to five business days is a great threshold since it allows me to plan my week better. For long-form articles, having at least two weeks is a must. It gives me time to find sources, outline the piece, write, revisit, and edit the piece before submitting it. Research papers and ebooks are complex projects that require more collaboration, so I work on these projects for three weeks, depending on their complexity.” –Geraldine Orentas, Gerie Media
“I prefer to have a week to complete articles. I feel this is a reasonable amount, while also respecting my time. Depending on the length of the article, I usually have a turnaround time of 48 hours for revisions. However, I never want to promise this, because I can’t predict what my schedule will be when a manager sends a request.” –Andra DelMonico, AnDel Marketing
Top 12 tips for communicating with freelancers
Finally, freelancers get to the heart of the matter – their best tips for managers to improve overall communication. Although they shared a wide range of best practices, several clear trends emerged. Read on to find inspiration for your own freelancer task management workflow.
- Freelancer managers should give freelancers all the detailed information they need in an outline (as the freelancers established above!)
- They should respect a freelancer’s time.
- During the editing phase, managers should give freelancers clear, constructive feedback for improvement.
- Managers should be encouraging and empathetic.
- Make sure freelancers are connected with, and on the same page as, relevant full-time employees.
- And if managers think they’re over-communicating, that’s likely a good thing (as long as it doesn’t take up too much of a freelancer’s time)!
Read on for more details and other communication tips to improve your relationship with freelancers.
1. Clarify goals with your internal team first, before contacting freelancers
“Make sure your internal team is clear on goals, deliverables, and timeline before you communicate to a freelancer. I’ve worked on so many projects that started with one set of goals set by a leader, which then had to shift because they weren’t in the weeds about how things actually got done, or goals communicated by a staff member changed because they didn’t have buy-in from upper management.” –Sarah Duran, Fruition Initiatives
2. Give freelancers as much information as possible for assignments
“Have a clear process on how you work with freelancers and what you expect from them. Having a smooth process makes it easier to onboard multiple freelancers and avoids any kind of miscommunication.” –Seema Nayak, AdChina.io
“Don’t give them just the bare necessities when it comes to information. Introduce them to other team members if their work is somehow connected. Give them all the information everyone else on the team gets, as well as access to sources of information they need. Freelancers may have a different type of contract, but they still need to be just as involved in the entire process as the rest of the team.” –Denise Mai, Digital Nomad Soul
3. Connect freelancers with relevant full-time employees
“Connect freelancers directly with the people they need to work with to get the work done. Oftentimes, freelancers will either work directly with an organizational leader, which separates them from the internal staff who are actually executing the work; or the opposite, work directly with someone who doesn’t actually have any decision-making power. Both of these scenarios can lead to inaccurate communication around project goals and bottlenecks in the process. – Sarah Duran, Fruition Initiatives
4. Use organizational tools to streamline communication
“Set up a Slack channel, or have a dashboard where both parties can monitor tasks and payments easily. Also, make it easy for your freelancer to receive payments –they work hard.” –William Chin, Your Digital Aid
5. Stick with one major communication method
“Choose one method of communication and stick with it. I appreciate managers who use one line of communication when managing work. This makes it fast and simple for me to reference previous communications. It also eliminates the risk of me missing a communication. Managers that use email, Slack, or some other recordable messaging system are the most effective.” –Andra DelMonico, AnDel Marketing
6. If you think you’re over-communicating, that’s probably a good thing
“I’d rather you over-communicate than not communicate at all. I really like using programs like Asana to set clear deadlines for multiple tasks within an assignment. That way, you have every expectation in writing, and who is to do what is clearly defined.” –Vickie Pierre, Expert Insurance Reviews
7. Communicate via video
“I’ve found video to be an underutilized medium when it comes to communicating with freelancers. Many people just find it easier to express themselves over video instead of the written word. It’s also a lot faster for many people and most managers who are short on time. The combination of audio and visual not only make things clearer, but can also help build the relationship since you’re actually hearing the person’s voice. There are dozens of free or low-cost video tools out there but I’m a big fan of Loom.” –Camila Reed
8. Give clear, real feedback for improvement
“Give real feedback so we can improve our work. Giving constructive feedback for each project ensures we can improve and keep bringing you top-level content.” –Rachel Tindall, Capturing Your Confidence
“It’s unlikely you and the freelancer will be on the exact same page from day one. Be willing to put in the work to guide the freelancer in the right direction. This might mean giving clear editorial direction, for example, so their work only gets better and better.” –Kelly O’Hara, Copy Goals
9. Know when criticism is constructive and when it’s unreasonable
“Constructive criticism is one thing and harsh, unreasonable criticism is another. Frame your comments and suggestions in the right way, to give constructive criticism.” –Kelly O’Hara, Copy Goals
10. Respect the freelancer’s time
“Understand we are not employees. Freelancers don’t work for you full time (most likely), so don’t expect us to attend tons of unpaid meetings that don’t really help us do our jobs. We also have other clients we work with, so our availability may vary sometimes. –Rachel Tindall, Capturing Your Confidence
“In-house managers often forget that freelancers are not full-time employees. Recognizing this will make everyone’s work-life better. While freelancers will always try to accommodate clients, managers have to remember that just like they work with different clients/projects, we do too and can’t drop everything to attend to their needs on the spot.” –Geraldine Orentas, Gerie Media
“Once you hire a freelancer and had your initial project meeting, keep subsequent meetings to a minimum and please have at least a mini agenda for yourself and some notes. For myself, it’s much more convenient to have people make comments on a doc and then address those comments rather than sitting in a video conference and going over things. Make sure a meeting is justified before asking for one.” –Rob Swystun
11. Have empathy
“Freelancers sit at a distance. Little bits of context and information are incredibly valuable to them. Take time to answer the questions that seem obvious to you as an employee. A big suggestion is to be willing to meet freelancers in the middle. Most companies want freelancers to jump on their project management tools and adapt to their work culture. But that’s just not realistic for a freelancer juggling many clients.” –Karen Miller, KMW Content
12. Be encouraging
“I think managers can gain a lot by encouraging their freelancers. This helps keep their morale high. When I get a ‘well done’ remark from a manager, I try to put in even more effort in my work. There have been clients who never appreciate the fact that I go out of my way to meet deadlines and always take on urgent projects, yet they get angry at the first mistake I make.” –Jabran Kundi, The Stock Dork
As our freelancers survey has made clear, the more communication you have with freelancers, and the more detailed the communication, the better.
Just be sure your communication respects the freelancer’s time – communication they can easily access and address in their own time is best.
Wondering about freelancer management challenges and misconceptions, from the freelancer perspective? Don’t miss this roundup!