17 Difficulties and Misconceptions in Freelancer Management [and How to Fix Them]

Struggling with how to best manage freelancers? You’re not alone.

And like most cases, you’re probably wondering how your peers are facing similar challenges.

What are other freelancer managers dealing with on a regular basis, and what steps do they take to get through them?

Today, we dive into answers shared by 23 experienced freelancer managers. Learn from their proven tips to help take your freelancer management (and relationships) to the next level.

10 major difficulties in freelancer management – and steps to solve them

Let’s start by looking at the most common difficulties freelancer managers face, and how they solved them.

1. Helping freelancers connect with the company

“Managing freelancers presents the obvious challenge of helping them feel connected to the company’s mission and standards, while working remotely or sparsely with us. We’ve recently implemented a monthly newsletter for our freelancing team to help them feel ‘in the know’ and provide perks. We also love to celebrate our freelancers who write several articles a week with things like gift cards to their favorite coffee shop, a handwritten card, or a shout-out in our monthly newsletter.” –Amanda Lutz, Clara Agency

2. Setting clear expectations

“All the difficulties and challenges I’ve discovered fall within setting clear expectations. Creating a job description for the role to list out the exact duties and responsibilities is the first step to solving this. From there, I’ve learned having a contract and service level agreement that outlines terms of payment, project outlines and deadlines, and giving notice (to name a few) is essential, because both parties know exactly what is expected in the relationship. It is much more likely to then retain a freelancer at that point because you put the work up front to ensure they know exactly what they are getting into.” –Melissa Reeves, Fortune Avenue Consulting

“The major difficulty was in expectations and reality. We were used to working with the same people who know our standards, so when we started working with freelancers, we faced a whole range of various creative and not-so-creative deliveries.

“Creating a detailed specifications template and customizing for each task has solved the issue. The only thing left is to figure out whether the person is detail-oriented and can stick to our requirements or not. If not, we would be looking for someone else.” –Roman Vasilenko, Rocket Labs

“One of the major difficulties for me was teaching all the newcomers how to do what I need. It appeared that there are so many details in the process that I couldn’t spend hours explaining everything verbally. I ended up creating concise guides to describe the process.

“Now I contact new writers only when they are familiar with the guide, and I guide them through the whole process by sharing my screen in Hangouts Meet and commenting on each step. This takes less than 30 minutes when they know everything from the guide, and there are almost no questions afterward.” –Nicholas Martin, Pest Control Hacks

“Freelancers are remote workers. Training freelancers is only made more complicated by having limited interaction with them. To overcome this, I have learned how to set clear guidelines, as well as goals/expectations to keep them aligned. The entire process of their assignment needs to be described specifically and clearly, and I always have to touch base early on in the project to make sure they are on track.” –David Sides, Second Eclipse

“The biggest challenge is helping the freelancers I manage get into the mindset of the client. When writing for different clients, you have to use different tones, voices, and words. I try to provide this context up front in the brief or, for bigger projects, hop on a call with my freelancers to let them know who they are writing for and what the higher level outcomes are.” –Stefan Palios

3. Communication difficulties

“The most common challenge I face when managing freelancers is poor communication. This fundamental problem can manifest in several ways including missed deadlines, incorrect assignments, and disengaged work. But a disconnect in communication can almost always be found at the root. I generally find our freelancers work and communicate better when you engage with them regularly as peers rather than just throw work at them all the time.” –Thao Tran, Voltcave

“The biggest freelancer challenge has been managing and tracking communication. You have to be clear on what your expectations are. We have a 24-hour response window. If we ask a question, we expect an answer in 24 hours or the next working day. If a contractor can’t work within those parameters, it’s not a good fit. Just like any other job, it has to be a good fit for the client and the contractor. It’s a two-way street.” –Katie Elzer-Peters, The Garden of Words

“Hiring freelancers carries the same problems that come with all remote employees. Communicating via email often causes miscommunications because it lacks tone, context, and nonverbal language. It is vital to be very thorough in assignment briefs to avoid these miscommunications. Phone and video calls also help avoid miscommunications.” –Eulises Quintero, Titoma

“Communication. Some freelancers are in a different timezone, so there have been a few times it was difficult to reach them immediately. What worked was having everybody’s timeline seen on the communication platform, and a set time for every step of the writing process (initial edit, copyedit, etc.) to follow.” –Sander Tamm, E-Student

“Every writer covers topics differently. There can sometimes be a disconnect between how you might write about a subject and what a freelancer will do with it. The way to overcome this is through communication. Some topics are best left to the writer’s discretion, while in other cases it is necessary to provide more guidance.” –Adam Rowan, Twelve Three Media

“The biggest difficulty is in communicating positives along with negatives. As an editor, its easy for me to focus on what needs to be fixed, and I accidentally made a lot of my writers feel like they were doing poorly at their work. I have learned to focus on the positives and use the sandwich method of giving feedback, sandwiching criticism in between compliments.” –Deborah Goldberg, USInsuranceAgents

Looking to improve communication with freelancers? Don’t miss this roundup on communication tips in freelancer management – from the freelancer perspective.

4. Managing freelancers’ varied schedules

“While we love how we can cast a wide net when recruiting for collaborators, staying organized and managing various schedules has been our biggest challenge. We often need to juggle multiple priorities at the same time, and work with freelancers from different backgrounds across different time zones.

“We’ve found using project management software and taking advantage of the latest tech has been a lifesaver. We create customized dashboards for projects in a tool like ClickUp or Trello, and task a member of our core team with overseeing projects and ensuring timely delivery. We also use Slack to communicate internally and share feedback, and avoid unnecessary emails as much as possible. Streamlining our project management process has helped our collaboration with freelancers massively.” –Bogdan Marinescu, Digital Trails

“We’ve been working remotely for a decade. One of our biggest initial challenges was coordinating work, due dates, and turning it in to clients. We solved this challenge by switching over to Trello and using some of their Integrations to automate a good portion of the process.” –Kristina Witmer, Witmer Group

5. Freelancers missing deadlines

“Delivering projects by meeting deadlines is big problem for freelancers. Moreover, it is hard for them to manage timesheets, and send them for approvals. This made us built projects and timesheet management features that are best suited for freelancers, and remote teams. This help organizations to collaborate on achieving bigger goals, and bring the distributed teams in one place” – Fred Wilson, nTask

“Missed deadlines. We resolve this by having systems in place that enable us to fall back on other freelancers in case we need to remain on a tight schedule. We also employ additional writers from Writeraccess in case they come in handy.” –Nikita Chen, LegitGrails

6. Finding the right freelancers for a niche

“We initially struggled to find reliable freelancers who were knowledgeable in our niche. A lot of freelancers focus on quick turnaround instead of quality, especially in a niche as agile as commercial real estate. We ultimately landed on a small handful of reliable freelancers with knowledge of commercial real estate markets and trends, and focused on managing this small team instead of a wide range of writers. Taking this focused approach on a small team made it easier to manage and cultivated better relationships.” –Teresha Aird, Offices.net

“As Latana operates in a niche space (brand tracking software), it can be difficult to find freelancers apt at writing about the topic. I take two approaches to solve this issue. The first is to train the freelancer in the area/topic, giving them a couple of assignments to get an understanding of the area. I give lots of detailed feedback so they can make a good go of the brief. However, if assignments still haven’t approved a few weeks later, I take the second approach and sadly have to say goodbye and look for another person to take their place.” –Joy Corkery, Latana

7. Understanding that freelancers are juggling other priorities

“The biggest difficulty our company faces in managing freelancers is ensuring the work is up to our standards, while also understanding they have other priorities beyond ours. The best thing we can do is to provide consistent, reliable, and well-paying work to make this a mutually supportive collaboration between both parties.” –Andrew Gottlieb, No Typical Moments

8. Finding reliable freelancers

“It can be hard to trust freelancers to produce the work when you start out, however as you continue to work withm, you find the ones you can trust to deliver. It can stink to pay someone who delivers less than stellar work or fails to come close to the promises they made. When this happens, I do my best to communicate how their next choice will affect future work from my company. If they do their best to remedy the situation by taking responsibility and fixing the issue, then all’s good and I’ll hire them again.” –Shannon Peel, MarketAPeel

“It took me a while to find good freelancers. I learned hiring the right people takes time. But, here is how I solved the problem: If you are looking to hire one freelancer, I would hire three to five for a test project, where you give them a sample project to work on (and pay them for it). Hiring can be made effortless and easy right from the beginning with a good guide to pre-employment screening.”

“This is an investment in finding the right freelancer. Whoever completes the project the best is the person you hire for future projects. Doing this saves you money in the long run because you can see if your candidate will be good to work with early on, rather than go through the process of onboarding someone who might not be a good fit.” –Andy Cabasso, Postage

9. Making sure freelancers understand your reader’s intent

“Some writers have difficulties understanding the reader’s intent. The most important thing is to solve the reader’s problem and give them the information they are searching for. We’re not trying to fill out an article with pointless words just to meet a benchmark. I ask them to imagine themselves in the user’s position, including why the user is Googling this specific query, which usually helps.” –Ernests Embutnieks

10. Respecting freelancers’ flexibility

“A freelancer is not an employee, and therefore they are entitled to keep their own hours. Of course, if the freelancer is working alone on a project, this may be fine. However, as soon as the freelancer needs to integrate into an existing team of employees, it is normally better for the whole team to keep similar hours. There are two ways to overcome the challenge of different operating hours: First, include a service level agreement in your freelancer’s contract, ensuring a standard response time during your office hours. Offer your employees flexible hours.

“Also, freelancers are free to move on as soon as their contract is over. There is no obligation for the organization to provide more work, and there is no obligation for the freelancer to accept more work. Whenever I use freelancers to deliver parts of a larger, ongoing project, it can create a problem if a crucial freelancer decides to move onto something new. The immediate solution is to offer the freelancer a longer, ongoing contract. You can also create talent pools by creating a bench of vetted, pre-qualified freelancers for a particular skill or project. You are then not dependent on one particular freelancer and instead, have a number of viable options to resource the next part of your project.” –Harriet Chan, CocoFinder

Misconceptions about managing freelancers

Many myths and misconceptions are still floating around about managing freelancers. Below, managers share their thoughts and shatter seven of them.

Misconception 1: Freelancers are unreliable

“A common misconception people have about freelancers is that they are unreliable or only short-term. Having started at my company as a freelancer, I know when you treat them with dignity, go the extra mile to show appreciation for their work, and present a compelling vision, it can become a long-term relationship that’s more mutually beneficial than you might expect!” –Amanda Lutz, Clara Agency

“That freelancers are not usually available or hard to get in touch with, and the work might not get done in a timely manner. We find these aren’t problems at all, and we attribute our scheduling to helping with this issue. It’s also a vetting process – you have to choose the freelancers who are most likely to work within your confines/schedules.” –Greg Corey, Porchlight

“There is a common misconception that freelancers are mercenary in their dealings with the companies that hire them. In my experience, however, the majority of freelancers care deeply about their work and want to do a great job for the people who give them assignments. Many of them take on freelance work as a full-time or part-time job. They want to cultivate strong relationships with the people who provide them with work so they can contribute to the organization and build their portfolio long-term, rather than just taking on a few assignments and moving on to something new.” –Adam Rowan, Twelve Three Media

Misconception 2: Freelancers can devote all their time to your business

“One of the biggest misconceptions is to expect a freelancer to devote 100% of the time, focus, and energy to your task, while paying for 20% of their time. We were in the same shoes initially and saw this a lot in our clients’ freelancer relationships.

“Freelancers are usually managing assignments from a few clients and perhaps a few different types of services at a time. The better you explain the task and expectations before starting, the healthier relationships and results you will get.” –Roman Vasilenko, Rocket Labs

“I often hear that colleagues think the freelancers we work with have to be available 24/7, and be ready to help when we need them at a moment’s notice. Many people don’t realize that freelancers have customers other than us that they have to tend to.” –Nina Neuschuetz, Case Systems

Misconception 3: It’s way too complicated to manage freelancers

“My personal misconception was that managing freelancers was too complicated. My first attempts were to accomplish as many tasks as possible without anyone’s help because I was afraid other people wouldn’t be able to understand me and complete the tasks on the same level or better than me. I just couldn’t believe there are professionals out there, who are ready to add their soul to the content and online products they make.” –Nicholas Martin, Pest Control Hacks

Misconception 4: Freelancers should only be used as a last resort

“I think there’s still a mentality of businesses using freelancers as a last resort, when dealing with last minute work or needing urgent support. But in the post-pandemic world, I foresee more companies taking a freelance-first approach, and consistently working with freelancers as part of their business model, thus being able to be more agile and adaptable. We’ve implemented this approach for a few years now, and have had the pleasure of working with extremely talented freelancers, who’ve definitely contributed to the growth of our business.” –Bogdan Marinescu, Digital Trails

Misconception 5: All freelancers want to become full-time employees

“One misconception is that all freelancers are looking for a permanent full-time position and they are only freelancing until they find one. Many freelancers have fully embraced the gig culture and love the freedom and range of experiences freelancing provides. The majority of freelancers are freelancing because they love it… and not because they have no other options.” –Katie Elzer-Peters, The Garden Of Words

Misconception 6: Freelancers will automatically save you time, without work on your end

“The hope a lot of people have when hiring a freelancer is that they will automatically come on board and save the manager time. The manager is looking to offload a task, so they hire a freelancer to be responsible for it, and now that manager can focus on other things. But, the thing is, without proper documentation and procedures for the freelancer to follow, they will require much of the manager’s time to actively manage them.” –Andy Cabasso, Postage

“I think at the onset, hiring freelancers seems like a way to have tasks completed without you having to be involved in the process. Freelancers definitely take a burden off you and your daily tasks, but open communication still needs to happen, as with any employee. Eventually, you may reach a point with a long-term freelancer where you don’t need to talk with them as often, but I find it usually takes months.” –David Sides, Second Eclipse

Misconception 7: You can’t create a freelancer role like an employee role

“I think many people think they can’t create a freelance role the way an organization would create an employee role, which is actually essential. Any role working in an organization needs the same clear boundaries, duties, and expectations to succeed. It also makes it easier on you as the manager because you will have agreements and SLAs to reference, and it can reduce miscommunication.” –Melissa Reeves, Fortune Avenue Consulting

In conclusion

We hope these tips will help you overcome some of the difficulties related to freelancer management, and to see through common misconceptions about freelancers and the process of managing them.

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