8 Things Freelancers Wish Managers Knew About Freelance Challenges

Are you a content manager looking for tips to improve your relationships with freelancers? This unique roundup might help you out. It offers a glimpse into the challenges and issues freelancers face, from the freelancers themselves.

We asked freelancers to bring to light – and debunk – the biggest freelancer misconceptions. They also open up about the biggest challenges they face, and how they can work together with their managers to overcome them.

And finally, our freelancers share some insights to help managers learn even more about the freelancer perspective.

8 misconceptions about managing freelancers

Freelancers share eight common misconceptions they encounter, and set the record straight for how to cultivate a strong working relationship.

Misconception 1: Freelancers can work for you 24/7

“Managers sometimes assume they are your only client. They also forget freelancers don’t work 24/7. I sometimes have to explain that I cannot complete work within hours of receiving a request. I also don’t work weekends, which can be surprising for managers.” –Andra DelMonico, AnDel Marketing

Misconception 2: Freelancers have lots of wiggle room for turnaround

“One of the biggest misconceptions managers have about working with freelancers is that freelancers have a lot of wiggle room in terms of turnaround and should be able to get things done last-minute. On the contrary, since we have multiple clients we work for, we need to make sure we are highly organized with our time.” –Seema Nayak, AdChina.io

Misconception 3: Freelancers work for clients rather than with clients

“Many managers assume freelancers work for them. I personally think freelancers work with clients. Freelancers should be seen as business partners and experts in their field who are happy to contribute to a project. There is a significant difference in the perceived value, which can have an impact on collaboration and performance.” –Denise Mai, Digital Nomad Soul

Misconception 4: Full-time employees produce better quality work than freelancers

“One common misconception is the quality of work is subpar or not as creative as a full-time employee. I actually believe that sometimes, the quality is better or more creative because of the wide array of companies freelancers usually work with.” –William Chin, Your Digital Aid

Misconception 5: Freelancers should upload and publish content without added compensation

“The most common misconception is that I will add content to the website directly or upload to social media directly for no fee when it wasn’t part of the project. Managers think uploading content directly to the site gives freelancers more freedom. It doesn’t. It just adds another task and should be paid for.” –Jabran Kundi, The Stock Dork

Misconception 6: Freelancers don’t need you to reach out

“A big misconception is that freelancers don’t need any human interaction and will just wait for you to reach back out. Many times, I’ve seen freelancers ghost managers after the managers don’t have a project for them for a long period. You have to build a relationship with them as an employee, even if they are a contractor, and build trust and loyalty for your project. Remember, freelancers are more than just content machines.” –Amberlynn Fraser, Oh Black Betty Agency

Misconception 7: Freelancers don’t follow a schedule

“One of the biggest misconceptions about freelancers is that we don’t follow ‘office’ hours. While our schedules might be more flexible, most of us still try to follow an office schedule that allows us to find a work-life balance.” –Geraldine Orentas, Gerie Media

Misconception 8: Freelancers are interchangeable and dispensable

“One misconception is that freelancers are interchangeable and dispensable. Good talent is hard to find, whether it’s a staff member or freelancer. When you find someone who is good at what they do, you’ll be much more successful if you engage with them regularly instead of having to onboard a new person every time to your company context, goals, and branding. In order to do that, make sure they know how much you appreciate them and that you’d like to engage with them on future work.

“On the flip side, don’t waste time with freelancers who don’t deliver quality work. Starting with a trial project is a great way to see what people can do and gauge their fit with your organization before engaging in a larger contract.” –Sarah Duran, Fruition Initiatives

Challenges freelancers face

What are the biggest challenges freelancers face while completing assignments and holding often various self employed jobs? Learn what they are, and how managers can play a role in alleviating them.

Not knowing the expectations from the start

“I think most freelancers struggle with expectations. This is why I like to set them early on in the collaboration process. Expectations about our ways of communication, my involvement with the project, and the creative freedom I’m allowed. Having a conversation about these topics when you first start working together is best. Otherwise, both parties can feel frustrated if they’re not getting what they wanted from this collaboration.” –Geraldine Orentas, Gerie Media

Making sure managers are understanding of their time

“As a freelancer who may not have traditional hours, I think the assumption is I’m available all of the time – that because I’m not at a nine-to-five, I have more free time to tackle my work. But that could not be farther from the truth. Many freelancers work multiple jobs, and are constantly juggling it all along with their personal lives.

“If anything, freelancers need managers to be understanding of our personal time. This isn’t to say freelancers shouldn’t have deadlines or structure. But if both parties can establish a clear-cut timetable, and be willing to communicate openly about scheduling challenges, the job and the relationship become much easier.” –Vickie Pierre, Expert Insurance Reviews

No clear, consistent communication

“Setting boundaries was a definite challenge at first, and asking for enough money to make the project worth working on – especially the longer ones. Being straightforward in all communication and expectations upfront is key.

“As a manager, I think it’s important to be cognizant of your relationship with freelancers. It takes a conscious effort to make us part of the team when we don’t work there full time, especially for long-term partnerships.” –Rachel Tindall, Capturing Your Confidence

“Communication is the main difficulty. If the manager is too busy to quickly respond to any questions about the assignment, then it’s helpful if they delegate someone to do so. This keeps the project moving and the deadline realistic.” –Emily Messing, EJM Design

“The number one challenge is always communication. On my end as a freelancer, I could do a better job asking the right questions ahead of time. On the manager’s side, it’s better if they give too much information rather than too little.” – Danavir Sarria

The main difficulty for me as a freelancer in the past came from fast-growing teams of freelancers with no clear communication of responsibilities or proper training. I think it is essential for managers to take the time for an onboarding process. This includes an introduction of new freelancers to everyone who works with them directly or indirectly.

“Job responsibilities should be clear to everyone. And all processes and best practices should be documented so everyone is on the same page for how tasks are executed. On top of that, I think regular team meetings are essential if several people are working in the same process – that’s just as important for freelancers as it is for employees.” –Denise Mai, Digital Nomad Soul

“I experienced a lack of communication during the first year I worked with one company. It was difficult to work with confidence when I wasn’t sure if my work was acceptable. Once the company restructured, I was placed under a manager. We started communicating with each other and teammates regularly through Slack. I received regular feedback and evaluations. The difference was night and day.” –Melanie Musson, Clearsurance

Don’t miss our other roundup for more tips on communicating with freelancers!

Personal time management

“The most difficult part about freelancing is juggling multiple jobs at a time. Aside from writing, I also do some SEO-related jobs, which have stricter turnaround rules for tasks. I had to learn how to manage my time more effectively to meet deadlines.” –Hazel Santos, Skill Success

“I find sticking to a schedule extremely hard. One way I overcome this is by taking on work with tighter deadlines. This may sound counter-intuitive, but a tight deadline helps me avoid distractions and get to work. My best contracts are the ones where I have to turn in work on a daily basis. They help me develop a routine that is essential for any freelancer.” –Jabran Kundi, The Stock Dork

“Time management is the biggest challenge as a freelancer. I strive to have a consistent workflow, but this can become difficult when a manager has poor organization and sends work requests at the last minute.

“It’s also difficult when a manager doesn’t know what they want. It creates a cycle of submitting work and receiving feedback. A freelance manager can make things easier by staying organized themselves and not waiting until the last minute to send requests. It helps when they have a clear plan and direction for each article. This eliminates the endless stream of edits as they change their mind on what they want an article to be about.” –Andra DelMonico, AnDel Marketing

Doing research in a short period

“Some articles require more research than others and research is the longest part of writing articles. You have to double-check the information you find for an article, which can be time-consuming when you consider the amount of information detailed in a 1,000-word article. To stay within your contract’s time limits, sometimes you have to sacrifice thorough research.” –Imani Francies

Disconnect between writing skills and niche expertise

“About six months ago I completed a test piece for a potential new client. Although they appreciated my writing and skills as a content creator, they felt I didn’t quite have the IRL expertise to talk about the subject matter on a personal level.

“I’d say this is a toughie for anyone who wants to hire a freelance writer. If you think about it, not all professionals in the industry have writing/content marketing skills, and not all writers/content marketers have professional skills in that industry. In other words, I might be able to write a nice piece for your farm’s website but I’ve never actually planted a seed in a field before.

“I think the onus in this case lies with the content manager, project manager, or editor. They can add the polish and bring in personal expertise where appropriate. Or you could work together to get input, quotes etc. from industry experts to level up the content.” –Kelly O’Hara, Copy Goals

Matching a manager’s needs to a writer’s skillset

“Managers need to know the writer they’re hiring has the right skill set, and the writer needs to understand what the manager wants. While this sounds simple, they are the biggest challenges in the writer-manager relationship.

“Managers should really think about the writers who worked well for them in the past and try to pin down what made them different.

“Managers should also have a list of ‘deal breaker rules’ they won’t accept. I’ve seen dozens of managers hire someone because they really needed a writer at that moment, only to be disappointed because they didn’t match their requirements in the first place. Stick with your deal-breaker rules and you can save everyone a lot of headaches.

“Also, when it comes to freelancers, don’t be afraid to ask questions. Share examples and create checkpoints. There’s nothing more frustrating than writing a massive piece only to be told it’s completely wrong. While the manager is partially to blame there, freelancers can head this off by sharing drafts and asking questions. Build check-in points where you can confirm you’re on the right track. If it’s my first time working with a client, I’ll always share an outline of the first piece before I dive deep into the actual writing.” –Camila Reed

Getting fair pay

“One of the biggest challenges I’ve faced is getting companies to pay fairly. Equal pay for equal work is important to me, and often if you come from an Asian country, companies expect you to charge less for the same quality of work. I think in the present time, this is a really important aspect for everyone to think about. I overcame this by politely declining work if the client didn’t meet my rates. And if there was a conversation, making them aware of how important it is to pay everyone fairly.” –Seema Nayak, AdChina.io

Best practices and tips for freelancer management

What’s the number one tip for managing freelancers, according to the freelancers? We’ve got your insider info right here.

Carefully track freelancer responsibilities

“Track daily responsibilities so you know what exactly each freelancer is doing and which tasks they have completed. This will ensure everyone is being compensated accurately for the work they complete.” –Imani Francies

Communicate, communicate, communicate!

“Communicate clearly and often. As a freelancer, I don’t want to ever doubt whether I’m getting you what you want. So feel free to steer me in the right direction, make corrections, and be clear in what you want for me and by when.” –Vickie Pierre, Expert Insurance Reviews

“I’ve worked with some fabulous editors and content managers over the years. Those who I consider to be the fabulous ones keep a clear line of communication open about projects, their progress, and my involvement. They’re well-organized and I know exactly what they require of me.” –Kelly O’Hara, Copy Goals

Remember that freelancers are not your full-time employees

“We’re doing work at a project or hourly rate, so if you want more (including attendance at a meeting), you need to pay for that time. Most likely, you’re not the only client we have, and although we (hopefully) enjoy all the clients we work with, if all of them scheduled meetings without paying for that time we’d never be able to get anything done.” –Rachel Tindall, Capturing Your Content

“Managers should understand that their freelancers are not exclusively tied to them. Thus, they should provide enough consideration in turnaround and communication. Freelancers tend to have multiple projects and clients at a time. While it’s okay to ask for continuous communication, things might not go well if a manager expects freelancers to constantly be there as if they’re full-time employees.” –Hazel Santos, Skill Success

Set a regular schedule for freelancers, possibly well in advance

“It’s great to have a regular schedule of work with a freelancer. This could mean sending out briefs and content needs on the first week of every month. This helps freelancers plan their time well and prioritize your work since they know what to expect.” –Seema Nayak, AdChina.io

Integrate freelancers into your team

“If you want to keep freelancers in the long run, make them part of the team. Introduce them to the other team members. Invite them to meetings. Keep them updated on new information regarding the project. Give them access to all the data they need for their job. Check in every once in a while to see if there is anything else they need. Don’t treat them as an external resource you can replace at any time. As with anyone else, if your freelancers feel valued and integrated, their performance can increase significantly.” –Denise Mai, Digital Nomad Soul

Consider letting freelancers set their own deadlines (within reason)

“Assuming the manager has enough flexibility, allow the freelancers to determine the deadlines themselves. Freelancers who fit their work in their schedule always perform better and have less stress.” –Jabran Kundi, The Stock Dork

Set clear standards

“Don’t be afraid to take the extra time to explain what you’re looking for. A skilled writer can take on several different styles and tones, but they need the right direction to pull it off.

“Consider the extra time explaining as an investment. There are some clients that I’ve worked with for years. I know exactly what they want because they took the extra time to explain and now they have a real asset in me!” – Camila Reed

“Freelancers want to deliver a quality piece of work. However, there’s a learning curve. Every manager has a set of standards, and invariably, they forget to communicate some of these. It helps when a manager keeps this learning curve in mind. Once a freelancer learns what you need, you can depend on receiving consistent and quality work.” – Andra DelMonico, AnDel Marketing

Pay your freelancers competitive rates, and refer them to your peers

“Finding someone you can rely on and come back to again and again is invaluable. Compensating people competitively and recommending them to others are two ways you can show a freelancer that you appreciate their work. Basically, show them that you respect them as fellow business owners.” – Sarah Duran, Fruition Initiatives

Wrapping up

Hopefully, these insights from freelancers have helped shed some light on ways to improve your freelancer relationships and become a stronger and more understanding freelancer manager.

Searching for more information on improving communication with freelancers? Don’t miss this other roundup from a freelancer’s perspective!