Effective freelancer management practices

Project tools
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Yuliya Mishchanka profile icon
Yuliya Mishchanka

No matter what people say, there will always be small projects that require professionals but don’t justify a full-time position. That’s where freelancers come in. But they operate by completely different rules than full-time employees — and in this article, we’ll explain exactly how.

Key takeaways

Icon with OK

Freelancers require a different management style due to the specifics of remote work and multiple concurrent projects

Building strong, long-term connections with freelancers pays off through increased efficiency in future projects

Modern management and communication tools are critical for coordinating remote work

The realities of freelance

Independent specialists, especially if they’ve been in this state for quite some time, come with a side of very intricate details – understanding these is the key to building proper communication and fruitful collaboration:

  • Communication barriers. Freelancers work remotely, often in different time zones, and may not always respond to messages quickly. The lack of regular face-to-face contact makes it harder to convey context and project nuances.
  • Quality and deadline control. Unlike full-time employees, freelancers juggle multiple projects at once, which can affect prioritization and meeting deadlines.
  • Integration into corporate culture. Freelancers are not immersed in the company’s values and processes, which may lead to mismatched expectations and outcomes.
  • Freelancers have different motivations. They are not building a career within your company and don’t rely on corporate perks. They are driven by interesting tasks, fair compensation, and the opportunity to add strong cases to their portfolio.
  • Their work context is fundamentally different. While your in-house employee is focused on one project, a freelancer is juggling several clients, each with its own requirements and cultural specifics.
  • They work for results, not for the process. Freelancers optimize their time and work methods to achieve the end goal. Attempts to impose internal company processes often reduce their efficiency, or may even result in them ending the collaboration faster than you expect.
Meme about communication with freelancers

Remember – freelancers do exist in a completely different cultural paradigm. They might enjoy a certain sense of independence, but it also comes with a constant feeling of uncertainty and social isolation.

Your cozy workplace might feel stuffy from time to time, but it is, in fact, a very nice grounding point.

Freelancers, meanwhile, have to make do without that constant “grounding” in a stable, solid job. A perfectly nice way to live, sure, but keeping these intricacies in mind will help you communicate with them better.

Smart team choices

You won’t pick your next outsource team using the same templates you’ve used for the in-house workers. Not because the first or the second are inferior to their counterparts in any way, but because the way they measure success is slightly different.

Here are a couple of things to keep in mind:

  • When evaluating candidates, pay attention not only to their portfolio but also to their communication skills. Set up a video call — it will help you assess how comfortable communication will be during the project. Ask questions about previous projects, especially about how the candidate handled complex tasks and dealt with changes in project requirements.
  • Check references from previous clients. Don’t hesitate to reach out to past clients directly — most are willing to share honest feedback about the freelancer’s work.
  • Create a small test assignment to assess the candidate’s real skills and approach to work. Just make sure to pay for such tasks — this shows respect for the freelancer’s time and helps you get higher-quality results.

You’ll be seeing these people via digital means only, so make sure there will be no low-ping static between you.

A 2022 study by Raluca Moise and Anca Anton looked at how freelancers build communication skills through online communities. By analyzing Facebook groups for communication freelancers, the researchers found that these spaces help freelancers share knowledge, solve problems together, and improve how they collaborate. The study shows that being active in such groups isn’t just networking — it’s real-time practice for communication, which is key in freelance work

The importance of trust

Micromanaging is, in general, a very shady concept that does more harm than good. Micromanaging freelancers, though? People who strive for independence and creative freedom?

A very good way to kill any kind of good partnership you were going for.

Here’s how to keep your trust levels steady and keep an eye on freelancers' efficiency and productivity levels at the same time:

  • A clear technical brief is the foundation of any project. Describe not only what needs to be done, but also why. Context helps freelancers better understand the task and offer more effective solutions. Include examples, references, and detailed requirements for the deliverables.
  • Provide regular feedback. Don’t wait until the project is finished to share your comments. Weekly check-ins help adjust the work direction and avoid major revisions.
  • Document all decisions. What seems obvious during a conversation can be interpreted differently a week later. Keep meeting notes, log changes to the brief, and confirm agreements in writing.
  • Contracts should clearly define the scope of work, deadlines, payment terms, and responsibilities. Include clauses on confidentiality and intellectual property. Don’t save money on legal support – a well-written contract protects both sides.
  • Create a centralized project space. All information should be in one place – documents, deadlines, everything in Taskee. Freelancers shouldn’t have to dig through email chains or request links repeatedly.
  • Use objective metrics wherever possible. Website loading speed, sales funnel conversion, and lead count – measurable indicators help avoid disputes over work quality.
  • Fair payment is the basis for long-term relationships. Pay on time and don’t try to cut rates just because a task seems “simple.” Remember: freelancers work not only with their hands, but with their heads, and their expertise has value.

Some of the most respected freelance platforms — like Upwork, Fiverr Pro, Toptal, and Expert360 – build trust through strict vetting, transparent reviews, and secure payment systems. Toptal, for example, accepts only about 3% of applicants, offering clients highly screened experts. Upwork and Fiverr Pro verify freelancer identities, showcase client feedback, and hold funds in escrow until work is approved, protecting both sides. These systems reduce risks for clients and signal to freelancers that their work will be fairly evaluated and paid.

Motivation for freelancers

Like working with that one guy from another country, but he refuses to become an in-house employee? Pieces of paper with some scary numbers on them are not the most efficient way of keeping freelancers with you for longer than you both initially planned.

Try some of these, and you’ll get yourself a trusty collaborator:

  • Professional development matters not only for full-time employees. Give freelancers the opportunity to work on interesting and challenging tasks. Good freelancers choose projects not just for the money, but also for the chance to grow professionally. Complex projects, new technologies, and unconventional solutions are what motivate talented people.
  • Share your project development plans — this helps freelancers see the long-term perspective of your collaboration. If you know that you’ll need similar expertise in three months, let the freelancer know in advance. This allows them to plan their workload and reserve time for your projects.
  • Flexibility is one of the main advantages of freelancing. Don’t try to control every working hour. Focus on the results, not the process.
  • Recognition works just as well as financial rewards. Public appreciation, LinkedIn recommendations, or mentioning freelancers in your company’s success stories motivate them and strengthen your reputation as a good client.

Honestly, these you should do for all of your employees, in-house or not, but that’s a story for another day.

Resolving conflicts

It didn’t work out in the end? Ah, well, that’s life for you. Sometimes, no matter how you plan and prepare, things just don’t work out.

Don’t worry, though. A bit of pre-planning and open-mindedness, and any conflict will be promptly resolved, or, at the very least, won’t cause any serious damage to your business plans:

  • When conflicts arise, look for the cause in the system, not in people. Most problems happen due to unclear requirements, missing processes, or unrealistic expectations.
  • Document all changes and additional requests. Scope creep is the main enemy of freelance projects. Any expansion of tasks should come with a revision of the budget and deadlines.
  • Have a plan B. Sometimes collaboration doesn’t work out – and that’s okay. Build extra time into your schedule for finding a replacement and handing over the work.

And really try not to make an outsourced employee a scapegoat, even though it’s one very guilt-free way of liberating yourself from any kind of responsibilities. The failure of the team is very often the failure of the management first and foremost, and this rule applies here better than anywhere else.

Measuring success

Tracking whether these nice fellers you’ve hired on UpWork are doing their job in all the right ways is also a challenge – traditional ways don’t work all that good here.

TLDR: it does require a bit of communication (horrible, we know) to actually understand if your freelancers are producing good results

  • Track key metrics: task completion time, number of iterations before final approval, budget adherence, and overall satisfaction with the results.
  • Hold regular retrospectives not only with freelancers but also within your team. What can be improved in the processes? Which tools should be introduced? Where is time being wasted?
  • Maintain a knowledge base of best practices and common mistakes. This will help new managers quickly reach an effective level of working with freelancers.

Interesting fact Icon with eyes

A study by Upwork found that by 2028, 73% of teams will include remote freelancers, and companies with established freelance management processes save an average of 40% of time when launching new projects.

Related articles:

To better understand freelancer motivation and career paths, check out our article How to become a freelance project manager: A step-by-step guide.

Want to dive deeper into successful communication strategies? Read How to collaborate effectively with remote teams: Tools and tips.

Learn how to ensure accountability and monitor results without micromanagement in Remote accountability: Keeping teams productive.

Conclusion

Freelancer management is a balance between control and trust. Strong teams see freelancers not as substitutes, but as partners with expertise and a fresh perspective.

The key is respect, clarity, and a long-term mindset. And to simplify collaboration with freelancers, use platforms designed with their specifics in mind — like Taskee.

Recommended reading Icon with book
Book about the impact of AI and freelancing on work

"The Human Cloud: How Today's Changemakers Use Artificial Intelligence and the Freelance Economy"

A strategic vision of the future of the freelance economy and methods for integrating independent specialists into corporate processes to maximize business results.

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Book about building trust in business

"The Trusted Advisor"

A methodology for building trust-based relationships with external partners and consultants by understanding their motivation and creating mutually beneficial cooperation.

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Book about negotiation and reaching agreements

"Getting to Yes: Negotiating Agreement Without Giving In"

A classic guide to principled negotiations, essential for effectively agreeing on terms and resolving conflicts with freelancers.

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