The rise of remote and freelance work in the IT sector has provided employers with greater flexibility, access to a global talent pool, and enhanced cost efficiency. However, every rose has its thorn, and managing a remote freelance tech team — or a hybrid team of freelancers and in-house members — poses significant challenges. Managers often find it difficult to ensure effective communication, maintain productivity, and foster engagement and team cohesion.
None of these challenges is insurmountable, though. Let’s take a closer look at the most common ones, along with some actionable strategies to tackle them.
1. Communication barriers, including time zone differences
The most fundamental challenge in managing a remote freelance team is ensuring clear and consistent communication. Freelancers may be located in different time zones, come from diverse backgrounds, and speak different first languages. These factors may cause misunderstandings and delays.
Solutions:
- Set clear communication protocols and centralize updates and discussions on a primary platform. Plan each project in detail, breaking them into manageable tasks with specific deadlines. Communication tools like Slack and Microsoft Teams can streamline conversations, asynchronous or not, and project management tools like Asana can keep everyone updated on project progress.
- Create some shared documents with all the essential knowledge for your freelance team to use when you’re not available. These resources can include answers to questions, step-by-step guides (you can leverage screen and camera recording tools like Loom to create tutorial videos), and more — think of it as handing on the baton in a relay race. Ensure the documents are regularly updated.
- Encourage regular check-ins to bridge any communication gaps, including one-on-one video meetings. Some members may feel more comfortable discussing issues and doubts in a one-on-one video call.
- If your remote freelance team works across different time zones, consider establishing core work hours at overlapping times, then schedule recurring team meetings at those mutually convenient times. In their book “REMOTE: Office Not Required,” Basecamp founders Jason Fried and David Heinemeier Hansson recommend “a good four hours of overlap to avoid collaboration delays and feel like a team.”
- Consider hiring freelancers in your time zone for convenience. Companies like Jobshark, Proxify, and Relevant offer skilled freelance developers who work within the client’s time zone.
- Last but not least, promote cultural awareness and sensitivity through training and inclusive communication practices.
By implementing some of these solutions (the ones that best suit your project), you may discover that it’s an advantage that your team is not sitting next to one another all the time. This arrangement reduces friction and pushes you and your team to establish effective and productive processes.
2. Building team cohesion
Remote freelancers may feel disconnected from a company’s goals and culture due to the lack of physical proximity. This sense of detachment can lead to decreased motivation and negatively impact collaboration. As a result, work may become more transactional rather than focused on teamwork and common goals.
Therefore, to ensure the success of your project, it is essential to foster a sense of belonging within your remote freelance team. But how can this be achieved?
Solutions:
- It’s key that your freelancers use the same tools as your permanent staff. While many major freelancing platforms may not permit this, you can consider alternatives like Jobshark or Proxify, which allow clients to use their own communication tools with freelancers, enabling them to build a good team spirit.
- Encourage interaction through online brainstorming sessions and team-building activities — such as coffee breaks or “get-to-know-you” and icebreaker games. If possible, organize in-person meetings once or twice a year.
- Every worker wants to understand the direction they’re heading in and the purpose of their work — and freelancers are no different. So, don’t let them lose sight of the bigger picture. Ensure they know how their work contributes to the company’s goals, and make an effort to share company updates with them.
- If you’re working with freelancers nearshored in Europe, it means they’re just a short, low-cost flight away from your office. It makes it easy to meet in person occasionally.
- Everybody wants to feel seen and appreciated. Establish a system where freelancers receive recognition for their efforts. Celebrate milestones and successful project completions, as well as birthdays.
3. Tracking productivity and performance
When physical supervision isn’t possible, managers may feel uncertain about whether freelancers are using their time effectively. This creates a dilemma: on the one hand, micromanaging is counterproductive and erodes trust; on the other hand, as a manager, you still need visibility into freelancers’ progress to meet deadlines and ensure quality. So, what to do?
Solutions:
- Set clear expectations and establish measurable goals for each project. Utilize project management tools to monitor progress; options include Asana, Jira, Trello, ClickUp, or Basecamp.
- Focus on outcome-based performance metrics rather than strict time-based monitoring.
- Foster a culture of transparency and consistency. As you encourage freelancers to provide regular progress updates, make an effort to consistently deliver on your promises as well. A straightforward, structured approach to deadlines can go a long way in building mutual trust.
- Schedule regular feedback sessions to help freelancers understand performance expectations and make necessary improvements.
4. Ensuring quality and full-time commitment
Some IT freelancers work on multiple projects for different clients, which may impact the level of attention they give to each project. Without regular oversight, ensuring they meet your quality standards can be challenging — and even confirming their full-time commitment, if that was agreed upon, can be difficult.
Solutions:
- Partner up with freelance platforms like Jobshark to access qualified IT freelancers who can commit exclusively to your project. Another advantage of using Jobshark is that it allows you to use your preferred communication tools to manage the developers, making it easier to ensure that everyone on your team is aligned regarding expectations and quality standards.
- Make sure that your freelancers have reliable equipment that matches the quality of your in-house team’s. Although remote IT freelancers often use their own devices, it is advisable to check compatibility with the equipment used by your in-house team. If you see a considerable gap, you can invest in purchasing and lending compatible equipment for them that will be handled back (for example, via mailing) when the contract terminates.
5. Dealing with legal and administrative hurdles
Hiring freelancers globally brings legal and administrative hurdles, such as varying tax laws, contracts, and payment methods. Ensuring that you’re compliant with international labor laws can be a daunting endeavor. While working with legal professionals who specialize in international freelance contracts is an option, it is also costly and time-consuming.
Solution:
- A straightforward approach is to use freelancing network platforms like Jobshark, which can handle compliance, payments, and taxes for you. You’ll receive a monthly invoice for the work completed, which helps ensure that your business stays free from any tax or compliance issues. This type of partnership ensures you get only the best part of hiring internationally — access to a global talent pool at competitive rates — without any compliance issues.
Key takeaways
While remote freelance teams are revolutionizing the tech industry, it isn’t always a bed of roses. Challenges do exist, but they are no reason to simply go back to traditional work settings (in-house and onsite). Instead, you can adapt to directly address the challenges and turn them into opportunities.
By focusing on building trust, setting clear expectations, fostering a sense of team cohesion, and partnering up with suitable freelance platforms to ensure compliance, managers can lead remote freelance tech teams to success.
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