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July 26, 2023 · 5 min read

Successfully managing projects with freelance contractors

In today’s fast-paced and dynamic business environment, many companies are turning to freelance contractors to harness specialized skills and expertise for their projects. In fact, it’s why we do what we do here: to get great companies the kind of talent they didn’t think they’d find.

One thing that comes up time and time again is how to effectively manage distributed contract teams, which requires a different approach than traditional project management. In this post, we aim to provide non-technical hiring managers, who may be working with contract employees for the first time or managing multiple contractors, with essential strategies to ensure successful project outcomes. By focusing on clear communication, monitoring, and motivation practices, you can foster productive relationships with your contract teams and push your projects over the finish line.

Set clear expectations up front

When you’re working with freelance contractors, setting clear expectations from the outset is crucial for the project’s success. When you’re onboarding your contractor, provide a comprehensive project scope, timeline, and list of deliverables to ensure everyone is on the same page. Clear expectations help contractors understand the project’s objectives, deadlines, and the specific results you are looking for.

Furthermore, specifying communication channels, the tools your team works with, and what work hours you’d like to overlap will help to facilitate seamless collaboration. Since contractors may be working from different locations and time zones, establishing a standard mode of communication ensures that everyone remains connected, informed, and on-task.

To maintain accountability, define consequences for underperformance or lack of responsiveness. While this is something we take on internally at, if you’re not working through us, it’s essential to establish a system that encourages contractors to meet their commitments while addressing any issues that may arise promptly.

Focus on regular communication

Maintaining open lines of communication is vital for managing remote contract teams effectively. Share regular progress updates, address blockers, and provide feedback through the contractor’s preferred mode of contact. Regular updates not only keep everyone on the team informed about the project’s status, but it also helps to identify potential roadblocks early on.

Make sure you’re responding to your contractor’s messages and requests in a timely manner, even if you don’t necessarily have the answer. A simple “You know, I’m not sure. Let me check on that and get back to you,” lets the contractor know you’re respecting their time and effort, while also reinforcing a culture of responsiveness and collaboration.

Fostering good rapport is also essential when working with distributed contract teams. Not every bit of communication needs to be about work! Encouraging casual dialogue helps to build personal connections beyond the formal project discussions. Teams that feel comfortable communicating openly tend to be more productive and collaborative.

Time zone sensitivity is also crucial in ensuring effective communication for dispersed teams. Understanding and accommodating different time zones can prevent unnecessary delays and ensure that communication flows smoothly. Finding a few hours a day or week where your contractor can be available at the same time as your in-house team will go a long way in keeping those lines of communication open.

Implement rigorous monitoring

Regular monitoring is necessary to keep projects on track and ensure quality outcomes. Request periodic status reports from contractors, such as weekly or bi-weekly updates, depending on the project’s length and phase. These reports should outline progress made, challenges faced, and plans for the upcoming period. 

Reviewing contractor work, productivity, and billable hours regularly can help identify any potential issues or inefficiencies as they come up, rather than finding yourself faced with larger setbacks later in the project.

Providing substantial feedback, both positive and negative, is critical for contractor growth and development. Recognize and commend excellent performance, but also address areas needing improvement. Constructive criticism fosters a culture of continuous improvement and empowers contractors to grow. This is especially important, as contractors have a tendency to move between companies, which rarely allows for some of that more introspective work you generally find when someone grows over time with a single company.

To align efforts and expectations, make monitoring priorities and key metrics known upfront. This transparency means the contractor understands the project’s core objectives and the metrics that will be used to evaluate progress.

Motivate and engage remotely

Effective motivation and engagement are fundamental for maintaining a productive and committed contract team. Express gratitude and appreciation for work well done; this simple act can significantly boost morale and foster a positive work environment. Who doesn’t love hearing they’re doing a great job?

Recognizing that they’ve reached a key milestone or priority by offering small bonuses or gifts can serve as powerful incentives for contractors. Celebrating achievements, no matter how small, helps create a sense of accomplishment and encourages continued dedication.

Wherever possible, offer schedule flexibility and autonomy to contractors. Empowering them to manage their work schedules and methods can enhance motivation and increase productivity.

Competitive compensation is vital for attracting and retaining top tech talent. While it is essential to offer competitive pay and perks to all team members, tech talent, with its high demand, often expects competitive compensation packages.

Wrapping up

Effectively managing projects staffed by freelance contractors requires non-technical hiring managers to adopt an adapted approach to traditional project management. By setting clear expectations, maintaining regular communication, implementing rigorous monitoring, and motivating contract teams, you can build highly productive relationships and achieve successful project outcomes.

Embrace the opportunity to work with diverse talent and make the necessary investments to create a collaborative and thriving environment for your contract employees. Remember, understanding what developers want and fostering authentic connections can go a long way in wooing and retaining top tech talent for your projects.

With these strategies in mind, you’ll be well-equipped to navigate the challenges and reap the rewards of managing contractor teams effectively. By building a strong and motivated contract team, you can drive innovation, achieve outstanding results, and ultimately lead your projects to success.