How To Manage Freelancers & Remote Contractors Without Losing Sleep

Working with freelancers can save a lot of overhead costs. That’s why 94 percent of organizations surveyed by Upwork report utilizing remote workers. However, managing freelancers remotely can be quite challenging.

Common challenges when working with freelancers are:

• Missed deadlines,
• Work quality,
• Lack of communication,
• Lack of trust,
• And, hiring freelancers

In this article, you’ll learn how to manage freelancers and independent contractors while overcoming these challenges.

Let’s get started.

Missed deadlines

Most clients don’t realize this. But, freelancers are often juggling multiple projects. Last-minute requests from clients can throw a spanner in the works. Or, an emergency may derail a freelancer’s schedule.

For a freelancer, it’s only a slightly delayed delivery. But, this delay could disrupt your entire schedule. 

How to manage freelancers to meet deadlines consistently

Here’re a few ways you can get work done from freelancers on time.

• Agree on a clear deadline: Ensure that both you and the freelancer are in agreement about the deadline. Make the deadline clear, including a specific date. Don’t forget to account for time zone differences. 
• Use milestones for larger projects: When working on larger projects, break down the project into manageable milestones. Review the outcome at the end of each milestone to make course-corrections.
• Plan buffer periods for a deadline: Re-work is a major reason for missed deadlines. Wherever possible, plan to get the freelancer’s work delivered before you actually need it. This allows for delays and re-work if required. 
• Plan for off-days: Like your employees, independent contractors also need off-days. These can be public holidays and vacations. When planning work, ask the freelancer to let you know in advance. So you can plan work accordingly.

Tools to help meet deadlines

Most project management tools come with task management features. These can help you deliver projects on time. Trello, Asana, and Toggl Plan are among the popular project management tools.  

Toggl Plan’s Project Timeline tool helps you visually manage work delivery. Along with task deadlines, you can also add color-coded milestones to your plan. Plus, you can also share a read-only view of the Project Timeline with the contractors.

In addition, you can also create a separate plan to track vacation and other off days.

Work quality

Finding contractors that are reliable in terms of quality can be a challenge. And as freelancers work with multiple clients, chances are that the quality of work will slip.

Poor quality of work often results in re-work. It, in turn, adds up delays and project costs, often resulting in failed projects.

How to get better quality outcomes

Freelancers deliver what you ask for. You can get quality work done by clearly explaining what you need. Here’s how:

• Have a clear outcome: Both you and your contractor should agree upon an outcome. Define the outcome clearly in terms of quality, quantity, price, and delivery. When things are not clear, ask, and encourage questions.
• Create a quality checklist: This checklist includes the quality checks that are performed before the freelancer delivers the outcome. That way, there’s no ambiguity when it comes to the quality of the delivered work.
• Provide all information needed for the task: It’s your responsibility to provide all the inputs a freelancer needs to complete the task. This information can quickly become lost in email and chat messages. That’s why it’s critical to keep all the necessary information in one accessible place. This way, you can prevent delays in to-and-fro communication.
• Accept & provide regular feedback: Once a task or milestone is completed, exchange feedback with the freelancer. This way, you can continuously improve the outsourcing process. Plus, it helps the freelancer perform the next task better. Feedback might be specific to the project, how they communicated, or even something broader like tips on working remotely.

Tools that help improve work quality

Dedicated checklist apps like Process Street and Checkli help you create checklists for recurring tasks. 

A better way, however, is to use task management apps that come with checklists.

In Toggl Plan, you can add a checklist to a task. In addition, you can also include a detailed description and attach files to a task.

Lack of communication

A common concern that clients have with freelancers is communication (or lack of it). Sometimes freelancers go into hiding and stop communicating completely.

Maybe the contractor found other work. Or, maybe they’re blocked and are slipping on a deadline. Or, simply going through a bad situation.

In any case, a freelancer blacking out all communication is one of the worst things that could happen to your project. 

How to manage independent contractor communication

Here’s how you can maintain regular contact with your freelancers:

• Communicate expected workloads beforehand: Let your freelance workers know the quantity of work they can expect from you in advance. This helps freelancers plan their work better. And, as a result, prioritize your work higher.
• Encourage freelancers to communicate delays early: Freelancers often tend to hide when work is blocked or delayed. Encourage them to let you know of such delays. That way, at least, you get a window to re-adjust your project’s schedule.
• Open synchronous communication channels: By default, most of your communication will happen over asynchronous communication channels such as email or a project tool. However, make it easy for a freelancer to connect with you via phone or chat, in case of an emergency.
• Be patient: Freelancers value independence. Send a message and wait for a reply. Also, don’t constantly check in on the work status. Instead, mutually decide on a schedule for updates and stick to it. 

Tools that help improve communication with freelancers

Most project management tools document task information. Also, they help users collaborate via task comments. 

In addition, teams also use some kind of instant messaging or chat software such as Chanty or Slack. These apps are great for quick questions, feedback, and reminders. Plus, they also integrate well with other tools, including project management apps.

Lastly, Zoom and Google Meet are great tools for face-to-face meetings.

Lack of trust

Incomplete projects, poor quality of work, lack of communication are just a few of the bad experiences clients have had when working with independent contractors. Naturally, there’s a trust deficit.

But that shouldn’t stop you from hiring freelancers. Once a level of trust is established, working with remote workers is smooth.

How to build trust with freelancers

While it takes time to build trust, here’re some tips that can help you get started.

• Pay on time: Freelancers need to feel assured about payments. Most freelance job sites use escrow accounts for payment assurance. However, when working with independent contractors, you may not have access to this facility. Ensure that freelancers are paid on time. 
• Use time tracking: Clients are often worried about being over-billed by freelancers. Specifically, when working on time and effort projects. To maintain transparency and prevent billing disputes, ask freelancers to use a time tracking tool.
• Make freelancers a part of your team: It’s unfair to expect freelancers to understand the big picture if they aren’t a part of your team. Invite freelancers in your project management and communication workspace. This way, freelancers can contribute better to the work.

Tools that can help build trust

In addition to project management and communication tools, you can use a free time tracking tool such as Toggl Track.

Some enterprise project management tools such as Mavenlink and Replicon come with inbuilt time tracking features. However, such tools are expensive and have a learning curve. 

Hiring freelancers

Hiring freelancers is an attractive choice. You save a lot of overhead costs including office expenses, taxes, and employment benefits. However, clients find it hard to hire freelancers that deliver in terms of quality and price.

How to hire quality freelancers & contractors

Here are a few tips to help you find and hire quality independent contract workers:

• Decide on the scope of work beforehand: Depending on the scope of work, you may need to hire a freelancer for a one-time job or on an ongoing basis. In addition, the work scope also helps you identify the necessary skills.
• Do a quick pre-work assessment test: Most freelance job sites have inbuilt skills assessment tests. When hiring people directly, consider using an assessment tool. Assessment tools help you save time by filtering out ineligible candidates.
• Consider a pre-work trial: In some cases, a pre-work assessment isn’t enough. You may want the contract worker to do a pre-work trial before offering a full contract. Often paid, a pre-work trial helps you evaluate freelancers on the job and gain the confidence to hire them. 
• Keep a database of freelancers: Hiring freelancers is almost as intensive as hiring employees. That’s why you want to keep a database of freelancers handy. That way, next time when you need someone, you don’t have to go through the entire process again.

Tools to hire freelancers

With over 57 million freelancers in America alone, there’s no shortage of freelance and micro job sites.

Upwork and Fiverr are among the top freelance hiring sites. In addition, portfolio sites such as Github and Behance are great for finding independent contractors with specific skill sets.

Finally, for pre-work assessment, you can use Toggl Hire or 25 other alternatives to it. 

In summary

Hiring and working with freelancers can be challenging. Hopefully, the tips and tools mentioned in this article on how to manage freelancers will help you.

For managing a project with a remote team, you may want to give Toggl Plan a try. It comes with project planning, task management, and workload management features. Best of all it’s a tool that your team will actually enjoy using every day. 

Get started with Toggl Plan for free