The Ultimate Guide to Hiring and Managing Freelancers

Freelancer and UpWork

Freelancers offer a new dynamic and an abundance of talent to a business. Whether you’re running a startup or an established company, adding freelancers to the team reduces overhead costs while increasing productivity. The flexibility of hiring these new contractors on a short-term basis and the potential benefits make it an attractive venture for organizations.

However, after you’ve hired them, you’re going to have to manage them. That’s where the challenges start. Managing contractors scattered across different geographical locations and time zones can be overwhelming. 

Working with a team of freelancers brings different expectations and rules. Now, with the right strategies and approach, you can build great relationships and work as seamlessly as possible.

How Do You Know If Freelancing Is for You?

Before you hire a freelancer, you need to determine if your business really needs them. Analyze your situation carefully and ask yourself if you need to outsource. Having a clear vision of what you need to achieve will help you make a wise business decision. For instance, if you’re doing all the admin tasks, ask yourself, “Is working overtime worth it?” You need to assess your company’s needs to determine if outsourcing is better than hiring someone internally. 

If you decide that hiring freelancers is the best move, you need to understand what you’re bringing to the table.

The Benefits of Freelancers to Your Business

  • Flexibility – Freelancers work with more flexible schedules compared to in-office employees. This means they can easily be available for an urgent project that just came in.
  • Affordability – Freelancers are also entrepreneurs. This means their base rate may be higher than the average laborer. However, with no overhead costs, bringing them onboard is more affordable.
  • Work efficiency – Freelancers work in a conducive environment that can boost their productivity. Plus, because of their flexible schedules, they have a better work-life balance. In return, their work efficiency is higher, which leads to more profits.
  • Short-term contractors – Unlike in-office employees, freelancers don’t require long-term contracts. They come in handy for tasks that require short-term contracts, and you don’t have extra personnel.

The Drawbacks of Hiring Freelancers

That said, managing a team of contractors has its demerits:

  • Lack of visibility – It’s easy to interact with a small team of freelancers on a personal level. However, as the number of freelancers increases, maintaining visibility becomes difficult. Keeping track of their skills, quality of work, and engagement can be challenging.
  • Reliability issues – There’s no guarantee that a freelancer will always be available. They can disappear unexpectedly when you need them for a project.
  • Increased risk – The freelancer will have access to sensitive company data, and this can pose some security concerns. That’s why doing thorough background checks is crucial. It’s advisable to hire people you’ve worked with before or recommendations from people you know.
  • Missed deadlines – Chances are, your freelancers have other gigs on the side. Keep in mind that they will always prioritize projects with the highest pay, and this could lead to delays or missed deadlines.

Once you determine freelancing is for you and understand how freelancers can help your business, the next phase is how to manage freelancers.

How Can I Manage My Freelancer?

Places to find freelance work online

When it comes to working with and managing freelancers, there are some key factors you have to consider. Your freelance team is probably made up of people from different backgrounds, languages, cultures, and religions. You have to treat them equitably and find ways to incorporate them into your business’ growth strategies and budgets.


Before you start hiring freelancers, you must define clear project goals and expectations. This will help you know exactly what to look for in a freelancer.

Project Description

Once you’ve defined project deadlines and deliverables, the next step is to craft a project description. This requires strong attention to detail, especially if you want to attract the right talent. You need to outline the job responsibilities and answer these questions:

  • What qualifications are you looking for?
  • How many freelancers do you intend to hire?
  • What skills and level of experience are you looking for?
  • How many hours can the freelancer expect to complete the project?

Finding Potential Freelancers

The right freelancer will benefit your company immensely. That’s why you should carefully screen potential freelancers before onboarding them. You can start looking at freelance recruitment websites to get started. Some popular websites include LinkedIn, Upwork, Craigslist, Guru, SalesForce jobs, and Fiverr.

Try different websites to find the best possible match for the job.

Have a Contract Signed

Once you’ve found the right freelancer and done a proper onboarding, make sure you have a formal, written contract in place. An employment contract signed by the freelancer will protect both parties. Such contracts outline the expectations, hours/pay, project metrics and scope, and company policies.

The contract may come in handy in case of any future disagreements or discrepancies. It’s advisable to go over the contract’s details with your freelancer to ensure clarity and consistency.

If you find the recruitment process too overwhelming or time-consuming, consider hiring a freelance recruiter. Delegating this task will allow you to focus on other crucial matters. All you’ll need to do is inform the freelance recruiter of your business goals and expectations.

Managing Freelancers

time tracking app for freelancers

1. Understand Your Freelancers

Many managers assume that the employer-freelancer relationship doesn’t come with the same expectations as a regular employee. While there’s some truth in this, it doesn’t mean you shouldn’t tend to freelancers’ needs.

Actively managing contractors and showing you care about them will, in turn, lead to them treating your business more highly.

2. Set Clear Expectations

To avoid misunderstandings, you need to be absolutely clear about how certain things need to be done. If you have a preference for how you want things done, it helps to explain it. Additionally, clearly outline the project goals so you’re on the same page.

3. Encourage Open Communication

Having open channel communication is highly encouraged when managing remote freelancers. To ensure a streamlined freelance workforce, be prepared to communicate a lot. Their quality of work will be driven by the quality of communication you provide.

You can communicate with your freelancers through email, phone calls, chats, or social media. Whatever channel you choose, let them know you’re always at hand to offer clarity and discuss ideas and schedules.

Additionally, take advantage of software to manage freelancers, such as Trello and Wrike. Such tools allow managers and freelancers to interact on a professional level. They can share updates, assign tasks, reschedule deadlines, and so on.

4. Build the Relationship

Instead of viewing freelancers as short-term, one-time contributors, work at building a relationship. You may feel like you don’t need to invest as much in a freelancer as you would a regular employee. However, a freelancer is just as valuable as your employee, and regular communication will help foster a relationship.

Make efforts to get to know them better by asking questions outside work. Talk about families and anything else that’s going on in their lives. When you build a relationship, you create a better chance of working with them again in the future.

How Do You Engage Freelancers?

5. Avoid Micromanaging Freelancers

There’s a reason the contractor you hired works as a freelancer. They want autonomy. Therefore, give them the chance to work without looking over their shoulder. Allowing them the freedom and space to work on their terms ensures you don’t overstep.

Of course, they will be working within the set expectations and project scope. Keep in mind that the freelancers likely have multiple projects ongoing. So, be sure to set reasonable deadlines.

6. Provide Feedback

You don’t have to give performance reviews with freelancers. But, that doesn’t mean you shouldn’t. Freelancers are humans too, and who doesn’t appreciate being told they are doing a great job?

Share your thoughts about their work and offer tips on areas you think they will improve. This will create an even deeper relationship and improve their performance.

7. Provide Rewards and Recognition

A little token of appreciation goes a long way. You might be thinking rewards should only be reserved for your employees. But, rewarding freelancers after the successful completion of short-term projects can be immensely satisfying. Not only will you build a good reputation, but freelancers will also put the best effort into their work.

How Do Freelancers Track Hours?

When you reach a point where you need additional workers on your team, it means you have projects beyond your capabilities. You will need to lay down effective strategies on how to manage freelance projects.

Managing multiple projects calls for collaborative work with your freelancers. But since you’ll most likely hire freelancers on a short-term basis, time tracking is crucial. You need to know how freelancers spend time on assigned tasks and how many hours will be spent until project completion.

What’s more, a time tracking tool will show you who is working on what, their progress, and if they will meet the deadlines. This way, no one on your team will be overworked. To enable your freelancers to track time properly, you’ll have to add them, along with the rest of the team, to their assignments.

Using free time tracking software for Mac and Windows gives you the data needed to estimate future project expenses and compare them to potential profits.  

What Is the Best Free Time Tracking App for Freelancers?

Freelance time tracking software allows you to maintain accountability and visibility. These tools give employees a way to measure their workplace performance, hours spent on a project, and pending tasks.

When choosing a time tracking software for freelancers, you’ll need one with multiple tracking options. Traqq offers both real-time and manual tracking options. It allows you to monitor employee computer usage to see their work progress every couple of hours. On the other hand, you can add time manually on assignments they have been working on at the end of a workday.

On project completion, you can pull the reports and analyze the entire process. The software gives you insights into valuable details like the total hours recorded and how the time was spent. You can then collaborate with your freelancers to make manual edits, where necessary, and process payment. 

If you pay your freelancers weekly, you can pull a weekly summary of their activities to check the total hours worked. The reports simplify payment processing.

So, why choose Traqq to monitor your freelancers’ hours? Well, this tool has all the essential features you’d want in a time tracking software:

  • Time Tracking – Traqq offers an automated tracking system that allows for easy customization. You can track time in real-time or edit the hours manually.
  • Reports. The reporting feature takes all the data and transforms it into readable and actionable reports. What’s more, the tool provides visual reports for easy interpretation.
  • Alerts and Notifications – Traqq comes with smart alerts and notifications to ensure that you don’t miss tracking your hours. You get notified every time you start working without turning on the tracker or whenever you’re idle while the tracker is on. You also get notified after each hour worked. This can help prevent overworking or forgetting to take breaks.
  • App and Website Monitoring – We all know the Internet is full of distractions. The app and website monitoring feature brings to your attention your daily app and web usage. The stats can help you identify the time wasters and find ways to eradicate them.
  • Activity Levels – Traqq makes it easy to analyze the activity levels of each freelancer. The data provides insight into individual capabilities and can come in handy when assigning future projects.

On top of all that, Traqq is a free time tracking software for freelancers. It doesn’t matter how big your team of freelancers is or your industry—you get all premium features at no cost at all!

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