9 Tips for Freelance Management (Without The Stress)

As companies add more freelancers, contractors, gig workers and consultants to their ranks, one thing has become clear: they need to simplify and standardize their freelance management.

Without a formal approach to freelance management, you’re more likely to face payment delays that strain your relationship with the worker, increase compliance risk, become disorganized, and struggle to level expectations.

In this post, we’ve compiled nine useful tips to simplify and streamline the way you manage freelancers, from hiring to onboarding to nurturing long-term relationships.

1. Assess your needs

Before you know who to hire, you need to understand your talent needs (today, and in the future). Perhaps your team is gearing up to launch a new project, and you know you need to enlist a subject matter expert. Or, maybe you simply need more hands on deck. In this case, it will be obvious that you’ll need to hire freelancers or independent contractors

Sometimes, however, it’s not so obvious. That’s why it’s important to understand the kinds of expertise and experience the work at hand requires, the scope of the project, the timeline for completing it, and your team’s current capacity. If you determine that your team lacks the time or skill set to do a certain type of work, then you’ll know you need to bring in non-payroll workers.

2. Hire strategically

A freelancer may seem promising on paper, but it’s important to thoroughly vet them before diving into work. In addition to the obvious requirements like relevant skills and experience, you’ll want to hire freelancers that are professional, trustworthy, communicative, and receptive to feedback.

Although assessing freelancers for cultural fit is less imperative than it is for full-time employees, it’s still relevant. After all, you still need to manage freelancers, even if that relationship is more hands-off.

3. Don’t rush through onboarding

You may be eager to get started with a new contractor or freelancer right away, but rushing through the onboarding process will not end well for you nor them. Hiring managers need to cover the following during onboarding:

  • Sign and store all relevant contracts, NDAs, IP agreements in a centralized place that is easy to access
  • Collect the freelancer’s contact information, bank account information, preferred method and currency of payment, and tax documentation (such as W-8 or W-9), and pass all of this on to your finance department
  • Request required equipment, data and/or systems access from IT

Unless you complete this during the onboarding period, you can end up dealing with risk exposure, non-compliance with tax and corporate policies, and even security breaches.

And, unless your internal processes for paying freelancers are working efficiently, it will be difficult to approve and pay invoices on time. Ensuring prompt payments should be among your top priorities if you manage freelancers, as delays can create tension and motivate great talent to stop working with you. According to PYMNTs, 29% of all freelancers’ invoices are paid late. This is a major shame, since 85% would pick up more work if they were paid faster. 

4. Provide a comprehensive briefing on the work

After onboarding, it’s time to introduce the worker to the projects or tasks you are hiring them to do. When briefing the freelancer or contractor on the work, remember that this person is not part of your company. They haven’t gone through regular employee onboarding, which means they may not be familiar with your brand, audiences, products, or business goals. 

Because a freelancer will lack this intimate knowledge of your company, it’s your job to give them all of the information and resources they need to understand their assignments and deliver great work. In addition to answering any questions they may have, you should clearly explain the objectives of the project, the desired impact of their contribution, the individual milestones, and deadlines. Many hiring manager rely on different project management tools to manage the on-going

5. Set expectations

If you already manage freelancers, you probably understand the importance of setting and upholding expectations. By articulating your expectations for both the freelancer and yourself, it will be easier to establish accountability. This will benefit you in the long-run, since you will probably not be supervising the freelancer’s work.

The most important expectations to align on include the quality of work, flexibility of deadlines, the frequency and channel of communication. Leveling on these points before the work begins will help you avoid surprises or uncomfortable conflicts down the road.

6. Plan work needs in advance

Throughout the course of a project, work needs you didn’t plan for may arise. Sometimes it’s unavoidable, but other times you can predict those needs with more comprehensive planning.

Before the freelancer begins working, it’s best to map out the entire project in detail and determine what the freelancer will be responsible for, as well as corresponding deadlines. This helps you avoid springing something on them at the last moment. Since many freelancers and contractors work with multiple clients, they may not be able to accommodate a last-minute request. By giving them as much notice as possible (and being realistic about scope and deadlines), it will be easier for the freelancer to plan accordingly and complete all of the work you need them to.  

7. Shift to freelance management on auto mode

There’s an entire class of software that’s designed to simplify and streamline the process of managing freelancers. Freelance management systems (FMS) centralize all of the required contracts and tax documents you need for managing freelancers, guarantee fast payments, ensure compliance with tax regulations and corporate policies, and prevent security breaches. An FMS eliminates the administrative burden you face when you attempt to do all of this work yourself, prevents human error, and keeps your freelancers happy.

8. Create a system for delivering and receiving feedback

Providing constructive feedback is essential to helping the freelancer deliver on-point, successful work. By creating a formal feedback system — such as returning edits or reviews within a certain number of days, having regular meetings, or providing written feedback — you can ensure the freelancer is positioned to succeed. 

This feedback system should work both ways. Invite the freelancer or contractor to give you feedback on your communication, the volume of work, the quality of support you’re giving them, and even the way you provide feedback. Work together to make working together a mutually beneficial arrangement.

9. Show your appreciation for their work

Freelancers don’t get the benefit of work parties, swag, or bonuses, but they still want to feel appreciated and valued by the customers. Simply by expressing your thanks, showing them the impact of their work on your business goals, and recommending them to others in your network, you can help your freelancers feel greatly appreciated. With that, they are sure to become more engaged, proactive, and committed to the work. 

Managing freelancers doesn’t need to be hard

You might be able to get away with ad-hocing your way through freelance management if you have just one or two in your ranks. But if you enlist more than that — or have any plans to increase your freelancer headcount — you definitely need a formal process in place.

By adhering to these simple tips, you can significantly reduce the manual work required to manage freelancers, avoid errors that lead to payment delays or compliance issues, strengthen your freelancer relationships, and keep your projects moving.  

Written by
Maya Rotenberg

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