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Improve Your Freelance Relationships with These 4 Essential Management Principles

With recent estimates putting contract and freelance workers at roughly 20% of the US workforce, their value for your company shouldn’t be ignored. Many business strategies rely on the flexibility of freelance work. When your company wants to expand, contracting with freelancers can help you navigate uncertain supply-and-demand situations. And consistent freelancers allow you to operate in smaller verticals without the costs of full-time employees.

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Effectively managing any employee takes effort, and how you approach managing freelance relationships can determine the success or failure of your projects. When you take the time to connect professionally and personally, you can create lasting freelance relationships for successful future projects.

Freelancers and contract workers make up 20% of the US workforce. Is your business strategy utilizing their skills and expertise effectively? Here’s what you need to know.

1. Set Clear Expectations

Before you hire any freelancers, sit down with all project stakeholders to determine your process and goals for the work you want to contract out. You are free to set expectations for any and all parts of your freelance process, but in my experience you can avoid the worst headaches if you address a few key areas:

  • Payment scales, including bonuses or reductions
  • Project ownership and stakeholder approval process
  • Project deadlines
  • Revision/adjustment responsibilities and feedback process
  • Consequences for subpar work
  • Contract length
  • Fireable offenses

By planning out your expectations, you can ensure all stakeholders are on the same page and responsibilities are clearly understood. You’ll also be better prepared to avoid applicants who won’t adjust well to your workflow or company culture. Clear expectations mean a higher probability of quality results—the first time—and less time spent correcting or teaching freelancers when they turn in projects, effectively accelerating your onboarding process.

When you take the time to connect professionally and personally with freelancers, you can create lasting freelance relationships for successful future projects.

On the other side of the relationship, clear expectations help freelancers do their work. The more information they have, the better they can apply their skills and the more time they can put into a project. Plus, if freelancers turn in poor work, they’ll know what timeframe and leeway they have for improvement before delivering any future projects.

Freelance Management Pro Tip

Freelance hiring requires much of the same considerations as in-house hiring, so seek out freelancers with diverse opinions and experiences just like you would for any other position. Tapping the same sources for freelance applicants can limit the overall quality and reach of your freelance projects, effectively trapping your company’s product in a box that no one is even aware you’re in.

2. Provide In-Depth Resources

Since communication with remote freelancers is more limited than with in-house employees (we’ll get to that next), you’ll want to prepare a treasure trove of resources to share with them before they get started on anything. Create shareable resources applicable to every freelancer you onboard (for example, documentation of the expectations outlined above), as well as one-off resources for individual projects.

Start by writing down any information your freelancer wouldn’t have knowledge of on their own:

  • Give them examples of your mission statement, specific goals, and target audience.
  • Provide details of your process overall.
  • List specific ways in which the deliverables that your freelancer creates must be different from your competition’s.
  • Elaborate on any parts of your projects that are based on in-house information or research.
  • Focus on the specific areas of your process that other freelancers have struggled with when contracting with you.

While it may feel like a hassle now, putting in time up front to create these resources means less time you have to put in later when a problem comes up. Plus you will be able to reuse resources for multiple freelancers and projects, again saving you more time in the long run.

While it may feel like a hassle now, putting in time up front to create freelance resources means less time you have to put in later when a problem comes up.

These resources also allow your freelancers to find answers to simple questions and act independently—something freelancers tend to excel at—before reaching out to you. Trust me, they’ll thank you for thinking of these things ahead of time so they can do their job as efficiently as possible.

Freelance Management Pro Tip

After reviewing your most-important project resources, don’t be afraid to make others based on questions or suggestions your freelancers have. You can build these from feedback you’ve gotten from freelancers or repeated questions you’ve received from other team members. High-level resources can be shared with new and old freelancers alike, as well as freelancers across different verticals to cut down on onboarding time and overall training time.

3. Communicate More Than You Think You Should

In-house teams are easy to communicate with and keep in the loop when problems or changes come up. It’s also easier to gauge tone and body language and adjust your communication accordingly in person. But people say “out of sight, out of mind” for a reason. Corresponding often and clearly with freelancers helps you avoid issues, lets you learn about any struggles they are experiencing, and keeps freelancers included in your process.

Watch out: it’s easy to blame freelancers for project issues, but the problems may actually be coming from your side.

Communicating with your freelancers shouldn’t be a one-way street. Regularly solicit feedback from them to improve your process going forward—whether you like it or not, they can often see what you might be missing. Sometimes people jump to blame freelancers for project issues when the problems may actually be coming from your side. Keeping an open mind when you receive feedback can protect you from becoming too complacent in your process.

Asking for feedback also shows your freelancers you respect them as experts in their craft and want them to clue you in about any frustrations they have. And going beyond the normal conversations (like sending and receiving assignments) can build a stronger rapport. Take extra time to update them about process changes, to give positive and constructive feedback, and to check in casually. These extra efforts help freelancers feel like members of your team. This, in turn, can increase their job satisfaction and drive to produce high-quality work.

Freelance Management Pro Tip

Check-ins and feedback require time. Your freelancers should be compensated accordingly. Contracts with hourly rates easily cover these moments, but if you pay your freelancers on a per-project basis, make sure their rates reflect both the project and process expectations.

4. Treat Freelancers Like Humans

When you primarily communicate with someone through email, Slack, or other project management programs, it’s easy to forget they’re more than text on the screen. Practicing empathy when working with freelancers is good manners and good business sense.

Freelancers who feel respected and needed are more encouraged to produce quality work—which benefits you over and over again. And in the contract and freelance realm, happier freelancers could mean they’ll prioritize you over other clients. Many freelancers contract with multiple companies at a time, and getting your company to the top of their client list can result in them creating more work for you.

Freelancers aren’t robots, so don’t treat them like it. Respect their lives outside of working with you and your company.

Keep in mind that freelancers don’t want to work with robots. Don’t be afraid to use some humor when sending emails and updates. Not every in-office interaction is monotone and directly to the point, and your contact with freelancers shouldn’t be either. Freelancers don’t live like robots, either. They have just as many life events, personal and career goals, and struggles to deal with as any other employee. Set reasonable deadlines, ask about and allow for vacation time, and understand that illnesses and emergencies may sometime delay deadlines. In short, respect their lives outside of working with you and your company.

Freelance Management Pro Tip

Make an extra effort to help freelancers feel like part of the team. Send them birthday cards, cards for work anniversaries, or get-well cards as appropriate. And use portions of routine check-ins to ask how they are and learn a little more about them as people. Any type of small act of kindness can build a trust in your work relationship that might have been missed with business-only communications.

Managing Freelance Relationships for Success

If you want your business to succeed with freelancers in your strategy, preparing a little extra can go a long way. Put in the effort and time on your end to show you respect your freelancers, and they’ll respond in kind.

Aaron Gates

Aaron Gates has five years of experience editing marketing, academic, and fiction writing. He’s supplemented his writing studies degree with an ACES certification in accurate, audience-focused editing, and he manages freelance writers for Clearlink to produce engaging content with trustworthy copy and conscious editing. He currently thrives in Seattle, where he’s found his destiny living in endless rain and hiding away in cute coffee shops. He also edits and manages peculiar—the lit mag he co-founded—and often meanders to a nearby bakery for twice-baked ham and cheese croissants.


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