How to hire your own freelancers

Mar 04, 2021

If you’re a freelancer and you want to get better at what you do, hire other freelancers.

First, it’s the perfect opportunity to recognize what it feels like to be on the receiving end of great (and not-so-great) customer service.

Second, it gives you the chance to shape the world of freelancing for the better.

And third, you’re likely to find more affordable, faster, more personalized, and higher-quality results with a talented freelancer than a run-of-the-mill agency (which you know, because that’s the value prop you offer your clients).

For example, I’m in the process of hiring a UX designer for my website. Go ahead, take a look.

You’ll see that my site does the job, explaining what my journalism and content marketing work look like. But it could be sleeker, right? I recently had an intro call with a designer and was so thoroughly impressed with his process — he sent me a beautiful, fully customized project proposal within a week of our call, summarizing what we’d talked about and mapping out a timeline for us to work together — that it inspired me to trash my own project proposal template and build a new one. (And move him to the top of my list for probable hires.)

As a freelancer, I’ve hired freelance artists, designers, and photographers. There’s something to learn at every step of the process.

How to approach hiring a freelancer

Hiring a freelancer to do a job, whether for your business, home, or personal life, can be just another chore on your to-do list. Or, approached thoughtfully, it can be a way to get great work done, improve your own business, and build community.

Before setting out, consider these principles for hiring a freelancer as a freelancer:

  1. Look for excellence. You want the freelancers who are working on their own because they love the freedom, not because they can’t get hired anywhere else. Hold a high bar and choose someone whose work you love and who you can learn from.
  2. Recognize the learning opportunity. I love being delighted, and I strive to delight my own clients. But as a team of one, I can’t pour unlimited time into researching new ways to level up my client service. Every time I hire a freelancer, I note what parts of their process delighted me and where my pain points were, and use those insights to improve my own business.
  3. Be the client you’d like to have. My favorite clients know what they want, don’t micromanage, and pay upfront and on time, so when I’m a prospect or client for someone else, I do all that, too.
  4. Know your peers. I find one of the hardest parts about freelancing is not having a built-in work community. When I hire other freelancers, I’m not just supporting their work; I’m getting to know them, recommending them to my network, and learning from and with them.

How to hire a freelancer

I’ve hired freelancers and had it go poorly (see: the cartoonist I hired to do a sketch for a holiday gift with whom I didn’t talk about revision expectations, and whose first draft I couldn’t have gifted without offending the recipient).

Here’s what I know to do now to make sure each job goes well:

Start with a clear job posting.

Spell out exactly what you’re looking for so that whoever you hire doesn’t have to pull it out of you. Answer these questions:

  1. Why are you doing this project? What’s your overall goal?
  2. What should the final outcome look like? Is it a 1,000-word blog, a 200x200 full-color logo, a set of ten edited headshots, a redesigned eight-page website? Be specific.
  3. Who is the audience for this work? What’s the background of the project’s recipient or end user?
  4. When is the work due?
  5. How much are you paying? How are you planning to pay it? One lump sum, a deposit upfront, hourly?

Make a decision and communicate it.

Pick someone based on the strength of their proposal or pitch. Use references, portfolios, and project samples to help. A paid trial is fine, but don’t ask anyone to do work for free.

If you posted your project somewhere public, like Upwork or a freelance Facebook group, follow through and close the posting once you’ve chosen someone so that other freelancers don’t waste their time applying. If you solicited recommendations from your network and freelancers have spent time sending you proposals, thank them and let them know you’ve gone another way. Ghosting someone professionally is just as rude as doing it to a mediocre first date.

Get in sync on specifics.

First, make sure you have a signed contract in place that you and the freelancer are comfortable with. It should cover:

  • Project scope, deliverables, and deadlines
  • Pricing
  • Payment schedule
  • Ownership
  • Cancelation terms

Then, sign off on a project plan. The freelancer you’re hiring should write it, building off of your job posting. Make sure it includes:

  • Goal of project
  • Steps taken to achieve that goal
  • Timeline
  • Revision / approval process

Let them do the work.

How much do you love it when clients are breathing down your neck, pinging you for updates every hour on the hour? Don’t be overbearing; let the professional you’ve carefully selected do the work you’ve hired them to do.

Pay promptly.

Upon receiving the finished project, pay immediately. Hear that? That’s just a chorus of freelance angels appreciating your net-10 timeliness.

Give feedback.

What did you love about working with the freelancer you chose? What could have gone better? Let them know. If they ask you to complete a survey or provide a testimonial, do that, too. Keep them in mind for referrals. You know how hard this work can be — take the time to make it a bit easier for someone else.

Go forth and hire

I firmly believe that you can learn something from everyone, and that you can learn more than most from your fellow freelancers. Go prove me right, will you?

Katherine Plumhoff

Katherine is a writer for outlets like Teen Vogue, The Wall Street Journal, and Slate and a content marketing strategist for companies like Headspace, Toggl, and PowerToFly.