Freelancers can be a big boost to your business. But you need to handle them carefully.

Freelancers are a lot like jellyfish. We live solitary lives, swimming blindly through the choppy waters of our careers. Many people find us strange or mysterious, but our day-to-day existence is pretty uninteresting. We’re content to mostly just float around and do our thing.

That said, if you ever come into contact with us, you need to handle us carefully.

No, I’m not going to sting you. What’s more likely to happen if you mistreat me is that I’ll collapse into a pile of goo in your hands.

I’ll explain in a moment. Let’s back up before we dive in. Maybe put on some sunscreen first.

The ocean is full of freelancers.

I’ve been a jellyfish—er, freelancer—for about a decade. I’ve worked for dozens of clients, from big businesses to individual entrepreneurs; from tech companies to law firms to authors, coaches, and psychologists. I run my own business, make my own schedule, and pay my own income taxes.

It used to be I was the only person I knew who lived and worked like this. But these days, everyone seems to be growing tentacles.

With millions of people unemployed right now, and countless businesses looking to cut down on labor costs, more and more people are becoming freelancers, and more and more organizations are contracting work out to them.

Indeed, hiring one or more freelancers can be a smart move for your business, particularly in this economy. By outsourcing certain tasks and projects, you’ll save significant overhead while maintaining quality—or, in many cases, improving it. I mean, you’re engaging with an already-skilled professional rather than training and developing someone in-house, and you only need to pay for their productive time. Did I mention the tax savings?

Freelancing can be good for workers, too, in terms of greater independence, flexibility, and autonomy. Plenty of people who work for themselves also cite “increased earning potential” as a reason for freelancing, but I’d rather not comment on that one personally.

For these reasons, it’s no surprise that many employers are switching from employees to freelancers, or converting some or all of their workforces into independent contractors. A September 2020 Upwork survey found that over a third (36%) of American workers now freelancetwo million more than in 2019—and market analysts expect that number to continue growing.

Using Ruby in Your Office

Why do freelancer relationships go wrong?

But it’s not all dollar signs and freedom and BMWs. There are gooey, messy realities to hiring freelancers:

  • How do you make sure they do the work?
  • How do you avoid getting overcharged?
  • Do you need to sign written contracts with them?
  • How do you keep them happy and motivated?
  • What does it mean to be a good client?

Too many businesses overlook these sorts of questions and assume the freelancing arrangement will simply work out. They soon discover they’re not getting what they hoped for as quickly, reliably, or cost-effectively. 

Other times, companies squeeze their freelancers too hard, and things fall apart. Pop—there goes the jellyfish.

Here are a few tips from a freelancer for treating your freelancers well, getting the most out of them, and keeping them aligned with your business goals:

Know what you’re getting.

Know who you intend to work with before you hire them. I realize this sounds obvious, but you may be surprised how many people decide to engage with freelancers on the strength of a referral—or even a gut feeling—alone. Someone might have a glowing recommendation from a friend or colleague, but that doesn’t mean they’re automatically the perfect fit for your business.

Ask a freelancer the following questions before you hire them:

  • What’s your rate? (Or: How much do you charge?)
  • What does your current availability look like? Do you expect your availability to change soon?
  • What’s your turnaround time?
  • How long have you been freelancing?
  • Have you worked with companies like ours before?
  • What information do you need from us before we get started?

It never hurts to ask for work samples or a link to the freelancer’s website. This is especially important when you’re hiring someone to do creative work, such as graphic design, writing, or video production, where subjective taste and tone make a huge difference. 

Don’t be afraid to ask for an estimate, proposal, or scope of work before delving into the first project. Get a sense of the person’s skills, style, time, and costs—and set your expectations accordingly—and you’ll avoid potentially painful conflicts later on. 

You may also want to draft a contract that covers matters such as payment terms, ownership of the work, noncompetition, and other issues you’d rather not engage in legal disputes over later. Any freelancer worth their salt will be happy to sign a contract, so long as it’s drafted fairly, but may want to negotiate details first. (If someone refuses to sign any agreement with you, consider it a red flag.)

Trust freelancers to do their best work.

You hired the freelancer you hired for a reason. Maybe you liked their portfolio, or believed in their proposal, or thoroughly enjoyed your connection with them over the phone. Whatever the case, trust in your decision, and have faith that your freelancer is doing their best to turn in the work you requested on time and under budget.

In other words, don’t micromanage. Try not to check in constantly, or ask to see work before it’s ready. Be patient and remain calm. Keep in mind that freelancers value their time and space. Hopefully, assuming you vetted the person thoroughly, you’ve hired a pro.

If a freelancer isn’t quite delivering or meeting your expectations, that’s when it’s time to start a conversation. But keep your feedback constructive and specific—and check your assumptions. Ask open-ended questions rather than leveling accusations. For instance, instead of saying “this isn’t what I wanted,” ask if the assignment was unclear, or if they could use more information or resources from you, or what their intentions and goals were in doing something a certain way.

Lackluster work, overcharging, and missed deadlines do happen. But they’re more often the result of poor communication rather than willful negligence on the part of the freelancer. Assume that the person you hired is working in good faith, and use that initial disappointment as an opportunity to learn and improve the relationship. If it turns into a regular pattern, however, know when to end things.

Keep the lines of communication open.

There’s a difference between respecting your freelancer’s autonomy and leaving them entirely in the dark. Everyone, no matter how busy or self-reliant, can use the occasional check-in.

I like to talk to each of my clients over the phone or video at least once a month. In an ideal world, we would meet more frequently, but work and schedules tend to get in the way. These conversations are essential—not just for aligning people on projects and priorities, but for maintaining camaraderie. Hearing from the people I work for helps me feel valued and connected to the work.

Communication also serves to help freelancers manage their time and money. I can get urgent projects done faster and better if I know about them in advance. If a client is reducing their freelance budget, having that information allows me to shift things around and hopefully pick up additional work to make ends meet. 

I can’t tell you how many times a client has ghosted me and then returned several months later with a new project I don’t have room for. If they’d sent just one email before disappearing to acknowledge the situation, I would have at least been able to anticipate that the work might come back.

Understand the differences between freelancers and employees.

There are important legal and practical distinctions between freelancers and employees. While both may work for your company, the two differ significantly in terms of how you’re allowed to manage and pay them.

This is a topic that deserves its own article (or several), but here’s a quick overview of the differences between freelancers (AKA independent contractors) and employees:

A freelancer…

  • is self-employed
  • pays their own taxes and benefits
  • controls when they work
  • controls where they work
  • controls how they work
  • uses their own tools
  • may work for several different clients

An employee…

  • is employed by an organization
  • has their taxes and benefits withheld by the employer
  • works on the employer’s schedule (e.g. 9am–5pm)
  • works where the employer decides (e.g. on-site or in a virtual office)
  • adheres to the employer’s rules and training
  • uses tools owned and paid for by the employer
  • usually works for just one company (or two, maybe three, on a part-time basis)

(If you’re not sure what your workers classify as, read this IRS article.)

Perhaps the most important distinction here is control. Freelancers control their schedules and working arrangements—you can’t decide for them. Essentially, freelancers give up stability in exchange for independence. If you can’t provide someone with reliable employment, you can’t expect them to be available whenever you want. 

But that also means freelancer payment terms are a bit more flexible than employee wages or salaries. Work with your freelancers to determine how and when they’d like to get paid, and come to an agreement that works for you both. No matter what, be sure to pay them on time. After all, they can walk away whenever they want.

Remember that freelancers are human.

Above all, when working with a freelancer, honor the person’s humanity. We all make mistakes. We all have bad days, emergencies, and mental health struggles now and then. Recognize that sometimes, life can get in the way of work, and that’s okay. A freelancer should never be responsible for a mission-critical process, anyway—that’s a job for an in-house team.

Be kind to your freelancers when they’re having a hard time. Better yet, be kind all the time.

Respect, warmth, and a little humor go a long way. Professionalism matters, too. I’ve received a fair share of emails that are nothing more than blunt requests (“please turn in by EOD”) or curt acknowledgments (“received”), or where the entire message is in the subject line (“can you check out this website and send me your thoughts ASAP”). I much prefer working with someone who addresses me by name and asks how I’m doing.

I understand why clients forget this part sometimes. I work with some people I’ve never met in-person. And we’re all accustomed to getting certain things done through online software and bots. But I’m not like your bank or your Amazon shopping cart. I’m not an app. 

I’m a jellyfish. 

I mean, human. Definitely a human.

Author Bio

Matt Lurie is a writer, editor, and designer living in the San Francisco Bay Area. To learn more about his work or hire him for your next project, visit