Startups: What to Know About Working With Freelancers

Freelancers can be a great marketing resource for small and growing businesses. You may not need a full-time resource (yet!), so a freelancer can fill a specific need, whether it’s writing, design, or fractional strategy roles.

Most of my clients are tech startups of varying sizes. Sometimes, I’m one of many freelance resources; sometimes, I’m the only freelancer.

I can usually tell when clients haven’t worked with a freelancer before. They expect the relationship to be similar to that of a manager-employee, where they can issue directives that I’ll follow. Or they’re disorganized, don’t know what they want, and can’t figure out how I can best complement their business goals.

If you’re an entrepreneur thinking about hiring a freelancer, congratulations! A good freelancer is often a niche expert and can be an amazing supplement to your team. But there are some things to remember as you start looking for the “right fit.”

Freelance isn’t code for cheap or unemployed

One of the biggest misconceptions about freelancing is that freelancers “can’t get real jobs,” and that they’re the leftovers, a lower caliber than hiring an employee.

When I first began freelancing full-time, I could feel the concern from my parents. Did I have enough work? Was I going to be ok?

It takes a lot of boldness to step out on your own. Many freelancers do it because they can earn more than they would as an employee. And they see freelancing as less risky since they’re not tied to a single source of income.

A freelancer might cost less than a full-time employee, but that’s because they’re (usually) not full-time. They’re not necessarily a “cheap” resource. If you break it down to a per-hour basis, a freelancer is probably higher than a full-time employee. After all, freelancers are also responsible for their own taxes and other benefits (like health insurance and retirement).

What you gain is flexibility: a resource for fewer hours, filling a specific need, or short-term help.

Read the freelancer’s contract carefully

Like many freelancers, I’ve been burned by clients. And guess what? Every time it happens, I update my contract to protect myself in the future better.

My deliverables are clearly outlined, and I have standard language. I can tell when clients read it because they’ll ask questions. And I’m willing to modify the language — but it must be discussed before the agreement is signed.

I once had a client who signed the agreement within minutes of receiving it. I was positive he didn’t read it. The client was a marketing agency, so I was writing for their client.

My agreement clearly states that I only do one round of revisions per deliverable. However, this agency had no such limitations in their agreement with their client. Each of the client’s stakeholders would individually review my drafts, resulting in requests for multiple rounds of revisions.

I pointed out to the agency that the language of my agreement didn’t allow for additional revisions. If the agency had realized this, they could have guided their client to consolidate feedback or negotiated more rounds of revisions with me before signing. But as it ended up — because the additional rounds of revisions were easily avoidable — I charged an additional fee for the extra rounds, eating into the client’s budget.

Freelancers will work with the information they’re given

As a freelance writer, I’ve seen every type of brief under the sun. I’ll get very detailed briefs that outline the exact topics to cover, along with persona information and how the content fits into the overall strategy. I’ll also get emails that say, “Can you write a blog post, about 1000 words, about X topic?”

As an expert in my industry (financial technology), I don’t need detailed briefs. I can take a topic and run with it. But if you want a specific outcome, you need to give your freelancer specific direction. Otherwise, your freelancer will write the content in the way they feel is most appropriate.

Here’s the thing: freelancers don’t have insight into everything happening at the company. While creating a brief feels like extra work, it gives the freelancer the necessary context that could change the direction of the content.

If you want the freelancer to craft content based on their expertise, that’s fine — but then don’t request a bunch of revisions because the output isn’t what you had in mind.

Freelancers set their own schedules

Most freelancers work with multiple clients, so they’re juggling a lot. Good freelancers are excellent at managing their workloads, but that means they’re rarely available on demand.

A “quick phone call” on short notice? Unlikely. Same-day edits? Often not possible.

My best clients have one of two cadences with me. Either the deliverables are due on the same day every week (and they get me briefs well in advance). Or they’ll say, “Let me know when you can have this done.” I’ll then communicate my earliest availability.

Good freelancers can be booked out for weeks or longer. I’ve had to tell clients — good clients! — that I can’t deliver something on a quick turnaround. As much as I’d like to make them happy, I have other deadlines looming.

Good freelancers are on the lookout for red flags

Like good employees, good freelancers have a lot of options. They don’t have to work with difficult clients. They’re quick to drop clients who don’t respect their work or their boundaries.

Sometimes, a job description alone can be a red flag. The company will describe a role that sounds like an employee but is listed as freelance work. The company wants to control when and how work gets done. (In the U.S., this is a big no-no and can get a company in trouble with the IRS for employee misclassification.)

My best clients are collaborative. They respect my schedule. They give me constructive feedback. They view my work as valuable, even though I’m not a member of the team.

On the flip side, my worst clients have had unclear expectations. Rather than respecting my work, they’ll treat me like a content vending machine — put money in, and content comes out. I’ve also been paid late, a sign that the client doesn’t value the freelancer as a professional.

I want to build long-term relationships with clients. I love hearing how my work contributes to their overall business goals. But I’m also quick to drop problem clients.

If you’re looking to hire a freelance writer, respect the person as a professional.

Think of a lawyer you might hire. The person is doing work for your benefit but works independently. A law firm is an outside business you hire for its expertise.

It’s much the same with freelancers. They’re a supplement — maybe even a replacement — for an internal team. But freelancers are running an entire business, and you’re not the only client.

And if you wouldn’t pay your lawyer late, don’t pay your freelancers late.

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