Content Leads: What Your Freelance Bench Wishes They Could Tell You

Every content lead I’ve ever spoken to has stories about flaky, disappointing freelancers.

Every freelancer I’ve ever spoken to has stories about nightmare clients.

If you work in content, you’ve probably heard both sides. Missed deadlines. Vague briefs. Ghosting. Scope creep. The list goes on.

But most of the time, there’s no bad intent. We’re all just trying to do great work with limited time and resources. We’re on the same team.

And like any good team, success depends on clear communication.

Unfortunately, there’s an awkward power dynamic between freelancers and clients.

No freelancer wants to risk losing a gig by speaking out of turn. Even if you're the kind of content lead who actively asks for feedback, chances are you're still only getting a filtered version of the truth.

So, I did the snooping for you.

I spoke to dozens of experienced freelance content marketers about what helps them do their best work, what makes someone their favorite client, and what sends them running.

This isn’t a call-out post. There’s no finger-wagging.

Think of this as a relationship manual. A behind-the-scenes guide to becoming the kind of client freelancers love working with.

If you’ve ever wondered what your freelancers really think, here’s your answer.

Freelancers’ names have been removed for anonymity. (And shout out to Ryan Baum for the idea!)

A good brief will get you most of the way

“Writers aren’t mind readers. Better writing starts with better briefs,” says Morgan Short, Sr. Director of Content and Web Strategy at Vendavo.

Or, to quote one freelancer I talked to: “If an article I wrote for you requires six rounds of content edits, the problem isn’t my writing. It’s your brief.”

And ChatGPT is not a great content strategist: “Please stop using AI tools to auto-generate briefs if you expect the end result to be original content that speaks to your audience.”

What’s usually missing from client briefs, according to freelancers?

The purpose of the piece of content

“A brief is more than word counts, keywords, or audience. You also need the why, the stakes, and what you want your audience to feel, think, or do.”

Freelancers can usually figure out a lot on their own, but they can’t know exactly what you want unless you tell them.

“Some clients think freelancers want total creative freedom — and sometimes we do — but what most of us want first is clarity. Please just be clear about the goal of the piece, what audience it’s for, what you’re hoping it’ll do. That way we’re not trying to guess what success looks like.”

Your product positioning

Many content briefs are missing the inside scoop on how you think about your product — and that’s a lost opportunity:

"The more info you can give me about your product or service, your ICP, and what sets you apart from your competitors, the better the content I create for you is going to be.”

The best briefs contain a short section that indicates how the product relates to the topic at hand.

You might also want to consider letting your freelance team get their hands on the product in question:

“If you want me to write about your platform, I need to be able to use your platform. Or at least see it in action once or twice.”

In some cases, giving freelancers access to the wider GTM team may add some extra depth:

“I think it's really worth having access to insights from the customer support team, to understand who you're writing for, what their pain points are and what they really want. Marketing and customer support functions are often not aligned, and a lot of valuable information that could be passed on to freelancers gets missed in the process.”

But don’t confuse being clear with doing a massive info dump. Freelancers don’t usually need the level of onboarding you’d give a full-time employee:

“You're setting me up to fail if you send me a 34-page tone of voice doc. Summarize your house style in a handful of bullet points, then send me a couple of examples of what you think are your best pieces of content."

💡If you’d like to know what a great setup process looks like, you might want to check out our guide to strategic freelance onboarding.

And, if you’re not confident about your briefing process, feel free to invite input from your freelancers.

“Let me work with you to figure out what kinds of briefs will be the most helpful and effective for us both,” suggests one freelancer.

Morgan says this approach has worked well for her: “I have a pretty great brief template now and I owe it to the freelancers I’ve worked with over the years who have helped me sharpen it.“

💡 Want your own tried-and-tested briefing template? Here’s our comprehensive B2B content brief, plus guidelines for how to fill it in.

Think partnership, not management

“It takes time to get used to the vendor-business relationship, especially if you're primarily used to managing full-time employees,” says one freelancer.

“The challenge I face most frequently is when the difference between a full-time employee and a freelancer is ignored or muddied (i.e., expecting immediate access to me or my calendar, very fast turnaround times, or additional operations support and team integration when the contract is for writing only).”

If you’re used to managing a team, then you may think of your freelancers as an extension of that team, and expect all hands on deck when things get hectic. But freelancers aren’t employees — they’re service providers.

As one freelancer bluntly puts it:

“Your emergency is not my emergency.”

This dynamic shows up most often around time expectations. Yes, it’s fair to expect freelancers to meet deadlines. But it’s not fair to expect them to drop everything and work on edits the second you send feedback, or to answer a 10 p.m. Slack message.

“If you don’t value my time, I won’t value yours. Emergency requests, next-day turnarounds, late-night pings. It’s just not sustainable.”

Set clear expectations and stick to them

Rather than assuming a freelancer can operate on your timeline, have an open conversation about what a reasonable workflow looks like.

Agree upfront on turnaround times for first drafts, revisions, and approvals. Ask your freelancers how they prefer to work and what kind of lead time they typically need.

Build in breathing room

“I feel like letting the writer choose a draft date inspires more creativity and leads to better content. Obviously, this means things need to be planned in advance — but once you have a strong idea pipeline, it’s easier to build in more flexibility.”

You’ll likely benefit, too. When freelancers have room to think and create, you get better, more thoughtful work.

“The less overbearing the client is, the better work I do for them. You can feel when a client respects your time and trusts your process — and when they do, you naturally want to go the extra mile.”

Tight timelines every once in a while are fine. But if last-minute scrambling becomes the norm, it’s a sign something upstream needs fixing:

“If content requests are coming in at the last minute and pieces you’ve poured time into are getting scrapped at the last second, that’s not a freelancer problem — it’s a business problem. Great content needs a clear runway, not just a wing and a prayer. Freelancers can flex, but we can’t keep building the plane mid-air forever.”

Invite feedback

It’s not all on you. Freelancers also need to step into the partnership role. Many assume that setting boundaries or asking for more time will be taken badly, says James Leach, the Content Marketing Manager at Omnipresent. “It's a sad indictment of the industry that people don't feel they can be that direct."

In fact, as James points out, boundaries are usually welcomed: “I loved that I had one freelance designer in my pool who would just say ‘No, I'm not doing that.’”

So, as the client, you may simply need to clarify that feedback (and pushback) is appropriate, especially if you’re working with less experienced freelancers.

Trust the expert you hired

One of the biggest frustrations freelancers shared? Being brought in for their expertise, only to have that expertise constantly second-guessed.

Feedback is welcome, but micromanagement isn’t.

“If you hire me as the content expert and second-guess my advice every five seconds, then nope, we are not going anywhere with that! Don't come to me six months from now asking why we haven't made any SEO progress.”

And avoid duplication of effort if you can: “Please don’t hire me as the content expert and then rewrite everything I send you by the internal committee. You are shooting yourself in the foot!”

That includes last-minute edits. Most freelancers will be happy to jump back in:

“If you've hired a writer, use them. Right up until the moment the words go live. I know you want to add an extra line about something you left out of the brief. But you hired us for a reason: to produce the best possible version of the message you want to get across.

We're agonizing over your content to make it as polished as it can be. Then we see it live a week later, and someone's had a go with the cheese grater.

Any good freelancer will be more than happy to give your tweaks a final check. (And we'll be flattered that we're being included as part of the final sign-off.)”

For example, one of my clients sends me an automated notification every time they publish a piece I wrote, with a note asking me to let them know about any typos introduced during the publishing process.

Ask for help

Don’t be afraid to ask your freelancers for more support if you need it:

“Something I’ve noticed now as a content lead is that we can sometimes hesitate to ask freelancers to take on more projects. It usually comes from a good place — we don’t want to overwhelm them or push too much onto their plate. But when I was freelancing full-time, I actually appreciated when clients would ask.

And more often than not, I wanted the extra work. I think there’s this unspoken worry that we’re going to burn someone out by offering more assignments, but really, freelancers are capable of setting their own boundaries. Just give them the option. Ask. Let them decide.”

And this probably doesn’t need saying, but don’t play games:

“I hate it when content leads do ‘surprise tests’ within briefs — burying something in the brief that doesn’t align with the rest of the assignment, just to see if a freelancer calls it out.

Freelancers might mistakenly think it links to an internal goal in some way and find a workaround to deliver on it. Also, it’s a huge breach of trust at the beginning of a new relationship.”

Try to make time to communicate

Freelancers know you’re busy. That’s why you hired them in the first place. But if you want the best possible work, it pays to carve out a little time for communication, especially at the beginning:

“I understand a lot of clients hire freelancers because they're time-poor, but the clients for whom I've done the best work are those who make an effort to engage in plenty of back-and-forth at the start of the relationship.”

In particular, try to update your freelance bench about changes in priorities. Even bad news is better than no news.

“It’s fine if the project you were going to give me gets nixed by the CMO! Just be honest and let me know, don’t ghost me.”

This is particularly key if you’re working in a startup where strategy pivots are happening all the time.

“In the startup space, using freelancers to build out your content team means you'll have to be extra mindful if you pivot. Make sure you clearly communicate how this will impact their work and honor existing contracts, even if you have to switch directions strategically.”

This doesn’t mean you have to hop on a ton of calls. A video message alongside the brief, especially in the early days, is more than enough:

“Sometimes, all you need to do when we need clarity on a brief is to record a Loom/Vimeo explaining what your strategy is, how you think I should approach the piece, and what the output should look like.”

Tell them what they’re doing right, not just what to improve

Most of the feedback that freelancers get focuses on what needs fixing. That’s fair, but if you want to be your freelancers’ favorite client, it helps to throw some positive feedback their way too. Otherwise, they’re likely to assume you’re not happy:

“It seems needy, but tell your freelance writers they’re doing a good job (if they are). I’ve encountered impostor syndrome so many times and thought, ‘Maybe the client didn’t like this piece and is going to fire me,’ if a client didn’t express any emotion about the work.”

Many freelancers work in isolation, without peers or mentors to provide support. A kind word from a client can be more powerful than you might think.

“It's a lonely profession out here. Without the services of a coach or a very dear friend, it's almost impossible to get genuine validation.”

This doesn’t need to be a heavy lift. Just a quick positive comment in the draft will go a long way:

“I love, love, love when you say ‘I love this sentence’ or ‘great thought!’ while writing comments on my v1.”

And it’s not just about a pat on the back — it’s also about improving performance over time. “We don't go to school for this. So this is how we learn on the job!”

Also, it’s probably worth looping freelancers into the results of their work. This doesn’t have to be time-consuming — just a quick note when a piece of work does particularly well can go a long way.

“I think most freelancers would love a peek under the hood. Even just sharing a little feedback like, ‘This one did really well,’ with some metrics behind it, or ‘Here’s what didn’t work,’ is super helpful.

It makes us better. It builds buy-in. It creates a feedback loop that benefits everyone. And for freelancers, that performance info can also be useful in pitching future clients or building case studies.”

In fact, you can even automate it. For example, send an automated email to your freelancers when their blog gets published, so they can add it to their portfolio and notify their sources.

Bring them in at the strategy stage

Too often, writers are treated like the last stop in the content production process — brought in after all the important decisions have already been made. But involving your freelancers earlier can dramatically improve the quality of the final piece:

“Content output would be a million leagues better when writers are involved and integrated earlier on. A writer needs context and time to gather data and capture knowledge from stakeholders, documents, etc. There's more to writing than just the actual writing. Please involve writers way before the late-stage act of doing the writing bit.”

Good writing doesn’t happen in a vacuum. Freelancers can bring sharper insights to your content if they understand the thinking behind it.

Don’t invite them to every meeting

Yes, context is important. Yes, looping freelancers into strategy conversations can lead to better work. But no, they don’t need to attend every recurring Zoom call on your calendar:

“I simply cannot join your weekly check-in calls or have you set up random meetings when you feel like on my calendar.”

If it’s not directly relevant, there’s probably a better way to share the information.

“Please don’t feel like you need to invite your freelancers to every team sync. Most of the time, we don’t need to be there. It’s one thing to include us in a Loom or give us a Fathom recording with a transcript — that’s super helpful. But a recurring Zoom invite for something that doesn’t directly involve our work? No thanks.”

Include freelancers when it adds value. Otherwise, share the context asynchronously and let them stay focused on the work.

Add them into (some of) your internal tools

Being looped into your internal processes can save a lot of back and forth.

“Add me to your tools! It's so much easier to add a link to a client's task card (in my own project management system) and then have the ability to go back to it to submit the assignment later on.”

Email threads just aren’t the best way to collaborate on content:

“Please stop emailing me. I have a few clients who communicate via email only and have never added me to their project management tools, even though I know they’re using these tools with their internal teams. It ends up creating a ton of back-and-forth – and “‘wait, did you ever submit that blog post’” messages three months after I did, in fact, email a link to the Google Doc."

That said, there’s a balance to strike. When you pile on too many platforms, you’re accidentally assigning unpaid admin work.

“One thing I really wish more clients knew is how much time it takes to manage all their systems. If you’ve got me in Slack, ClickUp, Notion, a payroll portal, Google Drive, and some other random login — that adds up.

If you’re asking a freelancer to join a platform or set up a profile somewhere, please make sure it’s essential to the work they’re doing. And be realistic about how much time you’re expecting them to spend in those tools. Because at a certain point, it starts to blur the line between doing the work and being onboarded like an employee, without the benefits.”

💡Relato makes this all much easier. With Workspaces, everyone on your team has the access they need, when they need it — including your freelance bench.

The best freelance relationships are built, not lucked into

When you treat freelancers like true partners — loop them in early, communicate clearly, give them space to do great work — you’ll get better content and a smoother working relationship.

And you’ll probably get their best effort, too:

“When I find clients who do these things, I want to keep working with them forever and I (admittedly) give them more energy and attention because they are sooo great to work with.”

At Relato, we’re trying to make that kind of relationship easier to build. We help content teams collaborate more smoothly with freelancers, so you can scale your content without sacrificing quality (or burning anyone out).

Because when freelancers have what they need to do great work, they usually do.