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How to Work with Freelancers: Your Step-By-Step Handbook

Sarah Brooks
June 30, 2022

You just woke up in a cold sweat.

(Grab the popcorn as we replay this nightmare.) 

You assigned a freelancer a 2,000-word blog post about closing sales deals. But you didn’t give them a brief. Or your brand’s style guide. Or really any direction at all.

They sent over the Google Doc, and it was written in Wingdings. It was filled with laugh-worthy, yet unrelated, memes. There was no big idea, no central theme. You tried to reach out to the freelancer, but both Slack and Asana were down. 

This nightmare scenario is obviously super fake. (Does Wingdings even exist anymore?) But there are real-life nightmare scenarios between clients and freelancers every day, impacting quality of work and your reputation. 

Poor client-freelancer relationships lead to low-quality (and low-impact) deliverables, extra time and resources spent fixing the work and turnover due to lack of trust or low morale.

It’s not one-sided, either. Plenty of clients have been burned by freelancers, and plenty of freelancers have been burned by clients.

Is there a better way? 

In keeping our freelancers happy, we keep our clients happy. We produce high-impact work with smooth processes, hands-on production and consistent feedback. To get to this place, you need the know-how to successfully work with freelancers at every stage in the process.

Introducing your freelance guide

I’m Sarah Brooks, a freelance content writer, content strategist and ghostwriter with more than 10 years of experience working with clients. And I’ve seen it all. 

No brief. Being asked to turn around a deliverable in two days for minimal compensation. Receiving urgent client emails at 10pm. Unfortunately, this can become all-too-familiar without a solid client-freelancer relationship. 

Beam Content is one of my clients (and, honestly, one of the best! While I am being paid to write this handbook, no one is paying me to say this. I mean it!). They partner with 12 freelancers to develop high-quality, impactful B2B SaaS content. The founders have worked both as freelancers and with freelancers. 

Why am I telling you all this?

On any journey, your guides matter. Since we know our stuff, you’ll get an inside perspective from both a freelancer and the client who partners with them. 

We’ll answer common questions like:

  • Why is it important to build a strong client-freelancer relationship?
  • What’s the best way to vet freelancers?
  • How should I onboard my freelancers?
  • How can I keep freelancers engaged?

In short: I got to write a fun article, and you get a first-hand account of every phase of working with freelancers.

Why the client-freelancer relationship matters   

“Do I really need to go through steps A to Z to form a strong connection with my freelancers?” 

The short answer is: if you care about your work, your team and your company, yes.

Here’s why a good client-freelancer relationship benefits you, as the client:

  • Long-term partnership – US companies spend an average of $1,071 training each new employee. Building a solid foundation with your freelancer sets you up for a long-term partnership: growing with the company results in less turnover, training time and costs. If you’ve spent any amount of time on freelance marketplaces, you know how hard it is to find a solid freelancer. Take the time it takes to keep them. 
  • High-quality work – When we feel invested in, we share our time and energy. Freelancers who have a good relationship with their clients will feel more empowered to create high-quality work, leading to more impact for the client.
  • Extension of your team – A strong partnership with your freelancer makes them an extension of your team. With fresh eyes, they’ll even make things easier for you. Maybe they’ll improve a longstanding process. Or provide you with valuable customer insights.
  • Positive reputation – Freelancers network with, pass leads to and share experiences with fellow freelancers. When the relationship is positive, it’s easier to hire additional freelancers, thanks to your good company reputation.
  • Top-tier freelancers – There’s a common trope that all freelancers are desperate for work. It’s actually the opposite: experienced, high-impact freelancers are often booked out for months with long waiting lists. They want what any freelancer or full-time employee wants: flexibility, consistency, respect and interesting work. Put these things front and center, and you’ll find the best freelancers.

When working with freelancers, follow four key steps:

  1. Determine who you need—then find them
  2. Have an introductory conversation and vet
  3. Onboard and assign the first project
  4. Give feedback and maintain the relationship

By keeping these steps in mind, you’ll build a long-term relationship with a freelancer you can trust—and they’ll deliver high-quality work that grows your business.

1. Determine who you need—then find them 

To build a team of freelancers, you need to determine who you actually need. Look at the deliverables and tasks you want to outsource, then map skills to those outputs. You can even reference job descriptions to help inform what you’re looking for.

Here’s why this step matters: skill sets are not often interchangeable. Designers can be skilled in web design or brand design. The best copywriter for your sales pages likely won’t be a great fit for your case studies.

The highest-quality freelancers tend to specialize in their craft. In the freelance world, it’s called finding their niche. It’s getting really, really good at a few things, or even mastering one thing, instead of dabbling in everything.

Next, set your budget. Decide on hourly rates or defined project fees, and set a range that you’d agree on. (More on freelancer rates below.) 

With all of these details in place, start building your freelance roster. A list of freelancers you can count on for both on-retainer (more long-term, ongoing gigs) and one-off projects.

  • Use your network. Don’t be shy. Share exactly what you’re looking for on social media platforms like LinkedIn or Twitter. Find qualified freelancers through your own network.

  • Partner with exclusive freelancer networks. Browse creative networks that compensate freelancers fairly for their experience and talent. Try Designhill for designers, Lemon.io for developers and We Are Rosie for marketers. There are hundreds to choose from; check out G2’s Best Freelance Platforms list for more.
  • Provide referral incentives. Work with your company (and even existing freelancers) to offer referral incentives for qualified freelancers. We are who we keep company with, so chances are your team will know some pretty awesome candidates.

Once you have your roster, spend time learning more about them. Review their website and make sure to read their client testimonials—the inside scoop on what it’s like to work with them and the quality of their work.

Beam recently hired eight freelancers. After Brooklin Nash, Beam's co-founder, put the announcement out on LinkedIn, he received 300+ emails from potential freelancers. 

When I asked him how he vetted good-fit freelancers from such a large pool, he pointed to two things: "Writing samples and communication, in that order."

It didn't take much, either. Brooklin spent about three minutes with each freelancer's work samples. "By focusing on what I knew would be important to our clients—conversational tone, specificity, solid grasp of complex topics—I narrowed the list down to about 60 freelancers who had a good chance of being a great fit."

That gave him the foundation to pick up the conversation with the most promising freelancers down the line.

2. Have an intro conversation and vet

First impressions set the stage for an entire relationship. Your initial outreach should be clear, friendly and open. 

Before you email your freelancer, remember: at the end of the day, the freelancer is ultimately in the sales seat. If you share vague needs, fret over the budget or misunderstand the skill set you actually need, you’re raising a ton of red flags.

Start by introducing yourself. Follow up with anything you saw on their website: testimonials, writing samples or specific results they’ve reached. Share a specific vision for your work together. End the email by asking to schedule a discovery call.

Here’s a potential blueprint for your conversation: 

  • Start with an intro. Speak clearly and candidly about the company, the team they’d be working with, goals and specific deliverables. Don’t forget to talk about yourself! Share your background and some personal facts to make that human connection.
  • Determine skill set fit. See if the freelancer can deliver on the work. Ask specific questions pertaining to the deliverables, any tools or programs and past results to ensure they have the proper skill set.
  • Note personality fit. The freelancer’s personality fit is just as important as their skill set. Listen to your gut throughout the conversation to determine how this freelancer would interact with you and the team. Do they communicate respectfully? Are they friendly? Do they seem interested in the work?
  • Chat beyond deliverables. When you respect your freelancer, they’ll grow more invested. So it’s important to learn how they like to work and make them feel valued from the start. Ask about their work and communication styles. Maybe the freelancer doesn’t work on Fridays (that’s me!) or only communicates via email. Take note of their boundaries and respect them.

  • Talk money. Talking openly about money has traditionally been frowned upon. But it’s a conversation you need to have. Make sure your budget aligns with the freelancer’s rates and compensate them fairly. If rates aren’t matching up, leave room for negotiation. 

Provide freelancers with a test project as your last step. This could look like:

  • Ideating on a creative campaign with a set of social media posts
  • Designing graphics for an upcoming webinar series
  • Creating an SEO-optimized blog post for your industry
  • Writing lines of code to enhance the user experience of a website page
  • Completing keyword research for a new landing page

This point cannot be overstated: compensate them! They’re putting in time and effort to create this deliverable that your company might even use.

TL;DR—don’t be this guy.

Whether they succeed or not, a test project is a learning opportunity. It gives them experience for the next project you’ll work on together, and shows you exactly what you’re looking for. Either way, they’ll be fairly compensated. If you part ways because they don’t have the skill set, no hard feelings.

3. Onboard and assign the first project

Once you’ve found your perfect match, it’s time for legalese. There should always be a contract between client and freelancer. It protects both you and them from any unexpected situations and keeps the relationship clear.

Work with a lawyer to create a contract, or build one yourself. Shopify shares a great guide for creating a freelancer contract, and many small-business programs like Bonsai, Wingspan and HoneyBook have pre-made contract templates. Even better, most experienced freelancers will send over a scope of work agreement for you to sign before kicking off the project.

Once you’ve both signed on the dotted line, it’s time to onboard your freelancer to the company, team and projects they’ll be working on.

This interaction is crucial: how you work together on the first project determines the freelancer’s level of investment and morale. It’s make or break, so you want to get it right.

Endless email chains are often a recipe for disaster. Instead:

  • Set them up in your systems. Ideally you’ll do this on the same day, so they can handle all onboarding emails in one batch. Invite them to your project management tool, payroll system and communication platform. (Who’re we kidding. Slack. It’s Slack.) Send them an email confirming your invites and timeline for signing up.
  • Introduce them to your brand. A freelance writer can’t create good content without a brief—or at least solid guidance from you and others on the team. A freelance designer can’t develop your brand design without your brand identity. Freelancers are only as successful as the foundational information they’re given. You must introduce them to your brand by sending more information than less. This includes: style guides; brand tone, voice and design guides; foundational brand messaging; how-to guides; educational content; and anything else they’ll need to know. You’ve succeeded if you get them everything they need before they can ask. Leave time and space for questions.

Once you take these steps, you’re ready to assign the first project. No matter if they’re a writer, developer or designer, every freelancer needs a brief. Freelance writer Kaleigh Moore shares that a great brief answers the 5 W’s: who, what, when, where and why.

A brief aligns your expectations to what is delivered. If there’s no brief, or it’s unclear, you’ll receive a low-quality result or a barrage of questions from the freelancer. Keep your brief clear, cohesive and make sure it answers the questions: why are we completing this work? What is the impact you’d like it to have?

Send clear instructions with the brief: the deadline, process for turning in the work and invoicing. Give the freelancer enough time to complete their project; nobody benefits from three-day turnarounds. If it’s more long-term, like a complete overhaul of brand design, assign multiple checkpoints to break the project down into bite-size pieces.

4. Give feedback and maintain the relationship

After the first project, you need to maintain the client-freelancer relationship and deliver feedback to strengthen their work.

Here’s how to share feedback:

  • Give constructive feedback. Be specific, clear and useful. Then, work together on strategies and timelines for improvement.
  • Learn to deliver negative feedback. There’s a fine line between being constructive and just plain rude. Your freelancer is another human being with feelings. There’s a way to deliver not-so-great feedback that is helpful vs. harmful; if you share feedback in a negative way, this could sever your relationship for good. 
  • Send evergreen feedback. If you share feedback on a live call, you run the risk of the freelancer misinterpreting your words as they quickly jot them down. Send notes via Google doc comments, a written email or a Loom video so the freelancer has your notes and can refer back to them.
  • Keep it simple. Perfection is a construct. You could theoretically tweak a deliverable into eternity, and it still wouldn’t be perfect. As two individuals working together, you need to reach a common ground to deem the work complete. Edit back and forth two times at most. Set clear timelines to keep the project moving.

It’s not enough to share feedback, assign projects and that’s it. Just like in any relationship, you need to make your freelancer feel appreciated and engaged. They’re part of your team and should feel that. 

This means you need to trust them along the way. You’ve done your part to hire the best freelancer for the work; now, trust that they’ve got the expertise to make creative calls and deliver on the intended impact.

Check in regularly with your freelancer, both on a professional and personal level, at least monthly. Lead by example—your partnership is an open forum where they can share anything with you.

Everyone likes a gold star on their homework. Boost morale and make your freelancer feel seen by giving them a shoutout in your Slack channel, or sharing their work on LinkedIn or Twitter.

Sometimes it’s as simple as just saying, “Thank you!” Use words or your actions: give them extra time to work on a deliverable, bring them onto a high-impact project or reimburse them for skill development. (Also: pay them on time.) 

More than anything else, consider how you’d like to be treated as a freelancer, then act accordingly.

In any client-freelancer partnership, expect the unexpected

Even if you check every single step on this list, you’ll still run into a hurdle. 

(Probably not the Wingdings hurdle, but hey, anything can happen.) 

Maybe you need to change scope halfway through a project. (Ouch.) 

Or the freelancer misses a deadline. (Not ideal.)

Whatever happens, jump over hurdles with grace. Be honest and open with your freelancer, and build trust that you’ll help them solve any issue. Go in knowing the unexpected will happen, and you’ll be prepared to act.

Now, go be your freelancer’s favorite client!

Upwork found that 53 million Americans are now freelancers. That’s one in three workers, or 34% of the total work force. 

As more workers go freelance, it’s vital to know how to work with them, keep them engaged and make them happy.

A solid client-freelancer relationship leads to high-quality work, lower costs from training and resource-sharing, an expanded roster of talented freelancers and a solid company reputation. 

In other words, there’s no reason not to create a good relationship with freelancers.

Let’s make strong client-freelancer relationships the norm—built on mutual respect, trust and great work. As brands continue to duke it out for customer attention, we need to nurture loyal advocates who can grow with us.

You’re ready—go be your freelancer’s favorite client.

If you’re a B2B SaaS company looking to outsource your thought leadership content, we know a great team that could help. Reach out to Beam Content and see what happens when you create impactful content from conversations.