The SMB Guide To Working With Freelancers

Morgan Williams, freelancer

Morgan Williams

September 17, 2021

As a business leader, there are so many goals to accomplish and projects to finish. But often, there isn’t enough time, people, or money to do it all. Luckily, that’s where freelancers (like me) come to the rescue! 

As a freelance writer, I support SMBs (like Trainual) by helping them execute on everything content. And I’m definitely not alone! In a survey done by Upwork, 36% of the US workforce reported freelancing in 2020.

And younger generations are hopping on the independent bandwagon faster than ever before. Statista found that 44% of Millennials and a whopping 50% of Gen Zers freelanced in 2020. And that means the market is only getting bigger.

But before you hire your first freelancer (or the next), use this comprehensive guide and checklist. It’s what my best clients do to outsource the work without sacrificing quality and keep us aligned. 

Alright, let’s dive in:

What is outsourcing?

Outsourcing is when a company hires a person or party outside your company to complete tasks traditionally performed in-house. Typically, the people you bring in are called freelancers, contractors, gig workers, or independent workers. 

League of extraordinary freelancers, activate!

Freelancers help you accomplish specific tasks and offer a range of services, including writing, graphic design, and web development. And in general, it’s less expensive to hire a freelancer to complete tasks (than create and hire an entirely new role). 

Unlike your in-house employees, your freelancers will work a bit differently (literally) because they only focus on one task within a larger project. Meanwhile, your in-house employees have several responsibilities that might span across several departments. 

For example, content freelancers will only write a blog for you (usually as one-off projects). While your content team plans the editorial calendar, researches topics, writes blogs, publishes those blogs, and distributes the content across your marketing channels. 

As a result, freelancers require less training and management than employees. They’re only onboarded on your brand and the project. And they work completely autonomously.

Why hire a freelancer?

There are probably as many reasons to hire a freelancer as there are types of freelancers. Because the reality is everyone’s goals are different and unique to their business. There is no one-size-fits-all solution. But there are the three (in my opinion, more common) reasons you might hire a freelancer:

1. Costs less than hiring an employee

In most cases, hiring a freelancer is less expensive than hiring a new role. Because you only have to pay for the specific service they provide. And you don’t have to pay for things like office space, tech tools, or employee benefits.

For example, the salary for a full-time software engineer might be $135k a year. And once you add in extra expenses (like recruitment, training, payroll tax, benefits, and sick time), the total investment hovers around $311k. 

On the other hand, a senior freelancer might charge $150/hour. But if you assume both people work the same amount of time (40 hours a week), the freelancer will only cost $294k for the year. That means you’ll save almost $17k by hiring a freelancer.
In other words, outsourcing saves you money in the long run – without restricting your ability to grow in the present. Because as long as freelancers help you accomplish goals, you can continue growing the business and increasing profitability.

2. Quick access to talent or expertise you need

If you only need a designer or developer a few times a year, opening up in-house positions for these roles doesn’t make sense. Instead, you should hire a freelancer and only pay for these skills when you need them. 

Plus, when you pick a freelancer from a pool of experts, you save the headache of scouting, interviewing, and onboarding new professionals. And that also means freelancing gives you immediate access (with apps or references) to any talent you need. 

For example, it only takes Trainual a week from opening the position to onboard a new freelancer. But in comparison, their full-time employees might take 36 days from opening the role to start onboarding. That’s nearly 30 days a freelancer could’ve spent executing.

3. Produce more work in less time

Since freelancers can work outside your business hours and work asynchronously, you have more flexibility than just relying on your 9-to-5 employees. For example, you could hire freelance social media managers to respond to comments and DMs after business hours. 

And since a freelancer only focuses on one task (versus a full plate of responsibilities), it’s easier for them to accomplish goals quickly. Whereas your employees might get pulled in several directions, so tasks get pushed aside.

When should you hire a freelancer?

The truth is it’s always a good time to hire a freelancer. Because let’s face it: There is only so much time in the workday for your team to get it all done. But there are several signs that your business needs to outsource some work like yesterday.

For example, when you: 

  • Don’t have enough time or people to complete a project (or fulfill orders).
  • Have a specific project that’s outside your team’s expertise.
  • Need to complete a short-term project quickly.
  • Are on a tight budget (AKA you can’t afford to hire an entire role).
  • Need a creativity boost (or outside perspective).

In reality, if you’re even thinking of hiring freelance, it’s probably time to do it. Because when you and your team don’t have the expertise or bandwidth, you need to raise your hand and ask for help.

What freelancers look for in clients

Now, let’s jump to the other perspective: The freelancer. For me, there are certain characteristics I look for in my clients. And the most important one is already having your ducks in a row – long before you come to me.

Here’s what I mean:

Know your business

When you understand your business inside and out, you can communicate what you need and how exactly freelancers can help. And, as a result, it allows freelancers to produce better work. Because when they know what you know (such as your value props, branding, and audience), they can execute tasks that align with your goals. 

For instance, when I first started working with Trainual’s content manager, Lo Kidd, she shared a Voice and Style (V&S) guide with me. The guide was incredibly helpful for freelance copywriters. Because it described in great detail (with lots of examples) what Trainual content should read like and feel like. Which gave me a great base to start writing from.

Have a clear scope of the project

Before reaching out to freelancers, you need to know the details of your project first. Otherwise, there’s no foundation for the freelancer to build off. Key components include:

  • Your overall goal.
  • Call-to-actions.
  • Supporting materials.
  • The process for working together.
  • The deadlines or milestones. 

For example, my best clients provide a shared Google Doc or shared folder with all this information. They describe in detail what topic they want me to cover and when it’s due. They link to any supporting materials (like web articles or internal presentations). And they jot down any of their thoughts or random notes that I may need to complete the project. 

As for Trainual, Lo has a fool-proof process for working with me (I’ll describe it later). But I don’t actually expect that from all clients. Because from my experience with Trainual, I’ve learned that this is rare for most SMBs (let alone having one for working with freelancers). Even though repeatable systems and processes help maintain consistency and improve results. 

If you don’t have a process for outsourcing work, just be open with the freelancer about where you’re at in preparation. Because in most cases, freelancers are willing to help and probably already have a preferred way to work with their clients.

Understand you’re not their only client

It's true!

Using freelance is like ordering from an a la carte menu. You only pay for a specific dish (or, in this case, task) and not the entire meal (all-inclusive service). So, for example, you shouldn’t expect a freelance writer to come up with your voice, choose the topic, or spend hours researching. Unless, of course, you hired them to do that. 

My best clients give me a topic, share all of their thoughts on it, and provide me with some research upfront. Then, once we agree on a deadline, they let me do my thing on my own time. They don’t breathe down my neck, ask for content on short notice, or expect me to do things outside the project scope.

Simply put, you don’t have unlimited access to a freelancer’s time. So, you need to respect their boundaries and let them work autonomously. And when you attempt to micromanage a freelancer, know that you only create more work for yourself – instead of eliminating it.

The outsourcing checklist

Now that we’ve covered the basics of working with freelancers, here’s a complete checklist for outsourcing any work. Feel free to use it whenever you’re ready to start scouting contract workers.  

🔥 Tip: Copy and paste this checklist into Trainual, then add any other assets you provide freelancers. That way, you don’t miss anything, and every freelancer gets the same great experience with your company! Try for free.

1. Clearly define the project or ongoing work

Again (and I cannot stress this enough), you’ll want to know the project details before hiring a freelancer. Here are the most critical questions to answer as you outline the project:

  • What is the freelancer responsible for?
  • What materials will you provide upfront?
  • What is the deadline? Or the ongoing schedule?
  • How will the freelancer get paid?

Use your answers to outline the project requirements. And be sure that you write it out in a way that’s easy to understand from an outsider’s perspective. Meaning, avoid any jargon and provide background information when necessary. 

Not sure if what you’re talking about is common knowledge? Then, bet that it’s not. Better to give too much information than not enough.

2. Scout for talent online or ask for references

There are tons of great apps and websites for finding contract work – like Upwork, Fiverr, and Thumbtack. Or, you can ask your peers, employees, and friends if they have any references. In fact, Trainual found me thanks to a shared connection with their marketing manager, Becky Winter. 

Once you find a freelancer, gauge their experience, examples, reviews (if available), cost (don’t judge on this alone), and turnaround times. You can also ask for a trial run before committing to a freelancer on a whole project. 

For example, I wrote a trial case study for Trainual before officially freelancing for them. And they decided (based on what I provided) that I was a good fit for the company. But that doesn’t mean you get the trial run for free. You still need to pay full price for their service and time – regardless of whether or not you move forward with the freelancer.

3. Clarify who owns the work upfront

Before moving forward with a freelancer, write up a legal contract stating that you own whatever materials the freelancer creates. Then, include the agreed-upon cost and how it’s tracked (by project, word, or hour).

If your freelancer works directly with clients, include a non-compete clause in the contract. This clause ensures freelancers can’t bypass you and work directly with your clients. And if you don’t know where to start, ask a legal advisor or search for a free contract example online.

4. Onboard freelancers

Unlike new employee onboarding, you only need to onboard freelancers on the branding materials and the project. This includes your value proposition, vision, voice, style, colors, logo, development code guidelines, or whatever else they may need to know. And it includes the project details you came up with earlier. 

You’ll also want to lay out the process for communicating and delivering materials. That might mean a mix of Google Drive, Slack, or a project management tool (Trainual uses all three). You could even assign freelancers to relevant subjects in your Trainual breaking down your outsourcing processes and expectations.

Also, consider how you’ll offer feedback and finalize tasks. I prefer responding to comments in a Google Doc, but you could also email or share them in your project management tools. Whatever you decide, set the expectation for how freelancers will receive feedback and what you expect them to do with it.

5. Use project management tools

A project management software (like Asana) helps streamline communication, deliver materials, and finalize projects. But it’s definitely not required for outsourcing work because you could easily work with free tools, like Google Drive or Microsoft OneNote. 

For example, Lo assigns me weekly projects in Asana, including any materials I might need and the deadlines. Once I’ve finished a project, I share my content via Google Docs, link it in Asana, and check off the task. 

That way, everyone involved in the project is aligned on where we are in the process and has access to my work. Then, Lo drops her edits, and I respond to them directly in the shared Google Doc. 

Also, if your freelancer charges by the hour, consider using time trackers, like Toggle or Clockify. While it may not work for every freelancer, it’s okay to ask for a record if you’re paying for their time.

6. Treat freelancers like partners

Resist the urge to boss your freelancers around. Instead, treat them as partners. Meaning, ask for their thoughts and respect their expertise. One way to do this is by providing constructive criticism that improves the quality of work and clarifies your expectations. And don’t forget to provide positive feedback as well.

For example, Lo doesn’t simply say she doesn’t like something when editing my work. She gives me precise feedback that improves my writing (or aligns it with the Trainual brand). For example, she’ll often ask for more detail, less detail, or examples of what I’m describing. And she often expresses appreciation for my work – which goes a long way in building a partnership!

Plus, it’s just as important to fulfill invoices on time. It helps build rapport, which can also increase your freelancer’s responsiveness. Because when you pay someone fairly and on time, they’ll be more likely to show up when you need them and deliver better work.

When I send invoices over, Lo responds within 24 hours that she’s seen them and is working on processing them. She then adds me to her email threads with finance. This lets me know when the invoice will be fulfilled as soon as she does.

7. Understand your tax obligations

While you should always speak with your tax consultant before hiring a freelancer, there are a few things you absolutely have to have in all contractual relationships. 

First, you should always ask for a W-9 from the freelancer. Second, you must issue a 1099-NEC (non-employee compensation) at tax time. And third, you should track the expenses incurred while working with freelancers (like Upwork fees or Fiverr costs). 

With Trainual, they rely on a software called Justworks. It makes it easy to get all of these documents signed and filed right. Plus, it allows both the company and the freelancer to easily access the documents they need come tax time.

Above all, here’s what you need to know: Outsourcing your work doesn’t have to be difficult. It can (and should) be easy, reliable, and efficient. But that starts with you understanding your business, outlining your projects clearly, finding a reputable expert, and creating a repeatable process. Then, quality execution will naturally follow.

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