Want to Keep Your Best Freelancers? Follow This Playbook

February 11, 2021

A friend who’s growing a content arm of his startup recently asked me, how do you keep freelancers engaged?

We’d just finished discussing the merits of working with a team of freelance writers versus hiring employees, and this was the pain point that came up for him. In his experience, freelancers tend to be less invested in the business than employees.

This makes sense; think of it from the worker’s perspective. Would you be more engaged with an employer who holds the keys to your entire paycheck and growth trajectory, or a client who’s just one of several companies you work with and responsible for only a portion of your income?

Remember: freelancers are running their own business, just like you’re running yours. They are invested in the success of their business. And that’s where the opportunity comes in, for by extension, they can also be invested in the success of their clients.

Work from a freelancer who puts in 20 hours a week can be just as high quality as that of a full-time employee. What matters most is hiring the right people, not the employee or contractor status you assign to them.

Now, that doesn’t mean you can hire someone for full-time hours and withhold employee status; part of respecting your workers is categorizing them properly. But my point is that you shouldn’t avoid working with freelancers or assume their work will be any less satisfactory than an employee.

When you hire the right people and create a culture of trust, the work will be good either way.

6 strategies for fostering freelancer engagement

In this post, I’ll offer some ideas for keeping freelancers engaged. I’ve used all of these strategies myself, so I’ve seen them work first-hand.

I’ll talk specifically about freelance writers and editors, since that’s my wheelhouse, but I suspect these ideas could apply to other types of freelancers as well. 

Whether you’re working with one freelancer or 200, here’s how to keep them engaged and producing high-quality work.

1. Pay well

Of all the suggestions on this list, this is the most important. All workers feel valued when they’re compensated well for their work. When your freelancers feel valued, they’ll put their best foot forward.

You’ll also land more experienced freelancers who do higher-quality work by paying well, and those workers are more practiced at maintaining relationships with clients. In other words, they’re pros who know how to keep you happy.

While most companies have budgets to stick to, think hard before you nickel and dime your freelancers — you may end up paying for it in other ways. For example, paying more for a well-written blog post might save hours of work for your editor, who is likely more expensive than your writer. If you’re the editor, it might save you time, which as a company leader is your most valuable asset.

The pay range for blog posts varies widely depending on the writer’s experience, the length of the post, whether it requires expert knowledge, whether you expect the writer to optimize for SEO, and more. 

Expect to pay between $150-250 for a blog post of 700-1,200 words, and $250-600 for a blog post of 1,200-2,500 words. If the post requires original reporting and interviews, it might cost more. 

While it’s nice to have a target word range to set expectations, I never pay by the word because it incentivizes volume rather than quality. Pay an admirable post or project rate, and your freelancer will want to work for you again.

2. Offer recurring work

Once you’ve found a freelancer that you’d like to work with long term, structure an arrangement so they can count on recurring work over time.

Every freelancer will choose a recurring project over a one-time assignment because getting new work is time-consuming and stressful. The flip side is true, too: establishing ongoing relationships with good freelancers saves you from having to find a new one every time you need it.

For example, rather than offering to pay a freelancer $250 for every blog post they write, offer $900 a month for four blog posts. You get more content without having to think about who’s going to write it. The writer gets the promise of $900 each month, which gives them ease of mind. It’s a win-win.

The tricky part for the employer is accurately estimating how much work you need from the freelancer, especially when you’re growing a startup and your needs are changing quickly. Remember, you can always increase or decrease the volume when you need to, so long as you give the contractor the 30 or 60 days’ notice outlined in your contract.

Another arrangement I’ve found successful is saying, “I’ll pay you $X each month to write up to Y posts.” Then it’s up to me to make sure I provide enough assignments to make that retainer worth it. 

If there’s a month when I don’t need quite that many posts, I still pay the writer as promised. At first glance, this gives the writer an advantage; they get the upside if they end up doing less work, and you don’t get to pay less when assignments are scarce. But there’s also an advantage here: you know you can rely on the writer for a certain amount of work. If you don’t “reserve” their time in some way, they might not be available when you need them.

You can also try, “I’ll pay you $X each month to write between Y-Z posts.” Some months will be at the low end of the range and some months will be at the high end, but your writer knows how much they’ll earn every month and you know how much you’ll spend. If you end up consistently assigning Y posts or Z posts, adjust the agreement and the payment accordingly.

If you have the luxury of moving slowly, contract with a freelance writer for several one-off pieces before agreeing to an ongoing relationship. Or offer the recurring work and agree to an initial trial period. 

The goal is to give yourself an easy out — not just legally, but also psychologically — if the writer isn’t as good as you expected.

3. Help them grow

Helping employees grow their skills and careers is one of the best ways to retain your top performers. This strategy applies to your freelancers, too.

For freelance writers, offer feedback that directly improves the quality of their work. Good writers want to see edits that make each piece better and help them learn over time. (Conversely, if a writer gives you push-back about reasonable edits, that’s a red flag.) Give them access to a great editor, so their work shines when it’s published and they get a chance to level up every time they file a post.

Ask yourself what else you can offer that will help your freelancers get better at what they do for you by deepening or broadening their skills. For example, if search engine optimization is part of your marketing strategy, train your freelancers on how to optimize a post. You could even bring in an SEO agency to teach them. This is the kind of perk that’s common in a full-time employee role, but isn’t as easy for freelancers to access. 

Trainings don’t have to be live (online or in person), though I find offering occasional live sessions improves rapport. They could also take place via recorded video using a tool like Loom, so your freelancers can watch whenever is convenient for them. 

Follow up later and ask for questions, or create a Slack thread for questions about that specific training. The goal is to make this training a two-sided interaction, rather than slinging a video at them with instructions. The slinging approach can work well for onboarding, but if your goal is to keep people engaged, add some interaction. As an added benefit, it allows you to see what your freelancers took away from the training, and you can watch their next few submissions to see whether they put it into practice.

Finally, you might even offer opportunities for growth that don’t directly benefit you, or where the ROI seems low, like paying for your freelancer to attend a conference. Here’s the thing: it does directly benefit you, and the ROI is likely higher than it looks, because it helps you keep your best freelancers. Finding new freelancers to replace your best people takes a lot of work, so it’s worth putting in some money and effort to retain them. 

4. Be respectful

Show you’re a nice human by being attentive to your relationships with your freelancers. Your work together is more than a transaction; you’re collaborating with someone who has needs and hopes, just like you. 

It sounds simple, but you’d be surprised how many employers neglect this piece — and as a result, wind up having to replace freelancers who’ve moved on to other clients.

Being respectful can mean different things in different settings, but here are a few basics that will keep freelancers working for you:

  • Pay on time
  • Do what you say you’ll do
  • Be kind

“Be kind” does not mean letting poor work slide. You can hold your freelancer accountable for submitting great work on deadline and also be understanding when they need flexibility for unexpected life events. 

5. Refer them to other companies that need freelancers

When you hear from a friend or previous colleague that their company needs freelancers and you think someone on your team would be a fit, make the introduction.

This might feel counterintuitive; what if the other company gives them so much work that your freelancer no longer has time for your assignments? What if the other company pays them more? What if they prefer working for the other company and give up working for you?

There is a risk here, but it’s usually worth taking. So long as you follow the other advice in this post — most importantly, paying well — your freelancers will want to continue working for you. 

Knowing you’ll send opportunities their way is a huge perk, because finding new clients can be stressful and takes freelancers away from paid work. An introduction to a new client, especially one accompanied by a recommendation, is highly valuable.

These introductions, which I also make through my consulting work, are one of my favorite parts of working in this space. It feels good on so many levels to introduce a great freelance writer to a company that needs them. It’s a win for the writer and a win for the company. And on a personal level, it helps me continue to grow my own network, too.

However, avoid connecting your freelancers to your direct competitors. If those competitors are smart, they’ll review the bylines on your site and recruit those writers anyway, which is fine (and you should use this strategy, too!). But don’t hand them your best writers on a silver platter. 

6. Create a mini freelancer community

Freelancers who work from home often feel isolated without colleagues. So if you have even a small group of freelancers, they might appreciate connecting with one another. 

I’ve done this in the past through a Facebook or Slack group, and some of the freelancers are good friends to this day. In addition to supporting one another, they often share work opportunities that aren’t a fit for them, so one of their freelancer buddies can benefit.

Establishing this type of group can also offer you an easy way to communicate with all of your freelancers at once. Back when we had a freelancers’ Facebook group for my content agency, we’d post opportunities for quick-turnaround projects so writers could see and claim them. This method was far easier and faster than emailing each freelancer individually to see who was free, or emailing the group and getting lots of emails in return.

Being a good client pays off

Whenever I hire a freelancer, my goal is to be their best client. When bandwidth is tight and they have several options for projects, I want them to choose to work for me rather than someone else.

Achieving that is partly about money. But it’s also about showing the freelancer that you value them and their work — and meaning it. 

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