How To Communicate With Freelancers

In A Coffee ShopFreelancing continues to rise.

More individuals are turning to freelancing. To make more money. To have more flexibility. Or simply out of necessity.

That means more companies are hiring freelancers as well. Some are doing it to save money. Some are doing it to have more leeway with hiring and firing. Some are doing it because it’s a way to find the best talent.

Whatever the reasons, freelancing continues to be a big trend in the workplace.

If you’re a manager, it’s important to know how to best communicate with freelancers. Especially those that are working remote. You’re probably already doing some of it, but odds are you’ll be doing even more in the next few years.

Here are a few tips I’ve learned after nearly a decade of working with freelancers…

1. Email First

Email continues to be the most popular form of text-based communication. Around 3.8 billion people have an email address and that number is expected to rise.

Email is simple. It’s mature. Even as new text communication comes along, they almost all require an email address to signup and use.

Text might be the one to take over, but there is now a little pushback against using text for work.

For now, and for the near future, email is the way to go. Texting might take over, but even in that case the same basic rules apply for using text to communicate with freelancers.

First, keep email as short as possible. The more text within an email, the less likely people are to read it and comprehend everything in it. It’s better to create a document or video to explain a process. Use email to share that with the freelancer you’re working with.

Second, try to keep the questions or requests to a small amount per email message. Asking more than 3 questions in one message makes it likely that they all won’t be addressed. Better to ask one question, get an answer and then ask another.

Email and all text communication allows people to consume and comprehend your message multiple times and at any time no matter there location. And that’s a major part of freelancing and remote work.

Phone meetings are certainly good for some things, but they’re difficult to coordinate and often take more time than necessary.

2. Document Processes & Set Expectations

Some companies hire freelancers because they want someone that can step right in and take off. Or they expect someone to bring their knowledge to improve current processes.

Even in those cases there is some onboarding necessary. And if it’s an entry-level position there are some unique onboarding things to do.

It’s a requirement to lay out the procedures and processes for what you want your freelancers to do. Chances are you’ve had someone doing them before. Maybe yourself. Take the time to document those so you can communicate what the job is to the freelancer.

Text and video work well.

During this process, also set expectations. Timelines for processes and things like that.

These are things you and the freelancer can reference when communicating about their work. And it actually saves a lot of communication because answers to common questions are in the procedures.

3. Track Performance

With expectations, it’s important to track performance. Let the freelancer know how their performance is measured. Then followup and measure it at set points throughout the year.

Every business mostly has some kind of performance metric for each task. Make sure you take the time to understand and set them for each position.

This allows for better communication around how you see the freelancer doing and how they see themselves doing in their tasks.

4. Set Expected Reply Times

One of the really tricky things with freelancer and remote working is response times to emails. Or calling back or texting back.

You might see it as reasonable to get a response within a few hours. The freelancer may see it as reasonable to respond within one business day.

Think through these scenarios and lay out expectations. It’s fine to negotiate with each freelancer. I find that as long as it’s discussed that you’re able to find common ground and you’re less stressed. You’re not sitting around wondering, “Why haven’ they responded…” when you know they respond every business day morning.

Communication today makes it feel that everyone can respond within minutes. Of an email or text or call. But it’s almost always not necessary and just because people can respond quickly doesn’t mean they should. And most tasks don’t require urgent responses.

5. Add A Personal Touch

Personal touch often gets lost in freelancer communication. It’s good to share who you are via email just as you would if you were working with someone in person. A little small talk can go a long way once in awhile.

Just sending a quick thank you at the end of the week. Asking how the person is doing and if they have plans for an upcoming long holiday weekend.

I find that the more you can build personal relationships, the better the business relationship gets.

6. More Positivity Than Negativity

It’s easy to be crass in email. Freelancers often struggle to find positive reinforcement from their work. They often only hear about the negative things they’ve done.

For example, a designer may turn in a design mockup and only hear about the couple things that need to be changed. When the entirety of the design may be wonderful.

It turns out that we need 5x more positive feedback than negative criticism for our health. That’s a lot more than you think and it’s work to build that into your routine as a freelance manager.


It’s different working with freelancers. You lose a lot of the in person subtleties in communication that you get in an office. But freelancing is a reality in our world and the trend is going more in that direction. Adapt now and become familiar with communicating with freelancers. It’ll help your managerial skills and reputation and performance. And hopefully these tips will help.

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