How To Make The Most Out Of Your Freelancers By Treating Them Well

A gift hamper: little things can really make your freelance team members feel more valued

I’ve observed a number of those who would typically occupy the purchasing seat in the buyer-freelancer relationship recently ask a somewhat eyebrow-raising question: how can we treat our freelance writers (or other resources) well?

Let me be honest: I think that the freelancing world / gig economy is currently in a pretty bad place right now.

On the supply side (freelancers) there’s way too many of us with often highly disparate costs of living fighting for the same work in (often) the same places. The result is a race to the bottom.

Nevertheless, it’s impossible to deny that demand for freelancer is enormous.

It’s growing. And the world is moving rapidly in the direction of remote work.

Therefore, while I think that the state of the freelancing market today is best described as “somewhat lamentable” I expect things to change. Because they will have to.

Therefore, I always try to answer the question “how can we retain our best freelancers?” Because I appreciate that there are clients out there who truly want to “do good” in terms of how they treat and manage their freelance resources.

Over the years, I’ve had some great clients who excelled in making their freelancers feel like valued team members — almost on par with employees. I’ve also had clients that communicated very much the opposite viewpoint through their actions, which, yes, always speak louder than words.

So without further a-do, here are my tips, from five years working with entrepreneurs, agencies, and companies, about how treat freelancers well — and consequently get the most out of them.

Remember That They’re Humans And Treat Them Accordingly

There’s something inherently dehumanizing about the experience of working remotely.

Zoom calls have made it much easier for us to get immersive experiences with our clients, but ultimately, us freelancers are a collection of pixels on a screen to our clients.

I’ve made the points to freelancers many times that this fact is actually hugely significant.

It explains — I believe — why so many clients unfortunately treat freelancers poorly. Why they seem to treat us with disrespect.

The good ones don’t, of course, but if you do this for any length of time it’s impossible to ignore that crummy clients are a significant problem in this “industry.” (Tip to freelancer: remember what Shakespeare said about people who protest too much. Sometimes this is your tip that the client actually doesn’t!)

The best way to keep your best freelancers is to remember that they’re humans and treat them accordingly.

They have families, spouses, hobbies, and interests. They’re real sentient human beings with personalities and interests outside of getting your work back by deadline.

Would you ghost somebody who showed up to your office every day and worked as a key member of our team (please tell me the answer is no)?

So don’t do it to your freelancers.

Make Them Feel Included (Within Reason)

Something as simple as inviting your freelancers for an office fun day could really help show that you care about them as an organization

A freelance client in Tel Aviv once invited me to a freelancers’ day during which they were buying in lots and lots of pizza and beer.

Sadly logistics prevented me from making the trip from Jerusalem (plus, how far does one really want to travel for pizza)? But I still remember the invitation to this day with fondness and put that particular client in my mental bucket for “clients that were nice to work with.”

Little gestures like this — that cost large companies almost nothing — really show freelancers that you, as a company, care about them as people.

Don’t make freelancers feel like out-of-house for-hire pariahs and exclude them from everything except the project management system.

If they’re an integral part of your team, even if they’re only on contract, then it’s courteous to make them feel included.

Concrete suggestion: a card or a gift hamper around the holidays (the same client who invited me for pizza always sends me one) is a pretty low-cost way to signal “we care.”

But equally:

Don’t Treat Them Like Employees

Many companies — particularly early stage startups where “all hands on deck all the time is the prevalent culture — have absolutely no idea about how to manage freelancers. Like none at all.

As freelancers, we sell our money for our time. It’s the only way that we can make a living.

Therefore asking for “free stuff” is not only cheeky but actually threatens to derail our business. We can’t do it. But in order to maintain the relationship we might feel pressured to say yes. So it’s always uncomfortable.

Here are examples for asking for things that you mightn’t think may smack of “we want free things” but really are (at least to many):

  • Requests for endless meetings
  • “How about getting on just another demo to check with our CTO?”
  • Requests for endless revisions (on writing deliverables)
  • Unnecessary phone calls

Our time is valuable.

The best way to show that you care for your freelancers and respect what they do is to understand that. Pay them for their time. And don’t ask for it for free.

(Freelancers: create a strong contract and control scope.)

Don’t Be Overly Robotic

Here’s a pet peeve.

It really comes back to the idea that freelancers are more than project resources.

I once had an account manager for two years at one of my clients.

To this day, I know almost nothing about him and he knows almost nothing about me.

Any attempts at small talk — which I initiated — were rebuffed. Eventually I simply stopped trying.

Some freelancers absolutely hate small talk but personally I find a complete absence of it makes a relationship feel oddly sterile and clinical.

Consider, when appropriate, asking your freelancer how their weekend went or what their plans are around the holidays.

It might open up a warmer and more fruitful relationship than might otherwise have been possible.

Always, Always, Pay Your Invoice On Time

There’s no bigger kick in the teeth as a freelancer than moving mountains to get deliverables for a new client in on time only to have them miss their first payment deadline.


Do you play your employees predictably?

Then extend the same courtesy to your freelancers.

Nothing makes me want to continue working with a client less than late payments. Particularly if it’s the very first one.



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Daniel Rosehill

Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.