Getting to a point in your freelance career where you’re too busy to do it all and can afford to outsource is an enviable position to be in.

But it’s likely all very new to you. Many freelancers haven’t had experience hiring people or managing a team so it can all be a bit intimidating. For this reason, among others, freelancers will put off hiring the help they need, often until it’s too late.

But if you’re ready to take the leap, we’ve got some tips to make this a simple process that benefits both parties.

Don’t go for the cheapest option

No doubt you understand the frustration that comes from knowing that some freelancers will charge pennies for their work. It brings the value of everyone’s services down when people know they don’t have to pay very much for a freelancer.

Lead by example and don’t head over to Upwork or Fiver when the time comes for you to hire someone. Do your research and budget for a quality freelancer, just as you hope clients will do for you.

Set expectations clearly

One mistake that commonly happens with freelance and remote workers is that the expectations are harder to set without those face-to-face interactions. Things get lost in emails, people misunderstand things and so on.

It helps to have everything down in writing so that you can both refer to a contract where necessary. If they don’t bring up a contract first, don’t be afraid to take the lead. Get everything in writing at the beginning as this will set you both up for a successful partnership.

Regularly check-in

If you plan to hire someone on a regular basis, it’s important to have regular check-ins either weekly or monthly. This gives you a space to share your thoughts on the partnership and also make plans for the future. Any issues can be brought up here and resolved without them getting buried under workloads.

Use instant messaging

If you hire a team of freelancers, then instant messaging groups can be really helpful. This allows everyone to communicate openly together. No more wondering whether that person has seen that email or whether you remembered to tell everyone about a new update.

Everything can be posted within the chat and referred to simply. Choose a platform like Slack or even a Facebook or Whatsapp group is better than nothing.

Be flexible

The key to freelancing is flexibility. It’s probably one of the main reasons why you got into it in the first place. So, make sure you’re flexible with your own freelancers too. That means flexible working hours and working out a compromise on deadlines that is realistic (particularly if they work in another time zone).

Stay in touch

If appropriate, try to stay in touch with freelancers you’ve hired in the past. You could use their services again, or they could even use yours or at least recommend you to someone else. But in most cases, people won’t do these things unless prompted.

Shoot over a quick email to check how they’re getting on. It could make all the difference. Just don’t go overboard with it and email them every weekend.


It’s easy to get hiring people wrong but the key is to mentally reverse the roles. Would you be a happy freelancer in this position? What would you want in this scenario? What have you struggled with in the past, with clients or bosses?

Use your experience as inspiration for how you deal with your new freelance partners.


Are you looking to hire a freelancer? Head over to Twitter to connect with some of our freelance followers.


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