Working with freelancers – 4 tips to avoid the headache

Freelancing has become more than just an additional side-gig for creatives and professionals looking to boost their income – it evolved into a lifestyle, much like the 9-to-5 workday or part-time work. Some even refer to freelancing as owning and running a small business, which nowadays makes a lot of sense. Once in a while, there comes a time where instead of hiring an in-house team member, a company is considering hiring a freelancer on a project basis. While it has worked for multiple companies in the tech industry, it has it’s a fair share of difficulties. Read more to find out what are the 4 tips to working with freelancers… and avoiding unnecessary headaches ?


  1. Communicate precisely
  2. Don’t micromanage
  3. Reward on-time delivery
  4. Pay them on time (no-brainer)

Helpful links:

7 reasons to use freelancers for your small business needs
Hiring freelancers vs. full-time workers
Guide to freelance project management

How flexible working allows working with freelancers 

working with freelancersWhether you have a small piece of work to delegate or you need to hire a freelancer to extend your team, you’re aware of the challenges of working with a new, remote team member. Different timezones, lagging video calls unfinished tasks might be some of the struggles. However, more and more companies decide to hire freelancers. Forbes did a great piece highlighting how hiring freelancers has risen in the last couple of years. Additionally, thanks to platforms like Upwork, freelancers and hiring companies now can benefit from a more transparent work environment thanks to building up profiles with information about employment backgrounds and track record. More and more tech companies embrace flexible working hours, which allows teams and freelancers to find a better fit when establishing their go-to work schedule.

So having that in mind, here are a few tips that will help you stay efficient when working with freelancers.

Communicate precisely

It sounds like an obvious one, but who didn’t experience having to deal with a manager reviewing your work by something along with the likes of:

“I like the design, but it’s a bit… 2016-ish” ??‍♂️


“That’s a really well-written article, but it kinda lacks the identity of our brand, it doesn’t sell” 


These or similar quotes are a fine example of providing confusing and nonprecise feedback, which is one of the essentials when it comes to efficient working in a business environment. Dear managers/bosses/supervisors – how do you expect a freelancer to deliver their job if they don’t understand the provided feedback?

You can do it, just be precise and to the point 🙂

Don’t micromanage

woman working on computerOkay, while I’m not in any way a fan of micromanagement (who is, duh?), there’s a fine line between a hostile over-the-shoulder micromanagement that doesn’t even promote efficiency and setting up regular check-ins and status updates within your team. There’s a simple way to gauge if your “hey, show me what you’ve been working on” e-mail is productive – would you yourself like to receive this from your boss? If no, set up official meetings where every invitee knows’ that’s the time to share assignment and project updates.

Remember: micromanagement is inefficient and significantly lowers morale

Disclaimer: Of course, if somebody didn’t deliver their job according to the deadline, it’s time to step in.

Reward on-time delivery

Another no-brainer. This doesn’t need to mean giving a huge bonus or promoting a freelancer to VP, but a simple “thanks, awesome job Steve” can really work wonders. Additionally, if you see that the freelancers deliver great content on a regular basis, talk more on perspectives – more serious involvements, raises or even equity incentivizing. Nothing works better than having someone on board for the right reasons, not only for the paycheck.

man working on computer

Pay them on time

That’s a really short one. Respect the people you work with. Pay them. On-time.

Don’t be a jerk.

You can also encourage your freelance counterparty to leverage some technology to ease the time reporting if you’re paying them on a time basis. TimeCamp has all the things you need to have your freelancers work in a transparent and measurable environment.


Obviously working with a new team member, especially if it’s in a remote setting can be tricky, but if it weren’t worth it, no one would be doing it. Keep these guidelines in mind and deliver better results throughout projects and milestones.

Best of luck, and remember. Teamwork makes the dream work ?

Feel free to share your thoughts in the comments – let’s hear your stories!

Working with freelancers – 4 tips to avoid the headache

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