How do I enforce a deadline with a freelancer?

Managing freelancers is very different from working with full-time employees – you can’t set working hours for one thing, which can make it feel like deadlines are a bit pointless.

After all, what can you really do to make sure they meet it? But setting (and enforcing) deadlines are both important and expected, so here’s how to get it right.

Pick the right freelancer

woman writing on paper

Picking the right freelancer is key to making sure they meet your deadline. Ratings and testimonials are a great way of figuring out if their past clients have been satisfied with their work.

If they’ve got bad ratings and you see numerous complaints about missed deadlines, they’re clearly not the right person for a project with a tight or essential deadline.

Equally, if you need work doing quickly it’s better to pick a more experienced freelancer who’s done that sort of work before, rather than someone who’s still learning and will naturally take longer.

Picking the right freelancer in the first place will mean you don’t have to do much enforcing – it’s likely they’ll meet the deadline without any issues.

Set a reasonable deadline

man working on laptop sat next to a large painting of a clock

If you want your deadline met, make sure it’s actually possible to do the work in that time! People often seriously underestimate how long it takes to produce creative work.

For instance, just a minute of animation can take a month to complete, and that’s with a whole team working on it! Similarly, logos are deceptively simple.

Designing a high-quality logo is a lengthy process, which involves research, and the creation of multiple concepts before it gets anywhere near a final draft.

Creative tasks are rarely the sort of thing you can rush through in a couple of days, and if they are, expect a rush rate to be added on to the cost. If you set an impossible deadline, expect it to be impossible to enforce.

If in doubt, discuss the desired deadline with freelancers and see if it’s feasible. Be willing to adjust it if you’re told it’s just not possible. If you involve the freelancer in this process, you’re less likely to have problems further down the line.

Don’t keep changing the deadline…

Don’t set a deadline then start ringing your freelancer asking if you can push it forward. The freelancer will have a workflow, and will most likely be working on multiple projects at the same time.

Randomly changing the deadline will totally disrupt their work. They won’t take you or your deadline seriously if you mess them around like this.

There’s nothing worse than a client who rings a freelancer at 4:30 on a Friday afternoon to tell them that the project that was due in 2 weeks is now urgently needed for Monday morning.

…But be willing to be flexible

Sometimes life gets in the way. When you set your deadline, have a bit of wiggle room built in for unforeseen circumstances.

The project might turn out trickier than expected, or if you’ve asked for a lot of revisions this will obviously make the project take longer. You’ll be less stressed about enforcing your deadline if you take potential delays into account.

For example, if you need packaging for a massive product launch, don’t make the freelancer’s deadline the day before!

Use milestone payments effectively

woman holding dollar notes in lap

If you tie milestone payments to certain deliverables, you can keep the project on track.

After all, money is always a fantastic incentive! Plus, it means you’re frequently checking in with the freelancer and you’re not going to discover right at the end of the project that you despise something they did right at the start!

Frequent review meetings and communication let you flag up any problems and these smaller deadlines help the freelancer to organise their work, as they can divide a big project into more manageable chunks.

What if I keep having problems?

jigsaw puzzle with one piece missing

We’ve all missed deadlines and sometimes it’s unavoidable.

The first time it happens, ask the freelancer what’s gone wrong – if they’ve been ill or had personal problems, obviously you should be sympathetic.

But if it happens again and again and the reasons seem to be plain old disorganisation (and you’ve done all of the above) it might be time to pull the plug and find someone more reliable.

Also, make it clear to any freelancers you hire that if they’re going to miss the deadline they should tell you in advance. Silence as the deadline soars by is even more annoying.

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Becca is the Marketing Executive at Twine. She loves literature, music, film and make-up. She spends a lot of time complaining about the mismatched angles of her winged eyeliner and stalking drag queens on Instagram. Otherwise, she’s helping Joe by writing blog posts and keeping Twine’s social media running.