The Startup
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The Startup

5 Surefire Ways to Annoy Your Freelancer

Avoid these common pitfalls when commissioning a freelancer

Photo by Good Faces on Unsplash

Like finding a good used car, truly great freelancers are hard to find.

When you find one, you’ll want to keep hold of them. Part of this is forming a good relationship to keep them delivering for you and prioritizing you as a client. When that rush delivery is needed, being a good client means the answer is more likely to be a ‘yes’.

It’s not just about “being nice”, it makes good business sense as well. Keeping your freelancer happy is a fast track to your own success.

Many clients don't always realize that hiring a freelancer is a 2-way street. While you are offering them money for their services, many successful freelancers have worked hard to build a loyal base of clients that they work with. This affords them a choice with who they work with.

If you aren’t a great client, then odds are they won't want to take on further work from you — no matter how much money you wave in front of them (unless it’s obscene — everyone their price, right?)

Self-employed people already know the value of freelancers. As well as being one, many freelancers employ them to handle different parts of their business. Yet, these tips are just as much for you as for anyone else. They help to crystalize where the breakdown might have happened with people you have employed. You might also think about reverse engineering them with your future clients.

Breakdowns in freelancer/client relationships are often unintentional missteps on the behalf of the client. Others can be slightly more inexcusable. Let’s take a look at the best ways to keep your freelancer sweet and develop a great and lasting relationship.

Pay them…on time.

Financial disputes are one of the leading causes of divorce in the US. The same is true with other relationships too. Nothing is likely to make freelancers stop wanting to work for you than not getting paid on time.

Most freelancers will chase up late payments with a quick email. In most of these situations, the client apologizes with genuine comments of forgetfulness. This is fair enough…once. However, recurrent late payments become a massive headache. Keeping tabs on everyone who hasn't paid, chasing them, dealing with the excuses, it ultimately just ends up being a better business decision to not work with you. It’s nothing personal, honest!

Many online platforms (Fiverr, Upwork, etc) use some kind of escrow service to protect both parties. When working directly with a client this isn't always the case. I left direct freelancing and started working on a freelancing platform because chasing invoices became a colossal pain. It was the best decision I ever made. I know I’ll get paid every time and don't have to spend valuable working hours chasing people for payment. It’s a great way for freelancers and clients to structure their working procedures to keep the relationship positive.

Don’t Add New Things to the Remit

Freelancers don't like it when you move the goalposts. If you have provided a project and then halfway through decide to change a significant component of it, be prepared to pay for the time it takes to make all these changes.

It also puts doubts into the freelancer's mind on whether they want to work with you again for 2 key reasons. Firstly, you appear to not know what you want. What’s to say you won't move the goalposts again further down the line. Secondly, it gets a bit dull for the freelancer. Reworking a project that you were 80% through and taking it back to square one feels like you are undoing all your work. Even if they are getting paid for it, freelancers are likely to get bored with working on the project all over again. You don't get the best work, they get fed up with the project. Nobody wins.

Not providing all the information upfront

This taps a little into adding new things to the remit with a subtle difference, namely time management. Starting an order with a timeline and adding a comment like “I’ll send you the additional documents tomorrow” inevitably means that you are condensing the amount of time the freelancer has to work on the project. This new document you provide might fundamentally change what they are going to do. They can’t start the project, yet still, the agreed clock is ticking.

It also puts the emphasis on the freelancer to chase you if the promised additional information doesn't arrive.

A fairer way of doing this is to not start the order until all the information is available. Alternatively, you might agree on an extended deadline once you provide this additional information.


Most freelancers got into the field to escape the 9–5 and having a boss. While they will happily do work for you, most do not like the idea of having a boss. Being a micromanager reminds them of having a boss. They don’t like it. Please don’t do it.

Depending on the nature of the work, most freelancers will want to understand your project upfront. They’ll have long conversations to understand your proposal. They’ll discuss what deliverables you want. They’ll talk through any key requirements that MUST be included in the final piece.

This is done for several reasons.

  • They genuinely want to produce a good end-product.
  • They want to reassure YOU that they understand what you want.
  • They give you the opportunity to ask any questions.

Now is the time to set expectations. Layout the ground rules. Ask any questions about their competency. Once you have commissioned them, leave them alone. They know what they are doing. If you don't trust them to deliver what you want a) you need to get better about communicating your expectations upfront and b) you shouldn't have commissioned them.

Asking for updates

Employing a freelancer, especially online, is a bit of a black box problem. As the hirer, you don’t necessarily know anything about their writing processes, internal timelines, or other deadlines.

Asking for updates can be frustrating for the freelancer. You’ve agreed the work and the deadline. Just let them do it!

When you agree on a timeline to deliver a project (let’s say 5 days), it doesn't necessarily mean that the project needs 5 days of work. Instead, 5 days is the time it might take to complete the project taking into consideration all the other commitments the freelancer might have. It might be that they work on it on day 1. It might also be the case that they only start working on it on day 5. Either way, it’ll get delivered by the deadline — don't worry!

Avoiding these common pitfalls when commissioning a freelancer can help lead to a positive and prosperous relationship for everyone concerned.

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