Working with a Freelancer

I have worked with several different clients, all of which have been fantastic (I think I’m just lucky). Every one of them have had different approaches to working with me and, I’m assuming, the other freelancers they’ve hired. Likewise, I work in communication and special projects during the day, which requires me to liaison with several different freelancers, from translators to designers. I’ve picked up a few little tricks along the way that have ensured – both in my freelance work and in my 9-5 – that projects are completed on time and without too many of the inevitable set backs.

Without further ado, here are some tips for working with Freelancers, no matter what industry.


Before you start a project, set up an internal schedule for yourself for each of the tasks that need to be accomplish. This will help you plan out what type of freelancer you need (writer, translator, graphic designer, web designer) and will give you the frame work for a projected completion date – something that gives you a goal to work towards.

Once you know who you need and the projected completion date, you will be prepared to contact freelancers.


Regardless of whether or not you have firm deadlines for your project, it’s always helpful to give one to your freelancer, especially someone with whom you’ve just started working. This is two-fold:

  1. Deadlines are a great way to gauge a freelancer’s reliability. The most obvious question you will answer is if they can meet deadlines. The second is whether or not they give themselves and you enough time to work out any kinks or answer any questions. Everyone has their own style and their own system set up, so don’t be alarmed if they ask all of their questions at the beginning, throughout the project or at the end – it may just be their way of getting the project done. However, if their way of meeting a deadline doesn’t work with your project management style, you find out right away, rather than in a few months when you have an urgent project due.
  2. Deadlines help keep projects moving. I personally split projects up into “first draft submission” and “edits”. When a client gives me a due by date, I try to make sure that I submit a first draft before the due by date to ensure that, if edits are required, they can be done before the deadline.

Tip: Set a soft and a hard date – the soft date being one that you can afford to miss, just in case there are unforeseen problems with the project, more edits than expected and so on. Give the soft date to the freelancer and keep the hard date for your reference.

Another Tip: When working with a relatively new freelancer, always try to give at least a week for any project. Once you’ve built a relationship, you will be able to determine what works for both parties.

Style Guides

I’m often surprised at how few companies have a style guide. Style guides will tell a freelancer the specifics you usually forget are necessary – which type of English you work with (Canadian, British, Australia, American); what colours are used in your logo (if you have one) or on your website; how you like to apply italics or hyphens. All of these things are style choices. In the case of website and graphic design, it is always helpful to have a mock up of a standard page with the heading types and colours listed for each heading and subheading.

Consistency is professionalism.

Tone, Audience & Purpose

Though this should also be part of your style guide, the tone, audience and purpose will vary slightly from project to project. When you are first considering the project, jot down at least one adjective for each heading. For example:

Tone: Friendly, colloquial

Audience: people with aging parents

Purpose: to inform  

When you give the project to your freelancer, these three factors will give them a direction, which will help them to craft the project the way you want.


This is essential. This is also many-parted:

  1. Availability: If you’re planning to go away on vacation or will be M.I.A. for longer than 24 hours, let your freelancers know. This way, if they have questions, they’ll know to save them for later or will know that a response will take longer than usual. Likewise, they will repay the favour so that if you want to send them a project that requires a quick turn-around, you won’t be left with no one to send it to. 
  2. Content & Questions: Keep the lines of communication open. Most good freelancers will ask you any questions they might have. You should do the same.
  3. Confirmation: When you receive something from one of your freelancers, but don’t have time to review it right away, send a quick email to that effect and give an eta for when you will review it. Email isn’t always reliable – sometimes messages get lost in the void that is the internet… and sometimes they get filed without us knowing it. This confirmation will assure the freelancer that their work has been received.
  4. Problems & Concerns: If something isn’t working out or you feel that there is an issue with your freelancer, tell them. Be honest, open, respectful and polite about it, but still, tell them. It may be that they are not aware of the issue.


Feel free to say how you feel about the work that’s been submitted, especially if it’s the first project. However, be specific. General statements like “I don’t like it” or “it doesn’t work for our company” leave the freelancer wonder just what exactly she could have done differently. Most people are happy to do revisions, even start from scratch if necessary, providing they have the appropriate direction. When you receive something that you just don’t like but can’t figure out why, try answering these questions:

  • What about the text doesn’t work?
  • Is it the content itself?
  • Is it the word choice and if so, which words?
  • Is it the tone of the text?
  • Is it the length?
  • Is it the use of “is it” too many times?

The more specific your feedback, the better the second draft will be. 


(did I mention those already?)

If your Freelancer consistently (and by this I mean, 5 or 6 times with no advance explanation) misses deadlines, you might want to talk to them about their work load and availability. There are four reasons why a good freelancer will miss a deadline:

  1. The project was bigger than they expected
  2. They are overloaded with work
  3. Family or personal crisis
  4. The deadline was unreasonable (though most will tell you that in advance)

If you have a good relationship with your freelance writer, keep it by being open about your expectations and your disappointments. Most writers have developed a thick, scaly skin over their years of writing, though admittedly it is still possible to hurt their feelings. There will be well written projects and some that miss the mark entirely, but if you follow these tips, you will create a positive work environment for yourself and the people you hire.

Was this helpful? Do you have any additional tips? Share them in the comments.

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