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5 Questions To Ask Before Signing A Freelance Writing Contract

So you’ve decided to start using Upwork to make money as a freelance writer? That’s great! As somebody who has been doing this professionally for two years now, I know the process can work.

(NOTE: even if you’re not using Upwork in order to obtain your freelance writing jobs, this advice still applies to you)

That being said, though, just because you’ve decided to make the leap into freelance writing on Upwork doesn’t mean you’ll have all the answers to using the platform figured out right away.

You’ll likely be overwhelmed by the amount of job postings, you might feel like all the jobs are “scams,” and there’s certainly a chance you won’t even hear back from the majority of clients that you contact.

And guess what? That’s perfectly okay, and super normal, especially when you’re just starting out and you’re trying to get your footing in this new writing arena.

Embrace the overwhelm, but don’t let it scare you into thinking you can’t make money with Upwork.

You can, and it starts with knowing how to ask the right questions before entering into a contract.

If you have a client who is interested in hiring you for your writing services, here are five questions I highly recommend asking before entering into the contract:

1) What is the word count on the project?

For most clients, they’ll state this right in their job posting, but for those who don’t, be sure to ask about it, especially if it’s a writing category/project that you’re unfamiliar with.

For example, say you have a client who would like your help writing product descriptions for their new online store, but you’ve never done this kind of writing before. You might be unsure about the typical length of a product description, so make sure you ask! I’ve done product descriptions that were only 45 words, but I’ve also done ones where the client wanted a brand description, and the blurb was more like 500 words. Quite a difference, right?

Never be afraid to ask about word counts, and if the client says they’re more concerned with quality over word count, that’s great! It means you’ve found a client who really appreciates quality work, and isn’t just looking for meaningless words on a page.

Hold onto clients like this.

2) Does the project require images?

In my experience, when doing blog content for the fashion industry (i.e. my writing niche), many clients want images to go along with the blog post.

Because fashion is such a visual industry, this makes sense.

For other content, it might not be as necessary, but just be sure about all the deliverables before you sign onto the contract. While having to source a couples images here and there doesn’t take that much work, it can add extra time if you’re having to source 10+ images.

Also, when it comes to adding images for blog content, always be sure to make it clear to the client what kind of images you offer. For example, I don’t offer original photography on any of my articles, and I always make this clear to the client. I tell them I can source images from the internet and provide credit, or I can use free stock photo websites.

Remember: this isn’t your blog. However the client asks you to pick the images, that is up to them. Just be sure to pick ones that help illustrate the point you’re trying to make in your article.

Note: if you do have experience with photoshop, or you think you’d be able to provide original graphics with some other program, feel free to mention this to the client. You don’t have to be pushy about it, but it’s a great way to upsell your services and possibly make more money on the project. Just be sure to make it clear that you do charge extra for this service.

freelance writing contract

3) What is the timeline for the project?

Always ensure you’ve been given a deadline for a project before locking yourself into a contract.

There’s nothing worse for your reputation on Upwork than negative testimonials on your profile, which likely will happen if you don’t meet deadlines for your clients.

Be clear about when deadlines are, and, if you’re going to be splitting work up into multiple stages (i.e. first draft, second draft, etc.), make sure you have a rough timeline for that as well. This will also help you with scheduling your time, and ensuring that you don’t take on too much all at once. In addition, you’ll find having an agenda or some type of planner that allows you to write down deadlines will come in handy. (note: I use the Simplified Planner, and I’m absolutely obsessed with it, if you’re looking for a high quality planner)  

Also, if you’re just starting out on Upwork, always try your best to deliver top quality work in the fastest time possible. Don’t make the client think that you’re always going to be this speedy (this sets up bad expectations), but you can always say something like, “I had some extra time today, and was able to get this finished for you early. Excited to hear your feedback.”

Even when I’m not particularly busy and getting a project done early was no big deal, I always make my clients think I’m a little busier than I am.

Think about it: do you want to go to the restaurant that has a big line where everyone is eager to try the delicious menu, or is the little spot down the street that’s completely empty sound more appealing? Unless you’re super hungry, you’re likely going to be inclined to want to dine at a spot that looks to be popular.

The same goes with freelance writing. Never seem too available, but at the same time, be available. As much as that might sound like a contradiction, I think you all understand what I mean here. They key is to always take on the work, but just ensure the client doesn’t get the impression that this is your one and only job. You need to act the part of a professional freelancer, and create some demand.

4) What is the compensation for the project?

Probably the question that you’re least likely to forget, always ensure you’re clear with your clients about compensation.

This includes knowing if you’re going to be paid a lump sum for multiple pieces of work, or if you will be paid as you go. Basically just make sure you’re clear about the conditions of your payment, and when payments will be made to you.

While we’re on the issue of payment, I highly recommend pushing for a contract that ensures you’re paid for each piece of content you submit, rather than one lump sum for multiple stages of work.

For example, if the client tells you they want four pieces of content throughout the month, set up a contract that allows you to be paid for the articles one at a time instead of all at once at the end of the month when you submit. This way, if the client doesn’t like your work, or they suddenly disappear, you’ll know about it before you start on articles 2, 3, and 4.

Having said that, though, if you’re using Upwork, and the client is comfortable depositing funds into escrow for all four articles, you won’t have to worry about not being paid at the end. With Upwork, because the client deposits funds into escrow, if the client just randomly disappears after you’ve submitted the work, Upwork will release the funds to you and you’ll be paid without issue.

This has only happened to me on three occasions during my two years on Upwork, but it’s saved me from losing out on some serious money, which makes me so thankful that I’ve decided to use Upwork for a solid portion of my writing contracts.

I’ll also mention that currently, with most of my clients, I submit multiple pieces of content all at the end of the month, rather than one at a time. This is simply because I’ve been working with these clients for multiple months now, and I know what they want. I’m not worried about the articles not hitting the mark, because I already have a good idea of the tone I should be aiming for.

If you’re just getting started with a new client, I recommend suggesting to the client that you submit a paid sample piece, so that both you and the client can ensure you’re a good fit for each other before proceeding. This protects both you and the client, which I find clients always appreciate.

5) Are there any special considerations that I should be aware of?

Always ensure you tell the client that the more information they can provide to you, the more likely it is that you’ll be able to deliver top quality work to them. To this day, when I enter into a new contract, this is something that I always say to new clients.

For some clients, they may not realize something is not obvious to a freelancer, or they might just completely forget to state something that would change the entire scope of the project.

Keep in mind that some clients who are just starting a business may have multiple other things going on. While it might be nice to think the work you’re submitting to them is their top priority, it oftentimes is not. Because of this, it is up to you to ensure you’re asking the right questions that will help get you through the project.

Bottom line: if you have questions, or you’re not sure about something, never be afraid to ask about it. Trust me, the client is going to be much more frustrated if you deliver low quality work than if you ask a mere question.

This includes asking questions about the target audience for the writing, what the purpose of the writing is, what the tone of voice should be, and how the piece of writing will be used.

Think of it this way: imagine yourself sitting down to write the piece. If there’s anything you’re unclear about, I can’t emphasize enough how important it is to ask about it, because let me tell you, as someone who once completely got the target audience wrong for a piece writing, I now always, always, always ensure that I know exactly what the client is hoping to achieve with the piece.

Remember: your ultimate goal when writing for clients is to ensure that you’re making their vision come to life. In order to do that, you need to have as many details as possible about the project. If you ask questions, and the client isn’t concerned, don’t worry too much, but for the most part, clients are going to see your interest in the project, and they’re going to register it as a good thing. They’ll appreciate you more, and they’ll be much more inclined to leave you a positive review at the end of your contract, which I think is one of the key defining criteria for having success on Upwork.

Don’t be afraid to ask questions when it comes to working on freelance writing projects. Plain and simple.

Everyone approaches freelance writing differently, but these are the questions that I always ask when I take on a new freelance writing projects, and I hope they can help you during your next contract negotiation.

Don’t forget that freelance writing doesn’t have to be scary. Just try your best to ask all the questions that you need to in order to understand the project completely. Easy peezy.

If you want to dive in to this topic even deeper, and you’re looking for some tips that will help you find the best clients and deal with the difficult ones, feel free to check out my ebook on freelance writing.

My ebook, Freelance Writing Simplified, is over 100 pages that will take you from start to finish on how to get started freelance writing on Upwork. Even if it just helps one of you, it’ll have made my day.

Happy freelancing, to become a freelance writer

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