How to Use Upwork for Successful Hires (Get the Best Freelancers)

hire on upwork tips

Over the last 5 years, I have worked with hundreds of clients on Upwork and earned over $100k. I have also worked with freelancers on the platform and know how to hire on Upwork. But it’s not always been a smooth ride and I’ve had some less than pleasant experiences with clients.

If you are looking to hire a freelancer through Upwork for the first time – or have had a bad experience with a freelancer and you’re not sure why – this guide should help.

I’m going to take you through the process from posting a job to ending your first contract, with tips that I’ve accumulated through years of working on the platform as a freelancer. This will help you find the best freelancer and hire on Upwork to build your brand further.

Posting a Job

Whether you plan to invite specific freelancers to a job or let professionals apply from all over the world, here is what needs to be in your job proposal:

  • The role you need filled or the work you need doing.
  • The timescale for the project or the amount of work required.
  • ‌Any specific requirements for the freelancer (e.g., must speak a specific language or have previous experience in a particular area).
  • How you would like to pay (hourly vs fixed amount) and your estimated budget.

You might be tempted to make your job proposal vague to encourage people to apply to find out more… But please don’t do this.

Here’s why.

To apply for a job, it costs freelancers ‘connects’. These connects cost money and freelancers beginning on the platform will only have a limited amount to spend.

Wasting connects applying for a job that actually isn’t a fit for our skills, wastes our time and money. Those freelancers whose time has been wasted are less likely to apply to further jobs you post in the future.

Red Flags Freelancers Look For

Other ‘red flags’ that freelancers look out for and avoid include:

  • ‌Not verifying your payment method with Upwork before creating a job.
  • ‌Shortened links in the job description, whether it’s to your website or further details (un-shortened links that show the full URL are fine).
  • ‌Any request to discuss the job via phone, WhatsApp, Skype or elsewhere off the Upwork platform.
  • ‌Any sort of unpaid trial, or a promise of plentiful, long-term work if the freelancer drops their rate for the first milestone.

If your post has any of these red flags, you are not going to attract professional and experienced freelancers. Instead, you’ll get applications from the people that are so desperate for work that they’ll apply for anything.

The Dark Side of Upwork

You may be wondering why you should be concerned about freelancers that are desperate for work applying for your job. After all, you might get the work completed at a very low rate.

The truth is, there is a layer at the bottom of Upwork’s hierarchy that is filled with both predatory clients and freelancers. Clients who want to pay $1 a day attract freelancers who are so desperate for money, they won’t think twice about ripping off a client.

This side of Upwork is murky and there are plenty of horror stories from clients and freelancers alike. If you want to avoid falling into this predatory world, make sure you are offering jobs at a fair rate, so you attract freelancers who appreciate you as a client.

Job Proposal Questions

The questions you can add to the job description are a good way to vet freelancers. But if you just use the ‘suggested’ questions from Upwork, you’ll get generic copy and paste answers.

My advice is to use those questions sparingly, only for large projects, and make sure they are tailored to the job. If you add too many questions and make it a lengthy process to apply, fewer freelancers will take the time to fill it all out.

A reputable freelancer who has an hourly rate of $100 is not going to waste time filling out endless irrelevant questions when the next job post has none and offers the same money.

Shortlisting Freelancers

With a good job description and a little patience, you will receive a good number of applicants. The most popular jobs can attract over 50 applicants in an hour.

If your post isn’t attracting applicants, look at it carefully to understand if your expectations are too high or your budget is too low. For example, today I came across a job posting for an Amish writer to create an eBook – now I am no expert on the Amish lifestyle, but I am fairly sure there won’t be many using a computer or applying for Upwork jobs.

When you are shortlisting freelancers, you can choose a handful to interview further.

Extra Tip for Shortlisting

If you decide not to go ahead with the job, or you find a freelancer that would be perfect for it but they’re out of your budget, message them anyway. Being a businessperson is about networking. You might not be in a position to hire them for this job, but you may need them in the future.

I have had several clients who have hired me for subsequent jobs, after their business has grown to a scale that requires my services – but couldn’t hire me in the first instance.

Interviewing a Freelancer

When you are chatting with potential hires on Upwork, you’ll want to ask them about their previous experiences and your expectations.

It is also ESSENTIAL that you discuss what should happen if you need changes made to the work after it has been submitted.

Personally, if I have missed something in the brief or made an error, I will fix it without question. If you have suddenly decided that actually, you want something different than originally planned, I charge at my hourly rate.

As long as the freelancer has met the requirements that you gave them when you hired them, they DO NOT have to make the changes you need without further payment. The freelancer has met all the terms of the contract and it you decide that you no longer need the work or want it done differently, that is on you.

Communicate your expectations clearly and ask the freelancer if they have understood everything. If they agree and everything is documented, you have done all you can to ensure the freelancer is equipped to complete the job correctly.

man working at a home office desk

Agreeing on Price

Once you’ve provided more detail about the job, you may find that the freelancer gives a quote or timeframe that is beyond what you anticipated.

  • DO explain the budget you have to stick to, and the time frame you were expecting. Sometimes, a freelancer may be willing to compromise.
  • DON’T ask for free work or insist that the freelancer should work below the rate they have given you. If the glove doesn’t fit – you must acquit. Move on and find a freelancer that is in budget or adjust your budget to hire your chosen freelancer.

Freelancers are Professional Businesses

Remember, freelancers are not your employees. They have overheads and operate their work as a business. A freelancer will know what is profitable and they will know the value of their time and effort.

If my expenses are $30 an hour just to keep the lights on, cover everything I use to work from home, and keep my family fed, I CANNOT work for $25 an hour.

Upwork Charges Fees to Freelancers – They Factor Fees into Their Cost

Upwork charges 20% plus VAT to all freelancers for the first $500 earned on a contract. This is part of the Upwork Service Fee. After that, it drops to 10%. If you genuinely have a long-term project, asking for a 10% discount after the first $500 of the project may be a good compromise.

If a compromise cannot be reached, move on, don’t waste their time haggling, and find a freelancer that can work at your budget instead.

Update, April 2023: Upwork is adjusting their fee structure to a flat 10% plus VAT for all freelancers this year, so you may find that fewer freelancers will offer a discount after the first $500. This also means that there is less incentive to take on long-term work – it remains to be seen how this will impact the Upwork platform.

Hire on Upwork for a Trial

It’s totally okay to hire multiple freelancers for a paid trial. In fact, it’s a good way to test out freelancers’ abilities and measure them against each other.

I actually recommend you do this, if it’s within your budget and your requirements are very specific.

By trialling freelancers, you can quickly spot those that are overpromising and under delivering. You might find that a freelancer who has fewer qualifications exceeds your expectations, and you may save money knowing that freelancer can produce work to your expectations at a lower rate.

Sending an Offer

When you send an offer to a freelancer, whether it’s for a trial or the whole project, make sure it matches what you discussed at interview.

Furthermore, make sure the contract type is correct.

If you have agreed a fixed price for the project, create a fixed price contract. Even if your project may continue beyond the initial milestone, if you have a fixed rate (e.g., $50 per 1,000 words written) then you can use the fixed contract and add ‘milestones’ when more work is needed.

If you need to pay your freelancer hourly, use an hourly contract.

DO NOT send an hourly contract for fixed rate work. You don’t know if the freelancer is going to manually add hours and exploit your mistake.

Upwork Tends Not to Interfere

When a contract goes to dispute, Upwork is very aware that arbitration costs them money. They will do whatever it takes to prevent taking a financial hit, even if that means you lose out financially.

For the most part, Upwork encourages clients and freelancers to resolve the dispute themselves, without interfering at all. They don’t want the financial liability.

Stick to fixed contracts or hourly tracked time, both of which are protected for both freelancers and clients. If you’re using an hourly tracked time contract and you’re concerned about overall cost, either agree a fixed rate or get an indication of how many hours the freelancer anticipates it will take to complete the work.

Approving the Work or Requesting Edits

When the freelancer has delivered the work, try to respond promptly. If you cannot review the work in the next day or so, just message them to let them know when you will be able to reply with some feedback.

Trust me, waiting for feedback is absolute agony if the client goes silent and I have turned down clients requesting future work because they ghosted me on the original contract.

If the work is all good, hit the approve button (on fixed contracts) to release the funds to their Upwork account.

If it’s an hourly contract, you don’t need to do anything.

In either scenario, you should message the freelancer. Even if it’s just a “Good job, thanks.” It really puts our minds at ease and cements you as a communicative client that appreciates the work done.

Requesting Edits

If you need edits made, just ask. Outline what needs changing (bonus points if you can phrase it constructively and stay positive) and the freelancer should make changes or give you a bill for the additional work you are requesting.

Remember, edits made within the remit of the brief are fine. For any edits outside of the brief, you should expect to pay more.

writing feedback notes in a journal

Continuing or Ending Contracts

If you have ongoing work for your freelancer, just message them to ask if they are available. Then you can set up a milestone within your existing contract.

End the contract if you have no further work.

If you do not end the contract, it will remain open. Open, inactive contracts damage a freelancers account. If you need them in the future, they are not going to accept work if you have damaged their profile and prevented them landing other jobs as a result.

To close the contract, go to the contract page and click to close and leave feedback. Leaving feedback is INCREDIBLY important for freelancers.

Leaving Feedback After You Hire on Upwork

If you do not leave feedback, I am hesitant to work with you in the future. Firstly, because I don’t know if you were actually happy with my work, and secondly, I don’t want my profile filled with contracts that have no feedback. For potential future clients that check out my profile, that is a massive red flag.

So, take 10 seconds to select some star ratings. You don’t need to leave a comment, but it’s always helpful.

If you had an unpleasant experience, try to be respectful and honest in the review you leave. A good rule of thumb is to comment one thing the freelancer did well, and one thing that could be improved. Use the star system to highlight problem areas.

I’m not sure if I need further work

Well, then say that! Communication is important.

If it might be a few months before you have more work for the freelancer, tell them. They may be happy to leave the contract open. On the other hand, they may want you to close it and rehire at a future point.

Leaving your freelancer in the dark is NOT appropriate. We need to continue finding work and booking in clients. If we are unsure if you will suddenly pop back up with a large project, it makes scheduling very difficult. Don’t be surprised when we don’t have the time to accommodate you in this situation!


It’s great to hire on Upwork to connect with freelancers and find amazing talent to further your business or brand.

Overall, the biggest problem I find on the platform (as a freelancer) is a lack of understanding from clients. If you come at the process with the aim to get as much work for as little money as possible, with no respect for the people trying to earn a living, you’re going to have a bad experience as a client.

But, with the right attitude and the right approach to finding the right freelancer for your project, you will succeed. Good luck!

If you’d like to hire me on Upwork for content writing, take a look at my Upwork profile.

Isobel Moore

Isobel Moore is a quiet, quirky and creative “human bean” whose favourite pastime is curling up with a cuppa and a good book.

Over the past 5 years, her tea reviews at Immortal Wordsmith have helped thousands of readers choose vibrant tea blends and single origin selections from fine, organic, and responsible tea companies.

As a professional content writer with a qualification in digital marketing, Isobel has worked with market-leading tea brands around the globe to develop their content marketing campaigns and gain exposure. Her professional portfolio can be found on Upwork.

Besides a deep-rooted passion for tea, Isobel writes on topics ranging from food and travel to wellness and literature.

Favourite Quote: “Manuscripts don’t burn” – Mikhail Bulgakov

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