Top 10 Best Practices For Outsourcing Your Work On Upwork

If you’re looking to hire a freelancer online, Upwork is one of the most popular websites for doing so. It’s a great way to find experienced workers from around the world and has a wide variety of skillsets available at competitive pricing.

You can use Upwork for any kind of work, but most people hire freelancers there for writing, design, or programming projects.

In this article, we’re going to talk about how best practices can help you get better results on Upwork and how these practices differ from other platforms like Fiverr or Freelancer (which are also worth checking out).

Freelancing 101: Professional Best Practices on Upwork
1. Clearly define project requirements and expectations upfront.
2. Thoroughly vet and evaluate freelancers before making a hiring decision.
3. Communicate effectively and maintain regular communication channels.
4. Set clear milestones and deadlines to track progress.
5. Provide detailed instructions and guidelines for the project.
6. Establish a feedback loop to address any concerns promptly.
7. Monitor the quality of work and provide constructive feedback.
8. Build trust and maintain a professional working relationship.
9. Keep an open mind and be adaptable to changes or challenges.
10. Evaluate the results and learn from each outsourcing experience.

1. Stay Considerate And Friendly With Your Freelancer

As the employer, it’s your job to make sure that your freelancer is comfortable with the project you’ve assigned them. When that person is working from their home country, this can be a little tricky but it’s worth investing time and energy into maintaining a friendly relationship with them.

You’ll have much better luck getting what you want if your freelancer sees you as someone who cares about their well-being and happiness. So be polite, friendly, and helpful whenever possible! Ask about their personal life if they share something personal with you (and don’t forget to tell them more about yours in return). Check-in now and then just to see how things are going or if there’s anything else either of you needs at the moment.

The key here is respect: try not coming off as too demanding or demanding at all and definitely don’t treat them like they’re part of an assembly line!

Understanding why US freelancers charge higher rates than others can provide valuable insights into the competitive landscape. Explore our article on Why Do US Freelancers Charge Higher Than Others? to gain a deeper understanding of the factors influencing pricing in the freelancing market.

2. Choose The Right Contract Type For You

When you’re looking to outsource your work, Upwork will give you a number of different contract types to choose from. These include:

Fixed Price Projects

As the name suggests, with fixed price projects you pay a set amount of money upfront. Your freelancer receives this payment as soon as they accept your project.

Hourly Projects

With hourly contracts, payments are calculated on an hourly basis and made after the freelancer has worked for a certain number of hours (the default is 40). Payments can be made via direct deposit or PayPal if desired.

Specialist Contracts

These are non-standard contracts designed for specific types of work (such as logo design or web development). They allow both parties more flexibility with how they structure the project and how payments are received there’s no need for invoices or milestones in these cases!

Agency Contracts

Agency contracts allow you to hire multiple workers at once while keeping their access secure; they also give each collaborator’s information only when necessary so that others don’t accidentally see sensitive details like billing information or contact details without permission first

3. Give Your Freelancers The Information And Context They Need

Many freelancers will be new to your company and the field you are hiring them in. They should meet with someone from your team before starting work on your project, if possible. This is the best way to give everyone involved a sense of what is expected of them and how their work fits in with the rest of your organization.

The best way to communicate this information is through written instructions that include examples, links, and other relevant files that can be referenced as needed during the project duration.

Crafting a compelling portfolio is crucial for landing freelance jobs. Discover effective strategies for creating a portfolio that impresses potential clients in our comprehensive guide on How to Make a Portfolio That Gets You the Job. Learn how to showcase your skills and stand out from the competition.

4. Be Open To Change Orders

Over the course of your work with your Upwork freelancer, you may find that something comes up that needs to be changed. This is completely normal and part of the process. There are a few ways to go about this:

  • Communicate clearly with your freelancer, whether it’s via Skype or email.
  • Include details about what needs to be done, why it needs to be done, who should do it, and when they should do it by (if appropriate).
  • If a change order seems small and easy enough for an Upwork freelancer to do on their own without talking back-and-forth over email, then don’t worry about going through these steps just ask them nicely!

5. Hire For Skills And Not Just Price

When you’re outsourcing work on Upwork, it’s important to keep in mind that the freelancer is likely not a part of your team. You don’t want to hire someone who isn’t invested in your business and has no interest in reaching milestones with you. This is why it’s important to hire for skills and not just price.

You should find the right balance between price and quality when hiring on Upwork. While you may be tempted to hire cheap workers who will do whatever is asked of them without question or complaint. 

This could end up costing you more down the road if their work isn’t up to par or they decide that they’d rather take another job offer from another company instead of continuing working with yours.

In order for your freelance workforce to be successful (and hopefully stick around long term), look for candidates who have experience working with businesses similar in size to yours; this will help ensure there are no communication issues once they start working full time within your organization

6. Provide A Trial Period For New Hires

The trial period is a great way to get a feel for your freelancer. It gives both parties time to test each other out, which can be especially helpful if you haven’t worked with this person before. 

A trial period usually lasts no more than a week or two, but the exact length depends on the scope of work and how much time you want to spend getting acquainted before really moving forward with it.

I prefer shorter trials because they give me more flexibility when I need to switch things up it’s easier for me to decide not to continue working with someone after just a few days rather than after several weeks of working together! 

However, if we don’t get along well in our first week or two together there’s no point in continuing since we won’t be able to achieve much anyway!

As far as what exactly happens during our trial period: we’ll spend most of our time talking about what needs doing; discussing timelines (for both themselves and those who will do any necessary research); clarifying requirements from both sides; etcetera…

Before hiring a freelancer, it’s essential to understand the qualities and considerations that make a top-rated professional. Check out our article on Top Rated Freelancers: What You Should Know Before Hiring One to discover the key factors to consider when selecting a freelancer who can meet your project requirements with excellence.

7. Create A Client Success Guide

When you’re working with freelancers on Upwork, it’s important to let them know what you expect from them. This is why we recommend creating a client success guide.

A client success guide is a document that outlines your expectations for the work and how long you expect it to take. It can also include tips on how best to work with you so that both of your needs are fulfilled.

The best part about this method is that it gives both parties an opportunity to be clear about their roles in the relationship and set up expectations for future endeavors.

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8. Create A Safe, Secure Working Environment To Manage Files And Communications

To ensure your files are safe and secure, you should have a distinct work environment that is separate from the rest of your computer. This will help keep important information out of the hands of potential hackers in case someone gets access to your personal files.

To do this:

Use Upwork’s security features for file transfers and other communications. Upwork provides a way for you to send files securely through their platform, and they also offer an encrypted messaging system where you can communicate with potential contractors without sharing sensitive data outside of secured channels.

Don’t use general email or cloud services such as Dropbox or Google Drive for file transfer – these services are not secure enough for business purposes!

9. Celebrate Important Milestones Big And Small

It’s important to celebrate milestones big and small. An important milestone is one that you and your team have agreed on, such as having a project plan ready to go. A small milestone could be agreeing on a project timeline or submitting drafts of work for review.

Celebrating milestones will help keep everyone motivated and working hard. You should also encourage your team members to celebrate their own individual accomplishments with each other, and acknowledge them for their hard work when they do so!

A great way to celebrate these achievements is by doing it together in real-time via video chat or in an email thread where everyone can join in the conversation.

10. Go Above And Beyond For Your Freelancers With Additional Perks

In addition to providing them with a competitive rate and good communication, you can also go above and beyond for your freelancers. This includes things like providing feedback, referrals, bonus work, or testimonials/reviews.

You can provide feedback on the project they’ve been working on in order to help them continue improving their skillset. 

If they do a great job on one particular project, you may want to consider giving them another one so that they get the opportunity to experience more of the upsides of working with you.

Creating a compelling profile on Upwork is vital for attracting clients and securing freelance opportunities. Learn how to optimize your Upwork profile and make it stand out with our detailed guide on Upwork Profile: How to Create a Killer Profile. Implement these strategies to enhance your online presence and increase your chances of landing quality projects.


If you follow these best practices and use them to grow your business, then you will be able to successfully outsource work on Upwork. There are many freelancers who have successfully built their businesses using the platform, so you can do the same. 

Just make sure that the freelancer that you hire is willing to work within your budget and understands how long it will take them before committing to a project with them!

Further Reading

Here are some additional resources that you may find helpful for further exploration:

Outsourcing Tips: Discover valuable tips and insights for successful outsourcing in this informative article. Learn how to delegate tasks effectively and maximize the benefits of outsourcing in your business.

I Have Spent $30K Outsourcing Freelancers from Upwork: Here’s My Ultimate Hiring Checklist: Gain valuable insights from an entrepreneur’s experience of outsourcing freelancers from Upwork. This comprehensive hiring checklist will guide you through the process of finding and hiring the right freelancers for your projects.

Outsource Work: How to Get More Done in Less Time: Learn about the benefits of outsourcing and how it can help you increase productivity and efficiency. This article provides practical advice and strategies for effectively outsourcing work to achieve your business goals.

Frequently Asked Questions

What Is Upwork?

Upwork is a marketplace for hiring freelancers, where you can search for, interview, and hire the best talent in a variety of skills including web developers, graphic designers, and writers. The platform allows businesses to work with skilled professionals from around the world so they can focus on their core business.

How Do I Get Started?

A: To get started on Upwork simply create an account by clicking here. You will need information about your business such as what kind of job you are looking for or what type of services/products you offer so that potential freelancers can bid on open jobs matching your needs. 

You’ll also need information about yourself (or whoever will be managing all of this) like an email address(es), phone number(s), and experience working with remote teams or freelancers before they sign up! If not now then definitely check out our blog post “How To Get Started On Upwork In 5 Steps” which covers everything above plus much more!

What Is Upwork?

A: Upwork is a freelancing platform that connects businesses with skilled professionals. You’ll find a wide range of talent on the site, from website developers to copywriters, graphic designers, content writers, and more.

What Kind Of Work Can I Get Done On Upwork?

A: The types of projects businesses post are as varied as they come you might need help with advertising campaigns or research projects; cover letters or resumes; logo designs or business cards; writing blog posts or press releases; creating infographics or animations…the list goes on!

How Do I Get Started On Upwork?

If you’re using this guide to hire freelancers through the platform for your own business (instead of working for someone else), then here’s what you need to know about setting up an account and hiring your first worker(s):

Sign up for an account here. This will allow you access to all available talent pools within the platform by connecting it with your email address. 

Make sure that any information related to payments is correct before publishing any job listings this includes banking details such as credit card type/number and routing number (if applicable). 

Also make sure state laws allow certain types of transactions between yourself and workers outside its borders (e.g., if both parties live in California but transactions must be processed through New York banks due to tax collection requirements). 

Check out this page from Upwork’s help center which lists all supported payment methods).

Once ready go ahead and create jobs by clicking the “Post A Job” section under “My Workflows.” This will bring up several sections where different options exist depending upon what kind of project needs completing.

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