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Hiring Upwork Freelancers: A Valuable Employment Hack for Small Businesses

hiring upwork freelancers

In today’s economy, freelancers are more in-demand than ever before. Remote work is becoming increasingly common, and businesses are discovering the power of tapping into the global talent pool. One of the most popular platforms for hiring freelancers is Upwork, which connects businesses with talented freelancers from all over the world. In this blog post, we’ll explore the benefits of using freelancers in detail, and we’ll walk you through the process of creating a job post on Upwork. We’ll also share some best practices for evaluating talent so you can find the perfect freelancer for your project.

Why Hire Freelancers?

  1. Before we dive into the details of how to hire freelancers on Upwork, let’s explore the benefits of hiring freelancers in the first place. There are several reasons why businesses are turning to freelancers to help them achieve their goals:
  2. Flexibility: One of the biggest advantages of hiring a freelancer is the flexibility they offer. Unlike traditional employees, freelancers can be hired on a project-by-project basis. This means you can hire a freelancer to help you with a specific task, without committing to a long-term contract.
  3. Cost Savings: Another major benefit of hiring freelancers is the cost savings. Traditional employees come with a lot of overhead costs – you need to pay for their office space, equipment, benefits, and more. With freelancers, you can avoid many of these expenses. Additionally, because freelancers often work remotely, you can tap into talent from all over the world, which can be particularly cost-effective if you’re working on a project with a tight budget.
  4. Access to Top Talent: When you hire a freelancer, you have access to a global talent pool. This means you can find the perfect person for the job, no matter where they are in the world. This can be particularly helpful if you’re looking for specialized skills that are hard to find locally.
  5. Increased Productivity: When you hire a freelancer, you’re hiring someone who is focused solely on your project. They don’t have other distractions like traditional employees might, which means they can often work more efficiently and get the job done faster.

Creating a Job Post on Upwork

Now that we’ve explored the benefits of hiring freelancers, let’s dive into the details of how to create a job post on Upwork. The first step is to create an account on the platform. Once you’ve done that, you can navigate to the “Post a Job” section. Here, you’ll be asked to fill out some basic information about your job, such as the title, description, and budget. It’s important to be as detailed as possible in your job description – this will help attract the right talent and ensure that they understand what’s expected of them.

  • Job Title: Your job title should be clear and concise. It should accurately reflect the nature of the job you’re posting. For example, if you’re looking for someone to write blog posts for your website, your job title could be “Blog Writer.”
  • Job Description: Your job description should be detailed and specific. It should include information about the scope of the project, the qualifications you’re looking for, and any other requirements you have. For example, if you’re looking for a blog writer, you might include information about the topics you want them to write about, the length of the blog posts, and the tone of voice you’re looking for.
  • Budget: Your budget should be realistic and reflect the amount of work you’re asking for. Keep in mind that you get what you pay for – if you’re looking for high-quality work, you should be willing to pay a fair rate. That being said, you don’t want to overpay either. One way to get a sense of what the going rate is for your type of project is to look at other job postings on Upwork. This will give you a sense of what other businesses are offering and what kind of responses they’re getting.
  • Skills Required: When creating your job post, you should be sure to include a list of the skills required for the job. This will help ensure that you attract the right talent for the job. For example, if you’re looking for a graphic designer, you might include skills like Adobe Illustrator, Photoshop, and InDesign.
  • Deadline: Be sure to include a deadline for the project. This will help freelancers understand your expectations and ensure that they can complete the job on time.
  • Attachments: If you have any relevant attachments, be sure to include them in your job post. For example, if you’re looking for someone to design a website, you might attach a wireframe or mockup of the design you’re looking for.

Evaluating Talent on Upwork

Once you’ve posted your job, you’ll start to receive proposals from freelancers. This is where the real work begins – you’ll need to evaluate these proposals to determine which freelancer is the best fit for your project. Here are some best practices to keep in mind:

  • Look for Relevant Experience: Ideally, you want to hire someone who has experience working on projects similar to yours. Look for freelancers who have a portfolio or samples of their work that demonstrate their expertise. For example, if you’re looking for someone to write blog posts for your website, look for freelancers who have experience writing in your industry or on similar topics.
  • Pay Attention to Communication Skills: Since you’ll likely be working with your freelancer remotely, it’s important to hire someone who has strong communication skills. Look for freelancers who are prompt and professional in their responses. You might consider scheduling a call or video chat to get a better sense of their communication skills.
  • Consider Cultural Fit: When you’re working with someone remotely, it’s important to hire someone who shares your values and work style. Look for freelancers who seem like they’ll be a good fit for your team. You might consider asking them about their work style, their availability, and their approach to communication.
  • Check References: Before you hire a freelancer, it’s a good idea to check their references. This can give you a sense of how they’ve performed on previous projects and what kind of working relationship they’ve had with other clients. Be sure to ask for references from clients who have worked with the freelancer on similar projects.
  • Test Their Skills: Depending on the nature of your project, you might consider asking freelancers to complete a test or sample project. This can help you evaluate their skills and ensure that they’re the right fit for the job.

Hiring freelancers on Upwork can be a great way to access top talent, increase flexibility, and save costs. When creating a job post on Upwork, be sure to include detailed information about the project, the qualifications you’re looking for, and the budget. When evaluating talent, look for relevant experience, strong communication skills, and a cultural fit. By following these best practices, you’ll be able to find the perfect freelancer for your project and achieve your business goals. Happy hiring!


You have read this far, CONGRATS!  COntinue reading on as this will be the MOST BENEFICIAL section of this writing.  I am going to change gears and give you some very detailed specifics on HOW I evaluate talent.

The first key is to be very detailed in your description.  The more detailed you are from the beginning the better your chances are of getting the right talent.  Write clearly and concisely.

While YES the goal is to hire a qualified person for the position, you should be specific and detailed in trying to allow freelancers to disqualify themselves based on your description.  Yes, you heard me right. You are trying NOT to hire them (in a sense).  The more they can self-filter the less work you have.  After all, we want to relieve as much work and burden off of you, not create more.

So now you are getting freelancers responding to your job post.  You want to quickly figure out WHO is going to make it on your shortlist. There are two things you are looking for at this stage:  ACUMEN & EXPERIENCE.

Here is a quick list of things I look for to give them a thumbs down or a thumbs up.

  1. Job Completion Rate:  Greater than 95%  I have gone as low as 88%, but I really liked her resume and sample historic work.  I was straight with the freelancer in the messages and ask why it was so low.  She was able to give a reasonable explanation.
  2. Amount Earned:  I look for freelancers that have been on Upwork for a while and have earned at least $10K in revenue.  This will give a sufficient job history and a good sample of reviews.
  3. Freelancer vs. Agency:  I typically don’t work with agencies as it can skew their ratios of the above metrics.  Plus, I have a heart for smaller companies/freelancers.
  4. Language:  I want somebody fluent in my language so that it is not a barrier to communication.  If communication is a BIG component to the overall success of the position,  like a telemarketer, don’t simply trust that Upwork has verified them.  Request sample audio files of the freelancer reading a script.  Trust but verify
  5. Location:  I have hired freelancers from ALL over the world.  I am not opposed to working with freelancers in other countries.  It is actually kind of fun.  The challenges with working internationally can be delays in communication due to time-zone differences, cultural differences like holidays, etc.
  6. Historic Work:  I want to see multiple examples of their historical work.  If you are looking for a graphics designer to create a logo, social media images, brochures, or flyers –  Their historical work will give you a good idea if they have produced work that matches a look and feel that you want to accomplish.  Ask them questions about that specific project.  The same holds true with web designers, video production, content writers, and others alike.  Freelancers like website optimization companies get links to recent sites they have worked on and test the site’s speed.  Ask for referrals that you may contact…and contact them.  Read those reviews.  I could go on and on…but you get the point.

These areas above identify ACUMEN & EXPERIENCE and will get you a good shortlist.  But DON’T be quick to hire yet.  The third and equally important area that you need information on is their CHARACTER.  Trust me on this one.  I have rushed in to hire a freelancer without this and it has cost me time and money.  Just because they have the knowledge and experience does not mean they are a fit for you and your company culture.  If you overlook this aspect working with freelancers can seem frustrating.

Your goal is not a freelancer, but the RIGHT FREELANCER.

Below is a short list of questions you may want to ask to determine the right fit.  You will want to come up with other questions specific to you, the position, who they will be working with directly, your company culture, and more.

  1. What does effective communication look like to you?
  2. What does over-communication / micromanaging look like?
  3. What is the best way to organize a project?
  4. What helps you assure accuracy?
  5. What helps keep you motivated?
  6. What encourages you the most with project owners?
  7. What makes you want to work on a 2nd project with an owner?
  8. What would keep you from completing tasks on time (ie. too many projects, religious or social events/obligations, family issues, etc.)?
  9. What are three things I need to know about your culture that may be important for us working together?

Be perfectly clear about your expectations & share with them about how you operate and ask if that will cause any challenges.  Be Open.  Be Honest!


  • I can be very direct and results based.  My communication is candid, straight, and to the point.  Will this cause any challenges moving forward?
  • I am big on communication and require detailed updates on a regular basis.  Will this be a problem?
  • I have time constraints on this project.  It must be completed by (date/time).  Are you able to do this?
  • I am looking for this working relationship to be long-term and eventually grow in time, responsibility, and pay.  Is this of interest to you?

Lastly, if you want to have success in hiring freelancers, create an SOP (Standard Operating Procedure) that is detailed, and specific to the position you are hiring.   This will have information regarding how to perform their job, the tasks included, access information to necessary accounts, etc.

As you are working with these freelancers have them assist in developing and maintaining the SOP…put it in the job description.

Learn how to use I.D.E.A. to successfully onboard a new freelancer.

How will you know if outsourcing to a freelancer is right for you?

Here are a few questions you might ask yourself to help determine if outsourcing to a freelancer might be a good fit for you:

  • What challenges do you face in hiring good talent?
  • What recent costs of mis-hires have you experienced?
  • What tasks or projects do you do that could/should be handled by others?
  • What challenges do you face managing your current workload and team?
  • What systems do you have in place that could be adapted for remote workers?
  • What budget and timeline constraints exist for your upcoming projects?

I don’t know your situation, but for most businesses, it doesn’t matter if you are a solopreneur or a multi-million dollar C-corp, outsourcing aspects of operations can free you up to do what is important, allow your team to focus on what matters and exponentially increase your effectiveness and revenues.

Does your business provide you the freedom of time and money you had hoped for?  If not, let’s chat.

Christopher Moore Business Executive and Leadership Coach