How to Hire Better Freelancers on Upwork

So, you want to start scaling your business?

Most ambitious entrepreneurs reach a point where they can no longer increase their incomes without hiring employees. Time is limited so if you exchange your time for money, your potential is limited.

This limit may be $50,000, $100,000 or $1,000,000. The point is, you will reach a point where your growth is dependent on the people you hire.

Many businesses choose to hire full-time employees and there are many upsides to building a full-time team. Of course, every new employee can increase your business expenses considerably. If you’re making $100,000/year and you hire a full-time employee for $40,000, your income will take a short-term hit.

This is where freelancers come in.

Business owners can hire freelancers on a per-project basis, which allows for a lean, cost-effective business structure. Whereas salary employees are paid to show up, freelancers are paid for performance.

I’m a big fan of hiring freelancers and subcontractors. This approach allows me to hire specialists in different fields and only pay for the work I need done.

While there are plenty of ways to hire freelancers, UpWork offers one of the most effective solutions. UpWork is a network that connects freelancers with business owners and offers convenient management tools.

I’ve hired over 50 freelancers on UpWork, many of whom I work with on a regular basis. My hiring experience has taught me a few key lessons about attracting the right talent and scaling my business.

Business owners tend to have mixed results when it comes to hiring freelancers so I wanted to share a few ways that business owners can attract better talent that will help them scale their businesses.

The Pre-Hiring Process

If you want to build an all-star team of freelancers, you need to do some planning before you start posting jobs.

Business owners need to take the time to properly plan freelancer responsibilities. Freelancer tasks should be as unambiguous as possible.

We all share the same ultimate business goal: we want to make more money. There’s nothing idiosyncratic about wanting to hire a freelancer that will have a positive ROI. That said, you can’t simply hire someone to make you more money. As a business owner, it’s your responsibility to focus on the strategy.

Let me illustrate by example.

Assume you are running a profitable operation and you want to start ramping up your SEO traffic. If you create a job post for an “all-in-one SEO expert,” you could be setting yourself up for failure. SEO is a slow process that requires a range of different skillsets. Here are just a few:

• Keyword Research
• Content Creation
• On-Site Optimization (Non-technical)
• On-site Optimization (Technical)
• Link Building
• Outreach

Each of these components of the strategy take time. Furthermore, the results themselves take a lot of time. It may take you a few months to realize you hired the wrong person. Multiply that by a few wrong hires and you have a recipe for wasted time and money.

So, what’s a better approach?

Be specific.

• Hire a freelancer to do keyword research
• Hire skilled, niche-specific writers
• Hire an on-site SEO specialist
• Hire a site speed specialist
• Hire link building specialists and/or outsource to service providers
• Hire an outreach specialist

This may seem like overkill and sometimes a freelancer can manage multiple categories. That said, my experience has shown that this is a far more effective solution for two reasons:

1. It is more cost effective – If someone can research, write, and rank content effectively, they will undoubtedly be more expensive. Think about it, if you could build profitable niche sites that generate traffic and sales, would you not charge a premium price?
2. It delivers better results – Breaking a project into parts allows you to hire specialists in different areas. A great writer may know nothing about link building, and a site-speed specialist may have limited knowledge of on-page SEO. By hiring specialists, you can ensure you get the best quality in each area.

This approach doesn’t only apply to SEO.

A paid advertising campaign may require:

• A copywriter
• A graphic designer
• A landing page creator
• A PPC Specalist

A development campaign may require:

• A designer
• A front-end developer
• A back-end developer
• A website copywriter

The point isn’t that you should aim to hire the most amount of people.

You should focus on hiring the right people for the job and making sure your job description sets your freelancers up for success.

Once you have figured out an appropriate position, it’s time to create your job listing.

Creating Better UpWork Job Listings

UpWork is home to a range of different business owners and freelancers. Just as freelancer quality can vary, employer quality can vary as well (and freelancers know this).

If you want to attract the right talent, you need to put in the right work.

What Type of UpWork Talent Do You Want?

Every project has different specifications and business owners need to find the proper balance between quality and cost. For example, I could hire the world’s best graphic designer, but I would be paying a heavy premium. I could also hire the cheapest designer, but the quality is likely to suffer.

Before starting your project, you need to reasonably assess your budget and expectations. This will help you attract the right pool of applicants.

For example, let’s assume you want 2,000 word articles from mid-high quality writers and you offer a payout of $20. You’re unlikely to attract the talent you’re looking for. Someone who is willing to write 2,000 word articles for $20 is unlikely to meet your quality standards.

We all want the best quality at the best cost, but our budgets don’t always allow for all-star hires. Find the right balance between quality and cost so you can have the proper expectations before you post.

Setting Your Job Titles

Your job title is your pitch to freelancers. Remember, freelancers don’t have to work with you and the best freelancers have plenty of demand.

Make sure your title stands out so talented freelancers are interested. Here are two things to consider:

1. Be Descriptive – If you want to attract the best talent, you need to be as descriptive as possible. If you need a custom theme for WordPress, your title should be “Custom WordPress Theme Developer Needed.” This may seem obvious, but many people create broad titles.
2. Promote Project Benefits – If there is something about your project that stands out as a major benefit for freelancers, add it to the title. For example, if you are paying a rate of $100/article, mention that in the title. Similarly, if you need long-term work, mention that in the title.

Creating UpWork Job Descriptions

UpWork job descriptions serve two purposes.

First, they should provide a clear and accurate description of the job so you can attract the right talent. Be as descriptive as possible.

I usually make a list of three sections:

1. Project Details – A basic description of the job, tools we will use, examples, timeframes, etc.
2. Freelancer Responsibilities – Freelancer deliverables and more freelancer-specific project details.
3. Skills Required – All of the skills required to complete the job, including past experience, proficiency with certain tools, and more.

These sections should be as detailed as possible.

A post for “Tech writers” could attract a broad range of applicants. If you need tech writers to research, review, and rank new gadgets, mention that in the job post!

Pro Tip: I also like to include a section at the end that says, “answer the last question with the word “Peach” so I know you read this far.” This helps weed out some of the freelancers who apply for jobs in bulk.

Proper Screening Questions

Over the years, I’ve done a LOT of testing of screening questions and this section can be HUGE for attracting the right talent. When you have dozens of applicants, the best way to differentiate them is by analyzing their answers to your screening questions.

Here’s how I approach this.

First things first, don’t ask any question that doesn’t help you with the hiring process!

If you’re asking generic questions like, “what do you do in the face of adversity?” you’re unlikely to receive answers that make the hiring process easier. I may be biased, but I really don’t care how my graphic designers deal with adversity; I want to know that they can create kick-ass graphics.

Questions should be job-specific and the answers should provide great insights.

Here’s are a few examples you may use when hiring a landing page designer:

• What is your experience with landing page design? Please share some of your best work.
• Which tools are you comfortable using? (i.e. Instapage, LeadPages, WordPress, etc).
• Are you comfortable writing copy and designing custom graphics?
• Please share a link to what you believe is the perfect landing page (It doesn’t have to be yours).

Pro Tip: My most effective questions have been related to providing examples. I will ask, “Please provide a link to an example of what you believe to be the ideal deliverable for this project.” This helps a lot with understanding the intangibles. For example, if you’re hiring writers and they send a link to a poorly written article, you know they are a bad fit. If you are hiring graphic designers and they link to a bad graphic, you know they don’t share the same vision as you.

Seriously, take the time to think about the best questions to ask your freelancers. You’ll be glad you did once the applications start coming in.

Country Targeting and Pay Rate

Once you have a killer job post, you need to set some criteria for who can apply and how much you are willing to pay. As mentioned in the pre-hiring portion of this article, you should already have some basic expectations.

First, you need to decide if your work is country-specific. When I hire writers, I always look for native english speakers. When I hire developers and VA’s, I’m open to international applicants.

Second, you need to choose an appropriate pay rate. Price the job too low and you won’t attract quality talent. Price it too high and you may exceed your budget.

Pro Tip: My advice is to start at the low end of a reasonable range. If you know you can afford $25-$35/hr for a position, list it at $25 and see if you attract any good talent. If no one is applying, you can increase the pay rate or post the job again.

Inviting UpWork Applicants

Once your posting is live, the applications will start flowing in.

If you set up your job post correctly, you should be attracting some nice talent.

Of course, we’re not going to leave this up to chance. Some of the best freelancers on UpWork are not actively seeking new work. I always like to invite freelancers to my jobs so I can find the best talent.

Search for Ideal Candidates on UpWork

To find the ideal candidates, you’ll need to start searching UpWork.

First, let’s discuss the filters. Here’s how I use them:

• Country – Sometimes U.S. only and sometimes international
• English Level – Fluent or Native for writers. Any level for jobs that don’t require a strong understanding of English.
• Earned Amount – Over $100 for entry level jobs (i.e. writers) and over $1,000 for higher level jobs (i.e. development)
• Job Success – 90% and up. I will also filter by Top Rated and Rising Talent.
• Hourly Rate – Varies by project
• Hours Billed – Varies by project. 100+ for jobs that are likely to accrue hourly work (i.e. developers)
• Last Activity – Within 2 weeks.
• Talent Type – Freelancers
• Category – The category specific to my job listing.

Once these filters are set, you should have a list of qualified freelancers. Now, it’s time to find the specialists.

Finding specialists requires a bit of creativity. You need to think of the right search terms in order to find the right talent.

In some industries, this is easy. For example, if you just need a basic wordpress developer, you can search for a “WordPress developer.”

In other industries, it’s a lot trickier. For example, how exactly do you find someone to write about real estate? Of course, some writers will mention that they are specialists in real estate, but other qualified writers may not feel the need to mention it. Here are a few of my favorite searches to find qualified talent:

• Search competitor names – If you’re looking for a real estate writer, you could search for top real estate publications.
• Search certifications – Freelancers may mention certifications they’ve received and courses they’ve taken.
• Search keywords – Search for a range of keywords related to your topic. For example, if you’re looking for real estate writers, you could search for mortgages, real estate, refinancing, flipping houses, etc. The more specific to your project, the better.

Invite Your Ideal Candidates

Once you’ve found some candidates you’d like to invite to your job, it’s time to actually invite them.

UpWork offers a default message but I like to customize the message I’m sending (particularly if there is a specific freelancer I’d like to work with).

My message looks something like this:

Hey Mark, I personally reviewed your profile and I think you would be an excellent fit for this project. I was a big fan of the work you did on Project X. If you’re interested, I’d love to chat further.

Remember, it’s your job to attract the right talent. Take the time to attract the right people.

Testing and Hiring UpWork Freelancers

Once you’ve narrowed down your list of applicants, it’s time to begin the hiring process.

I always test a few freelancers when possible. I’ll always do this when hiring:

• Designers
• Editors
• Writers

For bigger projects like development, you may waste money if you test too many applicants. Instead, put more focus on the interviewing process. The rest of this section will be focused on test projects because I find a test project to be more effective than a long interview.

Test Projects

A test project is a smaller project designed to gauge the freelancer’s ability.

• In writing, this may be a 1000-word article
• In design, it may be a single graphic
• In research, it may be a quick research project

Your test project should allow you to test the quality and efficiency of a freelancer. I want to see that freelancers can provide a quality offering at a great price.

You can get a lot of insights from this process. For example, a $20/hr graphic designer may seem cheap until you realize she takes 5 hours to create a simple graphic. Similarly, a writer offering 1000 words at $20 may seem like a great deal until you review the quality.

If you want to make the most out of this “test project,” you need to provide the freelancer with detailed project instructions.

Creating Better Project Guidelines

Your project guidelines can make or break the success of your project. For example, if you just tell a graphic designer to “create an event flyer,” you’ve left a lot open to interpretation. If you list preferred fonts, colors, design styles, and examples, you are much more likely to get the results you want.

I like to create project guidelines that are detailed enough for freelancers to excel at their jobs. I will breakdown the project goals, share examples, and list out details.

If the freelancer fails, I should be able to point to a specific part of the guidelines where he did not meet the criteria.

How to Assess the Test Project

Once the freelancer delivers the test project, it’s time to assess whether or not they are a good fit.

My ranking system is pretty simple here:

• Rockstar – Awesome hire that deserves more work.
• Potential – A freelancer who could be a rockstar with enough guidance.
• Dud – Poor performance and unsalvageable.

Take an article writing test project as an example.

• A rockstar will deliver an excellent article that requires few (if any) revisions.
• A potential will deliver a great article that may require work on formatting, organization, or SEO-optimization.
• A dud will deliver an article with poor writing, organization, and/or research

In the last step of this process, we will discuss how to nurture each of these freelancer relationships.

Nurturing Freelancer Relationships

Your job isn’t done the minute you hire a freelancer. You’ve entered into an employee-employer relationship and you’re responsible for making it work.

Every freelancer has a different style, so you will need to learn the best ways to manage each individual. That said, there are a few things I find are helpful for every freelancer.

Provide Feedback

In the previous section, I mentioned that I only hire “rockstars” and “potentials.” Both of these types of freelancers need feedback in order to excel.

The rockstar may need some basic tweaking. Even if the work is perfect, you should provide specific feedback. If someone is proud of their work, they like to receive praise. If you receive rockstar-quality work and respond with “good job,” you are showing the freelancer that their work doesn’t matter. Give specific praise and keep your rockstars happy.

The potentials require a lot of feedback, especially in the beginning. Tell these freelancers everything that can use improvement (within reason). Make sure your feedback is specific and actionable. For example, if you don’t like an article, explain why. Does it require better research? Better formatting? A different tone? Longer content? Smaller paragraphs?

Give your potentials as much specific feedback as you can and you will watch the best ones grow into rockstars. If you find that your feedback is ignored, you can move onto the other candidates.

Rewarding Freelancers

Once you have a rockstar that has provided consistently high quality work, make sure he or she feels appreciated. I will often give my best freelancers pay increases, one off bonuses, or more flexibility.

Rewards don’t always need to be monetary, nor do they need to be excessive. For example, simply asking a freelancer if there is a specific type of work they’d like to do more of shows that you care about their satisfaction.

Similarly, on fixed price projects, a bump from $50 to $55 per deliverable, isn’t a huge pay increase but it shows you appreciate the good work.

Rewarding freelancers serves a few purposes.

1. It keeps the freelancer happy – You want to make sure your best talent wants to work for you (vs. finding new clients)
2. It keeps the freelancer accountable – If you bump a freelancer’s rate because she has been doing an excellent job, she now has more incentive to keep exceeding expectations.
3. It shows that you are appreciative – Rewarding good work is just good business. If someone is helping you make more money, you should be able to provide a little something in return.

What Are your Upwork Tips and Tricks?

Have any tips and tricks that you use to attract the best talent? Feel free to share in the comments below.