How To Hire a Freelancer on Upwork Part 1 and Part 2

Hiring freelancers is starting to become one of the best ways to find the most skilled people. Freelancer platforms like Upwork are no longer just a place to find the occasional logo designer. It’s a place where you can find some of the world’s top consultants, marketers, strategists, and other independent professionals.

So you likely already know why you should hire a freelancer and you’ve chosen Upwork as the platform to use. But how do you hire a freelancer on Upwork, and what are some tips for making it a successful endeavor? How do you not screw it up and waste money and time? This is a strategy guide so you can start building your freelance workforce. If you want the technical training of how to actually hire a freelancer using Upwork’s tool, then watch the video above which is associated with this guide. In that video, I walk you through the whole process. This article will focus mostly on the strategy to use in each step, while the video will focus on the technical how to and the strategy.


Step 1: Map Out The Job

Before you begin setting up an actual job post on Upwork, make sure you know exactly who you’re looking for and what you want them to accomplish. Sometimes you might not have all the details and you’re hoping that your applicants will help you finesse that. But get everything written out that you can. Make sure you answer these questions:

What problem in your business are you trying to solve? What goal are you wanting to achieve?

What have you done so far to try and solve that problem or achieve that goal? Did it involve hiring someone but didn’t work out?

Why are you looking to hire a freelancer to achieve this goal for your business?

What is the hoped for end result of the project?

What specific tasks are you already aware of that you know the freelancer will need to do?

What type of person will fit well with your team?


Step 2: Figure Out a Budget

You may already have an idea of the maximum money you can spend on the freelancer, either total for a project, or total each month for long-term work. And once you post the job, you’ll find that your budget doesn’t always match the freelancers that you want to hire. But you need to have an initial idea of what you can spend or want to spend.

And don’t get hung up on an hourly rate budget. That doesn’t help you because then you get stuck thinking about what you think the market rate is for a certain job. It doesn’t really matter what you paid your graphic designer employee per hour. What matters is how much do you want to invest in the end result that you’re paying for? A good freelancer won’t get stuck pitching his or her hourly rate either. They will focus on the total cost for the project or per week or per month to achieve X, Y, and Z.

Once you start talking to your top picks, you’ll learn a few things about what certain tasks and results cost, short-term and long-term. That’s when you’ll be faced with some decisions on whether to decrease or increase your budget, or whether to adjust the type of freelancer you initially wanted to hire. You may want the top expert but can’t afford them, so you have to be okay to hire someone who is less experienced but still likely to do a good enough job.

Overall, you need to have some flexibility in your budget because it usually changes by the time you enter into a contract with a freelancer, mostly for jobs you’ve never hired freelancers for before. You aren’t aware of the industry of what things cost for that task, and then the freelancers educate you on that. Be careful to never compare what the freelancer is charging to similar jobs your employees have had and their salaries or hourly rates. Freelancers are businesses and have a lot of overhead expenses to cover. A freelancer charging $75/hour is similar to an employee getting $40/hour for the same job.

And if you’re totally unsure about what things cost, just do a quick search on Upwork for the top freelancers in the industry you want to hire in and see what they’re charging. Look at their job history and see what the cost was of past recent projects. Don’t look too far back because prices change. You’ll get way more accurate data looking at freelancer profiles on Upwork than you ever will Googling market rates for certain types of freelancers. Market rates have very wide ranges and are hard to understand.


Step 3: Create Your Upwork Job Post

Now that you’ve done the preliminary work, it’s time to set up the actual job post. The main thing to remember here is that the best freelancers are just as picky about the clients they work with as the client is about the freelancer they hire. So, you need to sell the job with as much effort as the freelancer will put in to try and get the job. Be very clear in your expectations and deliverables.

Job Title

Choose a title that very clearly defines what work you want done. Don’t just say “video editor.” Explain what type of video editor. A better Job Title would be “Video Editor For Podcast Interviews” or “Video Editor For Short Commercials.” “Build a WordPress Website with Online Store Functionality.” It can be a whole sentence. Many freelancers who are busier make decisions only on reading the job post on whether to bother clicking into the job to read the description. So, be as clear and specific as you can be.

Job Description

I have hired people on Upwork and I’ve worked as a freelancer on Upwork. I’ve hired the best freelancers when I was very clear in my job post, thorough in my goals, and when I worded the description in a way that made it clear that I was looking for a freelancer to partner with. I was not looking for an employee. It’s very important that you understand the difference between hiring freelancers and employees.

As a freelancer, when I see a job post that is worded in a way where it seems like they are looking for an employee, I don’t apply to those jobs because I know that the client will not see me as a collaborator and partner. They won’t see me as a business owner. They will treat me like their employee. These types of posts usually include things like listing “job duties” and tell you the pay is $100/week, for example. There’s clearly no negotiating that. You don’t tell a freelancer what you’re paying them, they are telling you what they are charging and either you take it, try to negotiate it, or go with someone else. Also, when job posts list how many hours you’ll work, avoid descriptions like, “we need someone who can give us 20-30 hours per week.” That’s an employee job. Freelancers only devote a few hours per week per client so they can have multiple clients.

If you want to find freelancers who will be worth your investment, avoid like the plague any wording that makes it seem like you’re looking for an employee. I would even avoid using the word, “job.” It’s not a job, you’re hiring a business for a service. It’s B2B. So, communicate it like it’s a business to business relationship.

As you’re creating the job post, Upwork will ask for other parameters and requirements that you’re looking for. Use those features in order for Upwork to know how to surface the right profiles to you after you post the job. Because then you’ll have the opportunity to invite specific freelancers to apply.

Skills and Skill Level

Upwork will ask what skills you’re looking for. Select all that apply. Sometimes they won’t have the exact wording, so just pick something that is closest and keep it more broad in that scenario. It will also ask for skill level. “Intermediate” is a safe one if you want to attract experienced and beginner freelancers. But, if you have the budget for it and want an expert, choose Expert.

Then if you’re picky about the location of where the freelancer lives, you can select something there. Language and time zone barriers are the main things to consider here.

Finally, you’ll select a budget and type of payment contract, hourly or fixed price.

Step 4: Shortlist your favorites

Usually within an hour you’ll start to see proposals come through. Give it a day for enough proposals to get submitted, then go through them and shortlist any that stand out. Upwork gives you an option to mark certain freelancers as a favorite for the job. You don’t even have to extensively read through their proposal yet, but skim to get a sense of whether they are someone you want to know more about.

Also, reject any that obviously don’t make the cut if they don’t meet certain criteria. If you think you’ve shortlisted a few that look very promising, then you can turn your job post to private to prevent new proposals.


Step 5: Interview

Now take a closer look. Read through each proposal on your shortlist thoroughly. The freelancer who has the most relevant and not the most extensive proposal should be your top pick. I would ignore any proposals that seem like a copy and paste cover letter. The best freelancers know that you don’t care about all their work experience. You only care about what they’ve done that is most similar to what you want.

If they asked you any questions then you can answer their questions in Upwork messages. Then proceed to set up a call. The call is a two-way interview. The freelancer is interviewing and vetting you as much as you are vetting them. Don’t treat it like a job interview. It’s a business conversation to see if it’s worth doing business together and forming a B2B contract. Even if you’re only hiring one individual and not an agency, it’s still a business partnership. And the best freelancers know this and expect to be treated like a business owner.

Ask questions that help you fully understand the skill level and experience of the freelancer. Get a sense for their style and approach with how they do their thing. Ask them about their process and communication preferences to see if it aligns with yours. And these interviews don’t need to be more than 15 minutes if you’re prepared and focused. If you know in the interview that you want to hire that freelancer, then let them know, and start talking about the project, first steps, and expectations.

You need to fully understand what your role is in accomplishing the desired result as much as the freelancer’s role. You or people on your team will often play a part, but too often that part is not communicated clearly. A good freelancer will let you know regardless of you asking, but if they don’t mention it, make sure to ask.


Step 6: Sign the contract

Once you choose a freelancer, it’s time to hire them. The advantage of an Upwork contract is that you can pause or stop work at any time. You’re only committing to one week at a time unless you negotiate otherwise, but I suggest avoiding long-term contracts that don’t allow the freelancer or you to opt out because your priorities may change, or you may find you would rather work with someone else.

What type of contract should you choose? Hourly or fixed rate?

I’ll get into more detail on this in another post but for now, here is a quick overview of when you want to choose one over the other. Choose a fixed rate if the project is for sure a quick thing or a starting package with clear deliverables and timeline. And remember, the freelancer will have a say in this as well. If the deliverables are super clear and predictable, then fixed rate should work fine. If the exact tasks and time spent each week is unknown, then hourly is best.

Hourly has the most flexibility in being able to pause contracts and expand and shrink them depending on how much work you have for the freelancer to do. It also saves you administrative time because the freelancer logs the hours and Upwork automatically processes the payment. No need to fund projects, create milestones, or review and approve them. And you can set an hourly limit that keeps you under budget.

The big question is, should you allow manual time entry or make the freelancer use the Upwork time tracker? The Upwork tracker takes pictures of the freelancer’s computer every few minutes so you can check on their work. As a freelancer, I’m not a fan of that tool. As a client, I’m not a fan of it either. Why? When I did use it in the past, I never even checked the screenshots. If the freelancer delivered what I was paying them to deliver and the hours seemed reasonable and what we agreed to then I don’t need to micromanage their computer. It’s creepy. It’s unnecessary.

All that does is show that you don’t trust the freelancer. And it’s important to start a relationship with an initial level of trust. It’s very obvious if the freelancer isn’t doing the work you’re paying them to do. And as a freelancer, it makes certain types of work very difficult because they are forced to use their desktop computer for all work and if they aren’t clicking frequently enough Upwork delays logging time. What if you’re reading a book as part of your work? What if you’re on a phone call? There are so many tasks that I do on other devices or no devices and there is no way to track that time. Also, as a freelancer, I’m often logging into different accounts online and if Upwork snaps a picture of my computer, it captures those passwords, which is a huge security issue.

So, allow manual time, even with new contractors. Hold them accountable to delivering the work that you agreed on and all will work out. You’re on the right track in your business to even be choosing to hire freelancers. It’s a great way to scale with lower risk than hiring employees.

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