Upwork and other freelance marketplaces can be an invaluable source of help, especially if you are a small team or have projects that require a ton of manual repetitive work. They allow you to outsource smaller and more mundane tasks so that you can spend your time where it is most effective.

These platforms also allow you to turn your employees into managers, giving them added resources to get projects done faster. When you add in the ability to hire workers in different time zones, you can essentially add an extra 12 hours into the workday. It feels amazing to hand off work at the end of the day and show up the next morning with an inbox full of completed tasks.

In the past, I’ve used freelancers from Upwork for all different types of research projects, sales and marketing campaign work, report building, calendar work, billing, and even more personal tasks like sending out invites to events and thank you notes to event participants.

Throughout all of this, I’ve identified some ways to make working with “Upworkers” a breeze. Keep in mind these projects are typically easy and repetitive with clearly defined directions, milestones, and completion expectations.

But before we get into everything, keep these notes in mind as you are building your team...

Always remember these notes when building your freelance team!
  1. Remote teams don’t displace your current employees, but they can increase your employees’ current productivity and efficiency. It allows you to turn your employees into managers, focusing on what they really need to be doing as opposed to menial tasks and busywork.
  2. It will add more time to you and your employees' work-days. If managed properly you’ll be able to hand off work items at the end of the day and pick up where the freelancers left off in the morning.
  3. It can lower stress and boost the morale of you team. You’ll have more hands on deck to reduce the likelihood of employee burnout and keep your full-time employees' jobs more engaging and rewarding.
  4. You’ll either end up saving money or making more in the long run. By getting more done, having less risk of employee burnout, and having more flexibility to take on more projects you should end up in the green.
  5. While you’ll end up having a roster of freelancers, you’ll only need to employ them when you need them to complete specific tasks or projects. You pay a set rate per project or hourly rate, which allows you to be more efficient with your budget.
Now let's recruit the best team for the job.

With these in mind, let’s get into building the team.

How To Recruit

It doesn’t matter what your project is, there has been someone else hiring a freelancer for basically the same thing before. Before you even think about posting a project or contacting a freelancer through Upwork, you may want to seek out recommendations from peers who have already hired freelancers for similar projects in the past. They may already know the perfect candidate — In the past, I’ve recommended a bunch of different freelancers I’ve used in the past with success to friends’ startups.

Remember, there are two ways to hire someone on a platform like Upwork. Either you find their profile and ask them to work on the project, or you submit a job description to solicit responses. In reality both work, but having a job post up will allow you to consistently receive new freelancer submissions.

The Job Post

Before making a job post, take a look at similar postings on Upwork to understand what other companies are putting out, what the going rate might be, and how much time the average freelancer is willing to spend on similar projects in a day/week.

The description is VERY important. It is not only what candidates are reading to decide if they want to bid on your project, but it is also the first step in setting expectations, describing their EXACT role, and defining what success for the project looks like.

It is important to be as explicit as possible in the description. Keep these few things in mind:

  1. Write out every step of the project like you are explaining it to a three-year-old. This has nothing to do with the target audience, you just want to be as clear as possible in order to avoid miscommunication.
  2. There can’t be any confusion related to what is expected of the freelancer, or what the project is, the steps to completion, expected time commitment etc.
  3. While we want every hire to be a success, the reality is that won't be the case. If there is an issue with the work being done this is the first place to reference if there is a dispute.

After the project’s description there a few fields you can define like project length, type, and skill-set. We would typically look to hire people long term for various research projects so our projects would look like the following:

Keep in mind that while we are looking for freelancers with lower rates, going for the cheapest option may not be the best choice. Like any hire, you’ll need to compare the cost with their skill set, experience, review history, etc.

You are then able to define skills, experience, and qualifications. Some of this will obviously depend on your specific project but we typically required conversational English and at least 100 hours booked previously on Upwork.

You can also list a few questions that are required to be answered in any submittal. For example, if you are looking to build company lists from LinkedIn and Angel List searches that fit specific search criteria, and ultimately finding their social handles, your questions might look like the following:

You will be asked to answer the following questions when submitting a proposal:

  1. Do you have experience building lists from LinkedIn and Angel List?
  2. Please name one method you use for finding a company’s information if not entirely available on LinkedIn or Angel List?
  3. What software or methodologies have you used in the past to retrieve social handles or links?
  4. Why do you think you are a good fit for this particular project?
  5. What questions do you have about the project?

For entry-level freelance hires for menial tasks, this is really it in terms of engagement pre-hire. For more complicated tasks or larger projects there are a few other things you can do:

  1. Conduct a proper interview to asses their hard skills and soft skills, and to see if they fit with the current team.
  2. Ask them to provide a sample of exactly what it is you are asking. For tasks that are going to be on-going long term, this is a great way to avoid cycling through low performing freelancers.

After this, you are now ready to start building your remote freelance project team. You should start receiving applicants pretty quickly, but also do your research into potential candidates. For relatively simple research tasks you should be able to find tons of well-reviewed candidates you can contact and invite to apply.

Now are we ready to hire the team?

Before you bring candidates on board and working on projects, you will want to make sure to set them up for success. While we set this up, make sure to keep these items top of mind throughout the whole process.

Reminders for Setting Your Freelance Team Up For Success:

  1. You will hire more than one Upwork Freelancer — Even if your first project only calls for one freelancer, you will end up hiring more than one. This is because you will need multiple on-call for time-sensitive projects, late requests, freelancers that might quit, etc.
  2. The goal is to have long-term relationships with each freelancer — We want this person to become a consistent and reliable part of our team. As they work with you more often and learn your process, their capabilities will increase. You’ll end up having awesome long-term resources at your disposal moving forward.
  3. The work will never be perfect — This is something to keep in mind for all employees but especially lower pay scale Upwork freelancers. You get what you pay for so make sure that your expectations are in line with what you are going to be receiving as a final product. Make sure you review everything and keep in mind there are always ways to improve over time.
  4. You will end up firing an Upworker — If you are tracking work correctly, you should always be letting go of the underperformers and hiring in new talent. You will end up with a better team in the long run, but also a freelancer’s work can deteriorate over time. Make sure you are always keeping a fresh set of hands on deck.
  5. Freelancing is a two-way street — You need to be a good employer and project manager. You are going to be reviewed by those you hire, and the better your rating and reviews, the better talent you will attract over time.
  6. Freelancers ARE a part of your team - Just like any other team member all of your other best practices as well as office and team culture should transfer over digitally.
  7. Document everything - Not just for disputes but for improving process over time and making on-boarding easier down the road.
  8. Share your software, tools, and documentation - If you have tools at your disposal make sure your freelancers have access as well!

While not exactly rocket science, there are important aspects of the process that if handled properly will set you and your team up for success. Conversely, if carefree in setting everything up your results will likely be less than desirable. Now let's get to setting up that well oiled machine.

Let's go!

Set Up

Before pushing start on a project you should understand what you will need to set up for the freelancer and your team members who are going to be working with them. This might be access to Slack, Asana, Salesloft or any tools you might be using for the project.

Setting everything up properly in the first place can stop some hiccups from being able to occur down the road.  The Harvard Bussines Review found that when remote team members encountered common challenges, 84% said the concern dragged on for a few days or more. This can be an even bigger issue if the freelancer is in another timezone - let's make sure that doesn't happen.

Directions and Expectations

Direction & Expectations

Your initial job description should have contained an explicit set of directions for getting the job done. Even if this is the case this isn’t the only time you should be stating directions.

Whatever means of communicating you are choosing to work with, make sure to explicitly write out the directions again. This is always a good time to reinforce best practices and expectations, and doing so will ultimately lead to better results.

For an example, if the freelancer is tasked with basic research you should give a time limit for each piece of information to be found so that time isn’t wasted looking for information that isn’t available.

This is also a good time to establish expectations, whether it is the amount of time spent on the project, deadline or anything else. You can also encourage them to hit other goals, like time to completion, by promising more projects or some other incentive.

Communication

Communication will be key to the project completion, regardless of how you decide to get it done. I’ve always made a private Slack channel in our workspace for the freelancer and our team member who is managing or working on the project with them. This makes communication easy and referenceable. It also provides a place to share work, questions, and files easily.

Another big part of communication is to actually be available. The easier it is for someone to get in touch with you the more likely things will go smoothly, so remember to be as responsive as you would with internal team members.

Tracking

When the freelancer works on your project they’ll be required to log into Upwork itself. This is great because Upwork will track their time spent, but also take periodic screenshots of their work.

Also, make sure to track the freelancers on their work related to the project. As I mentioned in the last post, you should look to hire multiple Upworkers. You will be able to build up a strong team over time by building long term relationships with the top performers and cutting ties with underperformers. For a list building project, I’ll track the quality and quantity of their work in a Google Sheet similar to this:

We’ll be releasing workbooks for specific projects, tasks, and freelancer types of the course of the next few months, so if interested in getting these make sure to sign up. Starting with a well-made template is always easier than starting from scratch!

Documentation

This applies to more than Upwork, but remember to document everything. Everything you document has value, whether you are building an FAQ, handing a project off, rewording directions, adjusting job descriptions, or anything else.

In the past, we’ve turned this documentation into a handbook for both new team members and project managers, as well as new freelancers. It’s great to have a resource everyone can go to when the team experiences roadblocks.

Continuation & Accountability

We want each freelancer to become a consistent and reliable part of our team. As they work with you more often and learn your process, their capabilities will increase and you’ll end up building up some long term resources.

In order for this to be the case, you need to be a reliable source of work for the freelancer. They have the same goal of being a long term resource so make sure to stay in communication regarding new projects, reward top performers, and move on from unreliable workers. If you do this, it won’t be surprising to wake up to a Slack message saying “ Happy Friday Everyone :) I’m available for another one job.”

Rinse and Repeat

This is basically it. As you get more comfortable working with freelance teams you’ll be surprised as to the scope and complexity of projects you can get done, and just how reliable freelancers based around the world can be.

If you found this helpful, make sure to join our waitlist, as we’ll be not only releasing templates and guides for building freelance teams, but also other areas of scaling out teams.

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