How to Make a Good Hire on Upwork

This post is part of our series, Summer Scale Up. We’re helping you scale yourself and accomplish more.

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Outsourcing parts of your business is something that has the potential to completely change your company or freelance practice. It can accelerate your growth and free up your own time for tasks that use your talents if it’s done right.

I’ve found Upwork to be a quality source for freelancers and it’s worth learning how to make a good hire there. A couple of our virtual assistants and project team members were found there and we now have a process for making sure we hire the best person for the job.

  1. Don’t write a crap job description
    The first step to making a good hire on Upwork is making sure your job description reflects exactly what you need well. You’ll attract better candidates that way.

What qualifies as a “crap” job description:

  • Copying and pasting another company’s job posting just because the title of the position is the same. There is NO WAY that you are looking exactly for what another company is looking for. Do the work and really put the time and effort into communicating what YOU need because bringing someone else on, virtual or not, is a big decision.
  • Not putting in the time and neglecting to include enough information. If you only provide a few sentences about what you need and don’t include enough context, you’re going to attract candidates who will submit the same kind of low quality work.
  • Only focusing on personality/work style or skills. You need both hard and soft skills to make this important partnership work.
  • Sounding like a jerk who is looking for a subservient person. Actually, scratch that. If you sound that way, you probably are that way and it’s better for everyone that you don’t take the good candidates’ time so they can work for someone else who is a better manager/human being. Good work relationships are about mutual respect. Get in the mindset that you are looking for a team member.

A good job description includes:

  • A list of the top skills required to perform the job, including any technical skills
  • The length of the engagement
  • Performance expectations
  • Information about your company and/or product
  • How and when you will make your decision
  • What the work dynamic will be (communication via email or phone, teamwork required, whether you prefer someone who can work during the work week*, how you like to work, when the work needs to be completed, weekly time budget, etc.)

*There are a lot of freelancers who have full time jobs during the week and make extra money on the weekends with Upwork. Keep in mind that these candidates won’t send deliverables until the weekend. In many situations, this could work. Just keep in mind that a full time freelancer is quite different than someone who hasn’t yet made the move to quit their day job. Personally, I prefer someone who can make progress WITH me during the normal work week and I don’t turn my email off on the weekends so I’d rather not see updates from a VA on Saturdays and Sundays.

  1. Use your interactions with the candidate as measurement
    Don’t stop at their portfolio or reviews. Take advantage of the messaging capabilities of the platform and get a little back and forth going before you make a decision to hire or hop on Skype for a short interview. You’ll be surprised on what you can pick up from a texted conversation if you just pay attention.

Ongoing messaging is a great way to assess:

  • Timeliness– If it takes a while for the candidate to get back and you are moving forward with other potential team members, they might not be the most reliable. You need someone who is reasonably responsive and candidates will be the most anxious to get back when they are looking for new work. Not a good sign if they lag in these early stages. I usually look for an Upwork freelancer to get back to me within 24 hours and that’s what I expect once I’ve hired them as well. 
  • Intelligence– Blatant misspellings, sentence structure, and grammar mistakes will help you initially weed out the less talented. It doesn’t matter if what you need them to do doesn’t involve writing. Smart people read and develop writing skills from reading so a person with poor writing skills might not be that interested in learning and that is not a good hire, especially in the virtual world when they will be working independently and will have to figure some things out on their own.
  • Personality– Do they anticipate what you need to make your hiring decision by including details? Do they seem equally concerned about finding a good fit? Are they humble? Does their level of formality fit what you are looking for? Or simply, did you enjoy interacting with them?
  1. Don’t settle for the first applicant
    You’re going to find a better fit for you if you use a pool of applicants, first weeding out the ones you can tell you don’t want to hire based on their initial message to you, their portfolio and/or resume, and their reviews.

Then, after messaging back and forth with the remaining candidates, pick two or three that you 1) feel are the most capable for the job, 2) enjoyed interacting with the most, and 3) were the most timely.

  1. Take advantage of Skype
    Especially if the job will involve some interaction via phone or Skype, schedule a quick Skype call with your top two or three picks. There is a lot you can tell about a candidate in even just ten minutes.

Tip: Even if you will only require correspondence via email or text for the actual, it could also be a good idea to get your candidates on a video call. Once you make that personal connection, your hire will feel like they actually know you and will feel more accountable.

Do you have any tips for hiring freelancers? I’d love to hear them in the comments below!

Ludell Jones

Ludell Jones

Marketing Director at Eazl
8 years of digital marketing experience. Located in Chicago & San Francisco. Digital marketing & growth hacking lover. Online courses & entrepreneurship.
Ludell Jones

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