Even with their recent rate hikes, Upwork remains my go to resource to help me run my eCommerce businesses.  I use upwork to hire contractors to do everything from graphic design and web development to bookkeeping and data entry.

As someone who’s been outsourcing for close to 10 years, I’ve learned a few things along the way and in this article I’ll show you the process I use to hire contractors on Upwork.


Write a descriptive title

Use a title that attracts the right candidate.  Make sure to include keywords and be specific as to which tool/application/software you’re using.


Job title on Upwork




Task Good Job Title Bad Job Title
Fix a website bug
  • Fix the checkout page on my WooCommerce website


  • Fixa a bug

Design a Facebook banner ad
  • Design a banner ad for my Facebook Page


  • Design a banner

Write an article
  • Write a 500 word article on “10 best business apps”


  • Write an article for my blog


In the first example, I want to hire someone to fix a bug on my eCommerce site so my job description needs to be specific. The last thing I want is 500 applicants for this job, most of whom know nothing about WooCommerce.

Fixing a bug is a very vague subject and covers a broad spectrum. By specifying which software and where the problem is, contractors will know if they should bother applying.

 Write a short but detailed job description

If you’re a contractor, getting hired is a numbers game. The more you apply, the higher the probability you’ll get hired. You can’t waste time reading  a 1000 word job description.  As an employer I realize this so I keep my job description short and sweet.

Every job description should have the following elements:

  • 1 or 2 line summary of the task
  • 1 or 2 line of the requirements
  • An incentive
  • A price
  • A screening question


how to write a good job description on upwork

The contractor reading this job posting has a clear understanding of what I need fixed and how much I’m willing to pay to have it done. I’ve also included an incentive for additional long term work should performance merit it.

Contractors are always seeking continuity so if you can provide some sense of stability to then, they’ll go the extra mile for you.

Use a screening question

A contractors philosophy is always “Get hired THEN figure out what the client wants”. To avoid this, I use a screening question like “use the word XXXX when applying” at the bottom of the job description. This way, I’m assured the applicant actually read the job description in full.  Using a screening question will eliminate 50% applicants.

Hire by demographic

Political correctness aside, here’s a list of places I like to hire (and not hire) from:

Job Best Candidates Worst Candidates
Web Development
  • India

  • European countries

  • Pakistan

  • China

  • Russia

  • Bangladesh

Graphic Design
  • USA

  • Canada

  • European countries

  • Asia

  • Middle East

SEO Don’t outsource Don’t outsource
Virtual Assistants
  • Philippines


  • Pakistan

  • Bangladesh

  • Middle East

Social Media Marketing/Management Do it yourself
Fix small wordpress/website bugs
  • India

  • Bangladesh


  • China

  • Russia

What to look for in potential candidates

After posting a job, expect to receive applications in about 20 minutes. After 60 minutes, your talent pool will be flooded. To save time, here’s how I choose my top 3 candidates:

  1. Eliminate anyone who didn’t answer the screening question.
  2. Eliminate anyone with a feedback rating of 4.3 or lower.
  3. Pick 7 or 8 applicants and read their cover letter. If the cover letter is too generic, move on to the next candidate
  4. Read feedback comments, check qualifications and review their portfolio
  5. Pick the 3 candidates that standout and select them for an interview

Here’s an example of a job posting where I used “social media” as my screening question. Notice the middle applicant; they didn’t use the keyword and it appears to be a cut and paste cover letter.

how to hire on upwork

Interviewing candidates

While some people prefer to speak to candidates via skype, I prefer to chat with them on Google Hangouts though I could do the same on skype chat.

Interviewing candidates on upwork

In the interview/chat, I’ll ask the following:

  1. Are you sure you can do this job?
  2. Have you done something like this before?
  3. Can you provide me with some links of your previous work?
  4. How many jobs are you working at the same time?
  5. You are ok working with my budget?

Questions 4 and 5 are the most important. I don’t want a candidate who’s working multiple jobs at the same time or else they’ll be distracted. I also want to reaffirm my budget just so there are no surprises.

Paying contractors

Upwork makes it really easy to pay employees using an escrow system. The employer deposits the value of the contract in to a temporary account and then releases the funds as they fit.

NEVER release 100% payment to your contractor until you’re 100% certain the task is complete.

Depending on the complexity of the task and length of the contract, I pay my contractors in increments.

Task Payment Release Schedule
Complex task that’s expected to last more than 1 week
  • First task complete: 10%
  • 50% complete: 40%
  • 75% complete: 25%
  • 100% Complete: 25% + bonus
Simple Task (e.g. fix bug, write article, design banner)
  • Initial payment: $1
  • First draft complete: 50%
  • 100% complete: Balance + bonus

What to do when your contractor gets “sick”

“I’m sick”, “I’ve lost electricity”, “my dog died”. Get ready to hear every classic excuse as to why a contractor didn’t finish their work on time. When in doubt, FIRE and move on.