I’ve worked with freelancers for different reasons: to create an e-commerce store for a B2B food delivery company going B2C during the pandemic to hiring them to outsource operations in a VC-backed company.

These are lessons from hiring and working with over a dozen freelancers from marketplaces like Fiverr and Upwork.

Be specific

These guys will execute. Nothing more, nothing less. You need to be as specific as possible — to the pixel. The more ambiguity, the more margin of error, and the more errors. This can result in freelance projects ending up as a waste of time, energy and money.

Being specific requires explaining in detail what you’re looking for. This is an exercise in communication: using examples, providing evidence, being specific but succinct. This is an example of how I gave feedback to freelancers I was working with to build Soraya, an online supermarket that I helped build since the start of the pandemic (link to Coda page).

Only work with freelancers with top ratings

Using a marketplace like Fiverr or Upwork is a bit like trying to find water in the desert — it ain’t easy. Even if you stick with professionals with top ratings it’s hard to find someone good, but it’ll maximize your chances of doing so.

Onboard a freelancer according to the complexity of their work

Someone doing data entry will need a different onboarding than a product designer working on revamping the site. One of the key differences is how much extraneous information you will provide. People doing data entry might not need a detailed explanation of your business, while it may be a good idea to provide the designer with the strategic thinking of your company so that he can make proposals that align with that.

Be rigurous because your incentives are misaligned

Their interests are to invest as little time as possible as long as the project is accepted. As the person who hires the freelancer, this means you should both expect flaws and that you’ll be pushed to accept a deliverable. It’s natural, they just want to move on to the next project and it’s your responsibility to make sure the output is right.

What are the implications? Check the work thoroughly and be stringent with what you accept. Just as with any type of work, but especially with freelancers, the standard of work you produce as a company is the worst standard that you accept.

Limit your downside the first time you work with someone

I use these 2 tactics concurrently:

  • Fix-based pricing: this avoids people who want to overcharge you off you at the get-go
  • Having and abiding by a strict deadline: tell them that you will only pay them if they finish the project by the deadline you agree to, and ask them to confirm that they accept