How I lead an

Joe Leon
Steward On Demand
Published in
5 min readJul 25, 2015

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army of freelancers

by Joe Leon

“It’s 4:30AM on a Tuesday morning. Who is possibly texting right now?”

“Oh, that’s right. It’s daytime in the Philippines.”

My freelancer, Adam, just received the message I pinged him last night. It read:

8:25PM ET “Adam, I found another issue with the file you sent. It’s the same issue we’ve been discussing for the past few weeks. I’m pretty disappointed. Please ping me to discuss.”

Now awake, I texted Adam back. And by 5:05AM ET we had nailed down a new QA process to prevent any more data mismatches.

This is the life of dealing with an overseas freelancer.

I’ve been working with overseas and domestic freelancers for about a year now. They’ve helped me with everything from finding new leads and data entry to designing a blog and forming an LLC. In fact, freelancers are a core component of our business at Steward. Over time we’ve built an amazing team of experts, but for a while we struggled to find, vet and manage them.

If you’re currently outsourcing or plan to outsource a project, this post is for you. Learn from my mistakes. Leveraging freelancers to multiply your workforce can require a significant time investment, but it can be a very powerful business tool and I can’t recommend it enough.

I’ll start off with my two biggest takeaways:

1. Before hiring a freelancer, put them to the test. Design a paid trial to test for accuracy, competency, communication and speed.

2. After hiring a freelancer, always provide feedback. Always. It will take a lot of effort on your end, but feedback is the key to building a successful relationship with your freelancers.

Getting started

So, where do you find freelancers? I’ve successfully used Elance/UpWork/Odesk, UpCounsel and Fiverr. There are many more sources out there too. Just google the type of project you’re working on + “freelance marketplace” and you’ll find a bunch.

After you choose a freelance marketplace, I suggest posting a job. Make the job description fairly detailed, but not too long. After you post, you’ll receive a slew of in-bound proposals. There will be a lot of bad ones.

Quick tip: Quickly cull the candidate pool by asking them to answer a specific question in their proposal. (Eg. “What is today’s headline article on the New York Times website?”). Any candidate that doesn’t answer your question did not read the entire job description. Reject those proposals.

Selecting a team

Create a shortlist of 7–10 freelancers and set up an interview with each. I recommend using Skype to conduct the actual interviews. Here are a few questions you could ask the candidates:

  • Describe the projects that you’ve completed related to <your project>.
  • Do you have any references from those tasks that I can speak with?
  • What type of guarantees do you have? What happens if something is incorrect?
  • How will you handle volume as I grow?

You should get 3–4 solid candidates from your interviews. Plan to have your top candidates complete a paid trial (i.e. a test). Paid is key. It’s not fair to request a trial without compensation and you risk having your account locked as most of the marketplaces simply don’t allow it.

In the paid trial, you’ll test for accuracy, competency, communication-style, speed, etc. As you can imagine, designing the test is crucial. Since each task is unique, I’ll provide you with some trial design guidelines and an example:

  • Create an unreasonable deadline. Evaluate what percentage of the project they complete and the accuracy of their work.
  • Explain that this is a competition and the winner will earn your business. Push them to give you their best price in the context of their competitors.
  • Complete the task yourself, learn what processes work best and create an answer key. These will help you evaluate the candidates from both accuracy and process perspectives.

After the paid trial, rank the candidates based on the accuracy and speed of their work. Then, choose the highest scoring candidate with the most agreeable price. Tell your runner-up that they came in second and you’ll ping them in the future if things change. Don’t burn that bridge. You might need them.

Not sure how to get started with your paid trial? Here’s a quick example. At Steward, we provide on-demand sales research and operations support. Clients give us tasks like targeted lead list building or CRM data cleansing, to name a few. In order to keep our clients coming back, we need to balance speed and price while maintaining 100% accuracy. One common request we receive is to find a contact’s direct line. Here’s how we built our direct line-finding team.

Test Goal: Find a freelancer who can reliably find a person’s direct business phone number. (Not the 888–888–8000 number, but the contact’s personal extension)

Test Design:

1. Build a list of 50 people that span multiple industries and management levels.

2. Create an answer key (i.e.: find each person’s direct line). This will be time consuming, but by completing the test yourself, you’ll learn what results distinguish good contractors from bad ones.

3. Give the freelancers three days to complete the task and then evaluate them against the answer key. A passing score is 95% correct direct lines or higher.

Test Result: Most freelancers failed. But after several rounds (and a fair chunk of change), I found a great freelancer.

Managing your team

It’s impossible to provide a step-by-step guide for managing freelancers, since each situation is different. However, here are some general guidelines:

Expectations

Freelancers won’t always infer what you want and cultural and linguistic barriers can make communication even more challenging. Take the time to clarify your expectations with regard to budget, communication, project output and timeline. Explain everything multiple times and include a written copy for their reference.

Communication

Keep a line of communication open at all times (I prefer Skype Chat). Some freelancers will feel bad bothering you with seemingly minor questions. Encourage them to reach out no matter what. Get comfortable micromanaging. Until you develop a strong working relationship, you will need to hover a bit. Over time, you’ll give them more rope.

Feedback

Go over their work with a fine-tooth comb and provide feedback. Do not skip this step. As tempting as it is to correct tiny mistakes yourself — don’t. Instead, review their work, give them feedback and request that they fix their own mistakes.

A final thought

Managing a remote workforce is difficult. Managing overseas freelancers is even tougher. However, once you find your freelancer dream team, it’s relatively low maintenance. My team is awesome! We span 3 countries and I hold them to 100% accuracy standards. I enjoy working with my team everyday, even those rare days that I receive a 4:30AM Skype wake-up text.

And by the way, if you’d rather not deal with managing a team of freelancers to tackle your next project, I built Steward to help. Just email request@getsteward.com and we’ll get started on your task.

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