Related post: How To Hire & Manage Remote Teams

Why outsource? It enables you to hire from a talent pool that’s ~1,000x bigger than your city’s pool at a fraction of the cost.

Over the last three years, I’ve hired and managed 70+ contractors from 30+ countries in a wide variety of roles.

While there are certainly other people with more experience than me, I’m savvy when it comes to outsourcing, virtual assistants and hiring and managing freelancers.

I’ve compiled the best guides on the internet to save you time as you start building your own outsourced team!

1. The Complete Guide to Outsourcing by TimeDoctor 

This is the best internet guide that I’ve read. It’s thorough and jam-packed with just about everything that you need to know.

The one area of the guide that’s lacking is about how to hire on freelancing websites but I added an extra resource to fill that gap!

2. Virtual Freedom (Book): How to Work with Virtual Staff to Buy More Time, Become More Productive, and Build Your Dream Business by Chris Ducker

Chris Ducker is one of the most famous VA experts for good reason. His book is fantastic and is a must-read if you’re getting into outsourcing.

3. Upwork Guide: How To Hire Online Freelancers

This is the best guide to Upwork that I found. Eventually I’ll write my own but for now read this one!

4. 101 Tasks to Outsource to Virtual Staff to Grow Your Business! by Chris Ducker

Helpful list of ideas for things that you can outsource!

5. The Secrets to Find, Hire, and Manage Great Virtual Assistants by Foundr

This guide may be redundant if you’ve already read #1 and #2 but if you’re looking for more information, this is another helpful guide!

Three Bonus Tips From Me

UPDATE: You can read a longer, more detailed version of my tips here.

Eventually I’ll write a full guide for this topic, but for now I just want to hammer home a few key lessons that will help you.

1. Hire before you’re ready (a lesson from Tim Ferriss)

The best way to learn something new is by doing it. So if you know that you should be outsourcing or that you’ll need to start soon, start now.

Why? Because your first couple of hires are just learning opportunities for you so that you can start to understand the process. The sooner you start, the sooner you start learning and spotting opportunities to outsource more things.

2. Recorded screen recording/video training is the best way to train new workers

I do almost all of my training as pre-recorded screen share recordings using Screencastify (I record myself doing what I want the contractor to do while explaining my process out loud).

Video recordings allow you to show exactly how you want things to be done while giving the new contractor a live feed of what you’re thinking about while you’re doing the task. It’s much, much better than written only training.

I frequently use written resources but these are secondary and are used to re-enforce key principles covered in the video training.

By recording the training instead of doing 1:1 live training, it enables you to easily use the training on new hires if you need to hire more people or if the first person doesn’t work out.

3. Upwork basic tips

Upwork is the largest freelancer marketplace and it’s the main site that I use for hiring. Getting setup and posting jobs might feel complicated but it’s actually simple.

This is my basic process:

  1. Post a job
    1. Make it clear what you’re looking for
    2. Ideally, you have 1-2 questions that will enable you to weed out candidates
  2. Wait 24-48 hours for applicants to come pouring in
    1. Search for and invite 5-10 good candidates to the job posting while you’re waiting
  3. Ask a follow-up question to the 4-8 best candidates
    1. Pay close attention to how quickly they respond and every minor detail (this is a preview of what working with them will be like)
  4. Hire the best 3-5 candidates for a 1-2 hour paid test that simulates the exact job that they’ll be doing
  5. Hire the candidate that tested the best and get started!
  6. If the first hire doesn’t work out, then hire the next best candidate or start the hiring process over. Repeat until you find the right hire.

Some people prefer to do video calls but unless the role involves speaking or is highly dynamic, I conduct written only interviews. But obviously do whatever is best for you!

Hopefully, this is helpful. For more related information, check out the best guides to hiring and managing remote teams.