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How to Outsource Tasks – 3 Different Free Systems I Use

Outsourcing tasks to VA is one of the simplest jobs but often when not done well it can end in confusion, extra costs and the desired end result not being achieved.

This post is going to talk about the progression I have gone through assigning tasks to my VA and what I have learned along the way.

If you don’t have a Virtual Assistant here is where you can go to find out more about my approach to finding a VA in 15 minutes.

Below is the task management method I have used and progressed through. The idea of this post is for me to show you the 3 basic models I have used and hopefully provide some best practises for managing VA’s along the way. No system is ever perfect and it depends on you, your business and your current teams capability and size to see which one is right for you!

Basics of effectively Assigning Tasks – Who is doing what by when!

Whenever assigning tasks it is critical that they all fulfill the following. Any system below can work but it is important each task is assigned the following…

  • Clearly define the desired end result
  • Communicate when it needs to be done
  • Who is responsible for completing it
  • Define what reporting should occur, when do they need to report back
    • Always have the reporting back on progress be within a few days if the deadline is longer than a few days.

Balancing Act – Easy/Fast vs Robust/Scalable

Any management system needs to balance being easy/fast to use with the systems ability to handle the number of people/tasks.

Task Management Balance

Fast/Easy vs Robust/Scalable

Systems developed over thousands of tasks!

Below are 3 options I have now grown from and have some hard earned tips on what works best for each based on my experience. Each system will be custom to your team and experience!

My ODesk Experience to Date

My ODesk Experience to Date

System 1 – Easiest Method – Email

This is the easiest method of assigning and following up on tasks. Simply define the task and email it to your VA. But here are a few tips.


Here is an example of a normal email I would send to my team to take care of a new money website I wanted built. Often I won’t be linking to the  SOPs since they know and use them already and there is a lot of information in the custom Google document for the money site not in the email (about, contact, title, tagline, description etc) but here is basically what the email would look like…

Hi Team

New money site to be built….

VA1 – Please register at NameCheap account 1 and point nameservers to hosting 1 – Complete in 24 hrs and email me and VA3 to let me know it is done.

VA2 – Please get 10 articles created within 7 days from 2 different writers. Below are the titles. Let me know within 3 days when you have hired the writer and forward to me the first article. Once all articles are complete and uploaded to dropbox let VA3 and myself know. Follow the SOP here (link to Google document)

VA3 – Please build a site including custom logo and leave it no-index until the content is up. Have the site ready for content within 7 days from now.  Follow the instruction document (unique Google doc for money site) and SOP here (link to Google document).

VA3 – Once you receive the articles please publish them and let me know when the site is complete and ready for final review. Follow the SOP here (link to Google document)

Let me know if anyone has any questions.



Key Learning – Systematically Follow Up

One of the problems with where email falls down is the ability to follow up on every task you assign. Without a way to follow up you  can send out 10 tasks and some of them will be completed while others won’t and it will be tough to tell which ones have been completed and which ones haven’t.

Tools to Make Email Follow Up Easy!

  1. Boomerang for Gmail –You can get an email you send dropped back into the top of your inbox at a specified time. This means that when you ask for a follow up in 3 days when assigning a task you can boomerang it to your inbox in 4 days and if you haven’t received a reply then you can ask about the tasks status. Make sure to not select the “if I don’t hear back” because often you should/will receive a confirmation email that they received the task. Once you receive this confirmation email you will not receive the Boomerang unless you have the option picked “regardless”.
    1. Boomerang for Gmail – (limited free trial)

boomerang for gmail task management

  1. Yesware for Gmail – Yesware is a pretty interesting tool which does a lot more than just automatically reminds you to follow up. It has a whole array of interesting tools and I am only using a small percentage of its power. But it is an efficient way to set reminders to yourself to check on the status of the tasks you assigned via email.
    1. YesWare for Gmail – (Free)

YesWare Gmail Task Management

If you are using an email service other than Gmail and you don’t want to make the change you can follow the Getting Things Done system and have a folder for all waiting for information emails in it.


System 2 – Slightly More Complex but More Robust- Google Spreadsheet

This method takes a little more time from a management stand point but it can be very robust. The key here is to create a spreadsheet that everyone on your team has access to and it clearly shows who is doing what by when.

The columns on the sheet are the following.

  • #
  • Desired End Result
  • Next Action
  • Responsible
  • Date required to be Complete
  • Status (Not Started, In Progress, Complete)
  • Comment

The key to making this sheet work is using it! Each person with activities on this sheet needs to update the sheet each week. I send out a Google Calendar reminder for everyone to login and update the sheet.


System 3 – More Complex – More Robust – Online Solutions

After happily working with system #1 and #2 for years and occasionally trying out some free/inexpensive online project management tools I have decided I am needing to upgrade my teams ability to handle many diverse task requests. After analyzing the nature of all the requests my team gets the majority of the requests from myself and clients is in the form of either new projects/sites(20%) or tweaks to existing(70%). The spreadsheet control document for each bigger project (authority sites, private blog network service) are excellent at managing them, however the inevitable tweaks that are required can not all be handled through email/spreadsheet easily.

So after testing or reviewing of a few possible online project management tools – Trello, Get Flow, Asana, ZenDesk, FreshDesk and OSTicket

My realization is that most of the “project management” tools are best at organizing, defining and collaborating on larger not yet clearly defined projects. Whereas the solution I am looking for is more of a robust task management system where customers can assign tasks/tweaks as well as myself without going through my inbox for everything.

So I have decided to integrate OSTIcket (open source helpdesk software) for all my task management. Thanks to Spencer for pointing me to OSTicket.



I have not used this tool extensively yet but I am looking forward to all the potential integrations I can do to continue to automate many aspects of my business. Initially, I will be using it for task assignment then progressing to order fulfilment automation.

In the future I will give a more detailed report on how the OSTicket integration has gone and all the automation options that are possible.

About the Author Jon

I am a 36 year old husband, father of 3, engineer and a huge fan of developing systems to build useful and profitable websites. The reason I build online businesses is to provide financial independence for my family and yours AND so I can spend time outside skiing and biking with my family.
Jon Gillham, Online Entrepreneur

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