Website Income

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 33 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

Leave a Comment:

Neil Curtis says December 23, 2013

Thanks Jon, I’ve built myself a small portfolio of websites over the last year or so (6 in total), but up to now I’ve done everything myself, and continue to do so. I know I need to start outsourcing tasks soon, probably starting with updating content and other things like this just to keep them ticking over so I can focus on other bigger projects.

So I’ll definitely be looking back over this post and some of your other related posts to help me out.

cheers and great stuff


    Jon says December 24, 2013

    Good luck building up more sites! Hope this article will be helpful.

    Cory Buford says February 8, 2014

    Hey Neil,

    My wife, Heather, and I have been doing things on our own for the past 16 years and it’s the best way to learn. However, last year we finally made the move to outsourcing and it does make things much easier.

    Jon’s right when he says there is no secret loophole but we can always work together to speed up the process exponentially Best of luck and let us know if there is anything we may be able to do to help.

Shawn says December 23, 2013


We have used a number of different systems to try to get the most efficiency and I would give Podio a try as you can save data and provide task templates in the same location as well as who has a great task management option with tons of features (not free) but a great resource.

Kashif says December 23, 2013

Thanks for another gem of a post.

Just curious how you’re using And by the way, their pricing page show no free version 🙁

    Art says December 23, 2013

    Great article! Another great tool is Mxhero ( – it actually provides many of the above capabilities for FREE and with unlimited messages!

S.Saab says December 24, 2013

As usual great article, I’d like to add using Jing ( which is a free SW that captures anything you see on your computer screen, as an image or short video (up to 5 minutes), and lets you share it instantly again it’s FREE.
It’ll help to send video instruction to your VAs on how to do specific task or even ask them to do it for creating training material.


    Jon says January 5, 2014

    TechSmith has a lot of great products for communicating visually! I use Snagit and Camtasia…both are paid versions of what jing does. But I think jing has better sharing ability…I will add it to my list to try since waiting for a video to convert even though it only takes 1 minute still is a road block for me to just fire a video together fast.

Raweewan says December 26, 2013

Hi Jon
Your article is always great and I always get many ideas to apply with my online business. I’m not using VA yet, due to my income is still not much. I need to do it myself for a while. Well, Happy New Year 2014.


    Jon says January 5, 2014

    Thanks Raweewan. best of luck in 2014!

Doug Cunnington says December 28, 2013

Jon – Great article. The systems you mention outline the standard progression as the amount of work grows. I fall into the early stages of system #3…

Here’s a funny and shocking fact: The client I work for in my day job is a major, tier 1, telecom company. They use email and some weak spreadsheets to manage huge, multimillion projects. Seriously. They don’t even use MS Project which I’m *not* a huge fan of anyway but they don’t even use that. I’m trying to pitch the idea of using some simple task management software but you can imagine how hard it is to change old habits.

I’ve been using Asana recently and love it. It’s great for people with small teams, like us, since it is free. It’s also really simple to use and add new users.

OSTicket looks great for your purposes. I see the big advantage since you have many customer facing considerations. I’m definitely interested in hearing about implementing the overall solution and how you roll out the system.


    Jon says January 5, 2014

    Hey Doug, thanks for the comment. I think any system can work it is just a matter of working it the right way. The implementation will be key, getting adoption from the whole team!

    Victoria says February 28, 2014

    Doug – if you need the function of milestones and such, check out using InstaGantt with Asana. It is a plug-in/add-on specifically for Asana that is still in its beta stage and free. I have found it works really well.

Winston says December 30, 2013

One thing I’ve noticed about your work is you’re able to break things down and organize them quite well, specially when it comes to outsourcing.

Wanted to ask you about maintaining expired domains. I read in a forum somewhere that you can lose PA. They mentioned buying a few exp. domains that were over PA 30, which later became PA 1.

Does this happen?

    Jon says January 5, 2014

    Hi Winston, the backlink ecosystem is always in a constant state of change…some links are being built others are being removed. So if a sites link metrics were coming from only 1-2 sites and they removed the links it is possible. Another common scenario is that the PA of the is different from the PA of so that may be the reason for the difference.

    But to answer your question directly most sites will have link metric changes with time but I have not had a site go from PA 30+ to PA 1…my guess is either there was only a couple backlinks that got deleted or they weren’t checking the PA on the www.

Miki Vicioso says January 2, 2014

Looks interesting John! I think the less efficient is everyone submitting on an excel sheet! Just doesn’t look right. I seem to be using a lot Google Drive (for files, reviews, etc) and email templates using TextExpander (for mac). Keep it up.

    Jon says January 5, 2014

    Yah that would be a nightmare having 1 central excel sheet…Google Docs are great for collaboration. One document my team uses almost always has 1-3 people in it.

Raweewan M. says January 6, 2014

Hi Jon
I’m come back again. I want to ask you something. How much does it cost for 1 VA on any project per day and per months? And I read your blog. You’ve 3 VAs, right? Can you share me your budget each month for hiring them?

Jason says January 7, 2014

Nice info! What do you think is the best way to give your VA access to software on your own computer (like Long Tail Pro) and no access to other areas of your computer besides renting a Virtual Private Server? Thanks

Omar says January 7, 2014

Hi Jon!

Sent you an email about a product that might really interest you! Sent you an email to your gmail address.

    Jon says January 7, 2014

    Hi Omar, thanks for the email… the tool you are developing would definitely be a great step up from my email task management system I was/am using. I can assign tasks that get automatically tracked right from inside GMail…slick.

Brad says January 25, 2014


Got a quick question and the one that is holding me up the most with using VA’s like you have going on.

You have VAs 1, 2 and 3 performing tasks that cost money (register domain, content and log design). How are these task paid for. Are your VAs fronting the costs or do you have some other way of paying for them directly through your accounts.

Gilbert Cuevas says April 16, 2014

Detailed and very helpful. Outsourcing Business Tasks is the future of outsourcing. Though that may be limitless.

joey says August 18, 2014

the shared doc does not share? Please email me a copy asap -> Share to Get Access to Task Management Template

I shared it a few times, but there is nothing behind the share – please advise

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