Over the past five years I’ve had extensive experience with both systems.

A few years ago Google launched email/calendar/etc…hosting that you can use for your business email (click here). Basically this means you can have your company emails be setup on the Google system through your own domain.

The Google solution has a lot more implemented functionality than Outlook has by itself. In any case, they are replacements for each other, and so I think it is a fair comparison.

Organization

Outlook uses the typical folder structure for organization which works for most things. However, what I love about GMail is what they call Labels. You can use Labels like folders and move emails into a Label so that it is out of your inbox. But they really aren’t folders because you don’t have to move an email that has a label attached to it outside of your inbox, which is handy….especially when you are getting a lot of emails.

When I did contract work I was able to test and fine tune how I used the GMail system in managing 30+ emails per day. What I found very quickly was how much more organized and how much more I could be on top of things with GMail over Outlook. I could have a “to do” Label and assign any emails in my inbox that I wanted to tackle later to that Label, but still have them appear in my inbox. I made this to do Label red so that it stood out over all my other labels. When I got done with each to do item, I would move it out of that Label and possibly assign it to the Label I used for that specific project (if it wasn’t already assigned to that Label as well).

I would then have a label for each project that I was working on.

This allowed me to easily keep track of the emails I still needed to respond to and also reference emails that were sent several months ago. You can so something similar in Outlook with Categories, but it seems a lot more clunky and not nearly as user friendly as GMail Labels. Another point worth mentioning is that you can have an email assigned to multiple Labels, which you can’t do with folders (unless you send yourself the email more than once…which is a lame replacement for this functionality).

Search

I’ve always been dissatisfied with the search tool in Outlook. This is a feature that has worked extremely well in GMail. On top of that, I don’t have to delete any emails that aren’t spam…unlike what I’ve had to do with the Outlook systems I’ve worked with.

Even if I accidentally assigned an incorrect label to an email, I can usually find it easily in GMail just by searching. There have been times where I had emails disappear where I couldn’t figure out where they went in Outlook.

Offline Capabilities

This is the one aspect of Outlook that has the advantage over GMail, since it is an installed application. However, there is an offline GMail application you can enable from the labs that will allow you to do this.

Since I’m 99.9% online anyway when I work, this is not a big deal for me.  I also like the fact that I don’t have to have a program installed to check my email, and that I can just have it loaded through a tab on my browser. They have a system that you can install that gives you access to an exchange server through your browser, but it is not nearly as fast as GMail and it doesn’t work as well in Firefox as it does in IE.

Non-Email Uses

This is where GMail takes the cake for me. I can not only create my own documents and organize my own private calendar, but I can also share these things with anyone who has an email address very easily. I can write a document, share the document with my wife who can then also make changes (or maybe I only let her view the document). I can setup automatic reminders through the calendar, or setup meetings that I share with several other people. The interface between all of these different systems is seamless and incredibly user friendly.

On top of all that, I can even chat through my Google account right in my email window (through Google Chat).

When everyone at a company is using the same Google system for their email, this becomes even more useful. You can setup specific company calendars that everyone at the company can see and also create documents that only certain staff at the company can view or maybe edit.

Add-On Features

There are probably add-ons that you can install for Outlook, but I really haven’t been given or seen this option. With GMail, you have what they call GMail Labs that provide some really useful functionality to GMail. Over the last few years I have seen a ton of applications added to GMail Labs. Anything from Offline GMail to having your calendar events show up on your left sidebar to customizing what is displayed on the title bar, make this a very valuable function of GMail. Also, the added options for additional functionality make it exponentially more valuable than Outlook over a long of period of time.

Summary

With all things considered, I would say that I am able to save about 25% of the total amount of time I read emails, organize emails, create documents and calendar items by using GMail over Outlook. When your primary communication method is through email and the internet, this ends up being very valuable. Then when you consider how much more you can be on top of things by using GMail over Outlook, it really becomes obvious which one reigns supreme!

Of course, this is just my opinion. There maybe other benefits in using Outlook over GMail that I am not aware of.