Replacing Outlook with Google Apps Email (aka Gmail)

Replacing Outlook with Google Email (aka Gmail for Business) requires proper setup.

In my experience, the most common scenario is for a business to move its email servers to Google, but then completely drop the ball when it comes to setting up the web email client.

Sure, you can simply open a browser, login and there’s Gmail. However, this substantially reduces the probability that users will accept the web-based Gmail client, even though it has substantial advantages.

How to view your email settings

  1. In the top-right corner of Gmail, click the gear icon gear, then click Mail settings.



  • You will have to view your email settings repeatedly. Gmail automatically closes your settings each time you make a change and click Save. It’s an annoyance, but one that’s easy overcome.

General Settings

  1. Follow the steps above to view your email settings.
  2. Click the General tab.
  3. Set the following options:
Option Value Why you want this setting
Maximum page size Set each options drop-down list to the value shown below.

  • Show 50 conversations per page
  • Show 250 contacts per page
I like to see the maximum number of emails per page. This reduces the next to click next page.
Keyboard shortcuts Select Keyboard shortcuts on. Shortcuts are a key strength of Gmail. Once you get used to them, you’ll find Outlook mouse-intensive.
Browser Connection Select Always use https. If your admin has not set this up by default (which he/she should have), then you’ll want this setting to help secure your business email.
Conversation view Select Conversation view off. This is a matter of personal preference, but if you’re coming from Outlook then you want this setting to ensure that each email is displayed as a separate email. Trust me, conversation view is high on the list of reasons why users reject Gmail.
Desktop Notifications
  • Select Chat notifications on.
  • Select New mail notifications on.
Users have become accustomed to the little popup when a new message arrives. This setting helps preserve this functionality for users.
Signature Create a signature. Personally, I find it annoying to receive emails without a signature. It’s business. Customers, vendors and co-workers may want to contact you.
Attachments Select Advanced attachment features. This makes attaching multiple files easier…but your users need Flash.
  1. Click Save Changes.

Remove Web Clips

  1. Follow the steps above to view your email settings.
  2. Click the Web Clips tab.
  3. Uncheck Show my web clips above the Inbox.

Web Clips are a distraction and really should not be in email.

Enable Labs features

  1. Follow the steps above to view your email settings.
  2. Click the Labs tab.
  3. Set the following options:
Option Value Why you want this setting
Canned Responses Enable Improves email efficiency by using templates for repeat messages.
Default Text Styling Enable Allows users to set fonts.
Google Calendar gadget Enable See upcoming events in the email client. This reduces the need to switch to Calendar
Inserting images Enable Everyone needs to insert images in email. I can’t figure out why Google doesn’t include this as a default feature in the email editor.
Right-side chat Enable Makes initiating chats more efficient as you can quickly see who’s online on the right-side of your email.
Send & Archive Enable You must archive email if you’re going to use Gmail correctly. This button automatically archives each email message that you send.
Signature tweaks Enable This should be a default. However, you’ll want this setting as it’ll put your signature above previous messages in a thread.
Title Tweaks Enable This makes the web browser display the Label (aka Folder) and the number of unread messages in the left of the title. In other words, this features makes it easy for users to see how many unread messages are in their inbox or other Labels.


  1. Click Save Changes.

How to setup Labels and Filters (i.e. Folder and Rules in Outlook terminology)

Organizing email is one of Outlooks strongest features. Fortunately, similar functionality is available in Gmail.

Labels (aka Folders)

  1. Follow the steps above to view your email settings.
  2. Click the Labels tab.
  3. Scroll down past System Labels and Circles. You should see a Create new label button.
  4. Click Create new label.
  5. Enter a name for the new label, such as Customer Inc.
  6. Click Create.

Repeat the steps above for each Label that you want to create.

However, you’ll noticed that Labels by themselves are somewhat useless. The real power in Labels comes from Filters.

Filters (aka Rules)

  1. Follow the steps above to view your email settings.
  2. Click the Labels tab.
  3. Scroll down to the bottom of your Filters list.
  4. Click Create a new filter.
  5. Enter your filter rules. For example, you may want to filter all email from into the Customer Inc Label. To achieve this, enter in the From textbox.
  6. Click Create a filter with this search.
  7. Check Apply the label, then select a label in the drop-down list. To continue our example, you’d select Customer Inc.
  8. Click Create filter.
  9. Hint: I recommend that you check Also apply filter to ___ matching conversations. This will ensure that all old messages are also displayed in the new Label.

The Fragmentation of Computer Usage

Back in the 90’s I worked on Sun Solaris servers. Back then, there was an upstart operating system named Linux. Linux lacked the stability of Solaris and more importantly it ran on commodity Intel hardware. This may not sound like a big deal, until you consider that Sun servers of the day often had multiple inbuilt redundancies. A Sun server was really a cluster of multiple servers where a failure in one board simply meant that another board took over. This redundancy applied to all aspects of the server which largely explained why Sun servers were known to run for years and years without a reboot. If a part failed, you simply opened the server (while it was running), changed the part and closed it back up. Contrast this with the Linux/Intel servers of the day where a simple issue, such as bad RAM, meant your server was down.

At the time, Sun argued that there was no way that a Linux/Intel server could possibly compete against a Sun server. To this day, this argument is true.

However, what Sun did not consider is a radical change in the overall architecture. Today, each Linux/Intel server is still susceptible to failure. The solution was to use multiple Linux/Intel servers in a cluster. Now, if any one server fails, you simply remove it (while the cluster is running) and replace it with a new server.

Today, tablets (such as the iPad) and mobile phones (such as the iPhone and the various Android phones) are far to weak to compete head on with desktops/laptops. And, there are pundits showing computing curves that project the point at which a tablet will be as powerful as a laptop.

Frequently we hear the same question, “Will a tablet be your next PC?” This line of thinking misses the point. These hand held will not overtake the PCs power, they will simply change the social architecture of how we use computers.

Today, a mobile phone consumes a portion of “email time”. Here, I define “email time” as the total time a person spends per day reading/writing emails. 10 years ago, 100% of email time was spent on the PC. Today, a portion of that time is spend on a mobile phone, and for those with tablets a portion of email time is spent on a tablet. Thus, the PCs share of email time has steadily reduced.

With the rise of social media, some applications such as Twitter are being designed for these smaller screen devices. In theses cases, the small screen becomes a key selling point, rather than a performance weakness.

Further computing fragmentation is happening with the rise of online applications. As an example, Google Docs is not a direct threat to Microsoft Office. The inherent weaknesses of online applications dictate that Google Docs will lack the rich feature set offered by Microsoft Office for years and years to come. However, what Google Docs does do is fragment office software usage. At times, sharing is more important than power. In these cases, usage becomes fragmented between high-powered desktop software and relatively weak online software. Again, the issue is not when online software will become as powerful as desktop software, the answer is likely never.

As new technologies arise, the important question is not when the new technology will become more powerful than the existing one, but rather will social and technical architectures change so as to minimize the need for the older technology.