Make Outlook Work Like Gmail

I have been using Gmail exclusively for the past 8 years. In December, I started at a company that uses Exchange and Outlook 2013. The transition has been a bit rough. It's taken me many hours and countless Google searches to fine tune Outlook so I can use it productively.

The good news is that although I can't get everything I want, it is possible to get Outlook into a more than acceptable working state. In this post, I go through how to configure Outlook to make it mimic Gmail as closely as possible, and throw in a few tips about how to overcome some of the Outlook challenges.

I have divided this post into these sections:

• Conversation View: It's not enough to just enable conversation view. I'll cover what you need to do to really make it work.
• Search: Gmail, of course, revolutionized email searching. There are things you need to do to make Outlook search work effectively.
• Inbox Usability: How to make the inbox mirror Gmail as closely as possible, and other tips.

Setting Up Conversation View

Gmail pioneered conversation view, and now other mailbox providers have followed suit. With the settings I have below, I have gotten close to what Gmail has, but it's still not as good.

First, you need to set to conversation view by checking "Show as Conversations" under the View menu:

Your settings in the "Conversations Settings" is also very important.

1. Show Messages from Other Folders needs to be checked. This allows the conversations to show emails that you have deleted (archived) or sent.
2. "Show Senders Above the Subject" should be unchecked. I'm not sure exactly what is going on here, but all emails in the conversation are not showing up for me when this is checked.
3. The other two you can play with and set to your preference.

To sort your conversations by date, you will want to select the "Date (Conversations)" for the Arrangement options. Sometimes I change this temporarily. But this is where it stays under normal operating conditions:

Search

Outlook standard searching does not search all folders by default. You want to go to File -> Options -> Search, and make your settings thus:

And when you use the search bar within the inbox, do ensure that the drop down shows you are searching your "Current Mailbox" or "All Outlook Items". You usually don't want to be limited to the Current Folder or Subfolders.

Inbox Usability

There is no priority inbox functionality that I have found. But you can setup folders and rules to try to mimic it. That is beyond the scope of what I have yet explored. This section is simply about making how you read emails work as similarly as possible.

Here is what mine looks like (content grayed out). You'll notice there are some significant differences to a Gmail Inbox. This is because I am trying to replicate the Gmail experience, and there is some functionality gaps that led to this being the design that best replicates the Gmail experience. I explain more below.

First, I like to have no Message Preview. This means that there is one line for each email in a conversation - showing just the information about the email, not the email content.

You can go to the View -> Add Columns option to set the columns you want. Here is what I chose, that I think most closely resembles Gmail:

To change the font sizes, go to View -> View Settings -> Other settings.

You also need to decide how you want to present the reading pane. This is where you click on a given email in a conversation and get a view into what that email contains without having to double-click and open a new window.

The closest to Gmail is to select "Off". However, there is no handy functionality to quickly expand one email to see what is inside of it without opening a new window, which starts adding too many clicks when you need to review a conversation with more than a few emails. I have found that I prefer having the reading pane on the right.

That's It

There are lots of other settings I have played around with - alerts, notifications, etc... but they are all pretty similar to what is available with Gmail and don't cause a big productivity gap when switching from Gmail to Outlook.

If you have anything to add that will help me get closer to Gmail, please let me know.