Google Workspace vs. Microsoft Office

Gmail vs. Outlook: Which works better for business?

When it comes to email, calendar, and contacts, Microsoft Outlook has long ruled the roost, but Google Workspace’s combo of Gmail, Google Calendar, and Google Contacts is worth a second look.

Google Calendar and Gmail vs. Microsoft Outlook
Thinkstock / Google / Microsoft

Some people will tell you that social media, chat platforms, and videoconferencing have replaced email as the most important means of communication in the workplace. Don’t believe them. Email remains the lifeblood of business and will do so into the foreseeable future.

When it comes to email in the business world, there are two main products to consider: Microsoft Outlook and Google’s Gmail. Outlook has long been the standby in the workplace, but Gmail has been growing in popularity. Each has changed significantly over the years and continues to change. Because of that, you and your company may want to reconsider which you use for work today.

To help you decide which is best for you, I’ve put them both through their paces. I’ve examined their basic interfaces; how you create, read, and respond to messages; and the options for managing email. I’ve also compared Outlook’s calendaring functions to Gmail’s companion, Google Calendar, and Outlook’s contacts capabilities to Google Contacts.

A few notes about price: Gmail is part of Google’s licensed Google Workspace (formerly G Suite) package for businesses, and it’s free for individual use. Microsoft Outlook is available as part of Microsoft Office, which has a variety of different iterations for personal or business use, and is available as either an annual Microsoft 365 or Office 365 subscription or a one-time purchase (what Microsoft calls the “perpetual” version of Office). Individuals can use the online version of Outlook for free, but its functionality isn’t as robust as the desktop client's.

For this review I primarily worked using the desktop version of Outlook for Windows in Microsoft 365. Individuals and businesses who use the perpetual version of Outlook may not have all the features covered here. Because it’s a multiplatform world, I also tested Outlook’s macOS desktop app, mobile apps, and web app. Gmail is web-based, and I tested it in my Chrome and Edge browsers. Google also offers Gmail apps for Android and iOS, so I tested those as well.

With all that in mind, let’s get started.

Navigating the interface

How easy or difficult is it to get started with Outlook and Gmail — and more important, what’s the basic interface you’ll use every time you check your mail, write a message, or create a meeting? I compared Gmail’s and Outlook’s overall look and feel as well as their simplicity and ease of use.

Gmail

Gmail focuses, above all, on simplicity. As you’ll see in a bit, Outlook feels as if you need to have a PhD in order to master its basic interface. Gmail, by contrast, feels as if any grade schooler can get up and running right away. You start right in your inbox and see all of your mail, with emails you haven’t yet read in bold. Click the one you want to read to open it. That’s all it takes.

Similarly, to create a new email, click the Compose button on the upper left of the screen. (Google is in the midst of rolling out some interface tweaks, so you might see either a pencil icon or a plus sign on this button.) Want to search your mail? Start typing in the “Search all conversations” box, and results appear immediately.

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Gmail’s interface is clean and straightforward, making it easy to use. (Click image to enlarge it.)

But don’t let the simple interface fool you; Gmail packs a lot of power for working with messages. Move your cursor over any message in your inbox, and icons appear to its right for a variety of mail management features, such as archiving the message or marking it as unread.

More options appear when you open a message. At the bottom of the message you’ll see clearly labeled buttons for replying to the sender, replying to all recipients of the message, and forwarding the message, as well as buttons in the upper right of the message area for printing, starring the message as important, and more. Above the subject line is a toolbar of buttons that let you take actions such as archiving the message, reporting it as spam, deleting it, and more.

If you click the three-dot menu button on the far right within the message area, you get even more options, for adding the sender to your contacts list, blocking further messages from the sender, reporting the message as spam or a phishing attempt, and translating the message, among others. (There are several other ways to manage messages from the inbox and message window, which I’ll cover in the Managing Mail section.)

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Gmail has plenty of options for responding to and handling incoming mail. (Click image to enlarge it.)

Gmail has a preview pane like Outlook’s, and you can customize the way it looks, as well as many other things about the entire interface. Click the gear button at the upper-right of your screen to get to the “Quick settings” pane, and you can choose the “Density” of the inbox (how many messages appear in a given amount of space), the “Type” of inbox (such as showing important messages first, unread messages first, starred messages first, and so on), whether and where the reading pane appears, whether to show email threading, and a theme, which has a graphic look.

You can customize even beyond that by selecting the See all settings button near the top of the “Quick settings” pane. Just be forewarned, when you click that button you’re immediately thrown into the Settings weeds and may get lost in all the options.

But really, Gmail’s basic layout just works. This design principle — having a simple, straightforward interface with advanced features easily available on buttons and menus — makes reading and responding to messages a breeze.

Outlook

If you’re looking for a simple, straightforward, easy-to-follow interface for creating and reading email, you won’t find it in Outlook. Its default view in Mail, featuring three panes bristling with buttons and icons, topped by a Ribbon interface of startling complexity, makes it difficult to focus on what exactly you want to do. Microsoft seems to think more is better, but when it comes to email, sometimes more is less.

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Welcome to the confusing world of Outlook, which sometimes seems as if you need a PhD to use it. (Click image to enlarge it.)

It’s not just that the screen is cluttered with so many choices. Even doing something as basic as browsing your inbox can be confusing. A big part of the problem is with the program’s overall design — three panes, with the leftmost one (the folder pane) being divided into sections. Its topmost section is labeled Favorites, and beneath that it lists the email accounts you have set up in Outlook. On the plus side, you can use Outlook to simultaneously read and manage several mail accounts — something you can’t do in Gmail — but it does make the left pane more confusing. Each account has its own set of folders underneath, including Inbox, Sent Items, Deleted Items, and so on.

So what are Favorites, and how do they differ from the email accounts listed underneath them? Items in the Favorites list, which Microsoft calls “folders,” can be anything from individual mail folders to entire email accounts. You can add a folder to Favorites by dragging it there, or by going to the Folder tab on the full Ribbon and choosing Add to Favorites. To remove a folder, right-click it and select Remove from Favorites.

At the very bottom of the left pane are icons for navigating to Outlook’s Calendar, Contacts, and Tasks components. For once, Microsoft has made things simple and straightforward in Outlook — just click one of the icons to go to that component. There’s also a three-dot menu that lets you add icons for Notes, Folders, and Shortcuts.

To see the messages for an individual mail account, navigate to that account in the left pane and click Inbox right underneath it. The list of messages in that account’s inbox opens in the middle pane, showing the sender, subject, and time, and date for each message.

But Microsoft couldn’t resist cramming in more controls at the top of the center pane. There’s a set of tabs marked “Focused” and “Other.” This is a mail management feature called Focused Inbox that I’ll discuss later in the story. For now, suffice it to say that your more important email should appear under the Focused tab; you’ll need to click the Other tab to see mail that Outlook has deemed less important.

And to the right of the Focused and Other tabs is yet another menu for sorting your message list by date, sender, subject, and so on. These are all useful features, but putting them all at the top of the middle pane adds to the overall clutter.

The rightmost pane is the reading pane. When you select a message in the middle pane, its contents appear in the reading pane. The top of the message has buttons for replying to the sender, replying to everyone who has received the mail, and forwarding the mail.

Stretching across the top of the entire Outlook screen is the Ribbon, which in its default state has countless options and features. The Home tab, for example, lets you classify the message as junk, delete it, archive it, create a meeting with its recipients, move it to another folder, categorize it, flag it for follow-up, and much more. You’ll find similar options on the other Ribbon tabs, for sending and receiving, managing folders, and changing the view.

All that said, Microsoft seems to have gotten the message that not everybody wants to see every available option at all times. In 2019 it made a new, simplified version of the Ribbon available to Microsoft 365 and Office 365 subscribers.  

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The simplified Ribbon shows only the most commonly used commands on each tab. (Click image to enlarge it.)

The simplified Ribbon shows just a single row of buttons for the most commonly used commands. There’s a three-dot icon at the right end of the Ribbon; click it to see a drop-down menu that contains all the rest of the commands from that tab on the full Ribbon. It’s just as powerful as the full Ribbon, but it’s not cluttered with a bunch of stuff you rarely use. (You can toggle between the simplified and full Ribbon by clicking the small up or down caret icon at the very right edge of the Ribbon.)

There are other ways to simplify Outlook’s interface as well. In the Layout section on the Ribbon’s View tab, you’ll find options for controlling the folder pane (you can minimize it, customize what appears in it, or turn it off altogether) and the reading pane (you can have it appear to the right of the email listing, below the listing, or not at all).

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Turning on the simplified Ribbon, minimizing the folder pane and turning off the reading pane makes Outlook much simpler to navigate. (Click image to enlarge it.)

The upshot? If you use the default Outlook interface, expect to be bedeviled by complexity. But if you turn on the simplified Ribbon, you’ll find it a much more welcoming and simple email program. Still, that doesn’t make it as simple and straightforward to use as Gmail.

Navigating the interface: Bottom line

Gmail has a much cleaner and less cluttered interface than Outlook’s default interface. Those who prefer simplicity will find it a much better fit.  However, if you turn on Outlook’s simplified Ribbon, you’ll find Outlook far less confusing, even if it’s not quite as straightforward as Gmail.

Writing and responding to email

How easy is it to create and send a basic email message or respond to email? How about if you want to get fancy, by changing fonts and font attributes, attaching files and photos, inserting tables and charts? What if you want to spell-check or grammar-check your mail before sending? You’ll find all that and more in this section.

Gmail

As with just about everything else having to do with Gmail, creating basic messages is simplicity itself: Click the Compose button (with a plus sign or a pencil icon) on the upper left of the screen, and a “New Message” window appears. Choose your recipients, type in the name, subject, and body of the email, include any attachments, and you’re done. No muss, no fuss.

That isn’t to say there aren’t plenty of advanced features for creating mail. You’ve got eleven different fonts and four text sizes to choose from, and you get the usual control over font attributes such as bold, underline, and so on. You can also choose text alignment and indentation, and create bulleted and numbered lists in your mail. You’ll find these options in the toolbar across the bottom of the screen just above the Send button. (Click the underlined A just to the right of the Send button to hide and unhide the formatting toolbar.)

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Gmail’s compose window keeps formatting options handy but unobtrusive.

As for attaching photos, files, and objects, you’ve also got plenty of options, found underneath the formatting toolbar. The options are a bit confusing until you get used to them. For example, there are multiple ways to attach files. Clicking the insert icon (a paper clip) lets you browse your hard disk for files of any type. But there’s a different button for inserting photos (an icon of what appears to be a tiny mountain) that doesn’t bring you to your Photos folder as seems logical, but instead to your Google Photos account, if you have one. And yet another button lets you insert files from your Google Drive.

Other buttons on the same toolbar let you insert an emoji; insert a link to a file online, a web page, or an email address; and insert a signature. Until you get used to what the different buttons do, it’s quite confusing.

That’s too bad, because the insert photo option is a great one. You preview all pictures in a folder so it’s easy to choose the one you want, and you can insert the photos either as attachments or as inline images. If you send it as an inline image, when you click the image in your email, you get a number of options, including having it appear as its original size, the best size fit to the screen, or as a small image.

Aside from all this, there several other nice features. Clicking the three-dot menu icon on the lower right of the screen offers options to spell-check your message, apply a label to it to help organize your mailbox (more on that below), strip all formatting out of your message so it’s just plain text, print, and go to full-screen mode.

In addition, as you type, Gmail suggests words and phrases you might want to use — just hit the Tab key and they get inserted. When this feature, called “Smart Compose,” was first introduced, I found it offputting, because it interrupted my train of thought and was hard to ignore. However, I’ve since gotten used to it and have found it to be a surprisingly useful time-saver.

You get all the same options when you respond to an email. An additional time-saver is that Gmail can examine the content of the message sent to you and suggest text you might want to include in your response. Google calls it “Smart Reply,” and it’s turned on by default.

If you’d like to turn off either Smart Compose or Smart Reply, click the gear icon at the upper right of the Gmail screen and click “See all settings.” Scroll down to the “Smart Compose” section and select Writing suggestions off, or scroll to the “Smart Reply” section and select Smart Reply off.

Also useful is that Gmail lets you “undo” sending a message — in other words, take it back — during the first several seconds after you’ve sent it. After you send a message, a small “Message sent” appears, and next to it is an Undo button. Just click the button to recall the message. After the Undo message disappears, though, you can no longer take the message back.

Despite the confusing insert options, Gmail does a great job overall of blending simple design with powerful features when you create mail.

Outlook

While some parts of Outlook suffer from too many features crammed into too little space, that’s not true when it comes to creating new mail messages. Click the New Email icon on the far left of the Home tab on the Ribbon, and a window pops up where you fill out email addresses, the subject, and the content of the message. If you’re creating a simple message, that’s all it takes. Just click the big Send button and you’re done.

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Creating a new message in Outlook is straightforward. There are also plenty of advanced options available via the Ribbon. (Click image to enlarge it.)

Replying to emails is equally straightforward. When you’re reviewing messages in Outlook’s three-pane view, click a message in the center pane, and it shows up in the reading pane. The top of the message area has buttons for replying to the sender, replying to everyone who has received the mail, and forwarding the mail. Alternatively, you can double-click a message in the center pane to open it in a separate window, where you’ll see the same screen and get the same options as you do when creating a new message.

This being Outlook, those options are plentiful. You can access them via the Ribbon across the top of the composition window — and that’s true whether you’re using the regular Ribbon or the simplified version. We’ve shown the full Ribbon above so the commands are easier to see, but with the simplified Ribbon, any command you don’t see is available under the three-dot icon to the right.

With Outlook, you get more powerful text-handling features than with Gmail — for instance, you can use any of the fonts on your system and change the text to any size, not just a handful of choices for each as in Gmail. Changing text colors, making text bold, centering text on the page, and so on is a breeze as well. Outlook outshines Gmail by a wide margin when it comes to dealing with text.

It does a fine job handling attachments as well. If you use other Office applications such as Word and Excel, when you click the Attach File icon, a list pops up of the most recent files you’ve used on Microsoft’s cloud storage service, OneDrive. Given that you’re likely to send files that you’ve recently worked on to others, this is a big time-saver. You can also select any file on your PC to send by clicking Browse this PC after you click Attach File. To browse through OneDrive on the web, click Browse Web Locations. You can also easily send other items as well, including a business card, calendar item, or any item you’ve created in Outlook, by clicking the Outlook Item button.

All this is just the basics. You’ll find exceptionally powerful mail-creation tools on the Ribbon, and they’re well worth delving into. A few highlights: On the Insert tab, you’ll be able to insert tables, shapes, icons, 3D models, screenshots that you take using Outlook, links, bookmarks, equations, pictures from Bing, and more. The Options tab offers even more control over fonts, colors and effects, including the ability to use themes. You can also request a delivery receipt or read receipt when your message is delivered or read, delay delivering a message for a certain amount of time, and more.

The Format Text tab, unsurprisingly, gives you pretty much complete control over how text and paragraphs are displayed, and lets you create and select various text and paragraph styles you can reuse. The Review tab is where you’ll find options such as spell checking, a thesaurus, text translation, and having the text of your message read aloud to you.

Suffice it to say, if there’s something you want to do when writing and sending an email, you can do it in Outlook. Just check out the Ribbon.

Writing and responding to email: Bottom line

Outlook has far more features for creating and sending email than Gmail, by a wide margin. True, you’ll have to poke around the Ribbon to find them all, and you may never use them. But if you do want advanced options, it’s clearly superior to Gmail. And even if you’re not interested in fancy tools, the basic interface for creating a new mail message is easy and simple enough.

Managing mail

Email overload is one of the biggest productivity-sappers in people’s working lives. We work on multiple projects at once, and each of them deluges us with too many messages. It’s not just the sheer volume that’s problematic, but keeping track of them all. Something as simple as preparing for a meeting by reading all the email related to it in the last two months can take far too long, because the emails can be so hard to find.

To solve the problem, both Outlook and Gmail offer a variety of tools for managing mail. I took a look at how they stack up in this all-important area.

Gmail

Gmail offers a variety of tools for mail management. By default, your incoming messages appear in one long list, with the most recent at the top, and Gmail has separate tabs for social media messages and ad promotions. You can configure those tabs and others by clicking the gear icon in the upper-right corner of the screen and selecting See all settings, then clicking the Inbox tab at the top of the screen and choosing which tabs you want to appear and which tabs you don’t. You can configure your inbox in a variety of other ways from there, including turning the reading pane on and off, having Gmail put a marker next to messages it determines to be important (based on your past behavior and other factors), and more.

Like Outlook, Gmail supports conversation view, which groups emails with the same topic together. Unlike Outlook, however, it doesn’t handle email conversations with multiple threads well. In Gmail there’s no way to see separate threads within a conversation. Every new message is arranged chronologically, so you’ll have to scroll through all the messages and try to make sense of individual threads. In long, complex messages with many threads, this is exceedingly difficult to do.

Gmail’s most important mail management feature is labels. They’re similar to Outlook’s folders; however, as I’ll explain in a bit, labels can do a very useful trick that normal folders can’t.

Labels help you organize your mail by letting you mark messages — including not just received mail but drafts and sent mail as well — with relevant labels. Gmail offers several built-in labels, including Starred, Drafts, and Snoozed, but you can create your own labels as well. So, for example, you could create separate labels for every one of your projects, for future ideas, for budgeting information, and so on. Then you tag messages with the proper labels.

To easily keep track of all messages related to 2022 budget projections, for example, you could create a label called “2022 Budget Projections” and tag all relevant messages with the label, and they would all show up when you click 2022 Budget Projections in the navigation bar. Also useful is that you can nest labels underneath other labels. So, for example, you could create a “Revenue” label underneath the “2022 Budget Projections” label, and then “Ad Revenue” and “Subscription Revenue” labels under the “Revenue” label.

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Creating a new label to manage mail in Gmail.

Labels show up in Gmail’s left-hand pane, arranged in alphabetical order. So it’s easy to see them all at a glance and browse the appropriate one. Just click a label name in the left pane to see only messages tagged with that label. To create a label, go toward the bottom of the labels area in the left-hand pane and click Manage labels (you might have to click More to see this option in the pane). Then click Create new label and type in the label name. If the label will be a nested one, type the parent label’s name in the Nest label under text box. Then click the Create button.

What makes labels especially flexible is you can apply multiple label tags to a single message. So if you have labels for “Year-End Meeting” and “2022 Budget Projections,” you could apply both labels to an email laying out the agenda for the end-of-the-year meeting, if budget projections are on the agenda. Outlook’s Search Folders (more on those in a minute) offer similar flexibility, but using them isn’t as intuitive and effortless as using Gmail’s labels.

Applying labels to messages is simple. When you’re reading a message, click the Labels icon at the top of the message, just to the left of the three-dot menu icon, then select the labels you want or click Create new to create a new label. You can also apply labels to a group of messages by selecting them, clicking the Labels icon, and choosing labels for them. If you’re writing a message, click the three-dot menu icon at the lower right of the screen, click Label, and from the menu that appears, select the labels your want or click Create new.

I do have one nit to pick with the feature. I’m a big fan of keeping a clean inbox — that is, when I handle a piece of mail, I want it out of the inbox and filed away under the appropriate labels. That way, I’m not greeted with thousands of messages every time I look at my inbox. But tagging a message with a label in Gmail doesn’t automatically move it out of your inbox. By default, the message stays in your inbox, with the label(s) showing to the left of the subject in the mail list.

Gmail has a variety of other useful tools for managing mail, none quite as useful as labels. A “nudge” feature is fairly nifty; it surfaces emails you’ve received that you haven’t taken action on and/or messages you’ve sent that haven’t received a reply. If you poke around in Settings, you can find several more mail-management features as well, including the ability to set up filters to take actions on incoming mail, such as automatically applying a label to and archiving messages from a particular sender. (Gmail’s filter options are not, however, as extensive as those available in Outlook’s rules.)

You can do a great deal of mail management right from the inbox. Hover over any message in your message list to see icons that let you take quick actions on it, including archiving it, deleting it, marking it as read or unread, or snoozing it. Archiving a message removes it from the inbox but keeps it accessible via labels and searches, while snoozing sends it away temporarily and has it reappear at a later time of your choosing.

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Here’s how to snooze mail and decide when it should appear again. (Click image to enlarge it.)

You can also star messages that are important to you, so you can see them at a glance. To do it, just click the star to the left of the sender’s name in the message list. Right-clicking a message in the mail list pops up a menu with several more quick actions, including replying to the sender, forwarding the message, moving it to a label, marking it with a label while leaving it in the inbox, and muting it so it won’t show up in your inbox but will still appear when you do a search.

You can use the check-boxes at the far left of the message list to select one or more messages to perform actions on. When you do so, a toolbar appears above the message list with buttons for most of the aforementioned actions, plus a few additional ones like reporting the message(s) as spam and adding it to Google Tasks. (Click the three-dot menu icon on the right to see additional options.) The same toolbar appears at the top of the screen when you open a message.

Finally, if you’re looking for important mail, you can, of course, search using Google’s considerably powerful search tools. You can do a simple search by just typing your search term in the Search mail box at the top of the screen. But you can also use Google’s search language to get more fine-grained. Type: 2021 Budget To: Jim Florence In: Carlisle Has: attachment, and you’ll find a list of every mail in the Carlisle folder sent to Jim Florence with the words “2021 Budget” and with an attachment. There’s a lot more you can do as well, including using dates and so on. Go to Google's “Search operators you can use with Gmail” support page for a full list.

All this means that if you’re looking to manage, organize, and find mail, Gmail does a great job — if you’re willing to use the discipline to apply labels consistently. One important area where it falls short, though, is handling message threads.

Outlook

Outlook offers several tools to help you manage your email. You might have to spend more time than you’d like learning how to use them; however, they add up to considerable help in combating email overload and helping you easily find the messages you want.

The newest feature is called Focused Inbox. When it’s turned on, two tabs appear when you browse an email folder: Focused and Other. Outlook decides what it believes your most important messages are and filters them into the Focused Inbox list. All other messages are, unsurprisingly, put into the Other list.

Those who simply don’t like the idea of Microsoft making those kinds of decisions for them can click the View tab on the Ribbon, then click Show Focused Inbox to toggle the feature off; click it again to toggle it back on. When Focused Inbox is off, you’ll still see two tabs above your email list: one for all messages and one for unread messages only.

In practice, I find that Outlook typically makes intelligent choices about what should be in Focused and what in Other — work mail and personal mail is routed to Focused, while ad come-ons and newsletters are sent to Other. And you can make it more useful by training it — if a message appears in the wrong list, right-click it and choose “Move to Other” or “Move to Focused.” So the feature is a useful one. Microsoft should do a better job, though, of clearly letting people know what Focused Inbox is and how it works, especially since the feature is turned on by default.

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You can train the Focused Inbox by moving important mail into it and moving unimportant mail out of it. (Click image to enlarge it.)

Another tool Outlook offers to help you manage incoming messages is a conversation view with threaded messaging, which groups together the messages and replies within the same email conversation. Frequently, in long email chains with multiple participants, there are multiple threads going on. In a single conversation about a product rollout, for example, there may be one thread about changes that need to be made to a presentation about the product, another about the timing of the rollout, and so on.

Outlook does a better job of handling threaded messaging than Gmail, although not by default. By default you don’t see mail conversations as threads, and so can’t easily navigate them. However, you can turn threaded messaging on by going to the View tab and checking Show as Conversations in the Messages section. Any message with at least one response will have a right-pointing triangle to the left of the sender’s name, showing that there are multiple threads. Click the triangle, and all the threads appear. Click any thread and you’ll be able to navigate straight to it and read only relevant messages. It’s a tremendous time-saver when you’re stuck in an endless, complicated email chain.

Two other useful conversation-handling features are found in the Home tab’s Delete group. If you select a message in a conversation you’re not interested in, you can click the Ignore button, and Outlook will automatically move the current message and future messages in the email conversation to the Deleted Items folder.

Even more powerful is the Clean Up feature, which you can use to simplify mail threads and make them easier to follow. Perhaps the most annoying thing about long mail threads is how many times the original message and earlier responses are repeated because they’re quoted and requoted in people’s responses. That makes it much more difficult to follow long threads, because you have to scroll through multiple repeated messages. When you use Clean Up, it checks the thread, and if it finds the same message repeated multiple times, it deletes all copies of the repeated message except for the most recent one. I find this to be a big time-saver and annoyance-buster.

You can use the feature to clean up an individual conversation, all the conversations in a folder, or the conversations in a folder and all its subfolders. When you’re reading the conversation you want cleaned up, go to the Home tab, click the down arrow next to Clean Up, and select either Clean Up Conversation, Clean Up Folder, or Clean Up Folder & Subfolders.

Speaking of folders and subfolders, it’s easy to create them and move messages into and out of them in Outlook as a way to organize and keep track of messages. The biggest limitation of folders is that you can place a message in only one folder at a time, even though it might be related to multiple folders. However, you can use a feature called Search Folders to create virtual folders that group messages by various criteria. For example, you could create a search folder for messages from certain senders, those that are flagged for follow-up, or those that include certain words. This lets you have the same message in multiple folders. To create a Search Folder, go to the Folder tab, select New Search Folder, and select your criteria.

There’s one final feature that is somewhat hidden that can be extremely powerful for automated mail management — creating and using rules. Rules take actions on messages depending on their context — the sender, words in the email’s text, and so on. So, for example, you can automatically route all incoming email from your boss into the Boss folder, or route all mail containing the words “2021 budget” into the 2021 folder.

To create a rule, click the File tab, and on the Info screen, click the Manage Rules & Alerts tile. Under the E-mail Rules tab on the screen that appears, click New Rule. The Rules Wizard appears, listing all the rule actions available to you, such as “Move messages with specific words in the subject to a folder” or “Flag messages from someone for follow-up.” Click the one you want, and continue through the wizard’s steps to create the rule. That’s all it takes.

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You can easily create rules to automate mail handling in Outlook, using its Rules Wizard. (Click image to enlarge it.)

You can apply email rules not just to incoming mail, but also to messages you received before you created the rule. To do it, go to the folder where you want the rules to take action, select the Folder tab and click the Run Rules Now button. (See our story “Mastering your Outlook inbox” for in-depth instructions on using rules.)

There are a variety of other management tools scattered throughout Outlook, such as using colors to categorize mail. But none of them are particularly powerful.

However, Outlook does offer powerful tools for searching through mail. When browsing through your inbox or a folder, use the search box at the screen. By default, Outlook searches the current folder, but you can use the drop-down menu to the left to search its subfolders, the entire current mailbox, all mailboxes, or even all Outlook items. And you can get more granular: When you place your cursor in the search box, a Search tab appears on the Ribbon; it offers multiple ways to search, including by sender, subject, whether it has attachments, and much more.

As you can see, Outlook includes extremely powerful email management and search features. But they’re disconnected from one another and tend to be difficult to use or to remember how to use. So you’ll have to be a dedicated Outlook power user to get the most out of them.

Managing mail: Bottom line

Gmail does a better job than Outlook of combining simplicity with sophistication when it comes to managing and searching through mail. Many of the tools are available right from the main interface, with a few powerful options tucked away under Settings. However, if you want access to advanced tools like message threading or creating sophisticated rules for automated mail handling, Outlook is the way to go. And, of course, you can always use the simplified Ribbon to clean up Outlook’s interface.

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