27 Tips for Complete Email Mastery

Cody Cardarelli

Email. We all have it. We all hate it. From Outlook to Gmail to the Great Email Beyond, here’s how to make the most of it.

They say that the kids don’t use email that much these days. Doesn’t that sound dreamy? We adults, unfortunately, have no such luxury. For better or for worse, email is a major part of our personal and work lives.

We’re tempted to just leave it at that. But there’s no need to feel hopeless. We took a good, long look at the center of our communication universe with an eye toward improving, upgrading, and (hopefully) dominating it. The fruits of our labor are in the following pages. Enjoy! (Or maybe we should say, suffer less?)

Getting Intimate with Outlook

The road to email mastery begins with Microsoft’s ubiquitous email application

Using Outlook is one thing. Exploiting it to its fullest potential is another. Over the next two pages, we'll give you a few ways you can do just that, and then show you five other ways you can exist without Microsoft's seemingly ubiquitous personal information manager.

Photo ID

Photo ID: Microsoft now has its own built-in social connections.

The Microsoft Outlook Social Connector Provider for Facebook, new on the scene but compatible with Outlook 2010, 2007, and 2003, links your Facebook or LinkedIn account to Outlook and helps you keep on top of information you can use to blackmail… er, get familiar with your contacts. Plus, having pics of your peeps helps safeguard against wrongly addressed emails.

Fast-Action Screenshots

In Outlook 2010, you can insert a screenshot in the body of your email message. Click the Insert tab of the message you've created and select Screenshot. A drop-down menu appears, from which you can instantly select the current image in any nonminimized window. Even cooler, if you scroll down to the bottom of that menu and click Screen Clipping, you get a chance to crop and select just a portion of that image.

Get Your Xobni On

Xobni offers faster Outlook searches and connects to social media.

Xobni ("inbox" spelled backward) is an Outlook add-on that appears within the program as a separate pane and does a bunch of cool stuff that Outlook junkies will eat up. Xobni searches your emails faster than Outlook itself, extracts oodles of information, and features a deep connection with social networking sites. Outlook 2010 now handles the social networking angle itself, yet Xobni continues to maintain its rabid fan base. Check out www.xobni.com for more info.

Take Command of Replies

It sucks when you want each of your recipients to Reply to All, and one of them neglects to do so. But now you can ensure that the offending party gets with the program. In the message composition screen, click Options/More Options and look for Delivery Options in the drop-down list. Click Select Names and enter those you want to receive all future replies.

Harness Quick Steps

New to Outlook, Quick Steps are a series of macros that conveniently merge several separate actions—as many as 10, actually—into a single button click. And while Outlook's predefined Quick Steps are just peachy, customizing the macros is peachier still. To set up your own Quick Step, click Create New in the Quick Steps group (found within the Home tab), and fill in the blanks.

Seek and You Shall Find

Outlook 2010 offers more search parameters than a Dalmatian has spots. But it also allows you to save your results in fully customizable Search Folders. In the future, you merely access that folder when you need quick access to the results of those keywords and/or criteria. To create a Search Folder, click New Search Folder in the New group of the Folders tab and select from the available options. Or create your own parameters.

Message Recall Isn't All It's Cracked Up to Be

You know that intimate message you sent to your ex-girlfriend but tragically misaddressed to your new girlfriend? Well… Outlook now has a Recall feature (accessed via Move/Message/Actions) that should, one would think, save your sorry backside. Except it probably won't. You see, Recall will work its magic only if both email accounts are configured using Microsoft's Exchange and only if the message shows as unread and unforwarded. Moral: Do not misaddress.

Sync Your Team

Avail yourself simultaneously of the calendars of all your team members by creating a Calendar Group. Start by clicking Calendar just like you've always done, then look for the Manage Calendars group. Then click Calendar Groups and New Calendar Group. Choose a name for your group, then add your contacts.

Clean Up Your Act

Clean up your act by using Outlook's Conversation view.

Ever notice that 'round about the third or fourth message in a thread (aka “Conversation”), each succeeding message just gets longer and more cumbersome? Now you can do something about it. First, switch to Conversation view by clicking the View tab and checkmarking Show As Conversations. To clean up a conversation, go to the Delete group in the Home tab, click Clean Up and then Clean Up Conversation. Voilà, Outlook will take care of the redundancy.

Get out of the Import/Export Business

It is not unusual to successfully import and/or export PST files (the critical Outlook file that contains all your irreplaceable personal data) to and from Outlook. Unfortunately, doing so will not only eradicate certain custom elements, but may also set you up for a file
corruption or a ghost PST that won't close. We know, it's happened to us.

Our advice? Forget about importing and exporting altogether. Instead, close Outlook, find your PST file, and simply copy it to your backup device. To restore your PST file—say, after you've accidentally beaten your PC with a baseball bat—merely find that copied PST, recopy it where it won't cause a conflict, then open Outlook and instruct it to access that file (File/Open/Open Outlook Data File).

Our Top Five Outlook Alternatives

In the corporate world—and especially in those environments built on Windows—Microsoft's Outlook email client reigns supreme. But once you start poking around, you'll find that Outlook is far from the only game in town. Here, we present five of the most interesting alternatives for home and small business users.

Zimbra Desktop

Zimbra Desktop is open-source software and thus free. That it allows you to access email even when you're disconnected from the Internet and handles calendars, contact lists, and documents in a single application is even more reason to consider it. www.zimbra.com

Gmail

Is Outlook's entrenchment the primary reason it still dominates market share? Would web-based Gmail otherwise lead the pack? Truth is that the two offer very different approaches. In an environment where offline Inbox access and Microsoft Office merging capabilities are mandatory, Outlook is king. But Gmail delivers far more mobility, costs nothing, and is seemingly becoming the future right before our eyes. mail.google.com

Thunderbird

Fast, very fast, and in a strictly email sense, the equal of Outlook (and perhaps more intuitive to use with its tab-browsing style), Mozilla's long-established Thunderbird runs in any operating system and, like Zimbra, is free. It's also incredibly simple to set up, although add-ons are required to match Outlook's scope. www.mozillamessaging.com

Windows Live Mail

Effectively the successor to Outlook Express and Windows Mail—and better than both—Microsoft's Windows Live Mail is a good option for those who run in a Windows environment and don't need the added business-oriented features (and complexity) of Outlook. explore.live.com

eM Client 3

Purported to be the fastest email client for Windows, eM Client 3 boasts customers such as Toyota and Oracle. Available in either a no-charge Home or $50 Pro version (which includes backup and syncing to any mobile device). www.emclient.com

10 Ways to Fix Microsoft Outlook

The Maximum PC offices have been an Outlook shop for a long, long time. We started applying our brains to the matter of improving Outlook before realizing that your ideas are just as good as ours. We asked you to let the ideas (and gripes) fly, and these are the results. If you want to join the daily conversation about tech, point your browser to www.facebook.com/maximumpc .

Christopher Alden: I'd love to have a Gmail-style conversation view.

Robert J. Armitage: Better support for showing "new mail" in subscribed folders and sub-folders. For me only the inbox updates properly; I have to manually click others for the new message count to pop up.

Mike Tjepkema: Integration of "signature grabbing," where you can double-click someone's signature and dump it into your contacts. It's available in third-party software, but I want seamless integration.

Jp Allen: Fix Outlook Web Access for non-IE browsers. Better shared calendar/contacts. Threaded conversation view that doesn't suck so bad it gets turned off. Search that isn't beaten by third parties like the Globetrotters do to the Generals. More granular junk/spam filtering options. A far less bloated archiving option/format.

James Burt: The ribbon interface, may it go back to the hell-spawned pit from whence it came. Its inconsistent layout, big buttons, small buttons, icons with no name, etc., are frustrating. Add in the fact that I find myself clicking more to perform tasks that were one or two clicks in the past is irritating.

Cory Notrica: Add something like the Lotus Notes Swiftfile. It would be so much easier than building rules and clicking twice to file to recently used folders.

Ryan Case: My #1 most desired feature in Outlook 2003 and Outlook 2007 is smooth scrolling.

Suffer Spam No More

Use these antispam tips for junk mail protection worthy of a… Nigerian prince

Dear friend! I am the son of the late Nigeria's former minister of mines and power in the regime of the late former Nigeria's military Head of State. I have discussed with my family attorney how best to provide for you the information on blocking email spam. To unlock these mysteries, you need only supply $2,500 of your United States dollars. To show you my sincere interest in giving you these antispam treasures, I give you immediately a sampling of suggestions for reducing the amount of spam your inbox suffers.

Use a Complex Email Address

While using yourname@yahoo.com might make it easy for your friends and loved ones to find you online, it also makes it easy for spambots to track you down and pummel you with junk mail. To throw them off your email trail, consider using an address that includes punctuation or numerical values as well.

Check Those Checkboxes

When signing up for a new service, often times, you’ll be given the option of opting in or out of mailing lists and additional services. Before finishing your registration, be sure that you’re not accidentally signing up for something you’re not interested in by leaving checkboxes in their native state. Take the time to do it right.

Use Disposable Email Addresses

If you need to register for something online, consider doing it with a disposable email address, like those available from services like Ten Minute Email ( 10minutemail.com ) or GuerillaMail ( www.guerillamail.com ). Doing so will guarantee that your inbox stays spam-free.

Maintain Two Email Accounts

If you prefer to keep a record of what you’ve signed up for and when, a disposable email address just isn’t going to cut it. Instead, consider using a secondary email address solely for the purpose of signing up for online services, such as web communities, Internet shopping sites, and newsletters. The bulk of the spam your online activity generates will be sent to the secondary email address, leaving your primary account relatively spam-free.

Choose ISPs According to Their Spam Policy

Your Internet service provider should be at the heart of your antispam solution, not at the heart of the problem. When selecting an ISP, research its antispam policy: Does it penalize customers who engage in spamming? Does it host spamvertisment sites? How closely does it guard customer information? These are all questions that your ISP’s customer service representatives should be able to answer. If you don’t like what you hear, take your business elsewhere.

Unsubscribe Is Not Your Friend

Taking the time to unsubscribe from a service you never signed up for in the first place is a sure-fire way of letting spammers know that their aggravating messages are indeed being read by someone. Don’t encourage them. Instead, delete the email or…

Use Antispam Software

There are a lot of excellent antispam software packages, extensions, and services out there. Choose one and run with it. Installing antispam software like SpamFighter (free, www.spamfighter.com ) can dramatically cut down the amount of spam your inbox sees on a daily basis. For the holy grail of Internet privacy, you may also want to consider investing in a computer security suite, such as our favorite, Bit Defender Internet Security 2011 ($50, www.bitdefender.com ). Along with antispam protection, you’ll also get antivirus and antimalware protection, plus a large number of other perks.

Gmail, Pro Style

Trick out your Gmail experience with these 10 pro-level hacks

Whether you’re new to using Gmail or a seasoned veteran, we’re positive that you’ll find at least one of our awesome Gmail tips to be, well, awesome.

Create Custom Labels

Creating custom labels to organize your Gmail inbox is easy. From the mail menu on the left side of your browser window, click the More link, and then Create New Label. Enter a name for your new label in the field provided. You can repeat this process to create as many labels as you need.

Use Filters to Organize Your Inbox

OK, it’s time to put those labels to use. Click any message in your inbox. Locate and click the More Actions button at the top of the message window. Now pick Filter Messages Like These. You can now create a filter that will automatically sort and label your incoming email.

Bookmark Messages for Quick Reference

Find yourself referring to the same email message time and time again? Instead of hunting it down every time you need to take a peek, consider bookmarking the message instead. This trick works in any browser and can significantly increase your productivity if having frequent access to a particular email is mission critical.

Become a Gmail Search Ninja

Gmail’s advanced search functionality is a finding-stuff juggernaut. To enable these features, look next to Gmail’s search bar and click Show Search Options. You now have access to a number of search parameters that’ll make finding a message feel less like rooting through a haystack for a needle. Locating the message you’re looking for becomes even easier using this method if you’ve taken the time to create customized categories, filters, and aliases for your account. If this turns out to be more search functionality than you can handle, click Hide Search Options to revert to Gmail’s vanilla search bar.

One Address, Many Faces

You can use multiple Gmail address aliases to handle incoming mail. Just add a plus sign and a word to your Gmail address—yourname+news@gmail.com, for example—when subscribing to new services. All email sent to the alias will be sent to your inbox where it can be filtered.

Use Gmail Offline

Using online webmail while off-line? Insanity! True, but it can be done. Just install Google Gears and restart your browser. Open Gmail, and select Settings, then choose Offline. From here, you can enable offline Gmail access for use on your computer. Now that’s sweet.

Enable Free and Easy Gmail Backups

Gmail’s great—until it isn’t. When the service crashes, it crashes hard. To avoid losing any valuable messages, consider forwarding a copy of every message you send or receive to a secondary email account. To set this up, click Settings and then choose Forwarding and POP/IMAP. Boom! Instant backups.

Watch for Stalkers

To access a list of recent activity in Gmail, select Details in Last Account Activity.

To keep tabs on when and from where your account has recently been accessed, scroll to the bottom of any Gmail screen and from the “Last account activity” line, select Details. Doing so will grant you access to a list of locations, login times, and IP addresses that coincide with your Gmail account’s most recent activity.

See Who’s Sending What

Unsure about the origins of a message sent to you? Click the arrow next to that message’s Reply button and select Show Original. Doing this forces Gmail to show you the message’s pathing information. Copy the information to your clipboard and then enter the information in a service like MX Tool Box , which will look up the origin of the message.

Send Executable Files as an Attachment

For security reasons, Gmail won’t let you send an executable file as an attachment. You can get around this by manually changing the file’s extension before attaching it to your email. Provide the message’s recipient with instructions for changing the file extension back to its original .exe and Bob’s your uncle.

Set Up a Hosted Email Domain with Google Apps

A personal hosted email domain for the low, low cost of free? Yes, Please

Do you have your own domain and/or website? Thinking about setting up personalized email addresses to go along with them? Well, you can pay your ISP for the privilege, or you can quickly set up a free Google Apps account that’ll provide you with a Gmail account branded with your website’s domain, as well as a number of other Google goodies.

Here’s How It Works

To set up your account, navigate to the service’s home page at bit.ly/cEETyJ . Enter your site’s domain name. You’ll be asked to submit some personal information. You’ll also have to choose a user name for your administrator account (yourname@yourdomain.com, for example) and a password.

Now, scroll to the bottom of the screen and accept the service’s Terms of Agreement. Before Google will allow you to marry your domain name to your Google Apps account, you’ll have to verify that you actually own the target domain. If you agreed to the Terms of Agreement, there’ll be a confirmation email waiting in your inbox. The email contains a link that will allow you to continue the setup process. Find it and click it. Doing so will open your default web browser, where you’ll be asked to enter the user name and password you selected earlier in the setup process.

Once Google accepts your credentials, a Google Apps welcome page will open. Click the Activate Google Apps button. This opens a new page with two tabs: Recommended Method and Alternate Method. We advise using the recommended verification method: adding a DNS record to your domain’s configuration.

Adding a DNS record to your domain is an easy way to verify your site with Google Apps.

You’ll note a drop-down menu sporting the names of a number of popular ISPs. If your ISP is on the list, select it and follow the instructions provided. If your ISP is not listed, select Other and follow Google’s instructions. You can also verify the ownership of your domain by linking your Google Apps account to an existing Google Analytics account, adding a meta tag to your site’s homepage, or uploading an HTML file to your server. You’ll find those options under the Alternate Methods tab.

After following through on any of these methods, click the Verify button. Within 48 hours your new personalized Gmail address will be ready for action.

Six Great Alternatives to Gmail

Maybe you’re a unique and special snowflake that can’t bear to use the same email service as everyone else. Or perhaps you just feel like rebelling against something—anything. No matter the reason, you yearn to leave Gmail behind in search of a new webmail service. We’re OK with that, and we’re not going to try to talk you out of it. In fact, here’s a list of six alternatives to get you started. Just remember to write us once in a while so that we know you’re all right, OK?

GMX

If you’re looking to break free of Gmail, GMX is a great place to start. Offering users 5GB of email storage accessible via POP or IMAP and the ability to send attached files up to 50MB in size, GMX can hold its own in a blow-for-blow fight with Google’s email service. www.gmx.com

Hushmail

The folks at Hushmail pride themselves on providing a high-security webmail service to their personal and business clients. With the Hush Encryption Engine protecting your webmail’s privacy, you can be certain that your digital information is in good hands. www.hushmail.com

Inbox.com

Much like Google, Inbox.com is a veritable department store of online awesomeness. Aside from offering users 5GB of free email storage, the service also provides file storage, photo sharing capabilities, a virtual message board, and computer-side email notification and download clients. It’s hard to argue with that kind of value. www.inbox.com

Windows Live Hotmail

More than 360 million users can’t be wrong. Thanks to a number of recently introduced new features, one of the most popular webmail services in the world is now also one of the most versatile. Offering calendar, instant messaging, and online storage solutions, Microsoft has done Hotmail some serious justice in recent years. www.hotmail.com

Lavabit

Sick of spam? So’s Lavabit, and it’s got an email account with your name on it. By providing clients with an impressive mixed bag of antispam technologies, Lavbit makes for a sane email experience that’s mostly Viagra- and Nigerian prince–free. www.lavabit.com

Zoho

If you rely on your webmail for your business, you’re going to love Zoho. Offering a feature set similar to that enjoyed by Google Apps users, Zoho will brand your webmail with your company’s domain name, letting you send out emails in style. www.zoho.com

How to Have an Empty, Clutter-Free Inbox

Welcome to Inbox Zero, an email management philosophy that could change your digital life

A 2010 report by the Radicati Group estimated that roughly 90 trillion emails are sent per year. If you’re like us, you know that it can feel as though every single one of those messages somehow makes its way into your inbox in a bid to ruin your day or week before it has even started. (For many of us, this phenomenon is called Monday.)

Just looking at this cleared-out inbox makes us feel less stressed out.

Some of us manage the flow in a standard linear fashion. Others have developed complex, byzantine systems of folders, archives, and filters. Neither is right or wrong, but lately we’ve begun to wonder if we could do things better. Enter Merlin Mann’s Inbox Zero philosophy, which purports to help clear the clutter and cut your overwhelming inbox down to a manageable size. We’ll explain what Inbox Zero is, how it works, and why you might want to use it. Or not.

Origin Story

The underpinnings of Inbox Zero were culled from a series of articles that first appeared on Merlin Mann’s 43 Folders blog ( www.43folders.com ), as well as from the task-management Tao of David Allen’s Getting Things Done site ( www.davidco.com ).

Why the name? Because if you’re doing it right, every time you open your mail client or browse to your webmail, all new email must be categorized and dealt with, deleted or archived, immediately, leaving you with no messages in your inbox. For those of us who are greeted by thousands of old messages each time we check our email, this is a pretty extreme idea. Inbox Zero operates under the premise that everything in life, email included, can be categorized, and that the number of categories should be as few as possible.

The Five Categories

To get Inbox Zero neophytes started, Mann suggests five categories that email should fall under:

Delete or Archive

Email that has been read, resolved, or has no sway on your life should be immediately deleted or archived.

Delegate

If an email needs to be forwarded to another person in order to complete a task, forward it. That said, be sure to follow up and make sure the task is being attended to.

Respond

Not all email demands a response. Some can simply be acted upon. Entering a meeting into your calendar is a good example of this. In the event that you do need to send a reply to someone’s message, keep it short and to the point. Mann suggests that no email should be longer than five lines in length. While some of your coworkers, friends, or family might think you’re being snippy with them, you can deal with this by leaving an explanation for your brevity in an email signature.

Defer

If you don’t have enough information to take action on an email, or your response to a message is dependent on the work of others, come back to it later. The Inbox Zero philosophy demands that after you’ve read a message it be moved out of your inbox in one way or another, so set up a folder for deferred action. And don’t let this get out of control.

Do

If you can take care of a task sent to you via email, do so immediately and get it out of the way. Once the task is completed—you guessed it—delete it from your inbox. Or archive it.

That’s the bare minimum the Inbox Zero system requires. Depending on your job or lifestyle, you may need to throw a few additional categories or folders into the mix. Mann advises that should this be the case, it’s best to keep things as simple as possible. For example, if you feel the need to archive a message, maintain a single archive folder. Complex subcategory-driven filing systems only serve to stymie the email simplicity that this is supposed to achieve. As you receive new mail, each message should be addressed and dealt with immediately by mercilessly jamming it into one of the five Inbox Zero categories and perhaps a few user-created ones.

It’s easy to see how this could be an effective weapon in the war against inbox bloat and counterproductivity. By following the rules, users are empowered with the ability to whittle the contents of their inbox down to nil in no time at all. For anyone who receives a mountain of messages on a daily basis, this is a great way to increase your overall productivity, as less time spent on dealing with email means more time that you can spend on higher-priority tasks.

Drawbacks

The Inbox Zero philosophy may not be everyone’s cup of tea. For starters, if you don’t receive large amounts of email on a regular basis, there’s little productivity to be gained in clearing out your inbox on a regular basis, as your volume of mail is already manageable. If this is the case, we will gladly trade places with you.

The cluttered, nested-folder hierarchy directly contradicts the principles of Inbox Zero.

Some detractors argue that taking pause to wipe out the contents of your inbox on a regular basis is a waste of time, with far too many productive minutes lost to the sorting of emails for the sake of categorization. Others, especially those who manage multiple projects or have a number of clients they work for, find that deleting or archiving their messages can cause more harm than good when it comes time to track assignments or create an invoice at the end of the month. Laziness and time are also factors to consider here. No matter how many folders or rules you create to manage your chronically bulging inbox, if you don’t have enough drive or hours in the day to enact your organizational scheme, your efforts (or lack thereof) will turn into one big bag of organizational failure.

In the end, the best inbox management system—Inbox Zero or otherwise—is the one that works for you.

The 8 Worst Email Blunders of All Time

8) Birthday Bitch

London bank employee Lucy Gao was turning 21. A keystone moment in anyone's life, but for Lucy, it was also a reason to demand, in email, that every guest at her birthday celebration treat her like the royalty she wasn't. "I will be accepting cards and small gifts between 9 p.m. and 11 p.m.," was but one of Lucy's many diva-like pronouncements. Soon, several billion people were privy to all of them.

7) Out Damn Spot!

Secretary Jenny Amner accidentally spilled ketchup on her boss's pants while they lunched together at a local eatery. The next day, Jenny got an email suggesting she cover cleaning costs. She agreed, again via email, but only after citing the very real fact that her mother had died that same day, then chiding the exec for being such an uncaring tightwad, then telling everybody about it. Jenny's boss resigned soon thereafter.

6) Mmm… Spam

Irish Green Party member Eamon Ryan got serious in 2008, successfully pushing important antispamming legislation through that country's parliament. So how did the Greens commemorate such an accomplishment? By inviting, via email, in spamlike fashion, regional technology bloggers to participate in a "viral video" contest. Sure, we've heard of far worse spam, just not worse-timed spam.

5) Cruel Fool

April 1, 2011: The University of California, San Diego, alerted all 47,000 people who'd applied to the institution that they'd been granted admission—a massive miscalculation of approximately 30,000 potential students. Needless to say, it took days to undo the damage.

4) Poetic Injustice

Britain's Joseph Dobbie met what he felt was the woman of his dreams and soon thereafter adorned her inbox with a highly sensitive and very lengthy expression of his feelings. But Dobbie's would-be princess declined, laughingly forwarding his prose to her sisters, who then reforwarded it to the world. Apparently unfazed, Dobbie has since insisted he's received more overtures than mockery.

3) All Wet

When your country is in the grips of a killer flood, you gotta have a little sympathy, right? Wrong, at least in the case of a certain unnamed employee of Australia's Queensland Health. Seems the insensitive boob emailed a mass memo demanding that absentee staff furnish photo proof they were indeed flood victims.

2) Careless Whispers

Adultery, spanking, force-feeding, tickle torture. An episode of Criminal Minds? Well, maybe, but in this instance we're talking about staid old Cornell University. Two Cornell employees, John and Lisa, somehow misdirected their pseudo-BDSM perv-ersation to the entire campus.

1) Wang Chung

Peter Chung, filthy-rich investment banker by day, nonstop stud machine at night. At least that's what Chung led his compatriots to believe in what surely must be considered one of the most pompous emails ever devised. Begging for an additional army of condoms was just the start; Chung bragged openly about virtually every facet of his life. But his bosses weren't nearly so amused. When they somehow received wayward copies of the grandstanding, Chung was canned.

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