Email didn’t become a regular part of my life until well into adulthood, and I rapidly learned there were no hard-and-fast rules governing the rapidly evolving email frontier. I had to learn with the rest of the world as the rules evolved that “all caps” was the equivalent of shouting, and that it was rude to forward everything you thought was funny to your entire address book.

As email became a more integral part of my business life, the questions about what was the correct way to use it became more complex. And yet I had no Emily Post to turn to for guidance on the correct etiquette in this new form of correspondence. Or at least I didn’t, until I found “SEND: The Essential Guide to Email for Office and Home” by David Shipley and Will Schwalbe.

The authors of “SEND” aren’t etiquette mavens laying down arbitrary rules. Instead, what they’ve created — after years of heavy professional email usage — is actually a guide to improving the quality of communications via email. In 2007, when the book was originally authored, Shipley was the Op-Ed Page Editor at the New York Times, and Schwalbe was Senior VP at Hyperion Books. (A revised version was published in September 2008.)

“SEND” is an easy read, and makes an easy reference volume as well because of its organization. It is an essentially practical book, with advice that is easily applicable to the real world and illustrated by real world examples (with names changed to protect the innocent).

The first big question that the book discusses is deciding when we should even send an email in the first place. Many web workers tend to default to email communication for various reasons. “SEND” brings up alternatives such as fax, letter and phone, and suggests how to evaluate when they might be more appropriate.

After you’ve decided you actually should use email for your communication, “SEND” will walk you through how to best handle all the various elements of an email. In email we deal with questions of etiquette and with options that aren’t available or considered on paper. Who should we “cc:” and “bcc:?” Should we attach a file, and in what format? What should the subject line say? Should we use a read receipt? The book addresses all these questions, and more, by teaching us how to make these decisions for ourselves instead of just laying down absolute rules, because in email communication there are no absolute rules.

Besides the nuts and bolts elements of an email there is the content at the heart of it: the body. “SEND” defines six different types of emails (“The Ask,” “The Answer,” “The Facts,” “Gratitude,” “Groveling” and “Social Glue”) and discusses the particular concerns to think about when sending each one. There are also entire chapters devoted to two particularly problematic types of emails: emotional emails, and emails that could land you in jail. The latter chapter actually deals with all sorts of potential legal ramifications of emails, and gives basic advice on how to avoid them.

If you live (and work) by your inbox, “SEND” is a must-read for improving the quality of your email communication and avoiding costly missteps.

Has an email miscommunication ever caused you a business problem?

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Brazilian Jiu Jitsu

The beauty of Brazilian Jiu Jitsu (BJJ) comes from combining three core principles: patience, control and efficiency. These principles can be applied to your email management practices.

BJJ Fundamentals

To be successful in BJJ, the fighter must always keep two solid points on the ground at all times, and then have one free point in order to manage his opponent — thus becoming a stable triangle. (In geometry, the most stable shape is a triangle.) The two grounded points are what set the basis for controlling any movement your opponent can throw at you. Think of any incoming movement from your opponent as energy. You can manage the incoming force in one of three ways: you can stop the motion, you can deflect the motion, or you can move with the motion.

Now, let’s take these fundamentals and extrapolate them to email management!

Stopping Your Opponent

You basically have three kinds of emails. Junk mail that needs to be tossed, read emails that need filling, and unread emails that require some sort of action. These are your opponents.

Now don’t panic, remember your mantra: patience, control and efficiency. Start by getting rid of all the emails that have absolutely no value to you. Toss them. Remember our BJJ principle of efficiency: Get to the source of the zero-value emails. Be it Facebook updates or useless forwards from family and friends, stop them dead in their tracks. If you can’t turn them off at their source, make use of filters to route those emails directly to the trash. By making them bypass the inbox, you are practicing the art of stopping your opponent.

Deflecting Your Opponent

Now that we have the easy stuff out of the way, let’s start cleaning house with some organization of our read emails. I use Gmail, so I’m going to describe my labeling method, which uses Gmail’s labels, but you could use folders in any other client.

The great thing about Gmail is that there is no limit to the number of labels you can apply to any one message. That said, you will discover (as I did) that having too many labels just makes you a labeling junkie. Make use of your patience with this process because your labeling system will probably need to change over time. Remember that efficiency is the ultimate goal, so make use of global labels. What I mean by that is having a set of labels that can be used across multiple emails, regardless of who or what they are associated with — don’t make them too specific. For example, I use a “Peeps deets” label for any email I am sent containing a person’s contact information. (Don’t be afraid to use your own odd lingo for labels. After all, it’s your system.) Now start smacking those labels on your read emails and archiving them! Start with the easy stuff like friends and family, for example. With a system for organization in place and read emails archived, you are practicing the art of deflecting your opponent.

Moving With Your Opponent

Now we have the base of our triangle set: Our inbox is under control. We just need to deal with those unread emails that require some sort of action on your part (those in your inbox now and those still to arrive). Let’s get hands-on and start moving with our opponent.

You need to create a standard for how you handle each email that requires action. A good rule of thumb is if any action required of you can be done in less than two minutes, just go ahead and do it. That one simple rule will keep you from getting bogged down with a lot of emails clogging up your inbox that kill your flow. That said, don’t send off quick, knee-jerk responses to those 2-minute or less emails. To get the most of the momentum you are generating with your productivity, you will need to give every email your full attention. Be sure to respond completely and concisely, so that the most important information can easily be digested.

OK, so how about emails that are going to take longer than two minutes to deal with — the multi-action emails? First thing’s first: Open the email and identify the actions that are being requested of you. Next, create a label for the project and apply it to the email. This is the same label you will apply to any other emails that will be associated with the project. Now, identify your first most doable action to get the momentum going on the project. Does the action fit the 2-minute rule? If yes, do it, and get the ball rolling. If not, ask yourself two questions. First, am I the best person to be doing this? If not, send off an email to the person best fit for the action item and apply a global label of “Waiting On” to the project email to remind yourself that a response is necessary to keep the project going. Second, can this wait till later? You must decide when is the best time to handle the action item. If you need to handle the action now, apply the gloabl label “Action” to the email so you have a visual reminder that you are doing something with that email. If you can defer it until later because it is not a priority, apply the global label of “Review” to remind yourself that you will need to deal with it later.

That’s it! Now start the process over again, each time juggling only as much as you can handle. Keep up on your emails labeled with “Action,” follow up on your emails labeled with “Waiting On,” and keep an eye on those marked “Review.”

Your inbox should now be empty. As the emails start to pour back in, it is easy to see where you left off on a project, thanks to the labels, and you can easily get going on the next step of the project. You have truly mastered your opponent.

Oscar Avellaneda is a photographer and year-round cyclist living in Alaska.

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A friend of mine who is new to teleworking was complaining that her overseas prospects wanted to speak with her on the phone. Since she didn’t want to have to pay for international calls, she turned down these lucrative offers. “I don’t want my fees to be consumed by phone bills,” she said.

“You don’t need to use the phone, you can always use voice chat or VoIP,” I suggested.

“What’s that?”

It seems that not everyone who sets out to do web work knows how to establish their communication methods. There are many tools that allow us to sidestep more traditional — and usually more expensive — means of communicating with our clients, such as client visits and phone calls. For those who are just starting out, here are your options:

Email

Sometimes I still see online contractors with casual email addresses like “sexychick2009@example.com.” While you can use any email address to communicate with friends and family, stick to something more formal for professional use. If you don’t want to go through the trouble of checking multiple inboxes and notifying personal contacts about your new email address, you can easily use multiple email accounts instead, and access all of them via one master inbox.

To avoid having your email addresses plastered all over the Internet (and attracting spam), set up a contact form on your web site. In my experience, potential clients often prefer a contact form they can fill out on your site, since they don’t have to open their email client to send you a message.

Instant Messaging

Instant messaging (IM) is real-time text chatting over the web. IM is useful for real-time client support and quick exchanges that are too short for email.

Some people have trouble expressing themselves via instant messaging, so don’t make this your only option for client support. Also, if you have clients that aren’t tech savvy, they rarely want to communicate this way. Still, many corporate remote workers I know stay in touch throughout the day via instant messaging. Here are some IM applications you can use:

• GTalk
• Windows Live Messenger
• AIM
• Skype

If you need an IM app that allows you to handle multiple accounts using the same interface, you might want to look at Lifehacker’s roundup of the five best instant messengers.

Phone, VoIP and Voice Chat

Although it might seem simpler to have one phone line for both business and personal contacts, it’s wise to keep them separate. You don’t want to provide 24/7 phone support for colleagues and clients, and you don’t want your workday to be interrupted by a call from your mom, either.

But what if you’re working with people who are overseas, as in the case mentioned earlier? That’s where VoIP (Voice over Internet Protocol) comes in. Instead of using regular phone lines, VoIP transmits audio through the internet. We’ve covered VoIP here at WWD before, including how you can use it to cut business costs.

There are many available options for VoIP and voice chat apps, including Skype, Truphone, Vonage, Gmail Voice and Video Chat, Calliflower, Phonefusion One and FreeConference.

Fax

While I’ve never felt the need to purchase my own fax machine, there are still some situations that call for faxing. For those of us who primarily deal with local clients, a regular fax machine might be enough even if it’s a second-hand unit. But if you’re mostly working with people overseas, sending faxes back and forth can be costly. Online faxing solutions such as efax and MyFax can be much cheaper in the long run.

Postal Mail

If you’re wary about giving your home address out to clients and business contacts, you can use a PO box or take advantage of online mailbox services such as Earth Class Mail or its European equivalent, Swiss Post Box. There’s also Private Box for those who want mailboxes in New Zealand.

Establishing multiple ways for clients to communicate with you isn’t that hard. When you’re starting out, it’s usually enough to have two different ways for clients to reach you (say, email and phone). Should you need more, the apps and services above give you plenty of options to choose from.

How do potential clients usually contact you? Which method do they use the least?

Image by tecknare from sxc.hu

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Recently I discovered a new Labs feature that makes me love Gmail even more: the “Send & Archive” button.

I rely on email as my main line of communication with my clients, and I have a whole system worked out. I use my inbox like a to-do list. Clients email me tasks, and as I complete them, I move the message out of my inbox. Whatever remains in my inbox are the tasks that I need to complete; the goal is to have an empty inbox.

My old method was to reply to emails and then manually move them out of  my inbox with the “Archive” button, a laborious two-step process. That was until I discovered the “Send & Archive” button! Now I just click one button to send my response and archive the email out of my inbox.

To enable “Send & Archive”:

1. Click on the “labs” beaker
   
2. Scroll down to the “Send & Archive” feature and click the “Enable” radio button
3. Click “Save Changes”

Now when you compose messages you will have a fancy “Send & Archive” button seated very nicely right next to your now-archaic “Send” button.

I hope this method helps keep you organized. As a freelancer, I am often juggling multiple projects and like to make my life as simple and streamlined as possible.

What Labs features do you use to streamline Gmail?

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Wait no more! Clear Context, a San Francisco-based start-up that makes an in-box management plug-in for Microsoft Outlook has come up with a new product called, Contact Exporter for Outlook. Of course you will need their inbox management plug-in, a for-pay product.

The Contact Exporter is a beta feature in ClearContext IMS v4 that lets you create and export groups of email addresses found in messages stored in the Outlook folders you select.

What it essentially does is create a list of email addresses found in messages from a set of folders users choose. And these can be used to create distribution lists. You can create say, an email list for a birthday invite and export the list in the CSV format. You can export files and import them into any application that will allow you to import CSV files. Facebook and Socialzr are two such web services. I think this export feature is quite handy. If you want to know more, check out their website.

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