Features - The Fourfold Path to Email Enlightenment

Dennis Kennedy is a computer lawyer and legal technology consultant based in St. Louis, Missouri. His web site at http://www.denniskennedy.com collects many of his articles and resources and is the home of his blog.


A lawyer overwhelmed by the deluge of email heard that there was a sage who lived at the top of a nearby mountain. The sage, so it was told, had the solution to handling email. Unfortunately, it was a difficult and dangerous climb to the sage’s home which clung precariously to the side of the mountain.

Over many years and many messages for Viagra, human growth hormone, work from home schemes and fabulous Nigerian hidden bank accounts, the lawyer resisted making the trek to the sage. At last, one day the prospect of making the difficult and dangerous climb up the mountain seemed less daunting than opening the lawyer’s inbox.

The journey was arduous but the lawyer at last reached the sage. “I have come seeking the secret to managing my email,” said the lawyer. The sage marveled at a lawyer who sought advice rather than merely giving it.

“Three words,” said the sage. “Meditate on these three words and you will control your email rather than have it control you.” “Yes,” said the lawyer, marveling that anything could be said in just three words. “What are the three words?”

Pausing deliberately and speaking slowly, the sage said, “Protect your inbox. Concentrate on this and all good things will follow.” He went on, “And, if you are using Microsoft Outlook or Outlook Express, make sure you keep current on all the security patches and updates.”

Protect Your Inbox

Like the sage, I maintain that if you concentrate on the notion of protecting your inbox and make it your primary theme in guiding your email management efforts, you will maximize your success. It is amazing how well this three-word phrase will help you find and implement best practices in email management.

The maxim, “protect your inbox,” however, is a little short on specifics, to put it mildly. I have also developed a four-part practical approach to handling email that puts this maxim into action.

This “fourfold path” concentrates your action on four key “pressure points” at which your efforts can have the greatest results. It does not focus on unsolicited commercial email or “spam,” as it has become popularly known. Spam handling flows naturally out of the process. In fact, I would argue that over-focusing on spam will result in some negative effects on your total email management efforts.

By focusing on these four pressure points, a modest amount of effort will give you 80% to 90% of the results you wish. You will get the best results if you address each of the four points, but you can achieve impressive results by only working on one, two or three of the pressure points.

The four pressure points are: (1) before emails are sent to you, (2) when you send emails, (3) when you receive emails, and (4) when you read and/or store emails.

1. Before Emails Are Sent to You


People are often surprised by the amount of email that arrives when they submit information online or provide their email address on a web site. The collection of email addresses is big business and your own efforts largely contribute to the amount of spam you receive.

The approach you want to follow is a simple one. First, you want to make it easy for the people you want to email you to send you email and you want to make it difficult for the people you don’t want to email you to send you email. Second, you want to adopt a “multiple email address” approach and attempt to steer email to the appropriate address.

Let’s look at the second point first. One of the tried and true approaches to email management has been to use at least two email addresses. As a practical matter, you have a “work” email address and a “home” email address. Most people have a yourname@yourbusiness.com address at work and a yourname@yourisp.com that came with their Internet account at home.

Another common approach, which I advise, is to have a third email account through a free Internet email service such as Hotmail or Yahoo mail.

Once you have these email accounts established, go back and apply the first principle and make it easy for people to send email to the appropriate address.

First, make it a priority to reserve the work email address for business email. This address is the address you should use on your business card, on your firm’s web site and for clients and potential clients. You may give it out in public, but try to do so only in the business context. Move non-business email away from this account aggressively. For example, if you have a business associate who sends you jokes or attachments, simply say that your firm does not allow them and have the associate send this email to your home account. Business-related email newsletters should also be sent to the “work” email account. As a result, your work inbox should contain, for the most part, two things: business email and spam.

Second, direct “personal” email to your “home” address. Use this address for friends and family, hobby and other interests, and other non-business email. Ask business colleagues who use this address to direct business email to your work account. As a result, your home inbox should contain, for the most part, two things: personal email and spam.

Third, set up a Hotmail or Yahoo email account to use for online shopping and any other time you have to supply an email address where you have a concern that providing your email address will lead to unsolicited email. Use this account accordingly. This account will contain, for the most part, order acknowledgements and shipping information, other receipts and spam.

Some people will go so far as to set up one or more other accounts for email list servers or discussion groups. I don’t think that it necessary to go that far. A two or three email address approach will give you most of the benefits without adding the burden of checking multiple accounts.

Using this approach, you will have inboxes that are easy to “triage.” You can determine quickly whether a message is a “keeper” or not, and largely use your “delete” key to handle spam.

There are a few other useful tips for handling pre-delivery email.

First, understand the notion of “opt-in” and “opt-out.” Most of us prefer a policy in which we must opt in or explicitly choose to get newsletters and commercial email. In other words, we must check a box or do something affirmative to get the email. In an opt-out system, you will see, for example, boxes pre-checked for you. Understand what you are signing up for.

Second, pay attention to privacy policies and be wary of providing information when a privacy policy indicates that your email address may be sold, rented or given to third parties. In such a case, you will want to use the third email address discussed above.

Third, consider carefully whether you should join email lists that have high volumes. Email lists can be enormously valuable, but also can have traffic of hundreds of messages a day. Some lists may be configured to send you a single message that contains all the postings for that day. Joining any list should be done only after you have determined how you will manage the messages you will receive from the list.

Fourth, avoid replying to, unsubscribing from or, if possible, even opening spam messages. Some studies indicate that 90% of spam comes from about 200 companies in the unsolicited commercial email business. You want to stay off their radar screens. Anything that you do that shows that your email address is “live” invites further spam.

Finally, some ISPs have started to apply spam filters and antivirus checking before your email even reaches you. Taking advantage of this option or moving to an ISP that has this option can weed out the most obvious and offensive spam before it comes into your inbox.

2. When You Send Email

Ironically, what you do when sending email has a great impact on how easy it is to manage the email you receive.

Some of your options are simple and straightforward. You definitely want to use the standard features of your email software. Save email addresses in the “contacts” folder or address book so you don’t have to retype email addresses every time. Keep copies of sent email automatically.

Other options take just a little effort, but can really help you.

First, ask whether you are emailing from the “right” email address. Almost invariably, your recipient will simply reply to your email and the reply will come to the address you sent your message from. If you send a business message from your “home” address, the reply will not make it to your “work” address and you will lose some of the benefits you gained in addressing the first pressure point.

Second, use effective subject matter lines. To me, the intentional sending of email with a blank subject matter line is unforgivable. It does not help the recipient or you when you receive a “RE: [blank]” reply. Similarly, cryptic or overly simple subjects (e.g., “Agreement,” “For you,” et al.) do not help much. Using a subject such as “My Materials for 2003 Missouri SASFIRM Conference Attached” helps me find the email later and helps my recipient manage his or her own inbox and give my messages appropriate priority – a definite win-win. I also like the idea of adding the phrase “No Reply Necessary” to the subject line to help your recipient manage those types of emails.

Finally, use your head when deciding to forward or carbon copy email messages. A huge number of messages do not need to be forwarded (and many of the ones that are tend to be chain letters or potential viruses) and too many people routinely cc: a whole list of people. Take a second to think about what you are doing before you send emails to multiple addressees. Don’t add to the email volume problem.

3. When You Receive Email


At last we turn to what you do when you actually receive email. This point is the one most commonly focused on in email management solutions and is the object of spam software.

On the “fourfold path,” however, we have already seen that we can do much before we even get to this point. In fact, if we follow steps 1 and 2, we will have already reduced our volume and have a couple of inboxes in which we can easily determine what mail is important and what is not.

It is also at this point where paths can diverge based on personal preferences. I like to keep a very clean inbox that contains only items which require a response. Others like to move these types of messages to “action” folders or use chronological folders (“today,” “yesterday,” et al.). There is no one true path. You can do what works best for you.

People often have staggering amounts of email in their inboxes. On an email list I’m on, someone wrote in wondering how to handle the 29,000 messages in his inbox! Almost any system at all will be better than that system!

Your first step in inbox management is commonly known as “triage.” After I download my email, I quickly go through it and delete what I don’t need and read what looks important to me. Deleting messages makes it easier to focus on what is left, like separating the chaff from the wheat.

Here’s a very important point. You do not have to read or even open every email message. In fact, it can be dangerous to open emails that contain viruses and, as I’ve mentioned, simply opening spam can lead to even more spam. There is a technique in common use that uses a bit of code generally known as a “web bug” to invisibly let the sender know that you have opened an email. Web bugs and similar approaches tell the spammers that you have a “live” address and keep you on the spam list. If you think it is spam, delete the message without opening it.

Your second step is to create folders within your inbox. I’m surprised by the number of people who do not know that you can create these folders. That’s part of the reason I suggest that if you are going to take one computer class this year, take a class on your email software.

Yes, you can and should create a number of folders in your inbox (in Outlook, for example, go to the File menu, then New, then Folders). Again, you will get the best mileage by creating the folders that work best for you. I personally use fairly large subject categories: Client, Speaking, Articles, Newsletters, Contacts from Web, etc. Once you read an email and determine that you want to keep it, move it out of the inbox into the appropriate folder. Your inbox stays clean and you can find old messages relatively easily with little initial effort.

Even better, you can automate this process by using filters or rules, which should be your third step. Every email program these days has these features. A rule is a simple if-then management tool that you can apply to your email. The simplest is the “move to folder” rule, which most people consider to be essential for managing membership to an email list. This type of rule will “look” at incoming messages and based on the sender’s address, keyword or other factor, automatically route it to a folder so that it never appears in your main inbox. As a result, your main inbox stays clean and you can perform triage easily on the main inbox and then turn to the various folders.

In Outlook, for example, under the Tools menu, you will find a Rules Wizard that will walk you through the process of creating a rule. Even better, the Outlook Organize tool creates common rules with only a few mouse clicks and gives you the choice of running the rule on your existing messages in your inbox, making it a great way to clear out and organize an overflowing inbox. The Organize tool and the Rules Wizard (or their equivalents in other email software) also allow you to create rules to take care of standard spam and adult-oriented emails.

You can be as elaborate as you want with folders and rules, but I like to keep it pretty simple, on the theory that 20% of my effort will give me 80% of the results. While some people add spam filters and other tools, for most of us, the four steps in this article will take us a long way toward both handling received email and dealing with spam. I personally am not an advocate of spam filters because they are not perfect and I would rather delete a few extra spam messages rather than miss a message intended for me that contained a common word that triggered a spam detector.

4. When Reading and/or Storing Email

Much has been written lately about email retention and deletion policies. The issues are real and need to be addressed. For purposes of this article, I’m going to assume that you have developed appropriate policies and concentrate on only the email management aspects at this fourth pressure point.

While you might initially think that this issue arises at the point of storage or filing, it actually arises first when you read the message. Must you respond to the message? Today? Tomorrow? In due course? Does it require another action or forwarding to someone else? Do you need to keep it? Can it just be deleted?

I probably use a heavy finger on the “delete” key. Other people delete much more than I do and many delete much less. The guy who had 29,000 emails in his inbox triggered several postings to the email list explaining that there was a delete key and how to find it.

I clear my inbox by either deleting or moving to a folder. Ideally, my inbox will contain only messages that need a reply or action by me. Emails that don’t need replies go the appropriate folder immediately. Once I reply, the original email goes to the appropriate folder. I also evaluate whether the message is of a type that a rule can be created to automatically send it to a folder where I can deal with it separately with like messages, such as a newsletter.

After that, it’s a simple matter of file management. I tend to create subfolders on a semi-annual or annual basis, depending on size. For example, after June 30, 2003, I might move all the email in my Client folder to a subfolder called “Jan to June, 2003” and keep only the newer messages in the actual Client folder. This approach makes folders a bit more manageable and easier to search.

I also use my Newsletter folder as a poor man’s knowledge management tool. I keep about 6 months or so worth of newsletters in the folder before I delete older messages. That way if I run into situation where I think I saw something on a topic recently, I can do a quick search in that folder and generally find a reference.

Email programs also give you methods to archive and compress email. Using these features from time to time will also keep your email easier to work with.

I’m No Sage, But I Recognize Sage Advice

While I am not sure that I can solve your email management problems, this four-step approach will take you a long way toward getting a firm handle on your email and generally making your life easier. At its foundation is the idea of protecting your inbox, in a number of ways, so that what you see in your inbox is what is most important to you. There’s no silver bullet software solution to email management and I certainly do not recommend that you run out and get the latest spam tool. Email management is more a process, and an evolutionary, personal process, than a search for a tool. The better you understand that and work thoughtfully on the process, the better your results will be. Protect the inbox, grasshopper.

A version of this article appeared in the October/November 2003 issue of Law Office Computing.