Beware the Email!

In 20 years, email has become the dominant medium of communication in business, politics, and private life. It is irresistibly fast, cheap, and convenient. And it is a long way from being replaced. When I sent a request to a LinkedIn founder by InMail, he kindly responded, and then suggested we continue our discussion on email. The right kind of email address has even become a status symbol, with Human Resource managers disregarding the resumes of candidates with email addresses in domains that suggest a lack of sophistication.

But email is also mistake-prone and insecure, and it leaves more of a permanent record than most authors realize or wish. For reasons that are not obvious, email has encouraged loose talk and emotional outbursts that previous media didn't. Business letters, telegrams, telexes, and FAXes were written, edited, and distributed much more cautiously than emails, even though they were less subject to leaks. The wrong letter might have ruined a relationship, but not your reputation and your career, as a tactless email can.

Email systems should warn that "everything you send can and will be used against you." Those of us who started using email in a work group within a company in the 1980s received an education in the do's and don'ts of this medium that served us well when the internet expanded its scope. The past three decades, however, showed that many executives and public officials were not so lucky.

In the 1980s, the National Security Council (NSC) of the US used an early email system from IBM called PROFS, and staffer Oliver North mistakenly believed that "deleting" his messages to his boss, John Poindexter, had the effect of actually deleting them. Recovered from backup tapes in 1986, they were the smoking gun of the Iran-Contra scandal.

A few years later, the CEO of a major company sent two emails to two lists. The first message, to all employees, explained that the company's growth strategy required 1,000 of them to be laid off; the second one, to a selected few, explained that the layoff was needed to preserve their year-end bonuses. One of the recipients of the second message, however, forwarded it to all employees, causing them to receive both.

In 2015, Republican presidential candidate Jeb Bush, to show his internet savvy, published all the emails he exchanged with constituents as governor of Florida, including the confidential, personal data that his constituents had included in their emails to him. And now, his opponent Hillary Clinton is being raked over the coals by the press for using a private server for her official emails while Secretary of State, even though there is no indication that it did any harm, and many of the people going after her would be hard-pressed to explain what a server is.

Just don't count on email for security. If you want a message to stay secret, write it in Icelandic, encrypt it with a one-time pad, and send it by carrier pigeon. About email, you can find plenty of recommendations on filtering spam, not opening suspicious attachments, not clicking links, etc., Of course, we should follow these recommendations, but, rather than repeat them, I would rather touch on the few following, more strategic points:

1. Don't Blame The Medium
2. Write Your Business Emails Like Business Letters
3. Take Countermeasures to Avoid Sender's Remorse
4. Keep Your Email Archives Forever

Don't Blame The Medium

Some productivity experts bemoan the fact that professionals spend hours daily on email, but it's really no different than spending the same amount of time on hardcopy. Email, today, is the primary medium of person-to-person business communication. It is used to send meeting agendas and minutes, submit proposals, send invoices, receipts, reminders, complaints, etc.

It may not be the best medium for these tasks within an organization, but it is the default one you use with everyone you are dealing with across organizations, and with strangers half-way around the world.

Write Your Business Emails Like Business Letters

A business email is a business letter that is delivered electronically. It is faster and cheaper than paper, and it can include hyperlinks and attachments, but it is still a business letter, written for the purpose of obtaining a specific response from the recipient, while creating, maintaining, or enhancing a relationship. That we use a different word just means that we pay more attention to the medium than to the message. Not everybody does. My Russian correspondents, for example, call their emails "letters," and don't understand why we don't.

In a business letter, you state facts, without attributing motive or using any expressions that might offend or prompt the wrong response. You write "We couldn't find a record of you attending XYX school," not "You lied on your resume." You ask "What information do you base this on?" not "I know what people like you are trying to do." And you don't call strangers by their first names.

It is a centuries-old art, and it is not difficult to find advice or templates to help you cover all the points needed in an appropriate way for evey conceivable purpose. Email has not made this art obsolete. The complimentary clauses may be shorter, but they are still a necessary protocol.

Also, business letters often need to be vetted before they are sent. You don't want to be surprised by what a colleague sent out, anymore than you want your own boss to ask "You wrote what?" Unfortunately, no email client I am aware of lets you make the sending of an email contingent on approval by a list of reviewers.

You can, of course, send the message to them first as a draft and collect their feedback, but it's all on you. The email client does nothing to facilitate this process. The postal service didn't either for letters, but no one expected it to. More is expected from email clients, because, as software serving your organization, it should support its work flows.

Take Countermeasures To Avoid Sender's Remorse

Even though forums are full of users asking for a Confirm Before Sending option on email, the most common email clients still don't offer it. This includes Outlook, Gmail, Yahoo, Apple Mail, and Opera Mail. The closest Gmail has is a hold of up to 30 seconds, during which you can Unsend a message. Mozilla's Thunderbird has an add-on to prompt for confirmation.

If you order pizza on line, you will be shown the details of your order and asked for confirmation before you place it, but your trigger-happy email client will dash off a message to your best customer about a multi-million dollar project just on the basis of your clicking Send, or, even worse, accidentally pressing Ctrl-Enter.

Dropping a printed letter in a mailbox was as irreversible as sending an email, but the process of addressing and stamping envelopes came last, after the letter had been edited and approved. Email clients, on the other hand, prompt you for the destination address first, making the message ready for one-click sending before you have written a word of it. And, when your message is a reply, the destination is filled out automatically.

So what can you do to protect yourself? There are a few countermeasures you can take even if you don't have an email client that prompts for confirmation before sending.

1. If your email client lets you, use its Settings or Preferences to disable the keyboard shortcut for sending.
2. Write your messages before filling out recipient addresses.
3. Use another text editor to compose your messages, and paste them into emails afterwards. Unfortunately, formats may be affected.

In addition, chime in with the numerous email users on forums who are clamoring for a Confirm Before Sending options in email clients.

Protect Your Employees' Email Addresses

These days, companies will more readily give you an employee's mobile phone number than email address. Yet most use a common address format for all employees that makes these addresses child's play to guess if you know just one. An ACME employee gave you her business card at a trade show, and her email address is "[email protected]," from which you know that, most likely, all employees, from the CEO to individual contributors, with have addresses of the form <first-name>.<last-name>@acme.com. From then on, all you need is a list of names to spam the whole company.

Unless you want the whole world to know your employees' email addresses, give them email IDs that are random sequences of letters and digits, and use an email domain name that is not the company name. The ACME's Jane Doe then has an address like [email protected]. It doesn't affect her correspondents, because they have it in their contact list under "Jane Doe," but it will stymie the spammers.

Keep Your Email Archives Forever

The New York State government is currently being criticized for instructing employees to delete their emails after three months. What is that supposed to accomplish? Saving disk space at ￠10 a gigabyte?

The emails you send should be kept forever, along with those emails you receive that are of interest. The rest should be deleted immediately and flagged for future filtering. Over years, you may accumulated tens or even hundreds of thousands or emails. What if 20 years of records of your professional life take up 50GB of disk space? You can have it all on a 64GB memory stick that you buy for $!4, and it will be a great source when you write your memoirs.