Five tools to protect you from e-mail slip-ups

A growing number of tech tools are now on hand to prevent the all-too-common e-mail faux pas.

It's a rare e-mail user indeed who hasn't experienced the awful moment that can come right after hitting "send." It's the moment when you realize that you just said something you shouldn't have in the e-mail, and there's no way to get it back.

Such faux pas can be damaging to any user; for a business, it can be a disaster.

Need an example? Angelo Mozilo, former chairman of Countrywide Financial, drew considerable flak a few years ago by describing a mortgage customer's e-mailed plea for help as "disgusting." Unfortunately for Mozilo, he inadvertently chose to use that turn of phrase in a "reply" to the customer's e-mail, rather than forwarding it, as he intended to.

Not surprisingly, the lender issued a public apology later that same day. Countrywide and Mozilo, of course, have since left their own special legacy in the annals of time.

The risks aren't reserved just for high-profile CEOs at troubled companies, however. How can the rest of us avoid making e-mail mistakes of our own? Fortunately for us, an assortment of IT tools are on hand to help.

1. ToneCheck

Now in beta, ToneCheck is a software package from Lymbix that uses sentiment analysis to identify and flag emotionally charged sentences within e-mail messages. Currently offered as a free plug-in for Microsoft Outlook 2007 and 2010, ToneCheck allows users to set an individual tolerance level for emotional content. Using that level as a guide, the software monitors e-mails and a "Tone Alert" indicator turns red when the language used exceeds the user's tolerance level. Flagged sentences can then be revised accordingly.

2. Reply to All Monitor

Sperry Software's Reply To All Monitor, meanwhile, is an Outlook add-in that focuses on e-mail replies and especially replies to all. Priced at $14.95, the tool offers a number of prompts and confirmations to prevent users from accidentally revealing too much to the wrong people on e-mail. First, as its name suggests, the software asks for confirmation before you send a "Reply to All" message, thereby making you think twice about who will see what you're about to send. If you were BCC'd on a message, it also prompts you before replying so that you won't inadvertently reveal that you were an undisclosed recipient.

3. Safeguard Send

Another add-in from Sperry is Safeguard Send, which aims to help users think twice before they send an e-mail outside the company, for instance. Priced at $24.95, Safeguard Send can also alert users when their e-mail includes specific keywords, has a blank "subject" line or includes more than a certain number of recipients.

4. VaporStream

Aiming to prevent unauthorized or unintended copying, forwarding, saving and printing of e-mail messages, VaporStream is a cloud-based confidential messaging system that "vaporizes" messages after they're read. Priced at $7.50 per user per month, the technology integrates with current e-mail platforms -- even using existing e-mail contact lists -- and it allows the attachment of Microsoft Excel, PowerPoint or Word files. Rather than presenting a potential liability, however, such attachments get converted into unsavable images and are viewable only in the VaporStream attachment viewer. VaporStream uses military grade encryption, and a keyword filtering capability can prevent select, sensitive conversations from occurring at all. Free alternatives to VaporStream, incidentally, include KickNotes and Vanish, a prototype program whose source code is offered for free.

5. Xobni and Rapportive

Xobni and Rapportive are both tools that push the identities of those you're exchanging e-mail with to the forefront of your communications. Xobni, for instance, is an Outlook plug-in and BlackBerry app that not only helps users navigate e-mails and conversations but also pulls in data about contacts from third-party social-networking sites like Facebook to put them into context and remind users of key facts about their connections. Xobni is available in a free version as well as a "pro" version for $7.99 per month. Rapportive, meanwhile, is a free tool for Gmail that "shows you everything about your contacts right inside your inbox," in the company's own words.

The frequency of e-mail gaffes in business is underscored by this series of comics. Time to put some technology -- and thought -- to work to make sure you're not the next victim.

Follow Katherine Noyes on Twitter: @Noyesk.

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Katherine Noyes

PC World (US online)
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