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.

Join the Good Gear Guide newsletter!

Error: Please check your email address.

Tags instant messagingInternet-based applications and servicesapplicationse-mailproductivitye-mail securitysoftwaredata protectionemail

Our Back to Business guide highlights the best products for you to boost your productivity at home, on the road, at the office, or in the classroom.

Keep up with the latest tech news, reviews and previews by subscribing to the Good Gear Guide newsletter.

Katherine Noyes

PC World (US online)
Show Comments

Most Popular Reviews

Latest News Articles


PCW Evaluation Team

Azadeh Williams

HP OfficeJet Pro 8730

A smarter way to print for busy small business owners, combining speedy printing with scanning and copying, making it easier to produce high quality documents and images at a touch of a button.

Andrew Grant

HP OfficeJet Pro 8730

I've had a multifunction printer in the office going on 10 years now. It was a neat bit of kit back in the day -- print, copy, scan, fax -- when printing over WiFi felt a bit like magic. It’s seen better days though and an upgrade’s well overdue. This HP OfficeJet Pro 8730 looks like it ticks all the same boxes: print, copy, scan, and fax. (Really? Does anyone fax anything any more? I guess it's good to know the facility’s there, just in case.) Printing over WiFi is more-or- less standard these days.

Ed Dawson

HP OfficeJet Pro 8730

As a freelance writer who is always on the go, I like my technology to be both efficient and effective so I can do my job well. The HP OfficeJet Pro 8730 Inkjet Printer ticks all the boxes in terms of form factor, performance and user interface.

Michael Hargreaves

Windows 10 for Business / Dell XPS 13

I’d happily recommend this touchscreen laptop and Windows 10 as a great way to get serious work done at a desk or on the road.

Aysha Strobbe

Windows 10 / HP Spectre x360

Ultimately, I think the Windows 10 environment is excellent for me as it caters for so many different uses. The inclusion of the Xbox app is also great for when you need some downtime too!

Mark Escubio

Windows 10 / Lenovo Yoga 910

For me, the Xbox Play Anywhere is a great new feature as it allows you to play your current Xbox games with higher resolutions and better graphics without forking out extra cash for another copy. Although available titles are still scarce, but I’m sure it will grow in time.

Featured Content

Latest Jobs

Don’t have an account? Sign up here

Don't have an account? Sign up now

Forgot password?