If you've ever had an e-mail's tone misinterpreted, rest easy. New software ToneCheck allows you check your e-mail messages before you send them and flags sentences and phrases that might lead its reader astray. ToneCheck is the brain child of Matt Eldridge. After losing a deal due to appearing too pushy in e-mails to a client, he founded Canadian-based company Lymbix Inc . ToneCheck says studies show that e-mails are misinterpreted a whopping 50% of the time.

The software plugs into Microsoft Outlook and allows users to set their "tone tolerance," a measure of how much emotion they want to evoke in their writing. After scanning an e-mail, it cross-references the content with its database, which includes words, phrases, punctuation, and even emoticons, checking for signs of eight kinds of emotion: friendliness, enjoyment, amusement, contentment, sadness, anger, fear, and humiliation.

ToneCheck is built on the research of connotative intelligence researcher Wayne Chase. Connotative intelligence studies the unspoken meanings associated with various words and phrases. The software, which is available as a free download, is compatible with Microsoft Outlook 2003, 2007, and 2010. Support for additional desktop and web-based e-mail clients is promised for the future.