In real life, Matt Eldridge was a deal closer. But over email, he couldn't catch a break.
As a franchise salesman, potential buyers liked his pitch in face-to-face conversation, but he said they seemed put off by whatever he put in writing.
"They felt like they were getting pushed or I was aggressive. I didn't realize I was coming off that way," he said. "It was one email that was throwing the deal off."
So he did what any entrepreneurial-minded salesman would do: he turned his problem into an enterprise.
This week, his new company, Lymbix Inc., which is based in New Brunswick, Canada, launched ToneCheck. A program that plugs into the popular e-mail software Microsoft Outlook, ToneCheck scans email messages and flags sentences and phrases that might carry unintended emotion.
"The program was a need to scratch my own itch," he said. "I thought to myself, there's a spell check, there's a grammar check. There must be a check I can download into my Outlook to check my tone."
Eldridge said his company builds on the work of Wayne Chase, a ToneCheck advisor and Canadian inventor with 25 years of research into connotative intelligence, or the meaning associated with different words and phrases.
After users download the program, they are asked to set their "tone tolerance." The feature lets users decide how much of various emotions they are willing to communicate.
As ToneCheck scans each email, it cross-references the words and phrases against a massive database of words, phrases, emoticons and punctuation. When it finds a sentence that might convey more negative or positive emotion than the sender might have intended, it flags it.
For example, when the program scanned the below sentence, it said it exceeded this reporter's tone tolerance.
"It may be a necessary part of modern life, but email is such a pain. I hate the constant interruption and distraction."
ToneCheck registered the phrase "email is such a pain" as "humiliating" and determined that "I hate the constant interruptions" was "angry."
On the flip side, the program said the positive sentence below might also convey too much emotion:
"I loved meeting with you today. I really hope we can continue working together!"
The first part of the sentence was flagged as "enjoyable," and ToneCheck called the second part "contented."
The program seems, at times, to flag innocuous content. But Eldridge said that as more people use the service, the program will continue to get smarter.
"It really takes into account the emotions, beyond just positive and negative and gets into what people can really feel, whether it's friendly, affectionate or angry or sad or humiliating," he said. "Flagging that sent or phrase really gives you the ability to impact the end reader with the desired emotion."
The recently released beta version is free, but in the next few months, the company will add a premium paid version with more features, including suggested sentence and phrase changes.
Though some emailers may believe their writing skills are too good for automated help, social psychology suggests they might want to reconsider.
Nicholas Epley, a professor of behavioral science at University of Chicago's Booth School of Business, said a recent study of his showed that people correctly interpret emails little more than 50 percent of the time.