Like most people in the 21st century, Bob Kenny uses e-mail to communicate with his co-workers. Kenny, a child psychologist by training, is executive director of the More Than Money Institute, a Concord, Mass.- based educational and advocacy group that helps people use their money to act on their values. Lately, the psychologist in Kenny has become intrigued by how his staffers misperceive his e-mail messages.

For example, when he e-mails staffers that he would “really like” them to be at an...

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