Have you ever felt that punch-to-the-stomach feeling of clicking "Send and realizing you blasted an e-mail to the wrong person? As the CEO in the following case learned, one misguided e-mail mixed with some poor judgment can stir up a potent legal stew …

Case in Point: Kenneth Wold,46, applied for a manager job at an Idaho financial company. He e-mailed his cover letter and résumé. Within 10 days, Wold heard back, but not with the message he expected.

The company's CEO had mistakenly sent Wold an e-mail that was intended for a co-worker. The CEO's e-mail referred to Wold's résumé by stating, "Damn … He must be old—and just looking for something to do.

Wold never heard anything else. He assumed his application was rejected because of his age, so he filed a lawsuit under the Age Discrimination in Employment Act (ADEA).

The court sided with Wold and sent the case to trial, citing the smoking-gun e-mail. It said, "This broad, negative characterization of older employees is precisely the type of prohibited stereotype the ADEA seeks to remedy and gives r