You don't want to be Donna (so much so that Donna isn't her real name). You don't want to be Donna's apparent cad of a paramour, who won't be named here either only because his identity isn't relevant. And you probably don't want to be either person's employer.

One way to avoid such a fate is to start monitoring your outbound e-mail, says Roger Matus, CEO of Audiotrieve. His young company, founded by a group of speech-recognition specialists from Dragon Systems, makes a Bayesian anti-spam product called InBoxer that has garnered positive reviews since launching in July 2003. Audiotrieve is looking to extend that technology to help control outbound e-mail, a market opportunity drawing intense interest from a variety of vendors that recognize the regulatory burdens and legal liabilities spawned by irresponsible e-mail practices.

We'll get back to Donna in a minute.

"We started with the spam filter for inbound e-mail but discovered that the bigger problem was actually outbound," Matus says. "Inbound is an annoyance; outbound can cost you millions" in sexual harassment judgments and regulatory infractions. Forty-three percent of companies employing more than 20,000 actually have staffers spot check outbound e-mail, according to Forrester Research.

In getting started on its latest development effort, the Audiotrieve team asked itself this question:

"How do you take a spam filter and teach it about outbound mail? The first thing you need is a very large database of e-mail," Matus says. "Most companies really aren't willing to hand that over to you. They're very happy to give you lists of spam, because they don't care about that. But in terms of their own corporate executives' communications, well, we haven't gotten a volunteer yet. We asked several people, we promised to sign non-disclosures, but the moment we say 'I need to see all of it because we want to know about the stuff that's offensive, we want to know about the stuff that involves a business deal . . . well, you can imagine if I asked you for all of your mailbox."

I can imagine I'd hang up on him.

Fortunately for Audiotrieve, 176 former Enron executives, support workers and their correspondents (including Donna) had no choice in the matter. In March 2003, the Federal Energy Regulatory Commission posted online 1.5 million e-mails between these people that were related to Enron's crooked power-trading activities - a treasure trove not only for prosecutors but also software developers looking to engineer a language-based e-mail management product (note: if you follow the link above, you want the "Enron e-mail .pst" database) .