It was the perfect setup: a momentarily empty office at Sun Microsystems, the unattended computer of a new attorney. Mike Dillon just couldn’t resist. A few keystrokes and the deed was done—a resignation e-mail to the unsuspecting new hire’s supervisor: “It’s not working out.”

It was the perfect setup: a momentarily empty office at Sun Microsystems, the unattended computer of a new attorney. Mike Dillon just couldn’t resist. A few keystrokes and the deed was done—a resignation e-mail to the unsuspecting new hire’s supervisor: “It’s not working out.”Dillon, Sun’s general counsel and a renowned prankster, couldn’t contain his grin when Ted Borromeo, Sun’s vice president of employment and benefits, walked into his office distraught.

“He had this big smile on his face,” Borromeo laughs. “He’s a very mischievous GC; he makes work fun.”

While many general counsel of Fortune 500 companies are aloof and unreachable, pawning media inquiries off onto public relations lackeys, Dillon is uncharacteristically open. He authors a blog, The Legal Thing: Notes from a General Counsel, and he and his team have created a slew of initiatives that Sun has adopted in the past two years to cut legal costs and increase efficiency.

Dillon says the “peaks and valleys” of outside law firm costs, “depending on what type of work, what type of events are happening in your company, major litigation,” make it difficult to estimate those savings year after year.

“Where I can get a good gauge,” he says, “and what makes me comfortable that these initiatives are being very, very effective is on our internal spending. So over the last seven years our headcount as an organization has actually decreased about 25 percent. And that’s in a period when we have acquired a large number of companies and inherited their legal departments—and also the workload from those legal departments—and in an era where what our team is being called upon to support has gotten much, much more complex.”

Dillon, a youthful 51, has been known to show up at work sporting pirate’s garb—complete with hat, earring, wig and sword—to celebrate International Talk Like a Pirate Day. And although he doesn’t have swanky in-house digs (Dillon, like many employees of the Santa Clara, Calif.-based company, telecommutes), he can often be found in a temporary workplace at one of Sun’s many locations, closely connected to more than 165 legal department lawyers spread among 25 countries.

“When you work for a truly innovative company like Sun, you find yourself challenged constantly,” Dillon says.

Dillon followed Sun CEO Jonathan Schwartz into the blogosphere in August 2006. “Many in the legal profession and media questioned the value of an executive blogging,” he says of Schwartz’s experimental efforts, which ultimately led to 4,000-5,000 active blogs updated at least once a month by Sun employees.

“Newspapers would call to ask him about it and then ask me as GC, ‘How can you let him do that?’ I was never worried because blogging is a thoughtful process,” says Dillon, adding that heat-of-the moment e-mails and forwarded memos are much more disconcerting.

His blog focuses on what it’s like to be the general counsel of a global behemoth with revenues of $3.9 billion. And he uses posts to communicate with employees, other in-house counsel and law firms, and law students, who are a healthy portion of Dillon’s readership.

Hear Dillon talk about why he blogs.

While he can’t write about some of the most interesting aspects of his job for reasons of confidentiality (Sun’s recent acquisition by Oracle is one example), his blog posts may analyze pending litigation (sometimes to the dismay of opposing parties), highlight random and obscure websites discovered during late-night Internet surfing, or share thoughts on the changing legal profession.

Among the changes he’s helped bring about is the hiring and training of associates right out of law school rather than filling the upper ranks with costly former partners. Fifteen entry-level attorneys in six countries are able to quickly handle lower-level requests that may be key to a deal for a sales representative, freeing up experienced lawyers to address more complex issues.

A second management goal for Dillon was winnowing down the 450 outside firms that represented Sun five years ago for employment, intellectual property and general matters in the U.S. “It was very hard to implement any type of management over a population that large,” Dillon says. Today, Sun has relationships with 20 firms in the U.S., most with alternative billing arrangements—another hot issue for Dillon.

“I see a very different focus in [outside law] firms today,” says Dillon, who is a member of the board of directors for the Association of Corporate Counsel. “Many are pushing hard for flat fees.” And that push helps both sides of the in-house/outside divide.

“I loved the practice of law, but something didn’t feel quite right,” he says. “In law school I was trained to identify problems and find solutions. That’s hard when you don’t have information. Clients don’t want to pay to keep you updated because they don’t want to pay for the billable hour.

“In-house life is so much more enjoyable because clients bring you in on everything. At Sun, clients value our business judgment so much that they bring us in on everything, something that isn’t my job—the antithesis of law firms. As GC,” he says, “I want to do that.”

Dillon talks about management of his in-house team.

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