Being the meeting planner at Chester, Pa. — based software solutions company AdminServer might be a really fun job. That is, as long as you don't mind that nobody knows you are the planner.

And if you don't mind the months of subterfuge and investigative sneaking around by your curious co-workers.

The good news is that the man paying for the trips you would be planning, company founder Chris Doggett, is a fun-loving corporate chief who embodies the “work hard, play hard” image of an American boss.

He also loves a good travel mystery.

In October 2003, Doggett announced that he would send one lucky couple on an all-expenses-paid mystery trip. He invited all 24 employees and their spouses to a celebration dinner on a Wednesday night in Philadelphia. By then, he had upped the ante by saying the trip would be for two couples.

Everyone was told to come packed for a four-day/three-night trip that would depart after dinner. “The winner could be anyone,” they were warned. And bring a valid passport!

“We kept it secret just for fun,” Doggett says.

As excitement grew during dinner, Doggett dropped the real surprise on his staff: All 30 of them were flying to Orlando after dinner for a Celebrity Cruise to Nassau, The Bahamas.

Do It Again

Fast-forward to April 2005. Doggett wanted to top himself. By this point, its second year of the companywide trip, everyone knew they were going somewhere, but where remained a mystery right up until the end.

AdminServer employees and their guests gathered early one morning and enjoyed a Bloody Mary breakfast bar. Then they were herded aboard a train and taken to an out-of-the-way airstrip in Wilmington, Del., where a private charter jet was waiting for them.

“The 737 private charter was interesting, because we didn't have to tell anybody where we were going,” Doggett says. It wasn't until they reached cruising altitude that he revealed their destination: an all-inclusive resort on Paradise Island in The Bahamas. He had planned a variety of activities and events, including golf, fishing trips, and even a toga party.

“The Doggett Touch — the toga party — was my idea,” he jokes.

Although there were some problems with the resort and a last-minute switch to a different charter company, few of the attendees ever got wind of the trouble.

“I didn't know about that,” says AdminServer Marketing Director Jon Rottier. “The few select people who organize the trip continue to organize it while we're there. Chris takes control of situations like that without people being aware of it.”

Rottier has deep respect for Doggett, and he feels that the success of the company best speaks for Doggett's vision and drive. “I've been here a long time,” he says. (He was one of the first 10 employees hired.) “The neat thing about the trips is that, as much fun as it is to work here, when you walk through the office, all heads are down. We work in an office space with other companies where other people are leaving at five, and we are still here hours after that. Chris' generosity is the reason for our dedication to our clients and to the company. It creates great morale and a strong work ethic.”

Doggett even installed a flat-screen TV in the office that plays all the vacation pictures. “Sanitized, of course,” he jokes, “but it's everybody having a ball.”

Where to Next?

In May, AdminServer will take 130 employees on their third trip. The cost: $200,000 — far more than the $50,000 Doggett shelled out for that first cruise.

“If you're going to throw a party, $200,000 is not bad,” he says. “The way I look at it, if we have $10 million in payroll, that's 2 percent. It's an additional 2 percent of compensation that gets you a whole other level of employee loyalty and retention.”

Where is the group headed?

“It's a closely guarded secret,” he says. “It's fun for everybody to speculate. People get very serious about trying to figure it out. You would not believe it! I sometimes resort to misinformation and a campaign of subterfuge and double-dealing.”

A companywide e-mail has been distributed letting employees know that they need to be available for particular dates. Several more e-mails have arrived with clues. For the three weeks leading up to the trip, he will dole out even more clues, gift baskets, and then, finally, some information about what to wear. He is also planning a pre-party the night before the departure for those who want to stay over in Philadelphia.

Doggett stepped down as CEO of AdminServer in mid-January. But he says no one need fear that his successor will be any less interested in continuing the company's new tradition of mystery traveling parties.

“He's a toga man,” Doggett says with a laugh. “He drank the Kool-Aid.”