Secrets of planning a terrific off-site meeting

December 21, 2011, 5:39 PM UTC

By Anne Fisher, contributor

FORTUNE — Dear Annie: I guess it is true that no good deed goes unpunished, because our office holiday party — which took me six weeks to organize — was such a hit that now my boss has put me in charge of a three-day management retreat scheduled for mid-February. The location, a resort on a Caribbean island, has been booked, but so far the agenda is a blank sheet of paper, which is up to me to fill.

I’ve never been responsible for planning one of these before, so I really don’t know what I’m doing, but I’d like this meeting to be unique and memorable, and as productive as possible. Can you and your readers give me any pointers? — Smitty

Dear Smitty: Richard Moran sure can. A former Accenture (ACN) consultant and longtime Silicon Valley venture capitalist, Moran is CEO of Accretive Solutions, a Chicago-based consulting and recruiting firm.

He’s also the author of a string of smart and irreverent guides to success in business, including Never Confuse a Memo With Reality and Fear No Yellow Stickies. His new book, Sins and CEOs: Lessons from Leaders and Losers That Will Change Your Career, contains a chapter that might interest you. It’s entitled “Rome Is Burning and We’re Off-site.”

“Contrary to popular belief, retreats are really hard work for all who attend,” Moran says. “Foremost, there’s nowhere to hide. Anyone who monopolizes the airtime is assumed to be jockeying for a promotion. Anyone who doesn’t participate is assumed to have checked out.”

Trying to strike the right balance and still get some work done tends to stress people out, so Moran — a veteran of many great and not-so-great off-sites — recommends giving everyone a chance to decompress by building some genuine downtime into the schedule.

“Don’t close the windows,” he says. “Why go someplace beautiful if there is no time for the pool or golf, and people are locked in dark rooms from 8 a.m. to 8 p.m.?” A total lack of leisure breeds resentment, he observes, and that can torpedo the whole event.

One San Francisco financial company he knows of held a crucial annual long-range planning meeting at an exclusive ski resort, and then gave people no chance to ski. “The attendees were instructed that they could ski between 7 and 9 a.m. or after 5,” Moran says. “Unfortunately, the ski lifts opened at 9 and stopped running at 5.” That made people “so grouchy the entire time that nothing was accomplished.” Avoid that.

Some more of Moran’s tips you might find useful:

  • “People want to learn at meetings, whether it’s how to construct an effective plan or understand market dynamics,” Moran says. So “bring in speakers who can teach and entertain at the same time, and keep the sessions short.”
  • Never put a lawyer first on the agenda: “Sarbanes-Oxley compliance is neither new nor uplifting.”
  • Invite someone who will dance in the evenings. “The success of the entertainment depends on someone getting up there early in the evening to pretend they are on Dancing with the Stars,” says Moran. “Pay someone to dance if you have to.”
  • Accept the fact that whatever entertainment you line up “will never please everyone. If you had the Beatles play, someone would complain. Get over it.”
  • In meeting rooms, “spread out the chairs. I like my space and, if I have to sit too close to people in chairs that are connected to each other, I go to the dark side — probably better described as poolside.”
  • Check cell phones at the door. “At most PGA events today, all devices that can ring, ping, or otherwise receive or send messages must be checked at the gate,” Moran notes — and isn’t the business at hand at least as important as a golf game?

He admits that obliging people to surrender their cell phones and PDAs at the door may be impractical. “An alternative is to have everyone tape their thumbs to their index fingers upon registration,” he says.

  • Limit PowerPoint. “A surefire way to kill a meeting? Line up PowerPoint presentations from 8 a.m. to 4 p.m.,” says Moran. “Alternatives include discussions and meaningful exchanges.” Wherever possible, go with those.
  • What Moran calls tchotchkes, a Yiddish word for trinkets or souvenirs, “are so over. If you are thinking of cheap giveaways like key chains and Frisbees, don’t do it. People will see that expense and think it will cost them next year’s bonus.”
  • Be aware that “people will drink too much. You are not responsible for anyone else’s drunken behavior,” Moran says. “Put a sign over each bar that says, ‘Drink Heavily — Remember You Are Young, Marketable, and Willing to Relocate.’”
  • Assume that anything anyone does at an off-site could show up on YouTube. Mention it to anyone who seems to need reminding.

Perhaps most important of all: Present a realistic agenda. “Too many meetings include way too many items with wildly unrealistic timeframes,” Moran observes, with pie-in-the-sky goals that are the business equivalent of saying, “In the morning we will solve world hunger and after lunch, we will fix the peace process in the Middle East.”

Instead, as you fill up that blank sheet of paper, sit down with your boss and any other higher-ups with a stake in the meeting’s success and talk about what outcomes they see as both essential and achievable in the allotted time. Then construct your agenda accordingly.

Good luck — and don’t forget to pack sunscreen.

Talkback: What happened at the best (or the worst) off-site meeting you ever attended? Leave a comment below.