Professional ski-mountaineer and guide Chris Davenport has organized dozens of expeditions on every continent. Here's what he's found: it doesn't matter if what you're planning is relatively simple (backcountry hut trip, reunion in Costa Rica) or complex (remote paddling trip in Alaska); it's all about organization.
ESTABLISH A GROUP LEADER. Usually it's the guy who came up with the idea; he wants to do the trip the most. When there's a leader, all the others know what time they need to wake up and where they need to be.
CHOOSE YOUR TEAM WISELY. When it comes to any outing that's based on a sport, the group is only as fast as its slowest member.
DEMAND COMMITMENT. Start by establishing a cutoff date. If your trip is in April, people have to buy plane tickets by January or they're out. For a hut trip to a place that sleeps 12, I'll send out 20 invites. The first 12 to commit are the ones who are going.
KNOW YOUR GEAR. A once-in-a-lifetime adventure isn't the time to try out brand-new—or rent unfamiliar—equipment.
MAKE LISTS. Lots of lists.