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I've led quite a few groups through one of the biggest caves in Canada, and I've received leadership training from the Association of Canadian Mountain Guides through the Alpine Club of Canada.

Keeping your group together starts with establishing leadership. It's the responsibility of the leader to ensure that no one gets separated from the group. Every trip or excursion sponsored by the Alpine Club of Canada has a designated trip leader, even if all members in attendance are of equal ability, the trip leader is still respected as the designated leader for that trip.

Whenever I'm leading on a hike or in a cave, I always ensure that I'm out front, and check my shoulder occasionally to make sure the whole group is keeping up. It helps to have the slowest, or whomever you feel needs the most help close to you. This helps you set a pace that the whole group can keep.

With large groups it's helpful to have a second leader who takes up the rear, then you can know that the whole group is with you when you can see that person, otherwise, headcounts are helpful. I guided a group of 17 kayaks on a river this summer, and headcounts helped me out a lot. I had one leader in the front and one in the back, and I would float back and forth between the two. There were a couple times doing my count I came up one person short, and discovered the leader taking up the rear had unknowingly passed a boy at a fork in the river, and got ahead of him before the confluence. The boy kept falling behind because he was cold, so I ended up towing him for the rest of the trip.

It's also helpful to establish periodic check points; predetermined places where everyone regroups. In the cave I guide most frequently there are multiple rappels along the way, so it's easy to establish checkpoints because everyone has to wait at the top of the rappel for their turn on the rope, and we don't proceed until the last person is at the bottom of it. Even with checkpoints though, sometimes it's prudent to stop the group impromptu when the leader notices people are falling behind, and continue on again when everyone regroups.

All the suggestions above only work if you've established a leader. It's like herding cats if you've got people up front that don't take direction from anyone, so make sure you establish leadership and protocols at the beginning of the trip. If you don't, and you get half way through a trip and people are getting spread out too far, it may be prudent to stop the group and suggest that some order be established. I've spoken up more than once to offer suggestions to other leaders when I've recognized that a group, or member of the group was struggling with a climb, hike or other excursion.

As for hiking, it's mostly about group discipline and communication. From my experience, I find the following actions to be effective.

Put someone strong and fast to the end of the group - they should watch for anyone else not to lag behind. If someone can't keep the group pace, this last group member should notify others, and then the decisions are to be made about reducing the pace, taking some load off the lagging member etc.

Watch for the front member - if they're too fast, then don't hesitate to tell them to slow down. If they can't keep the slower pace - put someone else to the front.

If you, as a group member, see that the group is spread, then call for others so that faster would halt and wait for the rear ones.

Mind, that in different terrain and weather conditions you could allow different 'safe' distances between the front and the rear group members.

The simple solution is to put the slowest person in the front of the group. This does two things.

1. As long as no one passes, the group will naturally stick together.




2. It encourages the slowest person to speed up, as being in front causes pressure to go faster.

At the same time, a little spreading out is not a bad thing, because it allows the group to see who is the slowest and who might need extra help.

There was a trip that I was one where because the leaders were so careful to keep everyone together that it wasn't till much later that we realized how out of shape certain members were.

I very much recommend formally asking the group’s permission for you (or someone else the group designates) to tell them what to do as needed in order to keep the group together. Everyone tends to shrug and agree, and then that breaks down the momentary hesitation to say anything when the group is starting to split up. It’s much easier to prevent than fix.

Once that understanding is in place you can employ whatever tactic you want (putting one of the more capable team members in the “sweep” position at the end of the group, with the explicit agreement that they are empowered to set the group’s pace based on what they observe, seems to work well).

The concept is simple it’s the social aspect of execution in the moment (telling an older / more experienced / more grouchy person what to do) which causes hesitation so this upfront agreement really helps.

In the roller blading groups (50+ people) I've been in in Florida and NYC they have a sweep at the back whose job it is to make sure the slowest person is always with the group.

Everyone goes as fast as they like, but the leaders have a pre-planned route and take breaks at designated rest stops and wait for all group members to arrive (the sweep). Then they set out again.

Not everyone needs to know the route.

I would recommend rest stops at pretty areas, or where paths diverge, or places with seating or water. You can use walkie talkies for group leaders to keep in touch.

We had this as a constant issue when I worked in a school with a strong outdoor program.

Hiking

Slow people in front. In extreme cases, start them off 10 minutes early.

Slow person with a pacer. Individual behind the slow person encourages and gives tips.

Designated sweep. This is a responsible (and strong) individual who is last, and makes sure that people don't evaporate off the back end of the line.

Group leader generally travels at just sight range of front of group. So with a 25 person group, he may travel about position 8-10. When I ran trips about once an hour I would work my up to the front of the line, then drift back chatting for a bit with each person and looking at them to see how miserable or happy they were. Since it's a lot easier to go back than go forward my favorite position was to be where I could just see the first person.

System of whistle signals.

Two long blasts from behind. Stop the front of the line. Acknowlege with two short.
Two long blasts from front. Where are you? Acknowledge with two short. Used when you weren't sure how far back the other end was.
One long blast from behind. Proceed. Ack with two short.
Four long blast from behind. Proceed, but slower. Ack with 4 short.

We used fox40 whistles which are very loud, but unfortunately sound a lot like marmots. Hence all the 2 toots.

Two others we had in our list, but didn't use normally:

Three long blasts: "Come to me!" Three shorts "I'm coming" Three blasts is a distress signal. We tried not to use it unless necessary.

Canoeing

On lakes we had designated lead, point and sweep. No one went ahead of the lead, further from shore than point, or fell behind sweep.

Rivers were harder. Worst case was a 12 canoe brigade. The problem with rivers and small stream work, is that if a canoe gets wedged on a rock, you can get a pile up. We never had this actually happen, but we talked about it a lot.

On rivers we traveled in groups of 4 canoes. A group generally traveled in yelling distance, although everyone had a whistle to get attention. Usually the 2nd most experienced or skilled person would lead. He most likely to not get in trouble, and best able to say if this was beyond the group's skill. It also meant that there was someone at the bottom of the rapid to fish out the debris if someone dumped.

The last canoe had a highly skilled person too. He was the one who would have to dodge wedged canoes.

Groups traveled about 5 minutes apart. When we got to the next lake or long reach we would pause and regroup.

Dogsledding.

Group was split in half with one half going ahead on snowshoes breaking trail. The mushers broke camp, and would set out an hour later. We treated the two groups as being independent, sometimes not seeing each other all day. More commonly the dogs would catch up in a bit over an hour. Mushers would halt, and then catch up.

If the terrain was rough, mushers would have to park a sled and help the guy in front or behind get up the hill/over the creek bank, around the deadfall. On occasion, breakers would have to come back and help the sleds. On rare occasions the breakers got too far ahead.

Keeping the sleds in a group wasn't a problem. Dogs will go faster if there is a team in front of them.