We've hit that point in the winer season where I can take the time to write about some of my experiences in the summer. I did a lot of shepherding - trip leading, assistant trip leading, taking students out for their first time on the river. Because there are different dynamics depending on the context, I'm splitting them up by the circumstances, whether commercial, club, or just out with my mates.
In a commercial setting, there are two factors that aren't present in other settings. First, you never know who is going to walk through that door. Second, you're providing a service in return for a fee, so there is a contractual relationship to the trip.
When I say you never know who will come through that door, I mean anyone can show up. Unless they are clearly going to be dangerous to themselves or to others, you've going to take them out.
Most people are OK. People who decide to try kayaking, and are willing to pay for it, are generally self-selected to be healthy, moderately fit, and willing to put themselves in a novel and dynamic environment.
A few people walk up to that line, and someone, either a friend or their own bravado, convinces them to step over it, and once on the water, they need some attention. Maybe they're afraid, and you need to reassure them, or just keeping near them. Maybe they lack ability, and are going to be the slow boat that needs lots of coaching, or a tow. Maybe they're just oblivious, and having so much fun that they don't pay attention to danger, coming too close to a pier, too far out into a channel, or just plain horsing around.
We ha one couple from Canada who we took across the river and back at the shop. A husband and wife, both had some experience, the husband more than the wife. The wife kept asking why we didn't have bilge pumps for every single boat, which she said was the law in Canada (we had two for our four boats, and those of us leading the trip are trained in rescues). On the way back, the wind picked up and we had some chop. Her hands were tight and she only looked straight ahead, never turning her body. Her husband was far more comfortable in the swells, and had a smile hidden in his beard, like a dog hanging his head out the car window.
Another challenge is that it's possible to end up with widely disparate skill levels. There were at least three trips I was part of where we had one very skilled paddler, typically some Norwegian or Swedish badass who just wanted to try some urban paddling, and then we had two to five regular folks, in one case a second date and n another a group of buds celebrating a birthday. In these cases, we gave the skilled paddlers a longer leash but kept within communication range, and on the way back, one of us would go with the advanced paddler to get in whatever they wanted - speed, play, some wee beasties - before we landed with the main group.
The commercial part of these trips is rarely problematic, if you're clear about expectations up front. If someone pays to paddle out to the Statue of Liberty, they're going to want to see the Statue of Liberty nice and up close. If your group is too slow, you'll have at least one disappointed customer unless you find a way to get them there and back (in the particular case I am thinking of, we did). If you are foolish enough to guarantee certain outcomes, without language about skill level, sea conditions, and safe judgement of the trip leader, then you're setting yourself up for a bad conversation.
In one example, someone took out a commercial trip to circumnavigate Manhattan. Normally, this is about an eight hour trip. They got a late start, they got the tides wrong, they took someone who simply did not have the ability (and had to be towed three quarters of the way) and on top of it all, the weather was terrible, rainy and cold. It took them fourteen hours to complete, and while the clients were polite in their complaint, they did complain to the owner.
One final bit about commercial shepherding, which isn't exclusive to it, but more of a factor than elsewhere: people misrepresent their abilities. In my experience most people don't, because they're new to it. In some cases, people understate their abilities. because if you've been in this sport long enough, you get tired of braggarts. However, the problem people are the ones who know just enough to try and bull their way in . . .to some unknown purpose. They may try to parlay some lake experience and a single trip on Long Island Sound into representing themselves as a se kayaker, or they may have heard of braces and reverse sweep strokes and "back deck finish" rolls, but from YouTube or books. Worst, they may say that are BCU 2 Star or ACA Level 4 paddlers based on a course they took five years ago without much paddling since.
What I've learned to do is interview heir experiences. Have you paddled before? Where? What were the conditions like? how high were the waves, how strong was the wind? How long were you out, how far did you go? And so on. Watching their behavior as they answer is as telling as the answers they give. I'm not saying you need to be a lie detector, but based on their confidence, and how realistic their answers seem, you can get an idea of how prepared they actually are for a trip on the water.