You get really good at names

It helped that there was a clear correlation between a good trip and a good tip. In fact our boss swore it was causation. In reality it was as impossible to tell what the tip would be as what the weather would bring. In the morning we would pass around the clipboard with the schedule and attempt to build an image of the clients. Next to the name of their cruise ship was a descriptive row of paddling-related statistics: Name, height, weight, number of people in group, age, and special medical requests. Scanning the row I'd always hope for large groups. Large groups were easier to talk to for four hours. When I'd exhausted dad about baseball and the model of the kayak and the number of miles I can paddle in a day I could hang back and run through it all again with uncle Tom or Bill. Every other statistic was only there for speculation. People lied about weights and heights often. I'd stand on the pier gazing through the crowd shuffling off of the hulking cruise ships looking for someone who looks 6'3 only to have a man no taller than myself wander up to me. We had a number of specific kayaks that were specially fitted to accommodate guests with all body types. I had given tours to 5 year olds and 85 year olds, age didn't account for the wide variety of Americans and their levels of physical ability.

The group size was the only concrete fact I had to go off of before the group stood before me and I could size everyone up. Like I said, I enjoyed larger groups personally, 5-12 people was my sweet spot. This size of a group almost guaranteed that the group was all related to one another. Five people almost always meant a family. After all most people came on cruises for some occasion with their family. A bucket list vacation, or graduation celebration, or a full fledged family reunion. An extended family reunion was essentially a cash bonus, clocking in anywhere up to $300. They were immediately identifiable coming down the gangway. Two grade schoolers would wander in front of a cluster of uncles and aunts. I always bought a bright yellow paddle with me up to the docks, that way they could easily find me instead of the other way around. I simply planted my plastic pendant and waited for one of the kids to rush over. Then slowly the whole group would coalesce and approach. Uncle Matt or Mark had to stop in the restroom and I would have to loiter on the pier to wait while I introduced myself and sized up the crowd. On average there were three adult siblings, their spouses, a handful of kids between them, and then the grey haired matriarch and patriarch.
I became a formidable conversationalist. I don't remember ever struggling to make small talk or keep people interested. There would usually be an Uncle or the Grandfather who would jump at you right away. A handshake would seem the appropriate greeting for a man about to take you kayaking. First and foremost were names. You get really good at names. Knowing everyone by name is essential for good tips, should be the golden rule. Unsurprisingly, people like to be called by their own name. It makes everyone feel like there's camaraderie, a common goal, a relationship with a stake. Something akin but less formal than "team on three". Sometimes the Grandfather would loudly announce his whole family running through each by name, age, and relation. "And this is my wife Marry, that's Marry like Merry Christmas but with an 'A'". There's no way to forget that. Once Mark had returned from the bathroom I would lead the group down to our office, which was a run down houseboat moored to the dock of a charter fishing operation. The kids names were always easy to remember, especially the younger ones. I had their parents to thank for that. As soon as we got near the water I'd hear the parents reintroduce the children, "How can you be hungry David we just ate" or "don't get too close to the jellyfish Lisa they sting" or simply "Amanda stop". If the adults were not especially talkative you could hand the paddle to the kid and ask if they'd seen a whale yet, or what their favorite thing is to eat on the cruise ship. Informal second rule: This also, historically, helped increase tips. The parents had been in a small cabin on a boat with their excited kids for a few days by the time they reached us. We'd reach the houseboat and I'd help everyone inside. They'd take a seat along the sides of the boat on long wooden benches constructed to hold groups as big as 25.
This became a timed event. Records could be set and the goal was eight minutes. As soon as they sat down I was off, quickly reciting a memorized insurance disclaimer. I would do my best auctioneer impression and rattle off the risks and perils of "the inherently dangerous activity known as sea kayaking". What I said didn't matter much, everyone had it written on a clipboard bound paper in front of them. They'd all sign and then you'd begin the real test. Ideally when all the paper was tamped on the bench and slid into a manila folder only a minute had elapsed.