The Whether Man, the Ordinary Man, and Canby are three interesting individuals Milo meets during his journey to the Lands Beyond. Each of them encourages Milo to question his surroundings, which is a good thing… right? Well, kind of. These guys are so infuriating in their relationships to questions that it wouldn't be surprising if they turned Milo off to the question-and-answer game for a little while. But it's proof of Milo's good humor that he goes along with each of them and continues to be patient. What a guy.
The very first person Milo encounters in the Lands Beyond is the Whether Man. Milo's conversation with him gives a small example of just how wacky everybody else in the Lands Beyond is going to turn out to be. Even the Whether Man can't help twisting ordinary words around and giving them new meanings: "I'm the Whether Man, not the Weather Man, for after all it's more important to know whether there will be weather than what the weather will be" (2.11). The Whether Man brings out the idea of uncertainty and he's the first of many characters to encourage Milo to get away from the end goal of just making sense.
The ordinary man, on the other hand, is more interested in being extra special to different audiences than he is in answering Milo's question:
"You see," he tells Milo, "to tall men I'm a midget, and to short men I'm a giant; to the skinny ones I'm a fat man, and to the fat ones I'm a thin man. That way I can hold four jobs at once. As you can see, though, I'm neither tall nor short nor fat nor thin. In fact, I'm quite ordinary, but there are so many ordinary men that no one asks their opinion about anything. Now what is your question?" (10.33)
Like the Dodecahedron, the ordinary man has many faces. But unlike the Dodecahedron, the ordinary man's faces are all actually all the same. He just looks different in different contexts. How's that for a puzzler?
Finally, on the Island of Conclusions, Milo meets another question-related man named Canby. Canby has a lot of questions (namely, who am I?) but just one important answer. How did they all get to Conclusions?
"You jumped, of course," explained Canby. "That's the way most everyone gets here. It's really quite simple: every time you decide something without having a good reason, you jump to Conclusions whether you like it or not. It's such an easy trip to make that I've been here hundreds of times" (13.52-54).
Canby knows how to get to and from Conclusions, since he's jumping there all the time, but he's lost the sense of his own identity. He doesn't know who he actually is, and even has to ask strangers for his own name. Guess we need to really look inside ourselves for answers, instead of just, well, jumping to conclusions.