To a large extent the CD's job is one of those in which if you don't have anything bad to say about the cruise staff or the program, he/she is probably doing the job well. Despite the numerous public aspects of the job, a big part of it takes places behind the scenes in an administrative capacity.
That said, obviously you'll "connect" better with someone who shares your sense of humor, your personal experiences, your view of the world. But you can't expect that to happen every time. And, of course, it will be different for different people.
I felt that Jim Cannon was one of the finer CD's I've encountered (twice), especially when he was teamed up with Amanda Reed as SoHo. They made a superb statement for Celebrity as a place to have a lot of fun, but that also catered to ladies and gentlemen. I believe that neither of them is working on the ships anymore, and I think that's too bad. We also sailed with an RCL CD named Clo something-or-other (maybe O'Conner, O'Brien, O'Doul), whose Irish sense of humor just put me on the floor laughing. One day at a quiz thing that very few people showed up for, she regaled us with the story of how, when she worked for Renaissance, she was CD on a nudist cruise and had to escort one couple to the Captain to be married. She said that the bride wore a veil, the groom wore a bow tie, and that was pretty much it. Had me in stitches.
Most of the rest of them are interchangeable parts as far as I'm concerned, which isn't a criticism. Their jobs are very difficult and require tremendous stamina and energy. As a group they do a fine job.