This could be a difficult task, especially if you are attempting to sell him on using your services for a remake of the site. I would recommend the utmost discretion and tact, since the site is really his baby. You have to kind of praise, and criticize, and offer options, all at the same time. I don't know about web sites, but what I say for ugly babies is, "Madam, that is a remarkably good-looking chimpanzee you have there, but shouldn't you consider orthodontia to brighten that cheery little smile?" -- Jerry Muelver
I've had really good luck saying something like--"It's important that a site is updated from time to time so it remains fresh and vibrant. Even the best sites get stale after a while. So I'd like to offer my services...blah blah blah..." -- [Mark Henri]?