Direct answers:
Q) How do you deal with clients that make poor design requests? I know art is subjective but we also know what looks dated and may detract from a finish product in the eyes of the audience that will be viewing the product.
- Here's a shocking blow for you: the actual visitors? They don't care what your web site looks like. Really, they don't. Only "designers" and "site owners" care about "how it looks."
(there are some visual elements that are needed, but these follow function, not in the way most people assess "how it looks.") All they care about is finding their stuff.
See Web Pages That Suck [webpagesthatsuck.com] - it's true. So how do I deal with them? Swallow my ego and make it work.
Q) How much do you push and what tactics do you use to get the client to go your direction over theirs?
- I don't. "You can't change people, all you can do is change how you react to them." - my wife. Here is what I offer, if it doesn't help you and you don't see the value in it, we can't do business together.
(But this would never happen in respect to "design.") Q) Have you ever dropped a project because their design requirements were just to ugly or outdated?
- That would be silly. Design, IMO, is the least important part (see below.)
Q) If a client insists, what are some tactics you've used to "soften the blow" on the look of the site?
- Admit that it's my ego that needs to knock back a peg, it's not about me, it's about the business of making web sites work, no matter what I think of the "design."
---------
You really need to take yourself out of the equation and assume a more objective view. It's a hard thing to do.
Start with this:
What do **you** want out of this relationship? Do you want a "pretty" web site for your portfolio, or do you want to build a web site that will be of some advantage to the customer?
Right now you're probably thinking, WTH, how could an ugly design be effective? There are many examples out there, it's not the design, it's what it does. Start with Craiglist.org.
In the same way, you can **work** outside of yourself by making the site work the best way possible, and none of this has to do with the ugliness of the design. IMO, design is the least important thing of all, maybe even irrelevant. It's the ease of use and how well it solves the customer's problems, this is what makes it work.
I have a working example of this last week. From a series of designs, the client and sales rep picked one that is a putrefying combination of baby poo green and doggie doo brown, the entire design cries poo poo. Toss in what I like to call Stupid Web Tricks, things like transparent overlays (and make sure the text is legible laying over those high res <cough> images), lightbox effects, three columns across the bottom that can never align because they want to cram too much text that no one will ever read in there, a rotating slide show on the main page, an RSS feed they'll never maintain, and other fun stuff. As if that weren't bad enough, it was to be framed up in a CMS that is "supposed to work" on a Windows server but is generally only seen in the wild on Linux servers.
All of these . . . are challenges. Get past the putrid color scheme, get past the environment issues, build a site that will do well in the search engines with keyword rich URL's, a CMS that will allow them to maintain their site without a lick of HTML, one that will respond to their users well. Check, check, check, check.
It's in review this week, they think it's the hottest thing since sliced bread, and every.single.comment relates to "it **looks** really good.
No it doesn't. It's a poo-fest. But it's going to do really well, their customers will be able to find them, contact them, solve their problems . . . for all the reasons they are not mentioning. And that is the Holy Grail right there, not the design.
Does that help?