Here in San Diego I have heard many horror stories about web design projects gone completely wrong and plenty of positive stories as well. So what is the difference between the two? The reality of it is, that if it is not ability of the design company it must be communication between design and client that is lacking. This being said, both the customer and the designer should know exactly what they are trying to accomplish before ever even agreeing to do business with one another. This is not to say that there will be no curveballs during the process, but there needs to be a viable effort to eliminate as many of those curveballs as possible.
On the design side of things, the customer should be asked many questions, to the point that it is almost annoying. They should supply multiple websites that they like and explain why they like them. Also, you should see their logo and other print work, so you know what their brand looks like offline. Technical considerations are also a must. They should have a good idea of their exact sitemap and any considerations like e-commerce, Twitter feeds, blog sections, online payment options like Paypal, ect ect. This is certainly not an exhaustive list, but it will help to get the project started in the right direction.
Now from the customer side. What should you ask the designer? First and foremost, what are you going to need from me? Things like written content, images and logos can really hold the project up, not to mention the quality of all of those items will ultimately affect the outcome of your project. Make sure that the designer has high quality content and there will be no excuses on the back-end. Second, ask about communication. How are we going to manage the project and how will we communicate with one another? Via e-mail, phone, project management software or a combination of all are pretty normal, but when you need to get ahold of someone it is important to know the best line of communication. Last, but certainly not least, ask about a timeline for the project. Although there are countless numbers of things that can hold up any project, having a realistic timeline is very important. When asking about the timeline also ask about what types of issues can come up that may delay the project. Although many are unforeseen, there are a lot of experienced web designers that know exactly what type of things can delay a project.
All and all, just as with any successful endeavor communication is key on both sides of the table. Whether it is the client or the designer, if a solid roadmap is not put together before setting out, someone is going to end up frustrated. Make sure all the above questions and then some are addressed before starting the project, this way both sides will be smiling all the way J.