UPDATED: 5/18/2007 with some of my current wisdom
Some of the most common problems I run across when working with clients are things can easily be avoided by interviewing your clients ahead of time and working out the details before work begins. All to often beginner web designers are anxious to jump right into the design stages of a project or worse yet even coding. The following is a set of questions I send to all my potential clients that has enabled me to spot problems or raise flags right from the beginning:

5 sites that the client likes the design of irrespective to the content.
What are 5 web sites that you like the design of. These sites can be any sites on the internet. I ask them to provide me a quick description of what they like about the site, such as navigation, colors, fonts, etc. From here I can get a good idea of what the client’s tastes are. Now this may vary a bit from what the web site will eventually end up as, as the goal of the site may differ from what the client’s personal likes and dislikes are, but I find it is very much a good window into where the client is coming from.

3 people/companies/organizations they would consider their competition
This is particularly helpful if your client is kind of up in the air about the design they need. If you client’s market has a certain look and feel to it, you will most likely want to make sure you are competitive. These competition may also give you more insight into the clients market then they are able to provide in an explanation.

5 descriptive words they would want people to think of when they see their site (conservative, traditional, modern, goth, web 2.0, etc)
All pieces of marketing material, web sites included, attempt to convey messages quickly as possible through colors and style. This, even above your content, can put into a visitors mind their impression of you, your product/service and organization. If your customer wants to be the new hip hang out coffee bar they are going to want a theme that reflects that look and likewise a conservative law firm doesn’t want to look like a skating rink. Getting a feel from the customer about how they want to present themselves can dictate your color schemes, design elements and overall layout fairly quickly.

What is the web site goal… is it for people who hear about them and then go to the site, will be be people finding them through search engines, is it existing clients looking for support, etc.
While many customers just want a web site for the sake of having a web presence, a good web site also has a purpose. Whether is be to sell a product, provide support, showcase a portfolio… whatever, the design of the site, specifically the homepage is really dictated by what the client wants to accomplish with the site. If the client is trying to sell a product for example, a design focusing on product quotes and call to action statements will provide much more success to the clients goals. Following the same theory, a web site made to support a product a customer would find on the shelf in a store should have upfront access to FAQs and documentation.

What are your goals for the site today and what are your goals for the site in a future?
Does the client want to use SEO for the site right from the start? Will they be using it later? Should you build SEO into the design? While a good designer will try and make a flexible solution that will meet “everyone’s” needs, sometimes that isn’t cost effective and sometimes a clients desires don’t match their needs. Having a flash and graphic based sites are not going to be easy to maintain for customers who are used to WYSIWYG editors. Make sure your customer understand the “price” (time, money and skill) for the technologies they choose to use.

What sort of navigation is the web site going to require?
The design of a web site often is dictated by the amount of information it needs to convey. Simple and clean designs are in fashion… 2 or 3 links and big text areas, but this doesn’t work if your web site has 100 pages broken down in a hierarchy. Getting an outline of the navigation structure from the client up front dictates the size of the site as well as how you need to built in the navigation. Many design elements are dictated by the amount of data that needs to go into them. A small horizontal navigation doesn’t work really well if you need to put 50 links into it. Find out if the navigation is hierarchical and what NEEDS to be visible from where.

What are the expected deliverables?
When dealing with small clients or people who are new to the web, the line between web designer and webmaster is a blurry one. Make sure to clearly identify what is expected from you on delivery date. Make sure you aren’t expected to copy their 100 pages of text from their PDFs or their old site into your design and create all the necessary links… and if you are, make sure to include that time in your quote. I have done projects where I have scoped out a design and a template and gone 98% of the project showing the client the template with the understanding that I was the “designer” and then on delivery day “You only sent us 4 files, we have 62 pages on our site?”. A clearly defined deliverable list including the components as well as what you tested on will save you a lot of headache.

Who will be maintaining the web site/software once you (the designer) are done?
If you are fortunate your client will keep you on retainer to do all the updates to the site, however this isn’t always possible. If you client is going to be maintaining the site themselves (or having a 3rd party handle it), they may be planning on updating the content or design in a certain way, such as using FrontPage extensions, Dreamweaver or using the built in WYSIWYG editor in a application like Wordpress. These things should definitely be taken into consideration while designing the site or software as the customer might have expectations of how easy it is to edit or that editing will work in a certain fashion. To save yourself hours of headache in “support” make sure the client knows what skills they will need in order to maintain the software. If the client has never used Wordpress before and you implement a Wordpress site for them, most likely they will think of you as tech support for all their blogging 101 questions. Most likely you aren’t going to be able to avoid this, however knowing what the client is thinking and getting a basic understanding on what the client does and does not know, gives you the advantage in being able to prepare. I always keep articles and tutorials handy to send to my customers to help them learn what they need to know which also cuts back on my support. I also am very clear with my customers upfront about the scope of the project and let them know that support may be additional to the cost.

What web server platform will you be hosting your web site on?
Although not as important with static HTML sites, things like file and path names, server side includes and web applications like blog software and forum software are server dependent. With most of the work I do, my clients either have existing web space or are signing up for web space with a host and while the client may be smart enough to know they need Wordpress blog software, they may not know that running it on Linux versus Windows makes a huge difference when it comes to features and options.

Optional Questions for CMS Design Clients: What CMS do you want to use and what is the lowest version my design should support? What versions of the database (if any) and web server do I need to support?
You would be shocked how many of my clients are running old versions of software. This may be a question of resources, compatibility or even politics… but it is something you need to know before beginning. Template design in specific is very sensitive to changes in the core content management software so if you design a template based on the feature and functionality of one version of software and your client then needs it to run on something from 2 years ago, chances are you are going to have a headache. I definitely support letting your client know they are running on an old version (after all maybe they don’t know!) and sometimes I even throw in a free upgrade (particularly on easy systems like Wordpress) but you need to be prepared on delivery date to be able to take your designs from where you were developing/staging them and have them work on the clients machine.

Optional Question for Static Web Site Designs: Are there any special components you need in your site? Contact Form? Shopping Cart? List of store locations?
Will there be any dynamic components to the site? Anything that relies on a database? Things like contact forms and shopping carts seem abundant on any web site. With that in mind, a lot of customers think it is a quick and easy thing and forget to mention it. Anything dealing with “processing” (sending something to a database or email address) requires scripting knowledge and specific machine resources to complete. This may dictate what server platform you can host on as well as what knowledge the web designer will require. There are third party options to host these things off your web site, but most have a monthly cost associated with them. Finding out for your client if this is an expected portion of the project, determining if you have the skills or solutions available and clearing up any costs or requirements up front saves time and headaches down the road.

What is the target market from a technical standpoint; what browsers do you want to support as well as bandwidth considerations.
When a customer is rolling out their first web site for the first time I have found they have a tendency to over do it. They have spent a couple years on the internet most likely looking at web sites and been oooed and ahhed by all kinds of nifty flash, ajax, and other multimedia bits and bites. When they decide to make or have made a web presence of their own, they often want to include similar things so they will put on a good show. This sometimes completely contrasts with their target market. Knowing who is coming to the site is a huge variable in the design of a site. If the majority of visitors to the web site will be on dial up through AOL that is a whole different ball game from the geek market on broadband with Firefox 2.0. Explain to the customer why their desires may not be a match for their potential market. While you may be down selling your services a bit, you will most likely win when it comes to support or when the client puts their site to market and wonders why they are getting complaints of things loading to slow or certain things not working.

Can I use Public/Open Source Components and If So Are there Licensing Concerns?
Sometimes my clients want to resell my designs or provide them to their customers. This can be particularly tricky if things are licensed under the GPL or under a specific Creative Commons license. It is best to be clear up front if you need to use a 3rd party component that the client understand what it is and the responsibility they will be undertaking to maintain/upgrade that component. Make sure that they are comfortable with the license that the component is classified under. It isn’t your job to be their legal council but a simple “I would like to use X component in my design for the gallery, it is licensed at http://www.example.com/license.html. Can you please look it over and make sure that is acceptable?” It is definitely important to make sure that you make sure that your client agrees that you can use components that you didn’t write otherwise you may be voiding your contract of work and giving them a heads up on the license will save you from emergency phone calls “We tried to resell your template but our customer said we were violating something called the Gee Pee L? Do you know anything about that?”

Do you have all the resources available that I will need and can I see them before we start?
Lots of times my work entails modifications of existing sites or incorporating existing elements into my designs. Make sure your customer has access to the layered/vector or large sized logos they would want to use as well as any graphic elements they may have. As any graphic designer will know, you don’t want to spend hours slicing out or recreating logos from old single layered images (or if you have to do it, you want to get paid for it!). If they want PDF documents on their site make sure they have the PDF or find out if you need to convert them, again other things you need to plan/charge for. Check to see where the content for the site is coming from. I have found a lot of my clients hear the deadline of my project as the day their site will go live but then realize that there is no content in the site and they aren’t ready to roll it out. Bringing this point up in the beginning (as well as establishing a delivery date of the content if it needs to be authored, so that you have time to place the content) allows the customer to plan that into their schedule as well as budget.

What is their budget
You can’t get water from a stone and before you get into deep discussion about the design and business needs it is good to know you are not spinning your wheels. Lots of designers and consultants are gun shy when it comes to talking about money as they think it scares the client. I personally take a very straight forward approach when it comes to business and while I do believe in the concept of up selling your services, if the money isn’t there it just isn’t there. Sometimes the customers expectations are completely out of whack with the amount they want to spend. Once I determine a customers budget it allows me to be able to comfortably work with the customer knowing we are both thinking the same thing. If the budget doesn’t match their expectations I also am given an opportunity to be able to explain to the customer what I can do for them within their budget and perhaps even create a long term plan that starts out with a more minimal amount of money for a smaller set of goals and then grow that foundation as funds become available.

What is their time frame
Find out of there are any deadlines that need to be met such as a roll out of a new product or holiday season. When creating your delivery calendar keep in mind that customer will be way more comfortable if you can provide them some time between your final delivery date and their deadline for them to get used to the site both from testing and from a maintenance standpoint. Create milestones and explain to the customer the effects of missing milestones. I have found creating a custom calendar helps illustrate the point well as they can clearly see that missing getting you the content even in the beginning of the project can shift things months down the road.

By getting answers to these questions upfront I find that I don’t spend as much time spinning my wheels on clients who don’t have the budget or resources as well as I get the client to focus on what they want making my work more productive.

Comments and feedback, as always, are welcome and appreciated.