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I know there's not a cut-and-dried answer to questions like these, but there might be some guidelines I should be thinking of and it may help others as well. The case is as following:

I run a wiki community with a few thousand articles, and I may want to have it re-designed in the near future. Currently it looks pretty okay but there's a lot to improve especially when it comes to usability and a consistent style. Pre-fab designs are almost never what I'm looking for, especially because the website is so content-driven and focus must lie on good readability of the articles without losing the thematics of the subject (a rock band). Imagery and a certain dark style are very important with this band, so a good balance between readability and style will almost certainly have to be a custom job by someone who knows about these things.

The current implementation counts two basic pages (main page and article pages) and some variants like article edit pages, user settings etc which are mainly article pages with some extra elements. Apart from this the article contents can have so many kinds of elements (infoboxes, templates for different kinds of related content, etc) these will have to be designed too.

What should I look for when searching for a designer? What are good price indications, how can I tell if the designer knows about usability and can deliver what I want? Can I ask him to give me a first draft (for a small payment of course) to see if he fits the bill?

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I have a more altruistic answer below, but keep in the back of your mind the proliferation of templates. We were on the verge of hiring a Grade-A designer once when it struck us that her entire portfolio was derived from TemplateMonster.com. We asked her directly if she used templates (which would be OK to a point, right?) and it went downhill from there! :) –  Chris Adragna Dec 8 '10 at 18:38
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4 Answers

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Judging by your question, on thing to keep firmly in mind is the difference between a designer that focuses on general website design (user experience) and a graphic designer.

It is a very common mistake to hire a graphic designer to redo an existing site. Typically, while the new look will feel fresh, a graphic designer will not be able to greatly improve the overall user experience (that is simply not their job).

There are of course individuals that can do both tasks, but those are not common in my experience. I would for instance maintain that I'm a decent website designer but I lack all talent for graphic design. Thus I tend to bring in a graphic designer 'to make it look pretty'.

So if you just want to redo the graphics, hire a graphic designer. But if you want to improve the usability of the site make sure that you are not (only) hiring a graphic designer.

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+1 — I've been asked to implement some very pretty and terribly impractical and unusable designs over the years. Make sure you have a designer who understands all aspects of web design and not just art (or at least that they are working with someone who does understand them and can call the designer on the bad stuff). –  Quentin Dec 9 '10 at 7:42
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Consider their portfolio; make sure there is work in there that reflects the style you want on your site. Also ensure that they fully understand what your requirements are for the interface, and ideally see if they have examples they've done for others that can give you a sense of what you'll be paying for.

Also settle in advance how the mockup/review phase will proceed. This protects both of you by ensuring there is a common understanding for when the final design and coding can proceed and when the job is officially considered completed.

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Be aware that coming from diverse backgrounds or skillsets you often times will use different language or infer different meanings inside the same conversation. This is a contributing factor to becoming frustrated with each other.

You can overcome this by:

  • maintain an awareness of your differences
  • attempt to meet in person whenever possible. Being able to read a persons body language gives you the cues you need to know that they really Get what you mean.

The orientation I refer to is analogous to points made in the book Men are from Mars and Women are from Venus, but not (necessarily) due to gender difference.

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What should I look for when searching for a designer?

Look at designers' portfolios and (possibly) look up the designers of other sites which demonstrate the style and functionality you're after.

What are good price indications[?]

Strong, distinctive visual design is rarely inexpensive.

Given that you effectively have two requirements - artistic design and usable web implementation - you might consider having a graphic artist put together a layered PSD and then contracting a web designer for implementation as Kris suggested. (in my experience, that gives you more artists to choose from and you'll end up spending less on web design than you would if you were paying the same person to do both)

How can I tell if the designer knows about usability and can deliver what I want?

Let artists' and designers' portfolios speak on this point.

Can I ask him to give me a first draft (for a small payment of course) to see if he fits the bill?

It is typical to have several mockups put together before a final composition is selected, however, most artists will expect to be paid their full rate - this is, again, why it is important to narrow down which artist you'll work with by looking over portfolio material.

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