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So, Hacker News readers who have hired people based on resumes before: How would you feel, and what would you think, if you encountered this on an applicant's resume?
I would ask why there isn't a nonbreaking space between "Adobe" and "Illustrator".

I can't think of a single instance where I made a hire/no-hire decision based on a resume. The resume indicates that they're sufficiently interested/skilled in the kind of work we do to give an interview, and gives me an idea of specific things to talk about during that interview. That's all.

You could write "I implemented a Lisp compiler for StrongARM. Berkeley CS, 2002" on a polaroid of your cat, and I'd give you an interview. But Initech is probably going to be different.

I would wonder what the hell was going and why they were messing around with font sizes and diffent shades of grey on my black and white print out.

Its a nice concept but in practice it does not work. Props for trying it out.

I have done a lot of interviewing of programming candidates. If I saw a tag cloud like this, I would put this in the pile with the guys who list their skills and give themselves little unicode 'star ratings' like a movie review, in each skill. That is, 'only consider for interview if we are getting desperate to fill a seat'. It says the quality of the candidate is unpredictable but with strong odds of being flaky.
I bet this is a good way to get your resume sent straight to the "no hire" pile.

If I had a big long list of skills and technologies to list, I'd instead organize them by category (operating system, tool, language, whatever), with a bold heading and a linebreak for each category. That way you have a chance of it actually being readable.

Then again I haven't applied for many jobs.

I would wonder why someone who is a claimed expert (fancy color, large text and all) in copywriting has an extra 't' in Adobe Audition. :)
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Neat but non-technical HR reps who filter resume piles won't get it.

In general its best to write the resume to match the job description. Rather than listing all of your skills list only the skills that job requires plus a few extra closely related.

Listing too many skills can get your resume tossed because the resume reader will see a lot of Adobe products listed and think you're more of a graphic designer than a developer. Concentrate on what the job opening asked for.

I think this a pretty manufactured example. Does anyone list their skills as an randomly ordered, unformatted wall of text?

All that precious formatting gets lost and the meaning changed if it's copied into a plaintext email (you're back to a randomly ordered list) or printed (color text becomes light gray).

And how does one maintain that cloud? If you get better at something you have to increase its type size, alter its color, and probably change others since items in the cloud are supposed to be sized relative to everything else.

Rather than use a hard to maintain format that you have to explain (is everyone familiar with cloudmaps?), just use words and say I'm not so good at this yet.

Like henning says, the solution is just some simple organization:

  PROGRAMMING LANGUAGES
  CSS 
  Javascript 
  Some experience with SQL
  
  SOFTWARE
  Adobe Photoshop, InDesign, and Illustrator
  Basecamp
  Final Cut Studio
  
  OPERATING SYSTEMS
  Mac OS X and Linux
  Some experience with Windows
  
  Etc.
might work at the top or something in addition to breaking stuff down by category - would help you stand out a bit make it less boring if you've scanned 50 cvs that day already...
A terrible idea, just like how tag clouds are a terrible idea.

I was talking to some HCI folks recently, and they said that in a study people thought there browser was broken when they encountered a tag cloud.

Simply does not work.