Chris...my advice for a neophyte is first educate themselves first on what the different components of a system are (Robert Harley's Intro to High End Audio book is a good place to start) and to also learn what the terms used to describe audio performance mean (again RH's book has a glossary so does Stereophile website). Mastering the basic language used by the user and reviewer community is key. At the same time, have them take out a subscription of TAS and Stereophile and let them read it for 3 months. Range of products, terminology, etc...all starts to seep in.
With phase I out of the way (1-3 months depending on how curious, anal retentive, detail-oriented the person is will determine length of this phase), I would then, as Dan said, have the person decide on what is the maximum allowable budget they feel they can put up. If they can afford $20K but feel they only want to spend $10K because they are not sure, etc...tell them to spend the $20K (do it right the first time...the incremental method ends up costing a lot more when all is said is done).
With budget defined, I would ask them what software they already have. As that will determine priorities on where to spend on sources. If they have 5000 CDs and 0 vinyl, then the source is clear (digital player/transport with an accessible digital input so that PC/music server audio is also an option or a DAC/digital streamer if CDs are already digitized, etc...). Obviously, if person has vinyl and CDs ir digital downloads then a mix of the two and so on. With that figured out, phase 2 is the most fun and the phase in which I learnt the most and developed my sense of what to listen for and that is literally a 2-3 months of auditioning gear at bricks and mortar dealers. In Phase 2a (first couple of weeks or month), I would visit the available dealers in the locale, assuming there is more than one, and tell the dealer you are just starting out and this is your first system and your budget is $x and it needs to have the following sources, and here is my interest in music, and where the system will likely reside (common or dedicated room), etc... See what the dealer puts together and listen. Ask the dealer for their rationale for choosing the components and speakers that they did. Ask the dealer what one should listen for when auditioning a system. This phase also separates the chaff from the wheat in terms of determining which dealers really are want your business and are customer-service oriented. In this phase, one will start being able to develop biases/likes/dislikes. Remember the systems/components that drew you into the music emotionally and those that didn't.
Once Phase 2a is done, Phase 2b is another month or two of winnowing down the list of components one is interested in, doing more research online (reviews and forums), and going back to dealer(s) asking to listen to specific systems you have put together.
Repeat and rinse until you come up with the system of your choice.
Major caveat: if one does not have any local bricks and mortar dealers, then Phases 2a/b will have to be combines and compressed and achieved by scheduling dealer visits in advance when on business or vacation trips to a location where B&M dealers are available.
But if Phases 2a/b (i.e., demoing and listening for yourself) are not done, then no matter how much research one does, I believe any system you put together sight unseen and unheard is a crapshoot.
Sorry for the lengthy description but that was my process 7 years ago and it's probably one of the most fun times I had in this hobby.
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