One can be creative (which includes imaginitive) as all heck and yet still not know how to put that creativity into practice.
I can dream up all kinds of great images in my head but haven't got the art-making ability to put them on paper or screen. That's where I need some sort of processor, be it human or machine, to do it for me to my instructions.
I commissioned dozens of art pieces from the same professional RPG artist, Storn Cook, for two RPG books I published.
Maybe my experience is different to other people's, but the way I approached that was absolutely NOT 'here is a complete description of what I want you to draw, like sheet music for a musician or a recipe for a cook'. He's the artist, not me. I actively wanted his input and creativity, that was the whole point of paying him! It was also half the fun of making the book.
Here are some examples from the art brief I gave him:
CHAPTER HEADERS
These pieces are specifically designed to act as headers/bookmarks for the most important chapters of the book.
They should take up half a page each.
5. WORLD BUILDING
This comes from one of your own ideas Storn: “A GM putting blocks and shapes into a world over countries, stuff flying around in bits… sorta GM type leaning over a fantastic Sims layout or Civilization type land”. The only thing I would add to that is that there should be multiple people overlooking the layout, to represent the fact that the players create the setting of this game on a more or less equal footing with the GM.
6. CHARACTER GENERATION
This was one of your ideas: “A PC type as a schematic showing various aspects of character generation.. General Abilities, Traits, Flaws etc.” I’m not sure exactly how that would look but it’s definitely something to explore. Another possibility is to base something around Da Vinci’s famous Vitruvian Man diagram (the one with the man standing at a T position and also an X position, superimposed together in a circle. Maybe combine the two ideas?).
7. SUPPORTING CAST
An archetypal supporting cast for a fantasy game all huddled together ‘for the camera’. For example, a dwarf wizard, a scrawny young squire holding a sword, a floating skull, an innkeeper, a king, a barbarian, and a cloaked rogue/spy type character (could be an antagonist of some kind). I’m flexible though – only the floating skull is mandatory.
8. CONFLICT RESOLUTION
Two characters engaged in a hand-to-hand struggle – both from the Silver Age 1960s superhero campaign example. On one side we have ‘The Spirit of Liberty’ – a winged all-american hero, flag on chest, eagle mask helmet (face covered with a beak Hawkman-style), try to make sure he doesn’t look too much like the captain america style guy you did for the silver age campaign picture. On the other side we have EITHER ‘Grindstone’, a grey rocky strong guy hero made out of stone. maybe looks slightly demonic/gargoyle-like? – OR – ‘The Red Spectre’ – a cloaked figure (wearing a suit? evil looking robes?) who is able to turn insubstantial, possess people’s minds, and manipulate tendrils of gaseous/shadowy energy. Choose whichever of those two baddies you have the best visual ideas for.
There should be a caption underneath saying: ‘The Spirit of Liberty vs. [whichever enemy you use]’