Rutsahl
How does the process work?
Does he give you his ideas, have you draw something up and get back to him when you're finished, or do you both work on it together (like in the same room, with him watching you draw.)
How many rough drafts and back and forths do you usually go through with a particular piece of work before it's called complete.
Ben McSweeney
Usually I get a rough draft of the novel, which lets me start looking for seeds (here is a neat thing) and direct subjects (here is a neat thing that Shallan is specifically described as drawing), and from that we build a list for what we'll actually produce.
Unfortunately, geography prevents me from working in the same room with Brandon very often, but we live in the age of email and Skype so it's mostly just an inconvenience that we work around. Generally what I'll do is start drafting rough sketches, submit them for feedback, and begin a cycle where we spitball ideas and work back and forth until the subject's design is settled. Then I lay out the actual Shallan page itself, putting the subject into place and deciding what else we can include. Once the page layout is approved, I'll render the final illustration.
During the entire process I'm in a regular email loop with Brandon, Peter and Isaac. We make loooong email threads. Some designs take many iterations before we get it right (the axehound was particularly difficult), some designs are nailed down almost instantly (Brandon and I got on the same page with Shardplate pretty early). There's no way to predict how it will go until it gets going.