Do you hand in one sketch or multiple sketches?
The simple answer is that it depends. Sometimes I hand in one, sometimes more than one. "What does it depend on?" you ask.
"Why is there always a follow-up question?" I ask, in turn.
Concerned stare as I talk to myself... Fine. I'll elaborate.
First off, it depends on the actual art order itself. As I've mentioned before, sometimes art orders are extremely specific. When this is the case, for me the specificity of the description tends to suggest a single image. I draw that image on a piece of paper, scan it, and turn it in. Sometimes things aren't quite that simple, though. As an art description becomes more vague, there may be several options that come to mind. In cases such as this, I draw several images, scan them, and turn them in.
The second factor is the art director. Thus far in my career, I've never met an art director who would cry themselves to sleep over getting more than one option. In all reality, who among us doesn't like having options? I know I do. Art directors — being a lot like regular humans — like options too. What needs discovering is how important having more than one option is to any given AD. Now, I've had art directors who really liked to see more than one sketch every time. And, I've had art directors who didn't care one way or the other. Sometimes you get art directors who have a preconceived notion of what they want to see, and sometimes you have art directors who have no idea what they want to see and will let you know when you've come close. Getting a feel for an art director's personality isn't always easy, but it comes in time if you're lucky enough to work with them more than once. While sometimes the job itself dictates whether or not there's more than one sketch, sometimes it's the art director that requires it.
Even so, a normally decisive art director may still have no idea about a specific job and need to see more than one option. And this can happen even in the instance where the art order is rather clear and detailed.
The third factor that comes into play is deadline. Admittedly this is something that has only been a factor a few times in my short career, but it can be a factor. Sometimes a job is a rush job. And rush jobs need a quick turn around. In the editorial illustration world, the time between a piece's commissioning and when it's due can be mere hours. For me, the fastest I've had to turn something around has been a few days. When this has happened, everything has been quick and dirty. Ugly sketch that gets put together, nailed down, and approved as hastily as possible in order to set aside more time to paint. In these rush jobs, it's been pretty clear what was required of me. In fact, there has always been a verbal exchange between the art director and myself where we agree on a concept and visual direction before I even touch pencil to paper. The sketch is more or less the proof that I understood what we were talking about in the first place. So, it was more of a formality than anything.
Mind you, this does not exclude the possibility that you will have a rush job that requires more than one sketch. You might find yourself with some heady concept that's due tomorrow with an art director who has no advice on how to address the problem, or has no time to dedicate to the matter. You never really know what the circumstances may be. So, it's always possible that you'll find yourself putting together multiple sketches.
As I said above, sometimes I offer more than one sketch, sometimes I don't. With the clients I've worked with before, I know what is expected and they've grown to understand what I'm going to deliver. If it's a new client, I always offer more than one option out of the gate. It's a good rule of thumb. In fact, I'd say it's a good rule of thumb to offer up more than one sketch in general. You can never really go wrong by doing so. Above all, whether you've turned in one sketch or many, be prepared to do more sketches.
Throughout all this, keep in mind a universal truth of offering multiple sketches. More often than not, the sketch you're least interested in bringing to a finish will be chosen as the direction to go. My professors in college always spoke of this and I only half believed it as some hardened illustrator grumbling. Sure enough, however, it has proven true time and time again. The best defense against this is to not offer anything you wouldn't want to actually paint. Easy to say, more difficult to accomplish. Still, it's a goal to shoot for, and I'll be sure to let you know when I've achieved that goal, myself.