Howdy,
I figured I would do something I haven’t seen in a while. Write a full blown tutorial from a user of the community, so that you all can ask questions that I will answer if I don’t satisfactorily write about everything you want to know. To preface the following: I would not consider myself a pro but I am looking to make photography my career and have been living off of my photography for about nine months.
What I hope to cover is the full spectrum of:
1) Initial assignment
2) Planning
3) Testing
4) Shooting
5) Post processing
6) Final product
And if I don’t do it well enough, ask questions. If you don’t find it useful or want to rip on my image, go ahead, I’m not overtly sensitive… unless you are someone I respect and look up to, then don’t.
Here it goes.
1 Initial assignment:
Shoot a portrait of Kimi Pohlman, a sophomore softball player at the University of Washington (National softball title holders last season). Kimi is well known for her ability to steal bases, at the time of the portrait she was 37 of 39 attempts. That’s 2 outs on 39 attempted steals. This is background information I gathered from the writer of the profile for which I was shooting photos. I also checked out the schools’ athletics website to see her mugshot and get an idea what sort of face I was looking at shooting.
2 Planning:
I decided three things when thinking about doing the portraits. 1) I wanted her to be in the stadium. 2) I wanted her to be in game uniform or at least school colors. 3) I wanted her in two poses I could think of, leading off (which they don’t do in softball, see below) and sliding into the base.
I relayed these requests to the SID (Sports information director) responsible for the softball team [a media contact/representative that requests go through if you haven't done this yourself before]. The SID informed me that she would be in team colors and the field would be set up at a time before practice on a specific day for our meeting. She also said she would ask if Kimi would be willing to try to slide, as a player herself, the SID was concerned for Kimi getting injured trying to slide when she wasn’t in game with adrenaline pumping.
I agreed that if she did slide it would be brief, no more that one or two attempts. What I had envisioned was pretty simple for the leading off and the sliding pictures: a difuse main source [strobe into reflective umbrella] with a single rim light [bare strobe behind]. I envisioned the leading off picture to be taken from home plate down the line with the base in the bottom right of the frame, and the sliding picture a front on picture where the face is in focus and the energy of the slide is visible (dust kicked up).
I took out lights and arranged for an assistant to meet with me about 45 minutes before the scheduled shooting time at the stadium. My assistant Sang helped me set up the lights and I took some test shots of him in my lighting setup, taking into account the ambient exposures.
3 Testing:
Here I post some pictures that worked and didn’t work and did work until I (thought that I) got it all figured out.

One of the first test shots. You can see my strobes (this is reversed and I had him facing the wrong direction) the main to the right and rim to the left. Here I'm testing the ambient light vs. my strobes. I wanted a shallow depth of field so the overcast lighting was helping me out.

Down at the field. Realized my scale was a little off, lights are a little low for the new distance.

Snuck a little farther back (200mm @ f/2.8 on a 5d2) and found a field maintainer to locate a base to put down at first.

Had my assistant find a cup of field dirt to toss in the air above the model to give the look of a "dust trail". First attempt.

Better toss of the dirt. Wind was picking up but I wand the dirt a little out of the focal plane so it would look behind the subject.
4 Shooting:
I was painfully disabused of the notion that softball players lead off (they don’t). My assistant Sang snapped this shot of me directing Kimi to lead off when she let me know that softball players don’t. We all make mistakes. I had to readjust my lights to fix the location issue of the subject.

I'm instructing Kimi to do something that softball players don't do. You can see the location of my flashes here. Not quite 180 degrees off because I want the face to be a little better lit without shadows cast in the front. Courtesy of: http://sanghyuncho.com/blog/softball-profile/

Now that I have her in the right place on the base where she actually would be in a game. Lights need to be fixed a little bit as I'm now overexposed. Actually liking this framing better as the W for University of Washington is now more prominent and well weighted in the frame.

Another attempt at an action shot. The motion blur and body position wasn't working very well in the lighting.

Had her pose. Instructed her to move the right arm back a little. The 200 is a little distracting behind but I didn't notice at the time. This will be the frame I choose for this pose.

First attempt at the sliding pose. Head is down and I realized my light is catching the helmet more than I anticipated. Sang throwing the dirt is pretty good in this frame.
So I ended up with some pictures. The sliding pictures are overexposed. I should have noticed this in my test shots but I didn’t. Mistakes! I will make sure next time to not overexpose this way.
5 Post:

Not too much in the way of post. Slight levels/curves adjustments in Photoshop and a slight burn on the background. [If you click on this image link twice you can see a larger size.

Levels/curves, resize, sharpen, slight burn under the base but there's not much to do with the overexposure which is unfortunate because otherwise it is a decent frame. [If you click on this image link twice you can see a larger size.
6 Final Product:

Here's how it looks after being designed for the paper on the double truck (center fold in the middle of the paper). Designers took some liberty with the second image but it ended looking alright.
And that, in a very long, image laden post is the story. You can read the story here: http://dailyuw.com/2010/4/22/catch-me-if-you-can/