Below you can see the step by step progression of how I worked with the client to create their custom artwork and prints.   I keep in close contact with the client throughout the process to ensure a pleasing final result.

1)   First, the client determined the number of people which would be in the painting, the logos to be used and the text.   We decided upon a 22 x 30 inch format so the heads would be a good size (I cannot get good likeness and detail if working too small).   I used a head and shoulders cut and pasted from another caricature to help create a layout in Photoshop (first image).   I emailed back and forth with client until we agreed upon this layout below with all the positioning, the size of the logos and the text.    They provided me with attachments of the logos they wanted exactly, and even the font that they wanted the text to be painted in.   I numbered the layout so it would be easy to reference the photos they would send of their teammates and to place them in the order the client specified.   Client emailed me 20 close-up photos, front views, of each teammate and provided me with a spreadsheet telling their names (for reference), eye and hair color (sometimes it is hard to tell for sure in a photo).   I asked for high resolution photos for each one, which they were able to provide for most. 
2)  I used my light table to trace over logos and text and then painted the logos.   I also did a pencil placement of each head.   (Had to darken this photo for pencil to show).    I then sent this to the client to look at upon this stage.
3)  Next I did pencil sketches of each teammate, working on likeness and proportions.   I sent this darkened photo (to see pencil lines) to client for approval and feedback, along with closer up views of the sections of people.  At this stage, the client is looking for general likeness and proportion---details are sketchy and it is sometimes hard to imagine how the finished painted work will turn out.   This is a critical stage for the client to mention any issues with the likeness of a person or other detail (while keeping in mind it is a caricature and not a photograph and there will be some cartoony distortions that are normal) because the next stage is to go over the pencil sketch with marker, and once that is done it cannot be erased.
4)   After getting client approval on sketches, I proceeded to apply the marker (not erasable) to each person and then sent client a photograph of the result.
5)   The next series of photos will show the gradual build up of painted watercolor tones (not erasable).   I periodically updated the client with photos and toward the end we did a small amount of tweaking.
6)   At this stage I added some little logos the client wished to incorporate and then painted them.
7)   After approval of the above finished work in a photograph, I scanned the artwork to produce the perfect artwork image below, suitable for making the prints the client wanted.   I do my own scan work on a regular small scanner....artwork this large is scanned in about 12-16 pieces and then joined in Photoshop using a rotation, layering and touch-up process that is time-consuming.   The final scan shows the truest colors and detail, more than a photograph can capture.   Because of the time involved in scanning and piecing work in Photoshop, the client provides approval before this stage.
8)  Below is the original artwork which the client had me matte and frame, and the 20 smaller matted pieces the client ordered to give to each team member.
9)  Below are the photographs I worked with on this piece so you can see the likenesses.   The better quality the photo, the better the end results tend to be.   That said, some people are just more difficult than others to capture their likeness, so in a group photo there will always be some that are a little more "on" than others but please be assured I try my best on each one!  Also, as you can see in some of these, the client told me to change some hair lengths, etc.