One of my latest projects was to help a client come up with a family crest. Well when I say help I mean I illustrated and she just told me what to do.
This was her initial sketch of what she wanted and the final image is what we came up with.

After several emails and sketches we started to move forward. She wanted the classic animals protecting the crest and choose a swan and a bear (but she wanted the bear to look like the classic lions that you see in a crest) so there were a ton of elements added and changed.

Here is the final version of the crest once it was finally decided on. The process was several forms of media, traditional drawings for the animals, Adobe Illustrator for the placement and layout, and Adobe Photoshop for the coloring and effects added to the crest.
All in all it was around 25 concept drawings and samples and around a week of solid working to get it to her liking.

Pencil, Adobe Illustrator CS5, Adobe Photoshop CS5