I often shoot in nature preserves and areas where it's important not to disturb the surrounding plants or ground. Therefore, I avoid touching the plant and rarely, if ever, use a tripod. Whenever possible, I go out with a steward, botanist, or researcher who knows where and when the plants are blooming. I rely heavily on such individuals and wouldn't have gotten this far in the project without their trust and expertise. Trust is a key factor as many of the plant species on the endangered list are at risk for being poached. I have, on more than one occasion, agreed to keep secret the location of species I have photographed.
The best days for photographing shadows are days with bright sunshine and little to no wind. Early morning or late afternoon is preferred because of the long shadows. I look for shadows that make a nice composition, which usually means photographing several different plants until I find the right angle. It's great when I can photograph the plants in bloom, but some plants have more visual interest right before they bloom or as they begin to decay. Sometimes it's the seed pods or the remaining heads that make the most interesting shadow. I've also discovered that not all plants create intriguing shadows - some just look like blobs. This summer I'll be visiting some of the blobs again to see if I can get a better angle.
The other challenge is trying to get as much of the shadow in focus as possible, as the part of the plant closest to the whiteboard is obviously the sharpest. However, sometimes having part of the image out-of-focus adds to the composition and aesthetic of the image. So it's just trial and error, following my gut......and sometimes just working with what I've got. :)