To highlight your son/daughter on a Mac using iMovie (assumes you have some knowledge of iMovie):
Trim down your highlight video to whatever you want the coach to see.
Split each individual highlight at the spot where you would like to circle your player. (Highlight the initial section in yellow, go to "Modify" and then "Split Clip". That will split the clip into two sections.)
Click on the initial frame of the second part of the Split Clip so that you see the frozen image that you want to add the circle to). Then go to "File", "Share", and then "Image". Name it whatever you want, and then save it to the desktop (or wherever you know where to find it). That will save a still photo of the image you see in the iMovie window.
Open the image you just saved. This should bring it up in Preview. In Preview, go to "Tools", then "Annotate" and then "Oval" (or whatever shape you want to use). That will drop a red oval on the photo, which you can move and re-size however you want. Mine comes up red, but you can change the color if you want.
When you've positioned the oval over your player where you want it, just close out of the photo. The photo will be saved in the same spot you created it, but with the oval inserted in the photo.
Go back to iMovie, and then drag the photo you just created into the spot created when you split the highlight into two sections. You will be "dropping" the photo in between the two sections.
Then you can reduce the amount of time the photo will be frozen on the screen by clicking and dragging the left or right edge of the photo -- mine defaults to maybe 4 seconds, and I shrink it to under 2 seconds.
Repeat with each highlight. | 
