This process can begin when the entrepreneur has a final outline, or even finished manuscript, of their book. The cartoons need to be based on something!
With that in place, here are the steps I recommend for creating each of the illustrated sections of your book:
When Dan Sullivan and I started doing the Ambition Series books, we had a cartoon panel to correspond with each paragraph in the chapter.
Now, we rarely do that, often opting for a full two-page spread that gives a graphical overview of the chapter -- the gist. If it's a particularly involved section, though, we will still break it down into sub-sections.
Dan and I used to e-mail drawings and notes back and forth -- sometimes over the span of two weeks -- before we'd arrive on the final design for a chapter.
Not only was that time-consuming, I'd get attached to ideas I'd drawn, then have to let them go. Throwing out work is always frustrating for me.
Conversely, sometimes I'd just keep missing a point Dan was trying to make in his messages and sketches, which must have been frustrating for him.
These days, we have a video-call (our office uses Zoom), and sometimes we come up with a final rough of the chapter's pages in as little as fifteen minutes.
Even better, I feel completely confident going straight to final artwork (so we actually don't have to do steps 3 and 4 above anymore).
So our first review is of a nearly finished digital page, and the changes are minor -- improvements, tweaks, and additions, rather than a total rework.
As a result, our teamwork is exponentially faster -- and more fun!