I was kind of a guide on our Trans America in that I was the one who was a cyclist and had been looking into touring for a while. None of the three of us had toured before though. That said we all were experienced in various outdoor sports including backpacking among other things.
I did most of the gear choices and advance planning, but once underway we all contributed our as our various skills allowed. In some ways they looked out for me more than I did them, since in some areas, like putting on sunscreen, knowing enough to come in out of the rain, and eating properly for example, I am told I lack good sense
None of this is rocket science so a lot of guiding isn't necessary for folks with some basic outdoor experience and skills.