As far as the design 'sequence' goes when doing site work in InRoads, there is no clear-cut, textbook approach. Sorry. Specific tool-based 'sequence' is unique from project to project as well as from designer to designer. However, there may be areas of the design that can be approached systematically, like the driveway entrance shown above.
In some areas of site design, the modeling can take on a workflow-based approach, but it might not always be intuitive for a newer user. This is where understanding grading in general comes in. If you have a strong concept of what grading elements are needed to represent an area of your design, and understand their relationships, then it just becomes a matter of picking the right tool to help you execute the work. I believe this is where our industry needs to maintain the old-school mentorship approach to help new designers understand the 'design' methodology, unrelated to the software tools.
The best general direction that could be made about the design approach to use when working with InRoads is to start with areas of the site that you understand well and know about, and work from there into the areas of the site that you know less about. If you know the location of a building pad, then lay that out; if you know the location of a detention pond then create it; if you know that you are tying into an existing sidewalk or curb then begin there. Nail down and start with what you know about the design of the site. Hand in hand with that is, knowing what aspects of the site grading control other aspects of the site grading. Basically, what grading is dependent upon other grading?
When beginning, it's not as much about knowing the InRoads tools as it is about just knowing the design details of your site.
Some sites can be driven by a new, yet to be determined, site feature that everything else is stemming from. In this case, sometimes assumptions have to be made in order to get started. Don't worry about being perfect when you are beginning, just start with the best engineering judgment and direction available and move forward. You can always go back and change a part of the job that isn't quite working the way it needs to. That is just part of the overall design process. The key here is that you become more proficient with the tools of InRoads so that you can do this work quickly and effectively.