RWF has the right of it. (again)
I'm in a legal case right now that's very similar, as an expert witness defending another engineer's design.
The short answer is that you can go into your modeling program, and jack the inlets up really high, and then see where the HGL comes to in those artificially jacked up inlets, and that will tell you how much head it takes to drive the stormwater through the system as it was designed.
So then once you've established how much head it takes to push the design storm through your system, go back and look at the grading plan and see if the water can reasonably pond that high without spilling downstream. Then follow the water and see where the flooding problem starts. Etc.
Pay very close attention to manning's roughness assumptions, and check them vs manufacturer's recommendations, especially when it comes to HDPE or helical CMP pipes, which sometimes don't follow the "general guidelines" we all use. Also check those assumptions vs your local regulations.
That's the easy way. The hard way is to do dynamic routing of a design storm with a specified duration. (e.g. SWMM) The hard way often shows less actual flooding than the easy way though. Keep in mind that the Modified Rational Method, which is what most of these StormCAD style programs use to design pipes, isn't really a great way of determining what a true HGL in a pipe is, but rather it's a way to determine where the worst case HGL might land for a given 'year' storm. Those programs usually re-figure the intensity at each node in your network based on longer and longer Tcs, which means the I is dropping, which means the design storm it's looking at changes from node to node in the network. Any 'hydrograph' approach to the problem is going to choose one design storm of a specific duration and route that storm through your system.
If it's a legal issue, then you're likely best approach is to choose what passes for accepted practice in your region, which in my experience varies widely even just in the South East.