The drainage shed is determined by finding the total tributary area that drains to the area in question. The slopes shouldn't be a factor in determining this area.
For large areas one might use the USGS topographic maps. You would investigate upstream areas and draw a line delineating one drainage shed from another. Imagine where a drop of water would drain, towards your area or away from, as an example.
A customary rule of thumb is the modified rational formula can be used for determining storm run offs for 200 acres or less. Larger areas use the unit hydrograph analysis.
In urbanized areas, you might need to do a fair amount of research of as builts to determine if storm water is intercepted before reaching your site, for example.