A surveying device is operated to measure a surface profile of a terrain of a worksite and generate surface profile data indicative of the surface profile. A work machine is operated to move along a route over the terrain in accordance with an operating parameter and generates machine operational data indicative of the operating parameter. A navigation system determines the route and generates route data. A processing unit processes the route data, machine operational data and surface profile data to generate monitored operating condition data indicative of a monitored operating condition of the machine.