During recent decades, controllability and observability of linear time delay systems have been studied, including various definitions and corresponding criteria. However, the lack of an analytical solution approach has limited the applicability of the existing theory. Recently, the solution to systems of linear delay differential equations has been derived in the form of an infinite series of modes written in terms of the matrix Lambert W function. The solution form enables one to put the results for point-wise controllability and observability of systems of delay differential equations to practical use. We derive the criteria for point-wise controllability and observability, obtain the analytical expressions for their Gramians in terms of the parameters of the system, and develop a method to approximate them for the first time using the matrix Lambert W function-based solution form.