The skewness of the first time derivative of a pressure waveform, or derivative skewness, has been used previously to describe the presence of shock-like content in jet and rocket noise. Despite its use, a quantitative understanding of derivative skewness values has been lacking. In this paper, the derivative skewness for nonlinearly propagating waves is investigated using analytical, numerical, and experimental methods. Analytical expressions for the derivative skewness of an initially sinusoidal plane wave are developed and, along with numerical data, are used to describe its behavior in the preshock, sawtooth, and old-age regions. Analyses of common measurement issues show that the derivative skewness is relatively sensitive to the effects of a smaller sampling rate, but less sensitive to the presence of additive noise. In addition, the derivative skewness of nonlinearly propagating noise is found to reach greater values over a shorter length scale relative to sinusoidal signals. A minimum sampling rate is recommended for sinusoidal signals to accurately estimate derivative skewness values up to five, which serves as an approximate threshold indicating significant shock formation.