Prior investigations of the behavior of regolith on the surface of planetary bodies has considered the motion and interactions of individual grains. Recent work has shown the significance of cohesion in understanding the behavior of planetary regolith, especially on small, airless bodies. Surficial regolith grains may detach from a planetary body due to a variety of phenomena, including aeolian effects, spacecraft operations, micrometeoroid bombardment and electrostatic lofting. It is well known in terrestrial powder handling that cohesive powders tend to form clumps. We present an analytical theory for the size of regolith clumps that are likely to form and be easier to detach from a surface than their constituent grains, assuming monodisperse, spherical grains. The model predictions are significant for our interpretation of the surface of asteroids, as well as understanding a variety of phenomena on planetary bodies and designing of sampling spacecraft.