Conventionally, the work of adhesion at the nanoscale is estimated using an atomic force microscope with a tip of the size of 10 nm. It is pressed into a surface with nano-Newton forces and then retracted to ascertain when the tip breaks away from the surface. Thus this ensures “hard probing” of a surface. However there can be another configuration where the particle is barely placed into the surface when the work of adhesion attaches the particle to the surface and this can be called “soft probing”. In this configuration, if a birefringent particle is confined in linearly polarized optical tweezers, and then the surface is moved in the direction tangential to the plane, a rolling motion can be induced. Study of this rolling motion can also show the work of adhesion. We use this configuration to find the rolling work of adhesion of a 3 μm diameter birefringent particle on a glass surface. We go on to study the effects of changing the surface to a hydrophobic slippery surface like polydimethyl siloxane (PDMS). Then we go on to show that even 500 nm diameter diamonds bearing nitrogen vacancy (NV) centers which are birefringent due to the stresses on the crystal could also be trapped and rolled to generate pitch (out-of-plane rotation) motion with 50 nm contact diameters. We find that this mode of soft probing yields a work of adhesion of about 1 mJ m⁻² while the conventional nanoscale probing with atomic force microscopes (AFM) yields about 50 mJ m⁻².