Dipole moment of phenol is smaller than that of methanol. Why?

Dipole moment depends upon the polarity of bonds. Higher the polarity of bonds in molecule, higher will be its dipole moment. In phenol carbon is sp2 hybridised and due to this reason benzene ring is producing electron withdrawing effect.

On the other hand, carbon of methanol is sp3 hybridised and produces electron releasing effect (+ I effect). Thus, C—O bond in phenol is less polar than C—O bond in methanol and therefore, the dipole moment of phenol is smaller than that of methanol.