The Upper Hand & Other Grand Illusions is a series of vignettes that tell a story of courtship and intimate interaction. It opens with a confrontation in "Forever Love Is Tainted," focusing on the inner monologue of a man deceived. The song is a shot of reality, produced by Jelani Brooks to achieve a sound that is syncopated in melody, harmony, rhythm and texture. Each song thereafter documents a realization, "A Private Island" acting as commentary on the literal cost of getting to know someone. Drummer Terry Orlando Jones appears in great form here, and later on "Covered in Cloth," an acknowledgement of the moment someone invites you to move in.