His harmonic conception was "piano thinking" applied to the guitar and at the time seemed impossible - especially when considering the ease and smoothness with which he performed his chord passages even at break neck speeds! Wes just heard it that way and again, redefined the rules.
Wes was equally adept at harmonizing and playing a melody (the head of a tune) with his block chord approach, frequently adding uncommon and downright peculiar voicings to the harmonic framework of the song! Cases in point are the striking performances heard in the standard "I've Grown Accustomed To Her Face" and his original composition "Mi Cosa".
He played his chord phrases with a thumb strumming attack similar in articulation to his octave playing.
Wes Montgomery was a master of melodic invention - having the facility, emotional content, taste, and originality to turn any piece into an engaging musical experience.
As an improviser Wes was concerned with motif development, though in a natural and instinctive way.
He was the consummate story teller - leading an enthralled audience in chorus after chorus of inspired playing - revealing a motif here, developing it later, introducing a blues move, and then seasoning it with bebop modernism and chromatic tension.
Wes' motifs and signature licks ran the gamut from simple blues ideas to complex bebop phrases.
Like John Coltrane and Charlie Parker, Montgomery was always aware of where he was in the harmonic scheme of a song.
He constantly varied textures, rhythmic and harmonic complexity, and changes of register.
Finally, regardless of the tempo, Wes Montgomery retained lyricism, fluidity, and clarity - and above all else, "feel" in all of his improvising.
Wes Montgomery created many of his best solos with great concern for form.
Using the basic components of single notes, octaves, and block chords he pursued a definite strategy which was a general three tier plan usually occurring over multiple choruses.
Beginning with single note playing in the opening choruses, Wes would then progress to octaves and often reached a powerful climax of block chording in the final choruses.
These were sometimes made more exciting with the use of a blues based question and answer treatment of octave "punches" interspersed with repeating chord figures reminiscent of a big band "shout chorus".
Wes Montgomery's sense of improvisation was almost uncanny and precisely the sort of universal musicality which turned the jazz world on its' collective ear - attracting even the non-jazz listener to his ingratiating jazz guitar style!