Insightful questions Ian! The type of conditioning referred to in the Gita is not so much cultural (including values, politics, religion, etc…) but more so our tendency to identify with thoughts and physical sensations. As a society — we tend to overly attach ourselves to our thoughts of ‘I, Me and Mine’.
The Gita claims that we are awareness, however we have a deep habit of instinctually and instantaneously shining our awareness on thoughts and sensations when they arise. Once we break this habit of immediate reaction, there is now space for us to review which thoughts or sensations appear most salient to us. Choosing ‘new conditioning’ is the long and arduous road of being mindful of our tendencies, and strengthening our present moment agency to actively act differently!
I found the technique of Vipassana meditation as training to do precisly this. Training yourself to be aware of things without instantaneously reacting!
Homepage of Vipassana Meditation as taught by S.N. Goenka in the tradition of Sayagyi U Ba Khin