Self-awareness, particularly accuracy in decoding the internal cues of our body's murmurs, holds the key. Our subtle psychological reactions reflect the sum total of our experiences relevant to the decision at hand.
You should always have both but always start with the positive, why?
A conversation starting with the persons dreams & hopes leads to the path yields learning and vision. This positive conversation will extract some concrete goals from that vision, then ...
Tony Robbins says "Repetition is the mother of skill". This is true but with repetition you become proficient at the task as the task becomes more unconscious or automatic. This means you can pick up poor skills as well as good skills while practicing in a repetitive or drill manner.
Most of us think of the courage a leader needs as the courage that it takes to Fire someone or to have that really hard conversation with an employee...