Thought on Oliver Queen's incredibly shitty decision making and leadership skills. (TV only): I think this can be explained entirely from canon.
1) Both parents were members of a terrorist organization. Both parents cheated on each other. While young Oliver may have missed many specific lies, he undoubtedly picked up on the general atmosphere of dishonesty along with the whiff of self-righteous "everything I do wrong is for the greater good/deserved by the victim". Kids are sensitive to this stuff. There were strong hints that he and young Merlin both chose irresponsibility as an alternative to a version of adulthood they saw as worse than being useless. Father's dying words confirmed that he had spent most of his life doing wrong, and even when he started doing right deceived Oliver right up a minute before death.
2) His first mentor, later to become a Super-Villian Deathstroke was already Black Ops, very pro-deceit (by the "good guys") and very ends-justify-the-means oriented. He also got training from his doomed love; her death reinforced both that he was incapable of protecting those he love and that the virtuous are doomed.
3) Enslaved by Argus, run by "The Wall" - again, deceit, torture, murder "for greater good"
4) Trained by the Bratva, Russian Mob in leadership and dealing with "team".
5) During infiltration of league of assassins, personally trained by Raj Al-Ghul
He knows this is not the way to be. But a large part of him associated lying, deceit, and end-justified-the-means behavior of adulthood and effectiveness. Openess, honesty , trust are for losers. Another part hates that part of him. Sp when he tries to be honest,, to treat people well, to set limits on what he is willing to do to reach goals, the part that thinks all that stuff is for children and the irresponsible sabotages him. When he tries to go dark, the par that knows that is wrong sabotages him. So whichever way he chooses, he will always sabotage himself. :Cause the ruthless half will always sabotage the part that wants to be a boy scout, and the boy scout will always sabotage the part that wants to be Amanda Waller.
This post sponsered by two hours on hold at Social Security and still waiting.