The whole concept of characters 'hardening,' as in bad, pragmatic characters are 'hardened' and good naive characters are 'soft,' and that guiding a character along the right path means convincing them to 'soften their heart to the world' or something of the sort is inanely idiotic.
When dealing with people like Leliana in Inquisition, both in fiction and real life, the very last thing they need is some sycophant whimpering to them "I know it's hard...but you just need to have faith in the world...please, please do the right thing."
What should have happened is the Inquisitor getting in her face, grabbing her by the chin and commanding her "You'll follow my orders to the letter, and my orders are that we don't do this. If such a task is beyond your competence, I would happy to find you a position more suited to your abilities. You can serve the Inquisition by scrubbing floors. Am I understood?"