It never shows up in the transaction log, but in the NBA personal relationships are often the driving force behind a successful deal, whether it's a free-agent signing or a trade. In many respects the deal was constructed on the strength of a pair of relationships:
Olshey and Orlando assistant general manager Scott Perry had been friends for years, and Perry was aware that Olshey liked Harkless' game.
The Orlando front office sincerely liked and respected Harkless and wanted to make sure he landed in a good situation. These are the kinds of gestures that earn an organization goodwill around the league, and Orlando has developed a superb reputation around the league in this regard.