Social Engineering is a powerful tool. With the weapons gathered through Open Source Intelligence (OSINT) gathering and well crafted vishing or phishing a Social Engineer wields incredible power to do good. Unfortunately, for some the power of being a Social Engineer is one that they wield to show they are smarter than those around them and cause stress and fear doing damage to any potential relationship they or the department they represents. This discussion will be about how to create meaningful, targeted phish and vish in an enterprise while strengthening information security from the real world perspective of a CISO as well as a few specifics to avoid. In conclusion this presentation will cover the importance of trust and how social engineering can help build or destroy trust.