Trust is at the heart of all great creative work. In my experience, doing something truly unique and remarkable starts with a creative team willing to go there and stakeholders willing to trust in that high wire act. Educating Microsoft employees about how to keep their data, identity, and devices safe (which affects customers, as well) is serious business. In 2016, we were introduced to an outstanding team at Microsoft digital security who asked us to enliven their digital security training for Microsoft employees. The brief was to depict common scenarios that showed employees how to stay safe. Made sense, but we knew that could be a snooze to watch. So when our creative team led by CD/Director Kurt Reifschneider and ACD/Scriptwriter Graeme Hanson pitched a series of videos hosted by funnyman Luke Burbank, we were asking for a leap of faith. The Microsoft team was unblinking and believed in the idea the whole way. From an initial piece on phishing safety to several years of digital security training videos, employees at Microsoft responded with rave reviews and higher engagement in the training curriculum. The pieces were educational and fun to watch. The creative process was, as well.