The information security field is in desperate need of people with the technical skills and capabilities to fill a myriad of roles within organizations around the world. However, hiring managers and leadership are doing horribly when it comes to hiring and interviewing for these roles. Organizations are doing poorly trying to communicate expectations for a job, conducting interviews that make it impossible for candidates showcase their (limited or vast) experience, and some managers posture themselves so poorly that the candidates want nothing to do with the opportunity. This talk takes the experiences of the speaker as both interviewer and interviewee, as well as from others within the scene in order to let the people making hiring decisions know what they can do to get the people and experience they need for their teams. In addition, this allows for candidates to learn the limiting factors and challenges of hiring mangers face in hopes to prepare for and 'hack the system' to work around them.