Teaching, by its very nature, is a trial and error process. Experimenting with a variety of methods of pedagogies is an integral part of determining which strategies demonstrate the greatest possible learning outcomes. One would be hard-pressed to meet an academic instruction librarian without at least one concrete example of a teaching method or educational activity that was not a success within the library instruction classroom. However, these incidents are critical learning experiences that inspire instruction librarians to grow and develop their teaching practice, hopefully in tandem with student feedback, opportunities for assessment, and the support of departmental colleagues. The two authors of this proposal are both academic instruction librarians. One presenter works as an instruction librarian at a small rural university in New England; the other is an instruction librarian at a mid-sized private urban university in the Mid-Atlantic region. Although the presenters work at two very different institutions what they have in common is the shared experience of evaluating and refining their teaching practice as a means of improving student information literacy skills. Within this presentation three case studies will be provided, each of which will describe an ineffective teaching experience, an intervention to reflect on this failure, and the development and implementation of an alternative intended to address shortcomings of the previous method. Three specific components of information literacy instruction will be covered: online library tutorials as a replacement for one shot library sessions for first year students, a problem-learning based group activity in replacement of database and catalog demonstrations for first year students, and an interactive online game about citing and referencing instead of a lecture. The first case study discusses the creation of online library tutorials in Canvas for students enrolled in First Year Inquiry classes, a project undertaken due to a perceived lack of effectiveness of the traditional one shot. Assessment techniques and data will be shared as well. The next case study pertains to a collaborative and active-learning based library orientation for first year students called The Amazing Library Race. This method was adapted and implemented to reduce library anxiety among first year students and provide students with an opportunity to learn about the library’s resources and services in a discovery rather than lecture-based environment. Assessment methods and data analysis will be described. Lastly, one of the presenters will detail an online game created using the popular audience response system Poll Everywhere. The game teaches students fundamentals of citing and referencing in MLA format using a pop culture theme. This game was created to make learning about citing more fun and engaging, as the presenter perceived a lack of engagement during a previous lecture based approach to citation instruction. By sharing their own experiences with instruction obstacles, as well as changes made to overcome them, the presenters hope that their own failures and subsequent successes could be useful for other academic instruction librarians.