Libraries are constantly challenged to meet new user needs and to provide access to new types of materials. We are in the process of launching many new technology-rich initiatives and projects which require investments of staff time, a resource which is at a premium for most new library hires. We simultaneously have people on staff in our libraries with more traditional skill sets who may be able to contribute time and theoretical expertise to these projects, but require training. Incorporating these “seasoned” employees into new initiatives can be a daunting task. In this article, I will share some of the strategies I have used as a metadata project manager for bridging diverse generations of library staff who have various levels of comfort and expertise with technology, and strategies that I have used to reduce the barriers to participation for staff with diverse perspectives and skill sets. These strategies can also be helpful in assisting a new librarian with technology-rich skill sets to more successfully orient themselves when embedded in a “traditional” library setting.