This chapter explains that Baby Boomers are considered more accessible at the workplace, while Generation Yers feel that work should be left at work. Older generations see work as a means to end while younger generations strive for a greater work-life balance. Future generations require interactive communication and new forms of contact even with organizations that usually refrain from making comments. Younger generations are the texting generation, and it is necessary for them to know that slang and text type is not acceptable when communicating in the workplace. When communicating with Millennials, it is important to show them respect, to give them challenges, and to lead by example. In the workplace, formal communications and titles are preferred by the Traditionalist generation. When communicating across generations, it might be necessary to define the difference between Lots Of Love and Laugh Out Loud. Thus, the chapter discusses that training workers of all ages in the skills address the needs of the organization.