The Army NCO corps is an extremely diverse population of individuals from various ethnic, language, and socio-educational backgrounds. Being able to communicate effectively with Soldiers, officers, and civilians is an essential skill for all NCOs. However, recent research suggests that many NCOs have communication skills deficits (Ward, 2018). Before training solutions can be recommended, more research is needed to better understand the development of communication skills in NCOs and the most common challenges that they experience while learning these skills. The purpose of this research was fourfold: a) to map how interpersonal, written, and oral communication skills are developed both informally and formally over the course of a mid-grade NCO career (from E-5 through E-8); b) to identify skill gaps, c) to investigate communication challenges related to communication technology, generational differences, culture, English as a Second Language (ESL), and vertical and horizontal communication issues; and (d) make training recommendations. This research was conducted using semi-structured focus groups and questionnaires with 225 Soldiers, NCOs, and officers. Results indicate that the majority of communication skills are learned on the job, but that very little formal training is provided. The development of writing skills was identified as a particular challenge. Many NCOs reported that the development of writing skills varied greatly according to their senior leadership and Military Occupational Specialty (MOS). Further, results suggested communication challenges related to gender, but did not suggest significant differences related to culture, generational issues, or language. Results also indicate that while there is increasing use of texting as a primary method of communication, there is also emphasis on face-to-face communication when available. Finally, there is a need for on-the-job training solutions that are simple and fit into regular work activities. This paper will discuss these communication skills training challenges and suggest practical literature-based recommendations for resolving them.