Contracting is an integral component of both government (i.e., public) and private business. As part of the contracting process, contracting companies must submit proposals to federal agencies or private businesses; individuals who write proposals on behalf of contracting companies are known as proposal writers. Although proposal writers are central to the proposal writing process, they are only marginally represented in available literature on the contracting and proposal writing processes. Additionally, available literature is disproportionately influenced by industry and trade sources, versus academic sources, and completed by industry authorities. As a result, key findings from such reports may not reflect the feedback gathered as part of this research. This research utilized a 25-question survey with both multiple choice and free answer questions to gauge the most and least effective components of the proposal writing process. Communication and collaboration—internally within the proposal team or within the company, and externally between the company and customers, clients, etc.— were cited as both the most and least effective components of the process. Notably, however, communication and collaboration were not the most frequently encountered issues, as only 23.5% of proposal writers reported communication as a common issues. Instead, supporting resources (46.9%), time/ schedule (49.2%), and direction. instructions (44.9%) were reported as the most common issues that proposal writers encountered, although one in four participants noted that issues were not consistent across proposals.