Evolving communication technology, the increased volume of information needed by businesses and the intensified competitive environment have made internal company communication more critical to business success. The purpose of this multiple case study was to explore strategies for assessing the effectiveness of internal communication channels used by managers and leaders of three law firms in the Commonwealth of Virginia. The participating firms were recognized by their peers as being exceptionally well managed. Data from interviews and company documents were analyzed through the conceptual lens of channel expansion theory and the use of software coding to identify patterns and themes. Three important themes emerged: informal assessment strategies, indirect assessment strategies, and efficient versus timely assessments. The first theme suggested the effectiveness of an informal assessment strategy, depending on the size and complexity of the organization. The second theme reflected the effectiveness of an indirect assessment for organizations that lack the resources to support a more direct and specific assessment process. The third theme reflected the participants’ perceptions of informal and indirect assessments may be more efficient, the feedback from the assessments are often less timely. Managers may consider these themes in formulating communication policies. Small professional service firms, such as legal firms, provide important services to individuals, families, and businesses in their community.