A basic element in advertising strategy is the choice of an appeal. In business-to-business (B2B) marketing communication, a long-standing approach relies on literal and factual, benefit-laden messages. Given the highly complex, costly and involved processes of business purchases, such approaches are certainly understandable. This project challenges the traditional B2B approach and asks if an alternative approach—using symbolic messages that operate at a more intrinsic or emotional level—is effective in the B2B arena. As an alternative to literal (factual) messages, there is an emerging body of literature that asserts stronger, more enduring results can be achieved through symbolic messages (imagery or text) in an advertisement. The present study contributes to this stream of research. From a theoretical standpoint, the study explores differences in literal-symbolic message content in B2B advertisements. There has been much discussion—mainly in the consumer literature—on the ability of symbolic messages to motivate a prospect to process advertising information by necessitating more elaborate processing and comprehension. Business buyers are regarded as less receptive to indirect or implicit appeals because their purchase decisions are based on direct evidence of product superiority. It is argued here, that these same buyers may be equally influenced by advertising that stimulates internally-directed motivation, feelings and cognitions about the brand. Thus far, studies on the effect of literalism and symbolism are fragmented, and few focus on the B2B market. While there have been many studies about the effects of symbolism no adequate scale exists to measure the continuum of literalism-symbolism. Therefore, a first task for this study was to develop such a scale. Following scale development, content analysis of 748 B2B print advertisements was undertaken to investigate whether differences in literalism-symbolism led to higher advertising performance. Variations of time and industry were also measured. From a practical perspective, the results challenge the prevailing B2B practice of relying on literal messages. While definitive support was not established for the use of symbolic message content, literal messages also failed to predict advertising performance. If the ‘fact, benefit laden’ assumption within B2B advertising cannot be supported, then other approaches used in the business-to-consumer (B2C) sector, such as symbolic messages may be also appropriate in business markets. Further research will need to test the potential effects of such messages, thereby building a revised foundation that can help drive advances in B2B advertising. Finally, the study offers a contribution to the growing body of knowledge on symbolism in advertising. While the specific focus of the study relates to B2B advertising, the Literalism-Symbolism scale developed here provides a reliable measure to evaluate literal and symbolic message content in all print advertisements. The value of this scale to advance our understanding about message strategy may be significant in future consumer and business advertising research.