This work examines the differences in the way J.L. Austin and John Searle observe the meaning in the speech act theory, and in particular, the notions of direction and intention. On one hand, even though both philosophers consider language as an act of action, they are much different in pressing home the connection of utterances regarding performative social contexts versus the internal intentions of first sentence meaning constructs composed by the speaker. Based on qualitative and comparative analysis of both ‘How to Do Things with Words by Austin and Speech Acts by Searle, the paper outlines vital places of convergence, and divergence of the two authors in approaching the meaning of words and its usage in particular circumstances and intentionality. It proves that to Searle, intentionality takes center stage in the classification of speech acts whereas to Austin, meaning is placed in the context of performative and situations. In support of the argument, the paper points out that speech acts may not be given their meaning in terms of linguistic form, but rather a meaning in terms of context-sensitive and goal-directed application in the communication domain. This shows the interconnected role played by cognition and social structure in determining linguistic interaction and gives a better view of how utterances operate in real life communication.