Sentiment Analysis (SA) is a Natural Language Processing (NLP) and an Information Extraction (IE) task that primarily aims to obtain the writer’s feelings expressed in positive or negative by analyzing a large number of documents. SA is also widely studied in the fields of data mining, web mining, text mining, and information retrieval. The fundamental task in sentiment analysis is to classify the polarity of a given content as Positive, Negative, or Neutral . Although extensive research has been conducted in this area of computational linguistics, most of the research work has been carried out in the context of English language. However, Bengali sentiment expression has varying degree of sentiment labels, which can be plausibly distinct from English language. Therefore, sentiment assessment of Bengali language is undeniably important to be developed and executed properly. In sentiment analysis, the prediction potential of an automatic modeling is completely dependent on the quality of dataset annotation. Bengali sentiment annotation is a challenging task due to diversified structures (syntax) of the language and its different degrees of innate sentiments (i.e., weakly and strongly positive/negative sentiments). Thus, in this article, we propose a novel and precise guideline for the researchers, linguistic experts, and referees to annotate Bengali sentences immaculately with a view to building effective datasets for automatic sentiment prediction efficiently.