The expansion of the operational scope of a business informs the need to exercise diligence and sensitivity to the nature and demands of the operational contexts both local and international. Hence, the investigation into the influence of contextual intelligence on strategic leadership of telecommunication companies in the south-south region of Nigeria with foci on Rivers and Akwa Ibom States. Quantitative and correlational design was adopted. Four (4) telecommunication companies viz: MTN, Airtel, Globacom and 9Mobile selected based on their subscribers’ base and market share standing out of nine (9) major ones listed in the methodology constituted the population. Sixty nine (69) copies of the questionnaire accounting for 93% response rate were fully completed and used in the study out of seventy four (74) copies administered to senior staff and above obtained using Taro Yamene’s sample size determination technique from a population of ninety (90) respondents. Primary data were obtained from questionnaire. The findings showed that the four (4) hypotheses formulated around the dimensions of contextual intelligence comprising tacit-based knowledge, synchronicity and time orientations have significant influences on measures of strategic leadership made up of strategic direction and balanced organisational controls. The conclusion showed that contextual intelligence significantly influences strategic leadership of telecommunication companies in Rivers and Akwa Ibom States of the South-South region of Nigeria. The managements of telecommunication companies in these two States of South-South region of Nigeria were recommended to leverage contextual intelligence to better and enhance strategic leadership in their respective operational contexts.