As disaster occurrence continue to rise particularly in developing countries, cases of humanitarian crises have been growing. Thus, there is interest in paradigm shift to proactive response in anticipation of the disasters to save lives, livelihoods and save humanitarian actors from the enormous cost that they would otherwise incur in event of crises. This paper highlights the practical experience of developing an anticipatory action system that strengthened proactive response to disaster in Kenya, a country in which disaster occurrence has become a norm. It demonstrates practical challenges in pioneering this kind of a system that demands quality and appropriate data and expertise, while there is no central archive for all relevant data, gaps in coverage of early warning systems and limited capacity to access, interpret and use climate information for decision-making among risk management institutions. So far two anticipatory systems have been developed based on a data driven approach to predict and create anticipation of potential ravaging impacts of climate-related disasters; drought and floods. The systems are already attracting automatic funding allocation from donors to support vulnerable persons in the risky areas to take anticipatory actions to reduce risks and/or impacts of droughts and floods.