Information Technology (IT) can provide Small and Medium Enterprises (SMEs) with competitive advantage, effective management, and improved business performance. Decision making is an integral process of achieving a successful IT investment. SME owner-managers are usually the key IT decision makers despite the fact that they often do not possess sufficient IT skills. This study examines how SME managers search and prioritise information that guides their IT decisions. This study adopted a qualitative research method and conducted interviews with eleven SME owner-managers in Nigeria and South Africa to understand the process of IT investment based on the information available to the decision-makers. Owner-managers of small manufacturing, servicing, and retail companies were the participants of this study. Thematic data analysis technique was employed to analyse the data collected in this study. The findings of this study revealed that SME owner-managers face specific challenges like insufficient information to guide IT choice, limited resources when making IT decisions and lack of formalised approach to the decision-making process. The finding in this study provides an insight into strategies to formalise SME owner-managers’ IT decision-making process. This study concludes that, the formalisation of information searching process for IT choices in SMEs is crucial to achieving better IT investments.