Considering the volume of information technology (IT) project management failures occurring in businesses that strive to become fully digitalized, the present paper uses diagnosis and prescriptive analyses to propose effective digital solutions using qualitative secondary data from published research. Results indicate that successful technology project management (TPM) should consider highly qualified TPM professionals, skills, milestones, processes and budgeting in addition to observing standard project management methodologies tailored to the core business activities. The integration of artificial intelligence (AI) in information technology projects has proven to reduce project challenges while optimizing management of project scope, time, cost and resources besides big data management, automation, quality control, risk awareness and project productivity increase. Results revealed that digital-orientated companies have been allocating 46%, 46%, 52% and 39% of their budget to cover potential needs regarding digital upgrading on cloud computing, data security, ERP systems and project management. Furthermore, the key AI requirements for effective IT project deployment reside in apportioning 74%, 73%, 71% and 68% of the staff to security operations, Analytics platforms, Business workflow automation and cloud platforms respectively. However, the executors, the executors’ project implementation phases comprising analysis, design, test, setup, deployment, training and support should be aligned with the receptors’ project stages that include As-is process analysis, documented process, To-Be processes, process modelling, legacy system readiness, training and system support to guarantee a conclusive IT project deployment.