Computer is involved in every walk of* life. It is being used in education as an essential tool to enhance the academic activities from lecture delivery to assessment. Academic personals are keen to perform their activities through computer but lack of the particular software which limits the real advantage. Students become lazy in study if they know their assessment results late, By considering the great benefits of computer, we have developed quiz software named who wants to be IT professional (WVVIP). It has a sufficient variety of questions, where IT users can test their knowledge by attempting the right answer in a sequence but question stochastically taken from Question Bank with options and supporting life lines (50:50, Phone a friend, Audience). The software is fully based on artificial intelligence and incorporates the Microsoft Text-to-Speech engine. One can not only test his/her knowledge of IT but, he will be entertained and become artisan in the field of IT gradually. This paper elaborates the overall design, architecture and flow of WVVIP software and presents the numerical analysis and the assessment scheme.