In a growing world of Information Technology, entrepreneurs, start-ups and SMEs (small and medium-sized enterprises) require a good mechanism of delivering a good service. Information Technology Infrastructure Library (ITIL) is identified to be the best and most popular “best practices” framework. However, implementing ITIL not only is very difficult but there are also no best practices for implementing it. As a result, ITIL implementations are usually long, expensive and risky. This paper proposes an approach to identify and assess small business specific ITIL implementation and provide a roadmap for improvement based on the assessment results, business needs and guidelines. The proposed guidelines were used practically to assess and implement ITIL processes in a real-world digital agency.