The purpose of this paper is to identify the key elements in Strategic Outsourcing (SO) management that contribute significantly to the success of high performing SMEs. In this paper I shall clarify briefly what SO decision factors are affecting the success of high performing SMEs. After identifying these key factors, we can help SME managers and owners in their SO decisions, so through this approach they can better leverage external knowledge, technologies and innovation through correctly managed SO partnerships. The main concern of this paper is to show the importance of knowledge creation and knowledge sharing through SO partnership to SME managers and owners. Organizational learning is identified as very important for companies to be innovative and to stay competitive (Elango 2008)(Harland et al. 2005)(Marques & Ferreira 2009)(Hamel et al. 1989). I chose comparative case study as my methodology (Yin 2003), using primary data collected from seven SME companies located in Slovakia. They are to represent component suppliers in Business-to-Business (B2B) market, where end user data translates into product specification by OEM Company. This means that close relationships in the industry are very important, making it a good platform for knowledge sharing and for co-development activities. I used a structured five-scale questionnaire in interviews to locate the differences between company approaches to each key SO decision element. These questions represent key elements of SO management, identified in the literature (Kelley & Jude 2005)(Lorber 2007)(Hamel et al. 1989)(Stanko et al. 2009)(Marques & Ferreira 2009). This paper surveys where the main differences appear between high performing and average SME companies towards SO understanding in real life context. After analyzing the findings, this study concludes that the main differences between two groups of companies appear in SO activity identification, in project evaluation, in knowledge sharing and in monitoring market dynamics. High-performing SMEs in general approach SO activity as an opportunity to partner with suppliers to generate and share organizational knowledge and accept it as a strategic partnership. On the other hand though, average performing SME generally understand the SO projects as a supplier-buyer relationship, they do so with short-term targets and without any focus on long-term knowledge generation. This paper can contribute to the competitiveness of European SMEs by providing guidance in SO management by raising their awareness of key elements, which contribute significantly to the success of SO in the long run.