This paper aims to investigate how organizations should create the conditions to facilitate Design Thinking implementation to balance their exploration and exploitation activities towards innovation. Literature has shown diverse contributions of Design Thinking to companies. However, very few have discussed one of its natures of being a mediator to nurture companies’ capability to explore and exploit simultaneously and how Design Thinking implementation actions could foster this positive role. This paper has carried out a case study methodology to reflectively analyze three empirical cases in which authors have actively participated and has presented different approaches in three projects to reveal key factors that companies should take into consideration for creating the conditions for Design Thinking implementation. Implications for companies regarding the relationship with their organizational learning process have been discussed eventually. The research provides a deep understanding of how companies could facilitate Design Thinking implementation, highlighting which specific factors and conditions could enable its ambidexterity approach, especially for managers.