This paper aims at investigating how organizations should create the conditions to facilitate Design Thinking implementation for balancing their exploration and exploitation activities towards innovation. Literature has shown diverse contributions of Design Thinking for companies, however, very few have discussed one of its nature 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 its organizational learning process have been discussed eventually. Through the research, a deep understanding of how companies could facilitate Design Thinking implementation is provided, highlighting which specific factors and conditions could enable its ambidexterity approach, especially for managers.