This empirically informed report presents two innovative approaches to learning through work and working to learn from a secondary school in Germany, with both the school and its innovative development having received the German School Award. In one approach, the school's leadership team deployed the new "Challenges" school project for students' comprehensive educational development. In the other, the school initiated the possibility for teachers to gain practical experience outside the school by working full-time. In addition to their teaching duties, teachers can now work for a limited period in the private sector, thereby gaining valuable experience by shaping their professional stances and influencing their approaches to their students in everyday school life. This empirically informed report is based on desk research complemented by qualitative data gathered during a site visit. These data shall give a deeper understanding of how innovative actions initiated by the school leadership team can contribute to change within an educational system towards advanced teacher learning and transformative school development to achieve better student success.