Only when participants find themselves in authentic and real-life leadership situations, their management and communication competences develop and expand in a long-term effect. Good leaders create successful environments for their employees to thrive individually and as the entire company. In that sense, the mountain guide resembles the modern business manager’s job profile in a surprising way. Just like guests on a guided tour in the mountains, employees want to be challenged and encouraged; their functional competences need to be emphasized and developed. Therefore, both mountain guides and managers need to pay close attention to the motivation of their clients or employees. At the same time mountain guides and executives need to be able to handle their own doubts and uncertainties, articulate them properly and still make clear and binding decisions to ensure the success of the respective undertaking. We are putting these analogies purposeful into place in our leadership development programs to sensitize current and prospective managers for their demanding tasks and challenges. The outdoor environment offers perfect conditions to extract and address personal behavior in a respectable and trustworthy fashion in a destressed surrounding similarly to our team trainings.