Security-related topics like terrorism, large scale involuntary migrations and natural disasters are grounded in deep-rooted and complex societal problems. In order to promote safety, security management seeks to understand the nature of such problems, the contexts and systems in which they evolve, their different stakeholders, and corresponding relational dynamics. This chapter addresses those security challenges, which can be classified as wicked problems, and describes the complex systems in which they evolve. For such problems, systems thinking and complexity leadership are determinant for effective security management, as enablers of multi-stakeholder learning and innovation. Based on a multi-stakeholder methodology developed at Nova SBE (called wave-making) we propose a process that enables the development of co-created, practical and innovative solutions for wicked security challenges.