Why are risk decisions sometimes rather irrational and biased than rational and effective? Can we educate and train vocational students and professionals in safety and security management to let them make smarter risk decisions? This paper starts with a theoretical and practical analysis. From research literature and theory we develop a two-phase process model of biased risk decision making, focussing on two critical professional competences: risk intelligence and risk skill. Risk intelligence applies to risk analysis on a mainly cognitive level, whereas risk skill covers the application of risk intelligence in the ultimate phase of risk decision making: whether or not a professional risk manager decides to intervene, how and how well. According to both phases of risk analysis and risk decision making the main problems are described and illustrated with examples from safety and security practice. It seems to be all about systematically biased reckoning and reasoning.