This talk describes experiences and lessons learned while defining product requirements for small and large companies over a thirty-year period. From 1969 to the present the author has assisted or led teams in the definition of requirements for a wide variety of products and systems, including music information, produce delivery, power and process control, baggage handling, mail sorting, insurance, medical device and information, communications, taxation and even race horse breeding.

Often, the success or failure of the projects encountered depended on factors that were not immediately apparent to the project teams involved. At times team members would take the correct steps without realizing the consequences of a misstep. In other cases minor missteps might lead to catastrophe.

Finally, the talk presents a rationale for the perceived precipitous drop in software project completion rates since the 1960s and 1970s, and offer suggestions for better preparing computer science students to meet the challenges of 21st century software development.