In systems engineering, obliquity is a theory that proposes the best way to achieve a goal when you are working with a complex system is to take an indirect approach instead of a direct one. For instance, if you are running a large IT department and your goal is to help your company be profitable, the best way to achieve that goal is to think holistically and consider both the business and the technical needs of your company's employees. By concentrating on a goal that involves providing quality services -- and not just focusing attention on narrow financial metrics like unit costs and return on investment (ROI) -- your IT department will help employees work more efficiently and be more productive, which will in turn, make the company more profitable.
Obliquity has a lot in common with the principles of chaos theory; both concepts rely on the idea that, in a complex system, the factors involved are too numerous and too intricately connected to be easily understood. Therefore, just as we cannot be sure that long-range weather forecasts won't be affected by some unforeseen influence, we cannot be sure that single-mindedly striving for financial success is most likely to lead to our goal. The theory holds, for example, that individuals whose only concern is their own happiness are rarely happy individuals, and that companies that seek to maximize profits at all costs are unlikely to be the most financially successful.
The concept of obliquity in this sense was introduced by John Kay, a British economist and business writer. In his lecture "The Role of Business in Society," Kay explores the value of a holistic approach to business, and the paradoxical success of such an approach over that of a simple focus on maximizing profits. Kay quotes George Merck (founder of the extremely profitable drug company): "We try never to forget that medicine is for the people. It is not for the profits. The profits follow, and if we have remembered that, they have never failed to appear. The better we have remembered it, the larger they have been."
See also: Theory of Constraints