The wide world of ethics and law and related systems telling us how and what to do is well established, if not also clear and widely accepted. In a simplistic trine, it might be divided among things generally considered right, things generally considered wrong, and a no-man's land in between. For many of us, this in between is not all that clear and is complicated by the fact that we receive consequences for our decisions, sometimes because we just did not know or just disagreed with a client or stakeholder. Technology management, because of its direct involvement in changes to how and what we do, is understandably more likely to be faced with situations for which the rules of conduct were not designed or about which there is significant disagreement. This paper is not directed to rewriting the rules; it is directed to suggesting and identifying a number of areas in which there are better ways of evaluating situations and better methods for avoiding the risks of a less suitable choice. A checklist will be illustrated by examples, e.g., lying about your (hole) cards in poker is acceptable (or even better) but is not in a bridge game.