Problem: Project Task Estimation and the Culture of "Gotcha!"

I recently worked with an organization that adopted a mind-set in which it was assumed that the best way to keep project team members working hard was to unilaterally trim their task duration estimates by 20%. Suppose that you were asked to estimate the length of time necessary to write computer code for a particular software product and you determined that it should take about 80 hours. Knowing you were about to present this information to your supervisor and that she was going to immediately cut the estimate by 20%, what would be your course of action? You would probably first add a "fudge factor" to the estimate in order to protect yourself. The conversation with the boss might go something like this:

Boss "Have you had a chance to estimate that coding sequence yet?"

You Yes, it should take me 100 hours."

Boss "That's too long. I can only give you 80 hours, tops."

You (Theatrical sigh) "Well, if you say so, but I really don't know how I can pull this off." Once you leave the office and shut the door, you turn with a smile and whisper, "Gotcha!"

Questions: 1. How does the organization's culture support this sort of behavior? What pressures does the manager face? What pressures does the subordinate face?

2. Discuss the statement, "If you don't take my estimates seriously, I'm not going to give you serious estimates!" How does this statement apply to this example?