Depositions of the employee victim in a discrimination case is a key event. The employee must demonstrate that s/he can tell a coherent story and maintain some composure about one of the most difficult events in his/her life. Deposition strategy for the employer’s lawyer essentially is to obtain information from the employee. Often, the defense lawyer specifically seeks information from the employee that is damaging to the employee’s case. The defense attorney wants information he can use against you. See Pitts Law comments regarding what to expect at a deposition of the plaintiff.
So, there should be no reason to ask the same question more than once or twice. Asking the same question continuously is "badgering." Badgering is defined in the American Dictionary as asking the same question repeatedly. To ask the same question over and over, knowing what the answer will be is surely someone’s definition of insanity. Yet, so many of us do exactly that in a deposition.
More importantly from the defense lawyer’s perspective, when you ask overly harassing questions, you remove any hope of eliciting cooperative testimony. Many employees expect some degree of cooperation with their employer in a lawsuit. All bounds may have been crossed, but there will still be some residual expectation for some mininal cooperation. Once even the slightest cooperation appears foregone, the plaintiff will hedge on every question, no matter how innocent. And, in these days when settlement is such a part of every lawsuit, the amount necessary to settle will rise exponentially.
As Mike Maslanka says, the deposition is about the forest, not about the trees. So, us attorney types, we need to relax a little and "take a breather."