A significant decision made by the skilled mentor should be attention to the proper timing of direct challenges to the mentee’s facts and opinions.
The mentor must be particularly alert to the timing of an intervention—especially when utilizing the confrontive approach—because the mentor is relying as much on the psychologically right moment to introduce a point as much as on the actual intellectual weight of the issue under consideration.
Similar to the idea of a teachable moment, it is sometimes nearly impossible to separate the value of the comment from the readiness of the receiver to hear it. Mentors should be careful in the important early stages of the relationship that good intentions do not unexpectedly but dramatically transform into missed opportunities and even negative outcomes.
For example, a mentor who exposes—before a reasonable degree of trust has been established—a mentee’s thin veneer of facts or legitimate experiences could clearly be successful in winning an argument but deficient in the goal of assisting the mentee to reexamine flawed or poorly reasoned conclusions.
Mentors need to be properly concerned about implying that their own more sophisticated and seasoned reference points must always be automatically adopted as gospel.