I think that perhaps the cruelest feedback you can ever give someone is: “You are having a problem due to faulty judgment.”
The problem with this assessment is that it is both the height of arrogance and impossible for the receiver to do anything about.
It is the height of arrogance, because the only way you can criticize a person’s judgment is if you completely understand the circumstances they were in and the information they had available and still think that you could have used better judgment. It is an automatic assumption that in almost any given situation, you would do better.
It is also impossible for the person to do anything about it because if they truly try to do something about it, they are put in the position of having to second-guess every decision they make, a recipe for certain failure. Moreover, unless you expect them to continually come back to you to make decisions for them, they will be using the same judgment you criticized as being faulty to decide what normal reactions are the result of faulty judgment. If not actually an impossible situation by definition, it is at least an untenable situation that will ruin self-confidence.
If you ever find yourself wanting to criticize someone’s judgment, it would be well worth the time to attempt to determine exactly what mistaken assumptions are held that might be leading to bad decisions. Assumptions can be changed, and decisions will be improved accordingly. Forcing someone to question their own judgment is a form of torture, I think.
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