After reading the FAQ, this question might be considered as too-broad and opinion based. So if such is the case, please let me know and I'll preemptively stop the question.
Nevertheless, there has been multiple occasions where an associate of mine has vastly underestimated their level of competence in their field and ability to complete their assignments. Although I have reiterated the glowing reviews and feedback they have received from others and how their work stands above others, it would appear however that such a strategy does not work. They remain convinced that they are behind the curve and act despondent as a result.
At the same time, there are occasions where I have pointed out that certain goals or objectives (for another associate) might be out of scope and the skill level of the individual to reach in reasonable amount of time, i.e. finding investors to sink $18k to buy a car chassis for an engineering team working on electric cars when the team isn't even out of the conceptual stage. But the team leaders remain adamant on their success and abilities.
How do I reconcile the two sides of this psychological phenomenon?
Be more direct?
Utilize stronger words?
Use reverse psychology?