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I agree, Hawkeye has the leadership capability. However, I think the point being made is whether or not he is the best to lead a covert squad. I have to say that he probably isn't... and that Mockinbird (who has the training, the contacts and already leads a covert operation with the WCA) would make more sense.
I think Hawkeye wouldn't be boastful in this situation. He was given a responsibility and usually when someone gives him a responsibility he excels at it. Since it's a special responsibility...he will take it seriously. If it was just run of the mill hero work he might get complacent, lazy and arrogant.
Hawkeye wants everyone to respect him. When people show him that respect and make a special point of it he tends to come through.