User blog comment:Zathronas/Analysis by an author: Peter Port/@comment-12227301-20131214003834

Seeing how both of the characters have a history of their own, I'd say his confidence stems from (likely personal) experience.

If nothing else, Ozpin has led a "school" of this kind for a while. If there ever was a tight spot, which you can bet there are in their line of work, he is the one who led them through it. There would be ample opportunities to prove his leadership and descision-making skills to all who would be watching, such as an old-time student or teacher.

Also, the guy is almost TOO tertiary. Insignificant enough to warrant a plot twist, such as being Ozpin's mysterious correspondent. Plus, I get a feeling the two may have been partners in the past, or currently are on some other level. But those are hunches if there ever were ones. So they're off the record.