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They can be effective but most teams don’t get a chance to practice enough to pull of a traditional hook and ladder with much efficiency. Similar to a hook and ladder though, running designed plays where you intentionally have one or two guys in pitch position is something that is pretty common.

How often to hook and ladders work?

Depends on what format you’re talking about, but in general some sort of throwback or hand-off with a backside play developing for a big gain (post, wheel, etc) is pretty popular. Check out this blog from FlagSpin that goes into detail on deception in flag football and how to use it regularly.