Cryptic Messiah

What’s the deal with Jesus being so cryptic?  Particularly in the Gospel of John, he seems to be more of a riddler than a teacher.  He speaks of his death, his relationship with his Father, and morality in terms that we struggle to grasp now of days in hindsight, let alone the confusion he must have caused for original listeners of that historical era.  More often than not, Jesus says something, people sit their dumbfounded, he says it a different way, everyone leaves more confused

I suppose Jesus was setting people up to seek him sincerely.  Jesus told parables so that people had to dig a bit before finding him, and the same probably applies here. 

That being said, here’s my big question: Are we supposed to teach like Jesus?  Sunday school answer says yes.  Today’s conventionality says no.  Contextualizing Biblical times says maybe.  

I’m slow to publish an answer because deep down I just don’t get why Jesus was a riddler.  With masses of spiritual inquirers, it seems so counterproductive not to give them clear instruction on how to follow.  It’s almost like he wanted them to believe first and follow second – unconditionally trust him before he told them how to live.  It worked for Jesus as the Messiah.  If anyone else tries this it looks like recipe for a cult.  Maybe there is still a way to riddle people toward Jesus without getting in the way?