Sometimes, the Trickster Mentor or Zen Survivor has a lesson to teach the younger folks for which words won't do — only by setting them up to discover it themselves will it take. In some cases, it is because the lesson won't make enough of an impression if explained; either they have to go through it themselves, or they have to put it into their own words before it really registers. In other cases (especially involving mystical teachings) it is something that literally can't be spoken at all, at least not in any manner that won't sound like an Ice-Cream Koan to anyone who hasn't experienced it. A form of Taught by Experience.
Differs from Figure It Out Yourself in that in that trope the 'student' knows that they need some important information and the 'mentor' blatantly refuses to give it, while in this one, the student is usually oblivious to the fact that a lesson is being given at all until the moment of illumination.
See also: It Was with You All Along which is this with a Fetch Quest attached.
Naruto's teachers love this method like Naruto loves ramen.
Kakashi's first challenge is to seize two bells from his person. Fail to get a bell, fail the test, yet there are three students. The lesson is to ignore the built-in incentive for competition and work as a team. (Later we learn that this method is a strange, sadistic tradition amongst the Hogake-trained line.) They fail to realize this and are punished by only two of them eating lunch while the other watches (guess who), which was another test of character. They give Naruto food despite the rules and pass.
Jiraiya gets impatient teaching Naruto how to release chakra. So he pushes Naruto into a deep canyon so that he releases his chakra in a panicked rush. Yes... That is truly the ONLY way Naruto could learn it.
Ebisu wants to teach Naruto to walk on water, and gives a decent explaination how... but thinks it best that Naruto's practice water be boiling hot. Training from Hell excused with it's the only way they will learn. The counter-argument being that a student who has just been dunked in boiling water most likely won't have the best of focus - which is crucial to walking on water.
Recently, when sages tried to explain the fusion of different types of energy into the body, Naruto was at a loss. So one of the sages literally gave an Ice-Cream Koan.
Gamakichi: It's like how ice cream is even better when you add mint to the chocolate and vanilla swirl.
Papa: That's even harder to understand!!
Naruto: Oh! I get it!
Gamakichi: Hehehe... That's just how Naruto is...
In Fullmetal Alchemist, Izumi Curtis leaves Ed and Al, then just kids, to survive a month on an island without using alchemy because, apparently, that's the only way they will learn what her philosophy means. However, when they explain in short what they've learned, she laughs at them, suggesting she may have been just testing their determination to train under her. Worth noting is that in the manga, she had her husband's apprentice on the island as well, wearing a monstrous mask and wielding a stick, just to up the ante... and also to keep an eye on them should anything seriously bad happen.
Played with in Izumi's own training in an omake. She was put in the same situation, learned a slightly different lesson...only to discover she trained under the WRONG TEACHER! The alchemy teacher was next door, she got the survivalist! One quick beatdown later, she is on her unique path...
The Matrix can only be understood through direct experience. While the audience may feel the urge to scoff at this at first, it does make sense. Telling someone they have lived in a computer simulation their entire lives may be easy, but they're not going to believe you without proof. Also, as Cypher points out later, if they were upfront about everything, their recruits would be more likely to refuse.
Later in the film, Morpheus sets Neo up for the "grand illumination" form of this in order to make him realize that he is The One.
Double Subverted in All About Eve. Karen deliberates on her plan to help Margo to get over herself. She finishes with "there's not even a reason why I shouldn't tell her," then, as she picks up the phone, adds, "in time." Subverted again, when it turns out Karen is the one with her head up her ass.
Local Hero - Old Ben, a hermit beachcomber, legally owns the shoreline in a village an oil company wants to purchase, and he's the lone holdout. Mac the acquisitions executive tries to bargain with him; Ben scoops up a handful of sand and asks if he'd give a pound for each grain he's holding for the property. Mac refuses outright, and Ben points out that he can't be holding more than 10,000 grains, and he missed a good deal. Ben is clearly implying he doesn't recognize the true worth of the place but Mac doesn't get it - when the CEO arrives, Mac tells him "If he makes any offer involving sand, take it!"
Kind of the point of the whole book of Hosea. Why order a prophet to go marry a brazen prostitute? Because sure, God could easily just tell the Israelites they were cheating on Him with other gods just like a wayward wife cheating on her husband with other men, but talk is cheap and people weren't paying much attention to anything the prophets were saying just then. Hence the need for a realistic demonstration of the analogy. "Look how she treats this poor guy! And that's exactly how it is with you people and me: I take you in, give you all kinds of good things, let you share my good name, and this is how you repay me!?"
Ender from Enderís Game is put under a series of trials by his seemingly negligent adult supervisors in order to balance his kindness with ruthlessness, making him unafraid to kill when a crucial decision must be made — he ends up (unintentionally) killing two people to complete his main training. Mazer Rackham then ruthlessly punishes him in physical combat until he learns to let go of his instinctive mercy.
In The Dresden Files, Harry's lessons for Molly Carpenter, a reforming Warlock, involve this. He tells his cop buddy Murph that she's the kind of person you "have to keep knocking on her ass" because "If I don't, if I let her recover her balance before she gets smart enough to figure out why she should be doing things instead of just how to do them, or if she can do them, she'll start doing the 'right' thing again. She'll break the Laws again, and they'll kill her."
Another example shows up when he first takes her on: he throws a miniature sun at her face and screams at her to make him stop it.
Once Molly finally does learn those lessons, signified by a bracelet he'd had her wearing breaking, Harry explains that his own mentor put him through much the same thing.
On Arrested Development, extreme examples to "teach them a lesson" are present from the first episode, where Maeby conspires to teach her parents a lesson about being away from family by making out with her cousin and claiming she didn't know. Later in the series, it would be revealed that the Bluth kids have an aversion to being taught "lessons" in this fashion from their father using a One Armed Man who would lose his prosthetic arm in gruesome ways resulting from their actions.
One episode of Dead Like Me has Dolores Herbig have an employee fake a heart attack so she can teach the Happy Time employees a lesson about using the defibrillators to make grilled cheese.
As might be expected from a game with a Karma Meter, you can subvert this trope by taunting her for her weakness, mercilessly killing her and then continue your path down The Dark Side merrily kicking puppies along the way.
And Kreia in Knights of the Old Republic II.
Kreia defines this trope. There's even a scene on Nar Shadda, where you can choose to help a person in debt or not. Either way, she berates you and shows what happens for the worse, in an attempt to show you how far reaching your actions are. This is relevant because basically her whole motive for setting the events in KOTOR II into action is based on this philosophy.
Valve accidentally revealed the "Meet The Spy" video for Team Fortress 2 before its official unveiling - and subsequently added a "Valve Corporate Achievement" for "Failing to understand what 'Private' means on YouTube." The heading for it was "It's the only way we'll learn."
Case number four of Phoenix Wright: Ace Attorney Justice For All has very clear undertones of this, when you think about Edgeworth's awareness and motivations regarding the case.
This is the generous interpretation of Grand Cleric Elthina's, er, "hands off" approach in Dragon Age II. Despite being one of the most powerful political figures in the city, she refuses to be assert her authority on the grounds that "children learn best when allowed to learn themselves". As a result, anti-Qunari zealots have room to commit hate crimes and the Templars repeatedly inflict brutal punishments on the Circle of Magi.
Little Busters!: The whole game, and particularly Refrain, revolves around Kyousuke trying to impart this onto Riki and Rin. He knows he and the others are going to die, but just telling the two of them that they'll need to be strong isn't enough - he needs to force them to be strong in less dire circumstances so they gain some confidence and will know what they're capable of when the time comes.
In Justice League Unlimited, Wildcat has become such an adrenaline addict and rage case that he's joined an underground fighting ring, and it's just a matter of time until someone gets seriously hurt. Green Arrow arranges a bout and then fakes his own death in the ring at Wildcat's hands, forcing Wildcat to face "My God, What Have I Done?" before it happens for real.
This applies to the Cutie Mark Crusaders from My Little Pony: Friendship Is Magic. they have not yet realized that they can't force their cutie marks to appear and need some kind of epiphany. but from an in-universe prospective, they WILL learn this lesson because every pony eventually gets a mark. Also, their friend, Twist, already went through this and had said epiphany needed to get her cutie mark.
As mentioned in the Cruel to Be Kind page, one of the hardest things a parent/teacher/coach can do with a child's dream is let a child learn this way. If the adult hasn't convinced a child that pursuing a dream or goal could not only not pay off, but actually be harmful, sometimes the only way to make them learn is to let them try and fail at it. Whether or not the kid learns, or learns the right lesson, depends heavily on the individual child and the goal that can't be achieved. But, no matter what, it's hard for everyone involved.