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I think it's a problem when an organization contrives 'challenges' just to make life a little more difficult for the pledges or to shift onto pledges responsibilities that the entire brotherhood should share.
In my chapter, if a task or project needed to be performed, we did not dropped on associate members. The entire brotherhood would take part, demonstrating the need for ongoing commitment, showing that we took it seriously, and bringing the new members into sharing those responsibilities.
Many chapters decide that their pledges ought to be challenged and come up with absurd tasks. Someone recently whined that his headquarters had forbidden his chapter to set out tasks like requiring pledges to memorize the number of floorboards in the attic. Say what? Cry me a river. That's not a personal emotional challenge, that's a trivial arithmetical one. People don't grow from that; they're demeaned by it. People also learn a lot more about commitment by signing on to commitments in which everyone shares than they do by undertaking a series of tasks only to achieve the "right" (hah) to foist those tasks off on others. That's not commitment. Commitment calls for continued work.
Most of the events in Greek life that shape members' lives won't be things we can program; they're things that "just happen" that call on members to respond. In my small chapter (25-35 people while I was there), some of my most powerful experiences were when we gathered in a dimly lit room to talk about the things that were going on in our lives that we weren't sure how to deal with. (Sometimes that would include each other, and these gatherings helped to address problems between brothers that might otherwise have simmered for months.) But only initiated brothers were invited to those events. The question is how to give new members a taste of the real challenges of fraternal life and calls on them to start asking questions about who they are and who they're going to be without inventing bullshit tasks and scenarios.
Do I have an answer for that question? Not really. I know of a first step, though: new members can tell if the older members clearly take the organization, its principles, and its goals of personal growth seriously. If they see that, they become a lot more open to thinking about the commitments to principle and personal growth that fraternal life entails -- even if they don't yet know what the exact words for the principles are.
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