Why not set a format like top model.....
If you want to test the successful trait, then you have to train them as well.

So say, this week's challenge is wisdom, then have a challenge setting them up in a scenario that tests their wisdom. Then have a panel of judges consisting himself, Tony Robins, and NBA recruiter to judge who the most intelligent person is and telling them their weakness. And for the final 2, let them give an inspirational speech to determine who the real successful person is.