My learning cohort was asked "What is the greatest challenge to helping a person grow spiritually?"
I've often found that the greatest challenge is myself! I sometimes catch myself behaving like it's my job to fix a person. And really, aren't there already enough codependent relationships in the world?
A speaker at a retreat once described the relationship between disciples as "One beggar telling another beggar where to find bread." That's always stuck with me. In my better moments I resist the temptation to be Superman and simply come alongside a person to share the joys, struggles, and the hope we've found in Christ...
When my wife worked in human services she used to joke that the most wonderful word in the English language was "referral." Well, it's wonderful to refer people to the care of the Holy Spirit.
Challenge number two is: myself. Again. It's easy to take a method that works for me and assume that it will work for everybody in every situation.
I'm introverted. I feel the presence of God in the quiet. I like to read, journal, meditate and pray the daily office. These aspects of my devotional life are nonnegotiable. But they may do absolutely nothing for another person -- say, someone especially extroverted.
I guess I need to keep the end purpose in mind and remain flexible with the methods. The end purpose is that the person has an ever deepening romance with God. (Even if they'd leave me standing in the middle of a labyrinth while they trotted off to some happy clappy songfest!)
The third challenge I see is an expectation that a person will experience one magicial moment that will make them spiritually mature in an instant... No struggles, no discipleship, no dark night of the soul required. Patience is a virtue, little padawan. I guess that's doubly true in regards to watching someone grow spiritually.
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