Having been through a mentoring experience in my own right over the last 18 months I'll share my observations. As a bit of background, I've been teaching an indian guy who reports to me at work about life, the universe and everything. I work as a database administrator for a company of 400 people which has around 3 Terabytes of data managed in a trust relationship on behalf of its clients. My junior guy had lived a very sheltered existence before starting work at the company where we both work. He'd been a head-down/tail-up kinda guy for most of his life and had been so focused on getting educated, etc... that he had never really learnt how to live.
When I first started at my current employment the guy I was given the responsibility to mentor professionally was a bit taken aback. I came in, looked at the way things were being done and was horrified (having come from big shop IT into an environment managing similar amounts of data to a place where just about every administration task required direct manual intervention) and immediately started to make changes. I laid down the law and said "This is not good enough - we need to do this smarter and better!" My junior DBA's response to this was abject horror. I represented an immediate and tangible threat to the comfort zone which he had surrounded himself for most of his life. He was one of those people who are quite happy to do repetitive tasks step-by-step over and over again because they don't know any better. There was a LOT of friction in the first 6 months of our working relationship and in the end we needed to get some mediation in place because we just couldn't communicate about the same thing in the same way. There was his reality which said that everything had to be step-by-step and tiresome and he couldn't accept that there was a different way of doing things. On the other hand, my reality was that his perspective was flawed and I was throwing that in his face at every opportunity I got.
In the end, I changed my approach. I moved the focus away from what I wanted to what he wanted. If building infrastructure reporting tools I would ask him to make suggestions on how he'd like the data presented. If he wanted to do things in a more manual way than I intended I'd ask HIM if there was a better way. I'd ask some questions along the lines of "How much easier would it be for you if ...?" and he'd do a double-take as he realised that what I was suggesting was actually possible. By leading him to the realisation that what each of us wanted was effectively the same thing (more time to work on professional development and proactive systems management [or once we've reached industry best practice long lunches at the pub!]) then he was prepared to listen to the vision I was trying to sell him.
Once he realised that there was a direct benefit from the changes I was trying to implement he mellowed considerably and we now have a very easy-going working relationship. He asks me for career advice. I drag him out for pub lunches now and then. He asks my opinions about politics and economics. I ask him for his opinions about the latest test series. We discuss religion and make cultural observations and generally manage to communicate better than any two other people we work with. We occasionally buy each other a beer at lunch and we work together really well as a team. This guy is now as good a DBA as I have ever been - the only problem that he has is a degree of tunnel vision - once a problem is not initiated on a server he needs to ask for advice.
So how does this translate into advice about mentoring?
Well... there are four key lessons in my experience.
First you must build trust. Trust has to be earnt. My initial problems with my colleague fundamentally came as a result of him not trusting me. When I changed my approach from TELLING to ASKING (with some leading questions to follow up which would open up some cognitive doors) I had immediate success with the relationship building process.
Second lesson. A mentoring relationship requires generosity. Sometimes the fact that the protégé needs help has to be the most important thing on your mind. Another friend of mine has had several mentoring relationships (he's even taught me some very important lessons about dealing with people) makes a point of making people feel that if the need is dire enough that they can always call on him for help and support. I've known people who have gone to him ahead of their own FAMILY for help. Friendship has no office hours.
Third lesson. When I marched in, took control and started ranting about "the way things were going to change around here" people took great offence. Since I have adopted a more subtle and conciliatory approach (asking people what they want and then leading them to an understanding of how my solution gives that to them) my "mission" of modernisation and automation has been embraced more warmly amongst not only my own staff but by all the people in the company whom I deal with. It's always easier to take advice from a friend than an authority figure.
Finally, remember that you cannot force anyone to become a person they don't want to be. Someone who doesn't share your passions will never change their mind just because you say so. If you give them a reason to be passionate about the things that inspire you then they might just turn your way. EXPECTING them to do this will guarantee failure. ALLOWING them to do this will usually give you better odds.
Re: the initiation process... maybe the lad you're to be responsible for teaching should be consulted about how HE wants to be initiated into manhood? Then perhaps you can lead him to a vision which is acceptable to both of you and a deeper experience for the both of you.
I hope this helps.
Regards
Jeremy