Yeah personality definitely plays a role. What I've noticed is that when a player is under ~20y/o he is generally much more accepting of learning from someone with a different type of personality. Try to set it up so that your youngsters are tutored by people who are regarded as a "Similar Type of Player" or who are on the youngster's list of Favoured Personnel. For players who are 20-21, try and pair them specifically with someone who shares their personality and can nurture them.
The best thing you can do though, is to get an Asst Manager or Scout with stats of 18+ in Tactical Knowledge, Juding Player Ability and Potential Ability, and Working with Youngsters. I think this is the set of requirements (others should please correct if I'm wrong) to get good advice from your manager regarding who is best suited to train specific youth players. Just check in the coaching reports and you should see advice from the staff member on tutoring. The reccomendations still don't always work, but have a much higher success rate than randomly assigning tutors.
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