There's a screen that says you have a chance to level up your skills by training with a card that has similar skills, but I have yet to see a skill increase every time I train with a card with the same skill.
I figured it out, I managed to level my skills when I used the same card to train. I used shaman cards only to train the shaman and managed to level his skill up to 3. Sometimes it takes many times before you get a skill level though.
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