Faced with the challenge of combing long hair, I do the logical thing:
Assess the outcome I want to achieve. Then start from the crown, and comb down.
It took the gentle coaching from another with long hair, to show me how to have a more desirable outcome: A little one that does not feel tortured by her dad.
This I have done: Walk into situations, logically assess, without any sensitivity to the pain that may cause.
Now, I try and find people that will coach me on the nuances that I miss.