And in the interest of concisely answering the OP, if indeed it is based on sincerity:
I have had a few close relationships with NT's over the years. I do not claim to know what is bothering an NT, but I can usually tell there is something internally amiss even if they do not yet perceive it themselves. But I can't claim to know WHAT that something is, so in an effort to dig deeper, I sometimes try to put myself in their shoes to see what that could be. This effort would yield an accuracy of perhaps 50-70%, depending on the relationship and on how well I know them.
I am interested in an NT's "thinking side" but they are often dismissive of feelings so this can be off-putting and a barrier to closeness.
In some NT's I have sensed depth yet upon probing found none, or alternatively, none was chosen to be revealed to me. So I have learned to be judicious with assumptions in this regard.
Hope that helps you.