one thing to keep in mind is that he may not have even been pre-T, and even if he was, he may have been quite far along in his transition (socially and legally), so may be familiar with all he needs to do. I know that was the case for me - I was en route to start T, just waiting for family stuff, and already did the name change, was living as male (to the best of my ability, given my trouble passing) and gotten referrals for surgery. It was just a matter of waiting. I knew every step I needed to take, and what that entailed, I didn't really need or want additional support.
And I always had people coming up to me, well-intentioned, saying "hey, I can get you started on this." And it was hurtful. Sometimes these people were actually new to transitioning themselves, knowing less than I did, but assumed because of how I looked, that I was brand new at it. What was a real slap in the face was when I was on hormones and people did that - saying "hey, I can get you started on the path to hormones." To me, it made me feel like my appearance made me look like someone who was trying and failing. Maybe I was taking it too personally, but it sucks when you're on your way but people assume you're not and need help.