I think he did. I never heard him talk like that. Upset and almost frenetic. Well...for him. The conversation didn't start that way but once he really started talking about what was bothering him, it was like he just couldn't stop. I felt bad for him because all I could hear is "I'm doing this right, why isn't it having the results I expect?" He didn't say it but I could almost hear him say, "Will you tell me what I'm doing wrong here?" I think it must be really painful for an ESTJ to be doing everything like they should and everything is still all fucked up. He really didn't need much feedback from me except to listen and reassure him that no matter how things turned out to take comfort in the fact that he was doing the right things and to just continue. The real solution lies outside of himself and I don't think he is ready to hear that.

Poor guy. I really, really relate to that. I read this entire quote and wanted to bold practically the entire thing, just to emphasize how much I relate.

Seeing things that are wrong and being unable to fix them is definitely one of the most upsetting things for ESTJs (except for universally upsetting, tragic things, of course). I've vented at people in a very similar way to that - with practically your exact quote: "Will you tell me what I'm doing wrong here?" And you did exactly the right thing, in telling him that he's doing everything he can

Takes a huge burden off his shoulders. Reminding him that "it's not your fault".
Why does my ESTJ friend keep nagging me to socialise more? What if I kept nagging her to stop nagging her own child?
Well... to a degree, ESTJs nag by nature

because they care. If they don't give a shit, they won't nag you. But if they worry about things not going smoothly for you - if they're concerned about your well-being - etc etc etc - then they consider it their duty as a friend/family member to step in. Worst case scenario: something terrible happens, and if only you had stepped in, the terrible thing could have been avoided.
But that's more Te dominance, than ESTJ-ness. ENTJs nag too, right?
Can you lend me some Si...
Here. Use it well, young padawan.
The only time I kinda debate for the sake of it is to learn more about something. And even then, I don't think I'm debating. I ask questions to understand wtf is going on. Some people might think it's debate-ish. *shrug*
That's actually what I do, too.

Exactly what I do. I totally agree. I usually don't like "debating", unless I know for sure that it will come to a satisfying conclusion - because I hate those debates that end with some vague understanding of all the irrational emotions that form the basis of everyone's opinions of everything.

I like the debates that end with a lovely enlightening moment, and make you feel like you appreciate the other person more

Or that you've convinced them that you're right
Oh, and I know none of that it related to NPs. D:
It's still sympathetic, and that's what matters

It's actually nice to know that it isn't always type-related, in a way. Though I'm still confused about how I manage to get into debates and then get lost in them...

I thought conversations were things that are easy to follow when you're in them?
When any debate opens, this is where it will lead. I can completely identify with debating for the intellectual stimulation or to sharpen or focus my thoughts. That is the purpose of the debate--nothing more, nothing less. I don't want it to necessarily go anywhere. I love it but I have come to realize that other people don't enjoy this at all. It's either seen as confrontational or as you said, going nowhere.

Or feeling like you're being used as a sounding board, without your permission. I dunno - I like conversations that focus my thoughts, as much as anyone. But for whatever reason, they make more sense to me when I'm talking to Js. I've had very intellectually stimulating and thought-sharpening conversations with NFJs, but that's mostly because it ends up being a pretty linear conversation. Or else, it's like a flowchart, and there can be multiple conversations going on at once, but they're still pretty linear and therefore they still make sense, even if there are so many. If that makes sense.
Also, to be fair, I have had really, really excellent conversations with my INTP dad. Not DEBATES, but conversations, where we throw out ideas and neither of us presumes to have a position, or not. If I'm in a debate, I have a position. I may abandon it if I'm convinced of something else, but I always have a position. I don't consider it to be a debate if I'm position-less. Also, like mcmartinez said earlier, I would probably be asking questions, instead of making blanket statements (as my INFP friend was doing earlier), to make it clear that I'm not taking a side yet.
Hmm...I didn't know that an INFP would do this...thought this was more of a XNTP trait.
It was SO WEIRD! I'll give you a sample, when we were talking about an author:
Me: He had interesting points, but he really annoyed me. He would make these huge blanket statements about huge groups of people. It was frustrating.
Her: Yes, but consider his background; his family was killed by members of that group of people.
Me: But that generalization! It's so frustrating! I HATE those blanket statements!
Her: But think of his background!
God DAMMIT. It kept going around and around in circles like that! Complete type-related miscommunication. She was acting as if I should consider it OKAY for people to be irrationally biased. As if the argument could be won by the sheer power of her Fi alone. I can't debate with someone who talks like that; we operate on completely different concepts of what's rational or irrational! I doubt that this is the fault of her type - I mean, we all know that rationality isn't type-related. But... it was SO ANNOYING
(There was a lot more to it than that, but that's just an example)