Okay, you know how with some ESTps (it happens with other types, too, but I think most of my experiences with this have been with ESTps), people are a litttle afraid to approach them because if they say something the ESTp may make fun of it and make them look stupid? People around them sorta wanna be friendly with them, but often end up avoiding them out of fear of being ridiculed. But there's always one or two people... people who seem to be able to say anything to the ESTp, to tease him or correct, and he'll just chuckle, or if he's in a bad mood, make a remark (but not go off like he would on others). You know damned well that if you said the exact same thing, you'd be met with a cutting remark or even be totally bitched out, and you just can't seem to figure out why it's any different with that person.
I'm generally one of those people, the ones who are allowed to speak freely. There's a few tricks to dealing with ESTps. First of all, don't try to get too familiar too quickly. It's best to disagree with them or have serious conversations with them in private many times before attempting such a thing in front of others. It's important to establish three things with the ESTp. First of all, you like him. He's rough around the edges and fucks up sometimes, but so what? Everyone does that... he's cool even when he's not cool. Secondly, you must not be intimidated by him. His bullshit is a bit funny and his observations are generally correct and he's certainly quick witted, but this does not threaten you. Thirdly, you have his best interests in mind. No, you don't want to "help" him, just to point out a few things that will allow him to smooth things out a little bit around him in order to get what he wants. While he does want to be respected by those around him, he also wants to be appreciated as well. It's not an easy balance for him to find, so any snippits of information you can offer will be (silently) appreciated. Explaining why things are the way they are, why one of his co-workers behaves that way, what will happen if she does or does not do something, etc. will be appreciated, but it has to be done in a casual manner. He will begin to get along with those around him better and use your ideas to accomplish things. He will most likely take credit for these ideas, too. That's okay... don't talk about it with him. If you attempt to converse with on on the matter, he will get irritated because he's not sure how to respond. There will be a silent understanding between the two of you. He appreciates the information you've given him, and he appreciates it even more that you don't make him say so.
To others, all of this will come off as what is described in the first paragraph. You're "in" with him, but no one quite understands what you do any differently than others. It can help to give people tips on how to deal with him when he's not around. This usually involves being a bit of an ambassador for him. Explain why he behaves the way he does, what types of things are likely to get what reactions, etc. Yes, he's wrong when he does certain things, but they should focus on the reasons instead of that, and it's more likely that relations will be smoothed out a bit. I've seen ESTps become friends with bitter rivals because of this.
Too much effort? Doesn't sound like something you should have to do? It's okay... I don't blame you. Doing these things is relatively painless for me, so I do. If it grinds against your personality to interact with him like this... then it may not work out for you to try. *shrugs*