The very best person I ever knew was an ESTJ. He was killed a few months ago, just as our 20-year casual acquaintance had turned into a very deep friendship, and I'm still struggling with it. If he was a "typical" ESTJ (and based on what I'm learning, he seemed to be), then ESTJ's absolutely do have a very deep and insightful side. They just don't always express it the way other types might want them to or expect them to. That I tend not to have expectations in that regard is probably a huge reason why our friendship suddenly flourished the way it did when he tentatively asked for my advice. I never tried to foist any of my "emotionally analytical" tendencies on him, even when I sensed he was in turmoil. I just quietly made sure he knew I was there and let him come to me. To my eternal surprise, he did.
Based on my albeit limited experience, the kinds of "deep" conversations you're referring to are simply not where their primary focus of interest is. My friend was a doer, a decider, a person of action. He was also profoundly moral and deeply concerned with the welfare of others and living up to his responsibilities to them.
He confided very personal things to me and revealed a side of himself that I imagine few have seen, but the only reasons he did so were (1) he was going through a personal crisis, and his natural instinct when confronted with such was to resolve it in whatever way would be BOTH moral and effective, (2) the nature of his problem necessitated gathering the insight of others because he had zero problem with acknowledging when he was ill-equipped to handle something alone, and (3) he, for some reason even he couldn't explain, felt emotionally safe with me and suspected I might have a helpful perspective on it that he could factor into his decision-making process.
Without all of those factors, I never would have heard anything about it, but not because he wasn't a deep or insightful person. In fact, it demonstrated what I admire most about the type: it doesn't matter if something is uncomfortable for them to do...if it needs to be done, they do it. There was a ton going on inside him, but he didn't have a natural, compelling need to express it purely for the sake of expression. He had a very streamlined logical process.
As our friendship progressed, we were able to talk very candidly about philosophical and emotional issues, but they were always relevant to him or to me....so perhaps that was the only time he would have been interested in that kind of discussion. Maybe he needed it to have some kind of application to his own life or the lives of people he cared about...that I don't know. He was killed before we got that far, but, frankly, I don't think it really matters. The point is, there was enormous depth to his personality and character, it just wasn't loud or overt, and I loved that about him.
My take on ESTJ when it comes to communication (and please, any ESTJ's correct me if I'm way off base) is that they communicate what they think and feel primarily through their actions, and if they do verbalize it, it will be straightforward, concise, and honest. My friend preferred to approach things directly, candidly, and honestly, and he responded favorably to that approach from others. He had no patience or liking for hedging or equivocation (but could tolerate it in someone he loved and respected), and though he never had any trouble with how wordy I tend to be, he was rarely if ever wordy back. He didn't need to be. To date, he was the easiest person for me to understand, and part of the reason I joined this forum is to try to figure out why that is.
Everything anyone needs to know about an ESTJ is in the way they conduct themselves. Words are unnecessary, if one is paying attention.
ESTJ's are my very favorite type of people. They inspire me.