This work was written by a 55 year old Tolstoy and is nearly 30 years removed from his trilogy on childhood. From his testimony, he spent considerable time studying the Bible, reading commentaries and theologies, and discussing theology and moral principles with those around him. The result is something that might be termed Tolstoyanist Dogmatics, except that it is presented more as a novelist might do rather than as a blinkered theology professor. I have listened so far to about 1/4 of this work, so will give my preliminary impressions.
A key theme that Tolstoy is developing in the early part of this work is that the Biblical command, "do not judge", is an absolute command that covers all possible human judgements, whether individually or collectively. He goes on to judge that almost all Christian thinkers prior to himself have judge wrongly in their judgement of the meaning of this phrase, which he judges to be a primary Christian imperative. And he judges that he judged correctly.
From this description it should be clear as to what I think is the subtle flaw in his thinking: Humans have a brain and a free will so that we might make judgments, and I have no doubt that Tolstoy made tens of thousands of judgments in the process of writing his work that condemned judging. Don't we judge what would be the most persuasive choice of words in order to entice others to judge that our judgment is the correct one? And if he hadn't judged that his writing was worthwhile to others, would he have published it? Thus, he has already fallen into the trap of the Academic philosophers who dogmatically asserted that all dogmatic assertions are false. Only the dead can escape judging.
The problem that Tolstoy stumbles over is fairly basic. He quotes Matthew 7:1-2, "Judge not, that you be not judged. For with the judgment you pronounce you will be judged, and with the measure you use it will be measured to you." We must interpret this in a way that is consistent with the rest of scriptures. Thus, we go down a few more verses and we see Matthew 7:15-16, "Beware of false prophets, who come to you in sheep's clothing but inwardly are ravenous wolves. You will recognize them by their fruits". Is this not a command to judge? And if I judge wrongly with respect to a false teacher, will this not potentially be catastrophic?
The there are the contrasting verses, such as John 7:24, "Do not judge by appearances, but judge with right judgment". The issue here is not that judging is wrong, but rather that we should not expect to escape a final judgment where whatever standards we used are thrown back at us. It is a command to judge correctly, because we ourselves will not escape judgment. There are countless other verses to support this point, and once we go this way we are much more in conformance with Old Testament teaching. Thus, I take this command more as a "Beware when you judge!". Especially to be avoided are judgments that needlessly make pronouncements on the character of others. But how is a novelist to function if he never makes a judgment regarding the character of those he writes about? Stop it! Looney, you may not be directly judging, but you are implying that he is a hypocrite and thus judging by stealth!