Why do plans keep including apologies? It feels like the some fundamental aspect of planning is fundamentally screwed up if we keep creating situations where an apology is the appropriate reaction.
[If you're referring to the acknowledgement of imperfect plans], Back during Isan, Hazou produced an unoptimized plan that Kei felt Hazou-pilot should have caught (which is arguable in either direction, but that's a separate topic). This led to Kei immediately drawing severe and drastic conclusions about Hazou's state of mind and lack of care regarding his family's well-being, storming out. This event had notable narrative consequences, one of which is that Hazou-pilot now feels a certain amount trepidation and anxiety regarding sanity-checks with Kei.
Both then and now, the characters involved were placed under immense emotional stress. The preemptive acknowledgement of "these are unrefined, off-the-cuff ideas that may or may not be viable" allows Hazou's interlocutors to prepare themselves accordingly.
Regarding apologies, in this specific instance, the potential Hazou-apology-to-Naruto has already occured. However, my model of Hazou's feelings regarding Naruto are "frustration at Naruto, frustration at himself, and regret over the situation." If Hazou-the-character is about to die (as may be the case) then it's simulationist for him to apologize "one more time," as a sort of "if these are to be my last words to you, then let it be this..."
Perhaps there's a solution for preventing Hazou's missteps, but [past missteps are why] we [now] implement the "sanity check with..." line in the majority of our action plans. Because we-the-hivemind don't have cultural context within the EN, and Hazou-the-character is a teenager who grew up as a clanless kid in a foreign nation.