Speak the language of leadership--for example, if you tend to say "Help me understand...," then consider that the recipient of this "question" will probably hear it as criticism. They hear you saying: "you don't get it," or "you're wrong," or "I disagree," or "you're slow."
Another variation is: "I'm not smart enough to understand..." (whatever you are saying, proposing, analyzing, or suggesting.)
If you truly WANT to ping someone for understanding wthout telegraphing anything negative, try asking more childlike and direct questions, like "What is this?" or "How does that work?" If you want to be critical, then offer some kind, necessary, and candid feedback privately.