That he does manage to connect with a wide range of people is evident in the above linked video. It truly must grate on the Entitled Elite, as they endlessly repeat their statements that Trump HATES all but the White People, contrary to a plethora of evidence to the contrary.
First, and most critical, Trump has experience interacting with them. In his businesses, when dealing with employees, contractors, building inspectors and other government officials (many of them predetermined to say ‘No’), guests in his homes and his hotels, media representatives, lawyers, secretaries and other staff - both his own and in the offices of his contacts.
Even his employees who work on lower status jobs - kitchen staff, cleaners, landscaping workers, and others - generally repeat the same story, that Trump is cordial, polite, and never in too much of a hurry to interact. If he cannot address a concern at that time, he will delegate one of his staff to do so, and makes a point of seeing that the problem is resolved.
In short, he doesn’t ‘High-Hat’, in public or in private.
He is a genuine mensch.
Now, that doesn’t mean that he has a great character. He may, or may not.
Bill Clinton had much of the same Common Touch (now, don’t go THERE!). And we all know that his character, particularly with women, was severely lacking. I won’t even go into his long history of easy lies.
And, yet, even his enemies were often charmed.
It’s a trait that you can develop, with dedicated work. You may never be all that much of a People Person, but you can work to better your ability to connect. The start of that process is to care - genuinely care - about other people.
Some people are just incapable of putting their own ego aside to listen to other people. They believe they know pretty much everything, and are not interested in listening to other people - they only want to pontificate THEIR opinions, THEIR interests.
Cough, cough - Hillary Clinton?
Kamala may be, at heart, someone with insecurities that prevent her from making those authentic connections. She may care, but the people surrounding her have clamped down on her going ‘off-script’.
But, probably not. She doesn’t seem to be interested in changing at this point. And, her lack of success with keeping her staff (90% of them left their jobs, so far) would seem to indicate that caring about others is NOT one of her top 10 concerns.
A story in The Atlantic that is part of the customary “October Surprise” - actually NON-Surprise - is a polemic against Trump, based on scurrilous claims by John Kelly, his former Chief of Staff. A more nuanced assessment of Kelly’s performance is here.