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But the White House under Ms. Wiles is chaotic too, just in a different way. Unlike John F. Kelly, the president’s longest serving chief of staff in his first term, who saw his job as trying to prevent what he considered radical, unwise or even illegal actions, Ms. Wiles does not view her role as constraining Mr. Trump. Instead, she makes clear that her mission is to facilitate his desires even if she sometimes thinks he is going too far.

She attributes her ability to work for Mr. Trump to growing up with an alcoholic father, the sportscaster Pat Summerall. “High-functioning alcoholics or alcoholics in general, their personalities are exaggerated when they drink,” she said. “And so I’m a little bit of an expert in big personalities.” While Mr. Trump does not drink, she said he has “an alcoholic’s personality” and operates with “a view that there’s nothing he can’t do. Nothing, zero, nothing.”

In a sign of how much her job revolves around the president’s big-personality, stream-of-consciousness public comments, she keeps a free-standing video monitor next to the fireplace in her West Wing office with a live feed of Mr. Trump’s social media posts.