“I went to college across the river at Harvard and took a class in European intellectual history with my roommate Carrie. She was a brilliant literature student. My younger brother David, a water polo-playing pre-med sophomore, joined us too—but let’s just say he wasn’t as passionate about the subject.

Carrie went to every lecture and read all the books in the original languages. I went to every lecture and read the books in English. My brother? He went to two lectures, skimmed one book, and then camped on our couch for three nights while I tutored him for the exam.

Afterward, we compared how we thought we’d done:
Carrie said, ‘I’m not sure I fully explained the Hegelian dialectic.’
I said, ‘I don’t know if I connected Locke’s theory of property to later philosophers.’
David said, ‘I got the flat one.’
We were confused: ‘The flat what?’
He replied, ‘The flat A—not an A-, not a B+, the flat A.’

We looked at him in disbelief and said, ‘But you don’t know anything!’

That story illustrates a key insight: men tend to slightly overestimate their abilities, while women underestimate theirs. Research backs this up—men apply for promotions when they meet some of the criteria, while women wait until they meet 110% of them.”

What makes Sheryl’s storytelling so effective? She has a relatable, playful style that makes her message easy to connect with and remember.

Let’s now move to a very different storyteller—someone whose style is casual yet captivating.