A former deputy chief of staff for Obama explains how a meeting with the president's economic adviser taught her there's no such thing as a dumb question

Alyssa Mastromonaco meeting with Obama
Alyssa Mastromonaco meeting with Obama

(Alyssa Mastromonaco, far right, at a meeting in the Oval Office in 2013.The White House/Getty)

On a recent episode of the #Girlboss Radio podcast, Alyssa Mastromonaco shared some meaningful career lessons she learned while working for President Obama.

Mastromonaco served as Obama’s deputy chief of staff for operations until 2014. Today, she is chief operating officer for the news and entertainment group Vice Media.

One anecdote in particular illustrates how even super successful people can struggle with self-confidence.

As she told #Girlboss Radio host Sophia Amoruso, Mastromonaco was at the White House for a meeting on the economic crisis — and she was freaking out.

"I was, like, sweating through my shirt because I was worried that at some point Obama was going to turn to the Socratic method and just randomly ask me a question about quantitative easing and I wouldn't know what to say," she told Amoruso.

As Obama and his staff, including Treasury Secretary Tim Geithner and Obama's economic adviser, Larry Summers, talked about quantitative easing and other unfamiliar terms, Mastromonaco scribbled the words in her notebook so that she could look them up later.

Summers noticed, and he tapped her on the shoulder: "Come to my office afterwards."

Mastromonaco panicked: "I was like, 'Oh my god, he knows I'm dumb.'"

When she showed up at Summers’ office, he asked her, "What's that list you have?"

She told him, and he asked, "Why wouldn't you just come to me? I will tell you anything you need to know."

Then he proceeded to give her a tutorial on everything she’d found confusing.

"I felt so smart afterwards," Mastromonaco told Amoruso.

Summers explained, "If you knew everything I knew, what good would I be?"

Today, Mastromonaco said, she never gets upset with anyone for asking a question — and she certainly doesn’t think it’s stupid to admit you don’t know something.

shrug
shrug

(It's OK to admit that you don't know the answer.Flickr / Funk Dooby)

In fact, had Mastromonaco's nightmare come true and Obama asked her about quantitative easing, perhaps the best response would have been, "I don't know."

Stephen Dubner and Stephen Levitt, author of "Freakonomics," say that while it can be incredibly difficult to admit you don't know something, it can ultimately make you look smarter.

Pretending you understand everything, Levitt said in a 2014 Freakonomics podcast, "might keep your job for another week or another month, it might make people think you are good, but that's not the point. Really, the goal is to be good and to improve and to learn and to make things better. And the only way to do that is to start by saying, 'I don't know.'"