Mindful Leadership

What It’s (Really) Like to Hang with Sheryl

On Monday night I hopped in a cab en route to meet Sheryl Sandberg.

Yes, THAT Sheryl Sandberg.

COO of Facebook. Third-wave feminist poster child. Architect of the national love affair we’re having with women and work.

Maybe you’ve heard of her.

I had traveled to New York specifically for a reception to celebrate her book launch with a few other women writers. I didn’t expect to know a soul in the room but I didn’t care. To paraphrase former Google CEO Eric Schmidt, “When asked to join a rocket ship, don’t ask questions – just get on.”

I was getting on.

No, wait. I was leaning in.

The reception started at 4:30pm, but I had spent the whole day getting ready.

Classic New York blow-out? Check. (Seriously, those hairdressers are wizards.)

New dress? Check. (What does one wear when meeting a billionaire?)

I even bought $97 in make-up JUST to have someone else apply it. (Upon suggesting I wear false lashes to “enhance the cat eye,” the Sephora staffer was pleasantly surprised when I whipped them out of my purse. Please. I’m no lightweight in that game.)

So as I took a deep breath and walked into a private room of the Time Warner Center, I was ready to go toe-to-pedicured-toe with the best of Manhattan.

And there she was.

The Forbes-anointed “Fifth Most Powerful Women in the World” was tucked in a corner, chatting with another guest. I noticed right away that she was, in fact, leaning in – sitting super close to the woman – and I was also slightly relieved to discover she was a fellow hand talker.

So far so good.

I arrived early in the hopes that everyone else would be fashionably late and – as I scanned the empty room – it appeared my plan worked. So…..I grabbed a glass of wine and played a game of mental “good-cop-bad-cop”, debating whether to walk over and interrupt.

“Shit. She looks totally engrossed in that convo.”

“You didn’t get on two planes for a glass of cabernet. Go.”

“What if she ignores me?”

“It’s a RECEPTION jackass. Get over there!”

Another deep breath.

As I made my way to the guest of honor, she was still physically turned in the other direction. I got about three feet away and just stood there.

Like a creeper.


For about a minute.

Quite possibly the longest minute of my life.

And then, just as I was about to pull out my phone and pretend I had something REALLY important to attend to, she turned around and saw me.

“Oh, HIIIIIIIIIIIIIIIIIIIIII! Thanks so much for coming. I’m Sheryl.”

Um, yes, I know.

“Hi, I’m Emily Bennington. Thanks for inviting me to this. It’s an honor to meet you and – as the author of another book on women in the workforce called Who Says It’s a Man’s World – I just want to say thank you for kickstarting this conversation again.”

I said it so fast I must have come off like Raphie in A Christmas Story“I-want-an-official-Red-Rider-carbine-action-200-shot-range-model-BB-rifle-with-a-compass-in-the-stock.”

Thankfully, she was gracious.

“I have that book!”

I knew that too, mainly, because I’m the one who sent it to her. Anyway. I’m trying to play it cool, but let’s be honest. I’m really thinking, “HOLY MARY MOTHER. SHE KNOWS MY BOOK.”

We chatted for a few minutes and, slowly but surely, a crowd started to gather around us. And since there were only about fifteen women total in the room, eventually Sheryl just started taking questions from everyone professor-style.

“What policy changes would you recommend for women in the workforce?” (Paid maternity and paternity leave.)

“What do you think about the reaction to the book so far?” (Glad it’s sparked a discussion.)

“How do you feel about this new Lean In movement?” (It’s not a movement. It’s a community.)

After about 30 minutes of dialogue, I found her to be engaging, wicked-smart on stats, and surprisingly unfiltered about her own insecurities. At one point I mentioned that, while I was in New York, my husband was carpooling our sons, doing the evening trifecta of dinner, homework and bathtime, PLUS he had to sit in our first-grader’s class for an hour that morning to observe a few “behavior issues” at the teacher’s request. Still, when I thanked him for stepping up, his response was simply, “They’re my kids too, you know.”


Which is why I didn’t feel guilty or find it the least bit ironic that I had left my family to have cocktails in another state and talk about “balance.”

“Wow” said Sheryl, “good for you.” Then she told a story about dropping her son off at school in a blue shirt only to be told he should have been wearing green. “I beat myself up about it all day,” she said, “whereas my husband would have drove off and never given it another thought.”

It was refreshing to hear that the woman who is on the cover of Time magazine as I type can be thrown off her game so easily.

(Thank you Jesus.)

It was also an important reminder that – for as much as we try and put on a good show – NO ONE has it all together all the time.

We put our kids in the wrong shirt.

We get nervous when meeting our girl crushes.

We beat ourselves up.

But guess what?

Titans do it too.

So whether I have another opportunity to stand next to Sheryl Sandberg or not, I’ll always take comfort in knowing the distance between us is actually pretty small. And that’s all the motivation needed to stand up, march on, and, yes, lean in.