To say we were honored to host a conversation between the legendary Charlie Rose and Alyssa Mastromonaco, a high-ranking member of the Obama Administration, is a vast understatement. We’re delighted to share with our community highlights from the conversation between these two very grey individuals!
The evening began with a simple question and surprising answer. “Is politics your passion?”
Alyssa Mastromonaco is no doubt one of the most powerful people in Washington, DC. Her answer to Charlie’s question, “No.”
“If politics is not your passion, what is?”
And this, we discovered as she shared stories with us throughout the night, is how Alyssa lives in the grey. Nothing is more important than her relationships. Her whole career in the very interesting world of politics has been driven by her passion for people and her ability and desire to form genuine connection.
She lit up when recounting stories of her days campaigning for Presidency with both then-Senator Kerry and then-Senator Obama. The stories though were not about strategy or lessons learned from a hard fight. They weren’t even about the candidates themselves. Her stories were about she and her colleagues dealing with a “broke-down minivan,” becoming a team in the humble beginnings in a basement office, supporting each other through the twists and turns and ups and downs of campaign life.
Alyssa shared she woke up one day during the historical ’08 Presidential bid knowing that she was one of the luckiest girls in the world. It became clear through the conversation with her last night that this feeling wasn’t just coming from the incredible access or the enormity of what she was a part of, it was because of the people she was doing it with.
After sharing a number of interesting anecdotes, Alyssa described what she thinks makes for a great boss. David Plouffe, Obama campaign manager in 2008, manages his teams as a team member - horizontally, not vertically from the top down. He’s on a high wire and he expects that his team come up to join him there. He has a belief that “if you’re not scared, you’re not doing your job. Being a little scared everyday is what keeps you thinking ahead and gives you the ability to make decisions.”
Former Secretary Clinton takes the time to get to know her staff and treats them like family. Alyssa shared a charming story about when the team recently boarded Air Force One with the Clintons and Bushes to attend funeral services for Nelson Mandela. Secretary Clinton, knowing that Alyssa had just gotten married, organized the entire plane in song and “the wedding dance” to celebrate her recent nuptials!
It seems to us at LITG that Alyssa recognizes these qualities in great leaders because she has them herself. It was incredible to experience and feel the warmth and amazing energy she brought into the room. Being in the audience felt as though you knew her for years and were just catching up with an old friend.
Actual longtime friends/colleagues (with Alyssa they truly are one in the same) of Alyssa’s were in the audience and frequently invited into the conversation as she referenced them in whatever story she was telling. It became very clear that Alyssa isn’t one person while at work and another person with her loved ones - a common affliction in today’s culture. She’s not black-and-white, she’s grey, because she blends every part of herself together. Being 100% who she is, wherever she is, most certainly plays an important role in Alyssa’s success and fulfillment.
When Charlie asked what’s next for Alyssa when the Administration is over, Alyssa shares that she expects she will always remain in the Obama orbit. We thought that was a beautiful way of saying she’d continue to make her friends her colleagues.
Insights from Alyssa’s Grey Journey that you can apply to your own life:
Own your failures. She spoke of flubs and failures with no trace of lingering regret or disappointment. In fact, her advice was to own your failures. She shared that being clear and honest with herself about her failures helps her to make tough decisions.
Take risk. “If you win a campaign, that’s terrific. If you don’t, life goes on.” Risk makes life remarkable, take that chance!
Be kind. “I got where I am by hard work and by being a nice person.” Even if you feel you work in a competitive environment (is it really more cutthroat than politics?), we agree with Alyssa that genuine kindness will get you farther than anything else.