Lessons in Leadership: Q&A with Michelle Peluso

“Good leaders value and care about the people around them,” says Michelle Peluso, Venture Partner at Technology Crossover Ventures (TCV). “There is real satisfaction, real beauty, in making it to the top as part of a team.”

Michelle Peluso has been a White House Fellow, Chief Marketing Officer and board member. But she’s probably best known for her stints as CEO of Travelocity and Gilt Groupe, which was bought by Hudson’s Bay Company in February of 2016. Michelle recently rejoined TCV as a Venture Partner to mentor TCV portfolio company executives and help investment teams evaluate opportunities. We sat down with her to find out how she’s putting her experience to work to help up-and-coming leaders of tomorrow. In this interview, Peluso discusses:

• Why women leaders must take the torch from the pioneers of yesteryear
• How self-doubt keeps leaders free
• Why grace is the most important leadership quality

TCV: Women have made huge strides in the corporate world and many of them now run some of the most powerful companies in the world. Where are we along the equality curve and what’s ahead?

Peluso: Women of my generation have benefited enormously from those who came before us: the Elizabeth Cady Stantons and the Katherine Grahams. And there are so many extraordinary women leading the way now, but we must all grasp the unique opportunity to shape our world. We must all ask ourselves: What are we women going to do with this opportunity?

TCV: You’ve said having a daughter has helped put this challenge into perspective. How so?

Peluso: I’m the mother of a six year-old boy and a seven year-old daughter, who one day may choose to be part of the next generation of women business leaders. So I’ve thought a lot about what I want her to know about leadership — and particularly, about being a woman leader.

TCV: Why is it important that your daughter be a leader?

Peluso: I want my daughter to be whoever she wants to be and to do what she loves. But I will encourage her to lead in whatever work she chooses and at whatever scale, because it will give her the best chance of helping to shape her destiny and our world going forward.

TCV: So what will you tell your children as well as established leaders of technology companies about leadership?

Peluso: A successful leader, male or female, is someone who builds other people up. We’ve all worked with people who put themselves first and try to look good at the expense of others. But no organization can thrive without teamwork, and nobody makes it to the top alone. Strong leaders value and care about the people around them. True leaders take time to understand who their team members are, what they want to achieve and then help them succeed. There is real satisfaction, real beauty, in making it to the top as part of a team. When I started Site59 with a small group of friends, everyone thought we were nuts. But two years later we sold it to Travelocity, then helped lead Travelocity and still remain very close almost two decades later.

TCV: What qualities should leaders look for when they set out to assemble their teams?

Peluso: Find people who complement you, challenge your assumptions and make you consider all options on the table. That might sound obvious, but we commonly see leaders surround themselves with “yes people” who don’t do this. David Foster Wallace once said that going down this path to inadvertent close-mindedness is a form of self-imprisonment. Strong confident leaders, on the other hand, are self-critical and they actively cultivate self-doubt. At Travelocity, we used 360-degree feedback exercises that we shared with each other as a leadership team to keep us honest. There were times it was brutal, but those moments helped me understand how I could become a better leader and how we could function better as a team.

TCV: What’s the hardest lesson for young leaders to absorb?

Peluso: It’s the old adage: Keep it simple. Young leaders are keen to demonstrate that they have the ambition, vision and skill to handle complex challenges. But in a world of new opportunities, ever-shifting markets, and this deluge of data, the key is to simplify, to cut though the noise, to focus on that one primary product, that one inspiring message, that one crucial experience. Young leaders must learn to strip away complexity and achieve simplicity.

TCV: It all sounds so simple…

Peluso: But it never is! Everything breaks, sooner or later. And those difficult moments are when true leaders prove themselves. We’ve all heard how those hard moments shape us and make us aware of our full potential. So let me go a step further: good leaders must anticipate and prepare for those hard times. Strong leaders must make sure they have the mental and emotional reserves to be at their absolute best when others are at their lowest. This is the real test of leadership.

TCV: Are there any other leadership qualities you think are important?

Peluso: In the end, I appreciate grace. It’s one of my favorite words, so much so that our daughter’s middle name is Grace. I wrote her a letter when she was born to capture my hopes and dreams for her in life. I told her that if she reaches high enough, she will occasionally fail, and let herself down, or let others down. It’s precisely those moments when we all need grace to pick ourselves up, to forgive ourselves, to recognize all that is good in others, and most of all, to persevere, to simply never give up. We owe that lesson for all the young leaders who come after us.

TCV: Why did you return to TCV as a Venture Partner, rather than take another top executive position?

Peluso: I’ve long admired TCV and their focus on brands and management teams; their long-term philosophy, and their incredibly strong team and culture. It just feels right for me and gives me the platform and opportunity to share what I’ve learned with a new generation of business leaders. It’s a great feeling to help someone succeed.

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Venture Partners are typically independent consultants who are not employees of TCV but have a strategic relationship with TCV and/or provide valuable advice or services to TCV and/or its portfolio companies.