Diana Rothschild: A force of progress

Diana has been driven throughout her career by a single question: how can I have the biggest impact? By pursuing that question in multiple sectors – education, government, and business – she has determined the answer.

Sidebar: You’re a fourth-generation San Franciscan. When you were growing up, did you have a vision for who you wanted to become?

Diana Rothschild:  My dad was an international tax attorney. At dinner, he would talk about different business models, international business transactions, and how Russia–U.S. taxation might work after the Cold War ended. He knew a lot of incredible people who would come over for dinner. So I think I always wanted to do something in business, with business models that do good in the world. I didn't really know exactly what that would be, but I knew I liked to run things.

Sidebar:  It sounds like your dad was an influence, but taxes are obviously a little different from business models for good. Where do you think you got that wanting to do good component?

Diana:  First, I believe that people are innately good, and that we all have the capacity to express good. But a life-defining moment happened for me when I was 14 and my father passed away unexpectedly. I'm the oldest of four kids, and so overnight I became a second parent to my siblings. So many people did good things for us, and that showed me the value of doing something for someone, and how you can make a meaningful difference in their life.

Sidebar: Wow, that’s really difficult. Thank you for sharing that with us.

Diana:  Yeah it was a very defining moment. I think it led me to thinking about impact. I was the kid who asked, “Why do I have to learn the area under the curve in calculus class? How is this going to help me in the real world?” This line of questioning turned into asking: How can I have the biggest impact?

Sidebar:  And what has been your experience transferring that question into your career?

Diana:  I wanted to make the biggest difference in education – and I started by teaching summer school, where I had an impact on eight middle schoolers. That was great but not a very big impact. Then I got to run Autodesk's internship program for 200 high schoolers, and I was able to influence other Bay Area companies to give valuable and practical internships in exchange for academic credit. Finally, my freshman summer at Cal, I interned at the Department of Education in Sacramento (in the School to Career Department), which I liked, but there was so much red tape and things moved so slowly.
When I looked at these three work experiences – education, business, government – I realized business was the biggest lever. I saw how business was so operationally efficient that it could make a bigger change in education than either the government or the educational system by itself. I come at a lot of my work today from a capitalist view… but in the sense that doing good is good business. Doing good should reinforce profit which reinforces doing more good.

Sidebar: Can you give us an example of this in practice?

Diana:  I was working at Walmart, and I had ideas about sustainability. One day, I ended up on the elevator with the CEO, and I had 31 stories, literally, to tell Lee Scott what I thought about how sustainability and how stronger supply chains bring more profit to Walmart. It went well, and I got to be one of the first employees to launch sustainability at Walmart.
One of our first initiatives, back in 2005, was to start sourcing MSC (Marine Stewardship Council) certified seafood. It was a relatively new label, and it didn't really make sense on paper to do it, because it’s way more expensive to source – only catching the right size fish, not using big nets that sweep the bottom of the ocean, etc. But we learned that by sourcing better fish, we had less waste and spoilage, because the higher-quality fish lasted longer. It ended up being good for business, and the whole program impacted the bottom line in a way that we never could’ve imagined if we just went by our spreadsheets.

Sidebar: As a leader, you know people aren’t always on top because they know how to lead. What are the must-have qualities of a great leader?

Diana:  Here’s what I say to people on my team for what makes someone a successful account manager, and I think it applies to anyone looking to be a leader. First, someone who's analytical and strategic – who can see a vision and clearly map out the path to get there. Second is a bias to action. While it's nice to think of big ideas, at the end of the day it's about execution and ownership, while inspiring others to reach the vision in a way that maps to their motivations. Third is an important value – to choose optimism. Life is hard. Jobs are hard. So if you don't choose optimism, you might as well just go home. And I don’t mean rosy glasses everything-will-work-out optimism, I mean choosing optimism and having a plan, and then a backup plan.
Fourth, All great leaders possess an understanding of the motivation for each person on their team. Is their motivation problem solving, is it building relationships, closing deals, making an outsized impact, their family? As a leader, you can guide what projects you put them on, that will help them grow in their career faster. Understanding motivation also allows you to give individualized feedback in a way that will land.
Lastly, being the example that you want other people to follow is a sign of a great leader.

Sidebar: That’s a very holistic answer. I’m curious,have you ever navigated a situation at work where your personal values ran counter to what was being asked of you?

Diana:  I started work at a brand strategy agency the day after 9/11 and the economy was tanking. The only companies that wanted strategy work were alcohol and tobacco companies, two things that I do not partake in. I was put on a job for Lucky Strike cigarettes in Mexico. Lucky Strike had determined that the best way to relaunch their brand was to go after 18 year olds; they were very excited about going to universities and putting Lucky Strike ads everywhere, and I was supposed to help them do that.
I was pretty upset, and was like how am I going to do this? This runs completely counter to my values.
So I ended up finding this obscure law that said that you cannot advertise cigarettes within a certain distance of universities in Mexico. I came up with this whole argument why it wasn’t worth the legal costs associated with advertising near universities, and instead they should advertise inside these high-end clubs, where they could do super innovative ads. My thought process was like, “Look, if someone really wants to smoke, they're gonna smoke, so let’s advertise behind closed doors where people have paid a lot to have a night of fun.” That helped my conscience a little bit.
Sidebar: Classic. I love how you somehow turned that situation into a good thing. As a member of Sidebar, you’re committed to becoming the best leader you can possibly be. What’s something you're working on improving with your group?
Diana: Last week we had a really amazing conversation about assertiveness, because assertiveness is one of the qualities I’d like to show up more in my work. What I learned through that conversation is that my group was surprised, like, “Wait, how are you not assertive?” Before our conversation, I viewed assertiveness as showing up in a steamrolling, aggressive way that I just didn't feel comfortable with. But by defining what assertiveness is within our group and hearing others’ examples of assertiveness as confidence with clarity, it became clear that I am more assertive than I think I am (though I still have more room to grow there). This will help me better understand and exercise that trait in the future.
We’ve also had great discussions about how to reorganize teams for the next chapter of growth, and how to structure them in a way where people feel heard. Specifically, tough situations like managing someone who feels they are ready to be promoted, but instead is being leveled. It’s been really helpful.

Sidebar:  Glad to hear that. And what's surprised you the most about Sidebar?

Diana: Two things have been pleasant surprises - first, I came to Sidebar thinking, “This is going to be a great place for me to get help with things.” And while it is, what I actually enjoy most about Sidebar is helping other people solve their challenges. That surprised me.
And secondly, it's refreshing to bring up an issue to the team and realize I'm not alone in having this issue – that my issue is the same in a wide variety of industries. It’s great to hear perspectives across different geographies, different industries, different functions, and how they've solved it. It's sort of like phone a friend, but you get six very different takes, and some of them build on each other.

Sidebar: What were your initial impressions about your Sidebar group and what has been revealed about them as you've gotten deeper into the experience?

Diana:  My initial impression of my group was that each person in the group was super strong on their own. But I feel like we're even stronger together. When we're working through someone’s issue, it’s the combination of our perspectives that yields the right answer versus one individual perspective. You  need the benefit of multiple perspectives to create the ideal solution.

Sidebar: What would you say are some of your biggest accomplishments?

Diana:  Wow – I’ve gotten to be a part of so many incredible initiatives, maybe what’s better to reflect on is which opportunities I am most grateful for. When I think about it that way, then professionally, launching sustainability at Walmart was a big moment. Launching an incredible coworking space with on-site infant and toddler childcare so I (and over 150 other parents) could bring their children to work with them, and live and work on their own terms. And then being recognized by President Obama at the White House Summit on Working Families was a pretty cool moment. Launching ThredUp’s Donation Bag program and helping TaskRabbit find new business models were also defining moments.
I also love growing teams and I’ve had the good fortune to do that in consulting, retail, coworking, and in sharing economy companies. We've grown the Retail Account Management team at DoorDash from four to 14 in the last year, and our accomplishments with our partners have been nothing short of exemplary. And, importantly, I think people on the team really enjoy their coworkers and feel a real connection to them.
And personally, I'm proud that my husband and I bought a historic Victorian and restored it ourselves to a beautiful home to birth and raise our girls… and with space for chickens and bees and a garden. And, I can't take credit for it all, but my two daughters are incredible. They're absolutely amazing bright lights – smart, inquisitive, empathetic, and intelligent. I feel a great sense of joy from them.
Sidebar:  Quite a spectrum there, I love that. You mentioned your daughters. What's your biggest piece of advice for others who are navigating their careers as parents?
Diana:  I think it's really important that kids see what a strong work ethic looks like and for them to see what you do every day; the past few years have really helped us with that. They hear Gabe and me on calls all day long, and they pick up on so much. I actually took my 11-year-old daughter to my team offsite in New York last spring, and she ended up taking notes on the whiteboard, on her own accord. She has been incredibly helpful as I think through team dynamics and issues with clients. I literally talk to her about these things, and she has such amazing insight. So, yeah, showing your kids what work is, and how you do it. Bringing it up at the dinner table.
I think sometimes our society is, I don't know, so kid-focused that you end up losing your own identity. Your children are a part of your family unit and your family unit is all of you. It's not just the kid and their interests. I think having that kind of awareness is really helpful when my kids are struggling, for example with friends at school. It makes challenges feel less dire and all-encompassing.
Lastly, I think being really intentional about when you're present at work and when you're present at home. And I think it's really important to turn it off. Like, turn off the phone. I used to have my phone with me all the time. If a notification came up, or if I had a spare moment, I would check my phone for messages. Now, I don't do that. The phone stays on my desk and we have family dinner. I think my daughters have really appreciated me not being glued to a screen all the time. My daughter calls it a text Shabbat… she takes my phone away Friday night and hides it somewhere I can’t find it.

Sidebar:  That’s so wonderful. Tell me how you are  misunderstood?

Diana:  A sage mentor once told me, I think 15 years ago now, that there are two versions of Diana. There's this kind, gracious, charismatic, warm Diana. And then there's Tiger Diana. And Tiger Diana is driven and focused and like, “Everything's very nice, but I'm gonna go get that now.” Her feedback was that sometimes people might see one or the other, and my hope is that I blend both together, because they both have clear objectives and benefits. Similar to a Shambala Warrior, combining compassion and insight. I strive for high standards, and that can be done in a way that's gracious and collaborative, welcoming and thoughtful, and intentional. It doesn't have to be these two distinct versions.

Sidebar:  With someone who's achieved the objective success that you have, where do you draw the inspiration to keep going?

Diana: I'm a pretty spiritual person. And so every day I wake up and work to see and express God's qualities reflected in all I see and do. And those qualities are unlimited,  all-encompassing, and all good. I can't really imagine a bigger thing to be inspired by.
I see the proof in all of the goodness that’s happening – through my interactions with my team, through deal negotiations, through my girls, friends, health, and incredible opportunities to grow. Like, I see the flow. It isn't just blind belief that there is goodness in the world. And it’s inspiring to see it show up, repeatedly, every day.

Sidebar:  I'm glad you mentioned that, because your optimism is something that resonates throughout all the vignettes you’ve shared with us today. And I think there’s a lot of people who may be pessimistic about good in the world these days. So, is there anything I missed that you'd like to highlight?

Diana:  I think there's something about home – I'm very into creating home, whether that's home for my team members, or home for my family regardless of where we are.
We live in an increasingly digital world where we don't really have to talk to each other, and we could just stare at a screen all day and be incredibly productive. But humans are social creatures, and so I fly to New York every eight weeks or so to be with my team and partners, because if not, I'm not going to see them and build more meaningful, high-trust relationships. And so I think a big question for me is how do we grow and thrive in a remote-oriented world, while maintaining our human connections? That's super, super important. And it’s one of the reasons the Sidebar event last week was so awesome. Just to meet people in person and not just have it through a screen.

Sidebar: Well, Diana, you’ve dropped a lot of knowledge and inspiration on us today. Thanks so much for your time.

Diana:  You’re welcome. Onwards!