Diana Rothschild, Head of Strategic Partnerships at TaskRabbit
Diana Rothschild is helping to revolutionize how people work and make everyday life easier at TaskRabbit. She has been a leader and a champion of strategic partnerships and sustainability in both start-up and large corporate environments, including thredUP, NextSpace Coworking, Blue Skye Sustainability Consulting, and Wal-Mart.
Q: Why do you choose to spend your time mentoring others?
A: I choose to mentor others just because I've had incredible mentors, and I see it as a way to pay it forward. I've benefited so much from learning about the experience of others. When applying to Stanford Business School, I filled six pages with what mattered to me the most - the power of relationships, mentoring relationships. And I talked about professional mentors, personal mentors, and then what I call aspirational mentors, which are a combination of the two.
My father passed away when I was 14. He was an amazing man, and as an international tax attorney, he taught me a lot about business, even though I was just a kid. Since his passing, I've had incredible father figures that were equally amazing. They helped me learn and grow personally, academically, and professionally – covering everything from how to support myself and help my family, and get into UC Berkeley's competitive Haas undergrad business program, but also personal advice. One of my first major mentors/father figures ended up marrying my husband and me fifteen years ago this week!
“I love seeing people grow, and I love how mentoring can allow that growth to happen much faster. ”
Through mentoring, I've seen that I can help someone advance a lot faster. One of my mentees ended up negotiating a higher salary through me talking to her. She approached me, saying, "I think I need to leave this company because I'm not paid enough." I asked her, "Well, what if you just asked for more?" She said she didn't know how to do that, so I talked her through an approach. She ended up getting double her salary overnight! I love seeing people grow, and I love how mentoring can allow that growth to happen much faster.
Q: What have you personally gained from mentoring others?
A: There are three main things I've gained from mentoring others. The first one is joy - I experience joy from seeing others grow, and from seeing my mentees learn and challenge themselves and ideally win. That's something that I gain, is getting to see their success. Secondly, I learn a lot about how people look at things and think about things differently. A mentee might come to me with a problem, and this is how they're viewing this situation, and I might see the situation entirely differently. So I like learning how people think. And lastly, I get to learn about different industries from an insider's perspective. Through Ceresa, I mentored a VP of Product Development, getting to learn about their industry, their company, what it's like to work for a private-equity-backed company, etc. Seeing the differences in her experience vs. mine affected the advice I give her. I get to see my mentees win – which brings me joy, teaches me about how people think and gives me greater insight into different industries from an insider's perspective.
Q: To what do you attribute your success?
A: I'm curious. I'm always curiously learning. I want to grow and push myself to do better. And so I think that helps me push that ceiling or push that boundary. I've chosen to work on mission-driven things that matter, which allows me to bring my whole self to work every day. And I join companies where the cultures want that. And lastly, I attribute my success to the fact that I get to wake up every day and completely express God's infinite, incredible qualities.
Q: Were you always comfortable bringing your whole self to work in the past, 10, 15 years ago?
A: No. I think in some ways, I didn't know what my full self was. I told myself, "Well, I have to be very professional and have all my ducks in a row," which is important to do, but I didn't know my full self or my full capabilities. I wanted to fit the mold and be the good analyst, management strategy consultant, manager, or whatever role I was in at the time. I've seen what a company's culture celebrates. I worked in a company where combative discussions were valued, but that's not my style. It's easier to bring your full self to work when your values align with the values of your company. I think that is a huge thing.
Q: What is the impact that mentoring has had on your journey?
A: Mentoring has helped me shape my leadership and management style. As I look at my mentees' journeys, I see the people I manage day to day in a different light. When I hear about a situation my mentee is grappling with, it allows me to see my own team members differently and consider what they're working to improve or grow. Mentoring gives me an outlet to bring coaching and support to others that I don't work with directly day to day.
Q: What does good mentoring look like to you today?
A: First of all, it's important to build that trust and respect with my mentee and know my mentees' goal. If I know their goal, and they tell me the problem they're dealing with, I can help them solve the problem in a way that helps them also reach their goal. Just last night, I was talking with a good friend about some things that were going on at work. I was like, "What advice do you have on how to think about this?" She's asked, "Well, what's your career goal there? What are you looking to achieve?" And by answering that question, she's said, "Okay. Well, based on that, then here's how you could think about it." So, it's about getting to know the person's goal before diving in with advice.
“You need to be able to ask the right questions to unpack the real problem to help your mentee solve it on their own. That, I think, is the best form of mentoring.”
The second thing is being an active listener. A lot of times, when someone is struggling with something, it's what they don't say that's important. If you're listening to a problem ready to give that next answer, and not fully listening, you can completely miss the mark as a mentor. I'll ask very open-ended questions, like tell me more, why. Asking the "five whys" are always super helpful to get at what's underneath something, and through asking those questions, I'll notice, "Wow. So you started by saying you wanted help with this. It sounds like this thing over here is the real issue. What do you think?"
My third thing is not to have the right answer, but instead, ask the right questions. When I first started mentoring, I thought, "Oh. I need to know the answer to everything. I need to give excellent advice every single time." Actually, you don't. You need to be able to ask the right questions to unpack the real problem to help your mentee solve it on their own. That, I think, is the best form of mentoring.
Q: What advice would you give to someone who is starting to mentor?
A: As soon as you can, build trust and common ground with your mentee. It's not that you need to be best friends, but there needs to be a level of trust and respect so that when you're talking through issues, you have a space for working on things together in a productive way.
It's also important to align on what a successful relationship will look like and where your mentee envisions themself in X number of months. In one of my first mentor meetings, I was given a spider diagram of how she ranked herself on different elements of her professional and personal life. I gave her homework and said, " This is what you are today. But what do you want your ideal to be? And in what timeframe? Bring this to our next meeting." And that gave us something to work on, such as, "Oh. You are happy with where your health is, but you wish scores on family & time spent with friends were higher." This analysis helped me determine where I could best help my mentee and to set the right expectation, so she's not thinking she's going to get something else.
The last thing I would recommend is ask your mentee, in advance of the meeting, to share what they want to discuss in a shared document or over email. I do this before I meet with one of my mentors, my CEO, and I expect it now from my mentees. It gives your mentee time to plan what will make the time most valuable to them, and it allows me to think through things in advance, so we make great use of the time.
Q: Why do you choose to be a mentor with Ceresa?
A: Ceresa gives me a chance to share my journey, particularly my experience as a working mom. Supporting women is important to me, especially as we get to higher levels within a company and balance being mothers to our kids and caregivers to our elders. And now we're parenting at home, homeschooling, and working and leading our teams at work. Ceresa also allows me to broaden my circle with people who I might not have met otherwise. I'm interested in joining a corporate board, and I find that it helps to deeply know people in different areas and industries. Through Ceresa, I'm able to support people from other parts of the country and offer my entrepreneurial mindset and skillset to people in other industries.
Mentorship: integral to the Ceresa whole-person approach
At Ceresa, mentorship is an integral part of our leadership development process. The mentor-mentee relationship is a key component in providing the structure, and at the same time fluidity, necessary to facilitate pointed leadership and career growth for both the participant and the mentor.