Back to Blog

Developing Empathetic Leadership Skills – Recap

  • - LiveRamp
  • 9 min read

The past year was challenging on many fronts, no matter how long you’ve been working or what your work-from-home situation may be. Yet amidst the endless Zoom meetings, Anneka Gupta, LiveRamp’s President and Head of Products and Platforms, and Kamakshi Sivaramakrishnan, leader of the Drawbridge Integration and Identity Charter for LinkedIn Marketing Solutions and former CEO and Co-Founder of Drawbridge (which was acquired by LinkedIn in 2019), have found ways to adjust their leadership styles and attract and onboard top talent.

Listen in as they discuss their career paths, finding their voices, and how they’re using what they’ve learned to better support their teams, personally and professionally.

Listen Now!

Spotify | Apple | Google


“I used imposter syndrome as a forcing function to make myself more educated, learn more from people around me, and make myself more successful based on what’s unique to me versus trying to be someone else.”

Daniella Harkins:
That’s Kamakshi Sivaramakrishnan, former CEO and Co-Founder of Drawbridge, and this is “Saying the Quiet Part Out Loud,” a podcast from LiveRamp. I’m your host, Daniella Harkins.
I think we all walk around the office—well we used to, anyway—and see people that seem really confident. I know I do. And we think, that person has probably never felt imposter syndrome. Surprise—we all have, and we all do.
This episode gets into the feelings we have at work that are not always easy to verbalize but are important to talk about, especially as our work-from-home period continues.
Here’s Anneka Gupta, LiveRamp’s President and Head of Products and Platforms, and Kamakshi Sivaramakrishnan, leader of the Drawbridge Integration and Identity Charter for LinkedIn Marketing Solutions. Listen in as they discuss what they’ve observed as technology leaders, particularly during the pandemic, and how they’re using what they’ve learned to better support their teams personally and professionally.


Anneka Gupta:
It’s been about a year now that we’ve been working from home, which is hard to believe. When the pandemic started, I thought it was going to be two to three weeks of working from home and we would be back in the office again. It was a big adjustment for me, and for so many people on my team, to transition to this model where we’re “living at work,” as opposed to “working from home.” Kamakshi, what are some of the insights you’ve had around the challenges of managing teams as they from work from home? What have you learned about how to help on a more personal side, and how to help your teams be successful in this work-from-home model?

Kamakshi Sivaramakrishnan:
Honestly, I’ll just come out and say it. It’s been more challenging than I anticipated, though I think we will emerge as better human beings with a higher sense of empathy, not just in a professional context, but in a human context as well. One of the things that stands out to me is how much I internalized face-to-face interactions. It was such a normal part of our in-office behavior and adjusting to that in a Zoom context ultimately resulted in mistakes. In the office, along with having that face-to-face dynamic, you’re also able to read body language and you can lean in and people know you’re ready to speak. Now that the dynamic has changed to screen interactions, I’ve noticed it can be a challenge for some people to find their voice.

I couldn’t agree more. The first couple of months of Zoom calls felt like everyone was always interrupting each other because you couldn’t read the signal when it was ok to talk and insert your voice. At LiveRamp we use the chat functionality as a tool within meetings. What’s really dynamic is when the person leading the meeting pulls out points from the chat and highlights them as a way to broaden the discussion. It’s made our meetings more productive and allowed more people to find their voice, and it’s almost been easier to bring out different voices and allow more people to be heard and make their point without interrupting the flow of the conversation, which is already jilted over Zoom. It’s helped those who are less comfortable speaking out in meetings.

As a woman leader, do you feel a sense of responsibility to create more participation?

I have always been pretty mindful of that because of the path that I’ve taken through LiveRamp. At various points in my career, I didn’t feel comfortable speaking up even though I felt I had a valuable perspective. That still happens to me sometimes today. When I’m in a new situation with new people, I don’t always know how to insert myself in a way that doesn’t come across as aggressive or isn’t interrupting someone. So, I’m very cognizant when I’m in a meeting and I’m not hearing a perspective I think is important to the conversation. Sometimes I’ll ping someone in a private chat and say, “Hey, I want to ask you this question…,” so they’re prepared and don’t feel like they’re being singled out. It’s difficult, especially if you haven’t been thoughtful about choosing the participants for your meeting. Having too many can become untenable, even if you’re good at moderating conversations. It can be difficult to bring out all the perspectives in a productive way.

Speaking of your own career track, I’ve admired your rise within the ranks of LiveRamp, both as a private company and now as a public one. The dynamics are very interesting.

Throughout my career at LiveRamp I’ve had many different sets of peers and leaders that I’ve reported to and/or worked with. I’ve learned how to connect with people who are different than me, whether it’s upbringing, stage in life, or career experience. It’s easy to get intimidated when you’re the youngest or least experienced person in the room. It’s easy to think you don’t have anything to offer to the conversation. A big part of my career journey has been recognizing that I do bring value, even in situations where I experience imposter syndrome. When I start working with new people, I always try to focus on what I can I learn from them. Whether it’s a peer, someone who reports to me, or someone I report to, there’s always something to learn from others. Having the curiosity to ask questions has been a great way for me to build relationships and connections.

You are a trusted voice for your team when it comes to technology and product, but the conviction and contributions you’ve made to the success of the company gives you a seat at the table. You are the deciding voice in key aspects around product, technology, strategy, and customer success. I hope the people who are listening to our conversation are able to take tips from you about addressing imposter syndrome. We all feel it, and I hope we can learn that it’s normal, and not let it drag us down and hinder our career progress. You bring a unique perspective that others don’t have, and finding your voice and having courage around that is the platform you stand on.

Thank you. I have similar admiration for you. I’d love for you to share a time when you felt imposter syndrome and how you overcame it. How have you coached others on your teams to work through their imposter syndrome?

My experience of imposter syndrome has been interesting, and I’m sure you can relate, considering we share an entrepreneurial background. When I founded Drawbridge and began building the company, I took on multiple roles with the desire to understand the value of technology from a market perspective. What does it take to make a business successful? As a technologist, I tend to over-index on the technology aspects and don’t always have the understanding of the right balance between technology, product market fit, and business success. To be honest, I’m still a student of the industry, but back when I was starting out, my learning curve was steeper. I experienced imposter syndrome when I was in a room full of CEOs, regardless of whether they were from the same industry or our competitors. In many instances, those CEOs had more experience than me in building their company and what it takes to make products and markets successful. I had a fair amount of learning to do, but I used the imposter syndrome as a way to educate myself and learn from people around me. I also learned that I can be successful by focusing on what’s unique to me versus trying to be someone else. For example, we both know Scott Howe, CEO of LiveRamp. He’s a very compelling figure. When he stands on stage and gives perspectives on the industry and the market, it’s both inspiring and educational. I can find my own voice by learning from him—how he recognizes patterns and connects the dots, and from the experience he brings to the industry. But I can also stand on my own platform and be confident in how I connect the dots of technology and product to build something that’s unique.

You bring up an interesting point in that there is actually power in imposter syndrome that isn’t fully recognized. It forces you into the mindset of thinking, how do I learn, how do I get better? Often, people aren’t humble enough to recognize that they have something to learn, or they don’t approach a new situation with a beginner’s mindset.
Imposter syndrome is something to lean into and lean on. Instead of being put into a state of paralysis where you don’t feel like you can do anything, turn it around and use it as an opportunity to learn. It’s a powerful tool to propel yourself and your career forward.

Finding opportunities to learn and get better is something we constantly have to do. Another question that comes to mind involves the challenges of not only attracting new talent, but also nurturing and retaining talent. I’d love to learn your experiences at LiveRamp.

It’s been interesting. In the past 12 months, I’ve hired three direct reports, and doing the interviewing and onboarding during the pandemic has been challenging. The great thing about hiring people now is that it’s actually a lot easier to schedule interviews, which speeds up the process quite substantially. You can hire people much faster now, because you don’t have to require that they travel all over the place, so that’s been an unexpected positive outcome. Another challenge I’ve seen, and Kamakshi, I would love to hear your experience since you joined Microsoft shortly before the pandemic began, is starting at a new company where you’ve never met any of your coworkers in person. There have been a lot of challenges with that. There are definitely ways to be intentional about building connections, but especially if you’re managing a large team, people are not going to feel as connected to you as a leader as they are when they see you walking around the office and they have a physical connection to you. Over Zoom, that just doesn’t happen. It’s hard to get organic conversations going when you have to schedule a meeting. There’s technology out there trying to create those connections, and we’re testing a bunch of them out at LiveRamp, but it’s definitely tougher for people, especially those who are more junior or newer in their careers, to get access to mentorship and access to their leaders in general.

Great point. I completely empathize and sympathize with the problems and challenges. In many ways they’re the same, regardless of the organization’s size and scale. Technology can only do so much to foster organic connections. There’s still value in those “walking meetings” where you chat with someone you see as you’re walking around the office. One of my strategies is to be more vulnerable in a context that is applicable for my team. It’s okay to share something that went wrong in my day or if something isn’t going well with a particular project or strategy. Being able to share the human aspect of who you are with your team is extremely important. So hopefully, as we come out of this, we don’t forget how much we yearned for that human connection. I hope we continue to try to be better professionals, leaders, and humans in the post-pandemic era.

I couldn’t agree more. There’s so much I have learned with regards to both my work and my personal life, and having to show up as a more human leader for the people on my team. Those are the things I hope carry through for everyone post-pandemic. Well, Kamakshi, this was a wonderful conversation. Thank you so much for joining me, I’m excited to see what comes next. Maybe we can do a session in the hopefully not-too-distant future and discuss how we moved forward after this is all over.

Absolutely. It’s such a pleasure having this forum with you, Anneka. You’re someone I’ve admired for a long time. I look forward to the post-pandemic era where we’ll share our learnings, because there’s certainly going to be many more between now and then as well.