Career Growth Advice from Shailvi Wakhlu, business Leader | Career Tips for Women in business

2B Bolder Podcast – Episode 114
Featuring Shalivi Wakhlu

Episode Title: #114 Shailvi Wakhlu, Head of Data at Strava, talks about Data, Leadership, and Self-Advocacy

Host: Mary Killelea
Guest: Shalivi Wakhlu



Mary Killelea (Host): Hi there. My name is Mary Killelea. Welcome to the To Be Bolder podcast, providing career insights for the next generation of women in business and tech. To Be Bolder was created out of my love for technology and marketing, my desire to bring together like-minded women, and my hope to be a great role model and source of inspiration for my two girls and other young women like you. Encouraging you guys to show up and to be bolder and to know that anything you guys dream of, it's totally possible. So, sit back, relax, and enjoy the conversation.

Hi everyone, and welcome to another episode of the To Be Bolder podcast. I'm Mary, and I am so excited for today's show. We have a truly remarkable guest joining us, someone who has made waves in both the tech world and in being a leading voice for self-advocacy and a woman I greatly admire myself. Shalivi Wakhlu is an experienced data leader and self-advocacy expert with over 17 years of experience, growing impactful teams and building technology products.

Shalivi’s journey is nothing short of inspiring. She's held notable roles at Salesforce, Fitbit, and even served as the head of data at Strava. Shalivi has spoken at nearly 100 global conferences and coached nearly 500 individuals, helping them unlock their potential through the power of self-advocacy. Shalivi is also the author of the best-selling book, Self Advocacy, a Practical Guide That Empowers Individuals and Leaders Alike to Get What They Deserve in the Workplace. It is certainly a must-read for every career woman listening to this podcast. Fun fact, Shelby grew up in India, studied computer engineering at Illinois Tech, and now calls San Francisco home, where she lives with her husband and from what I hear, 60 plants. Thank you for being here. It's great to have you.

Shalivi Wakhlu (Guest): Thank you so much for having me on the show, Mary. It's such a privilege to be on a show that I've really admired all the episodes you've created. What an amazing body of work.

Mary Killelea: Thank you so much. Okay, let's jump right in. You've had an incredible career journey with roles at companies like Salesforce, Fitbit, and Strava, which I mentioned. Can you share a little bit about your path into the tech industry and what drew you to those positions?

Shalivi Wakhlu: Yeah, absolutely. I definitely come from a space where I knew I wanted to be in tech since I was a child. I was very excited about the world of coding and solving business problems that affected millions of people. As I grew up, I spent more time noticing how technology really influences the whole world. I studied engineering, moved into the data world many years ago, and with some of these companies that you mentioned, I've been very, very fortunate in my career to have worked for some really amazing brands. It was also quite cool that most of these brands had products that were used by hundreds of millions of people around the world. That was a huge part of what drew me to them. It affects a lot of people, so it was just fun to work on. Also, I am a data nerd, and the data sets that all of these companies had was really huge.

Mary Killelea: The companies that you have worked for are big names and very recognizable. I have worked for Intel, so I really only know one kind of corporate culture, if you will, and you've experienced various ones. Are they distinctly different, or did you feel like there's commonality?

Shalivi Wakhlu: I would say that I bucket most of my career into the startup world, and then there's the big company. There are only Salesforce, and I used to work for Monster.com. Those are the only big companies I worked for.

Startups have their own little vibe, their own little culture. I also mostly worked for startups in San Francisco, and they definitely have a very specific culture that they have. Salesforce, I love that company. It is one of the best companies with an amazing work culture that I've ever worked for. Since I've worked at Salesforce, I've tried to take parts of their culture into every other company that I've worked for, so definitely took that along with me.

Mary Killelea: Well, that says a lot about that company, and that's cool to know, because I always wonder how cultures are at different companies. You're known as a self-advocacy expert. What inspired you to focus on this area, and why do you believe it's such a critical skill to have in today's workplace?

Shalivi Wakhlu: Yeah, I think a lot of people who work in tech, and especially people who are from underrepresented backgrounds, I think there is an experience that comes along with that, where you eventually end up with situations where you have to advocate for yourself. For me, I am a woman of color working in a male-dominated field. I was also an immigrant. I have an accent. I come from a different culture. I think there were enough prompts for me to have had to be in positions that I had to advocate for myself.

And as time went on, I realized that there were some pieces of it which came to me very easily, and there were other pieces that were really hard. I eventually got to the point where I felt that this is a skill that I have to be intentional about. It's not optional for me to have the skill as I grow my career. Career moments are shaped by those individual steps that you take to try to steer outcomes towards your best interest.

Also, I think as a technologist, it's really not a skill that we are taught. This is not something that we are taught in college. It is not part of our curriculum. We are not taught so many of these pieces. I think that is what drew me to that area.

Mary Killelea: I love that. I love that it's like a quiet requirement that each of us should own for our own success. Over your 17 years of experience, what are some of the most important lessons you've learned about leadership and building impactful teams?

Shalivi Wakhlu: Yeah, I think for me, when I reflect back on my journey to leadership, I feel like the thing that stood out to me is that building trust is one of the most important goals that you can optimize for between you and your team. I really generally feel that leaders are in such a privileged position. You have the capacity to really shape the careers of all the people who choose to bring you their talents. With that privilege comes a hefty amount of responsibility. You have to be intentional about the trust you build. It has to be a two-way street. I think trust has its own components. You have to focus on clarity. People who work for you should not have to guess what you reward, what you promote. And there's a little bit of that authenticity and vulnerability that I think when leaders exhibit that, they are able to build trust in a much easier manner. It's a more clear interaction between both sides.

Mary Killelea: That's a great summary. I wish there were more leaders heeding your advice. I see gaps in the workforce. As the head of data at Strava, what were some of the unique challenges you faced and how did you leverage data to overcome those?

Shalivi Wakhlu: Strava was such a wild ride in a way. It is one of the largest sports data sets in the world. It was really cool to have that opportunity to shape what happens with that. I think for me, one of the exciting things that happened when I joined Strava, they were definitely in that very high growth stage. They had a lot of options. People in the audience are not familiar. People who are athletes in their daily lives like runners, cyclists, those people use it. With that, there was a lot of questions about where the company grows.

With a company like that, there are so many different directions. You can go into more sports or you can double down on the sports that you covered today and go really deep. That question of going wide or deep can be about demographics, can be about locations. That was one of the big things that I focused on. We had a lot of data to leverage. We know how people are adopting our product, how different demographics react to various pieces on our thing. That is something that I leveraged with the help of some of my other colleagues. We worked to create the company's three-year company strategy and answer those questions like should we go wide, should we go deep, how do we leverage existing pieces and tie them into something that's valuable to our users?

Mary Killelea: I think that's fascinating that you're talking about shaping the company's strategic direction because sometimes when you think of data or you think of tech, you think, okay, I'm only in this technology solve a problem world. What you're saying and defining your role was really using that data to go broad and add business value. I think that's remarkable.

Shalivi Wakhlu: Yeah, absolutely. I really sincerely believe that data is at its best when it is a partner to solving problems, not just answering questions. I was very grateful that I think Strava, when they hired me, they recognized me as someone who had subscription expertise. I was brought in as a data leader, but also to really hone in on the subscription piece.

Mary Killelea: Let me ask you this. For those listening who work with data and that are not being asked their opinion of the value, the data, or what the data could be telling the business, how do you encourage them to proactively showcase maybe their knowledge, their expertise, or the value that they bring to the business?

Shalivi Wakhlu: Yeah, I think that's a fantastic question because I think there are so many people who are excited about showcasing what can be done with data. Unfortunately, people sometimes really struggle with just finding the time to poke around and look for those interesting things that might catch the attention. I always advise people to take some of that time out proactively themselves and really focus on what is something that can affect really dollars of business. If we were able to answer this question better, we would affect X dollars of business.

I think at the end of the day, people love money and people love putting things in perspective based on the monetary impact that a different problem or a better problem to solve can have on the business.

Mary Killelea: This is a great segue because I want to ask you about data storytelling. I think your website, by the way, is fantastic. I went on there and I spent some time yesterday and the lessons and learning resources that you provide are amazing. Let's talk about, you developed a course on data storytelling. How can data storytelling influence business success, what we were just talking about, and what are the key elements of a compelling data narrative?

Shalivi Wakhlu: Yeah, I think we are now almost living in a world where people almost expect a data component to any story, even if you're trying to convince them. Anytime you're trying to influence people, I think there is an expectation that you use data to make that case in a stronger manner. Of course, there are many situations where primarily you're using data to convince somebody to do something. The one thing that I always start with that if you are in a position and you don't have to be a data professional for it, you could be a marketer, you could be in product or any function. If you are using data to tell a story, always remember it is not about the data, it is not about you, the storyteller. It is always about the audience.

Ultimately, you are trying to tell a story that makes the audience do something. It meets their needs, it speaks to their motivations, or it adapts to the messaging that they are most likely to respond to. That to me is that critical component of the data storytelling. Who are you even telling the story to? I would say the specific ingredients that I think have the biggest impact is focusing on relevancy. How can you make your story more relevant to who is listening and the call to action? How can you give people a clear takeaway about what they should do with your story?

Mary Killelea: That's wonderful. Another thing that I think comes up or maybe should come up more is data quality and how crucial it is for decision making. Sometimes people capture data but they may not know the sources or it might be dirty data or whatever. Can you tell us more about your data quality workshop and the strategies you teach to maintain high data standards? I think that's really cool.

Shalivi Wakhlu: Yeah, I really appreciate people who even care enough about data quality to know more. I have been running this session for data folks and those sessions are a little bit more technical. But I really derive a lot of joy when I run this course or this session for non-technical people. Not non-technical in the sense that they're not into coding on a daily basis. So product, marketing, other cross functional folks. My goal in these sessions is always to educate anybody. Just anybody who's ever working with data. I think when they understand the life cycle of data better, when they understand that these are the phases where bad data can be introduced, when they have a better understanding of that, they are also in a better position to prevent it. They're in a better position to put resources behind it or put a process behind it. Because I always say that even if there is a data team that is doing the final steps to improve data quality, it is a cross functional effort. It doesn't happen in a silo. It doesn't happen unless people don't really, as I say, put their money behind it and put time behind it. So when these cross functional partners are more educated, they are in a better position to improve data quality for the entire organization.

Mary Killelea: Absolutely. As a woman in tech, what are some challenges that you faced and how have you used self-advocacy to overcome them for yourself?

Shalivi Wakhlu: Yeah, that's a great question. I would also say that I think it's been hard for me to exactly identify which challenges that I faced in my career were because of my gender. Because I think, I'm sure you can resonate with this as well, that some challenges could be solely because of your gender. Some are amplified because of your gender. The others are just a little hard to tell. Would you face it anyway? I would say the one theme that stays constant, which is sort of an indisputable fact, is that if you have less examples of what success looks like for someone who looks like you, I think it's just harder. It's harder to picture yourself in a position of leadership, for example, you don't see leaders who are women or or who match your demographic in some way. I would say that that definitely was a challenge for me.

I often share this example that over 17 years and five companies, I've somehow had 16 managers, which I don't know, I just got lucky, I guess. But I haven't not had a single female manager, for example.

Mary Killelea: Really?

Shalivi Wakhlu: Yeah, it's wild. I have been a female manager for many people on my team. My last team, half of them were women. But I've not had it for myself. I've not had mentorship or sponsorship from a woman. I would say that that was definitely a challenge. Then I think that led to other challenges of not knowing how to advocate for myself in a way that would not end up having me just labeled as aggressive or difficult or things like that. I think that's something that women tend to worry about a lot more. I think it's fair because unfortunately, our industry does have that problem.

I would say for me, I eventually got to that place where I said, I have to advocate for myself no matter what. I can keep eye-treating on the messaging. I can keep eye-treating on the tone. I can keep eye-treating on how I say what and who do I say to. But ultimately, I have to say it. I'm never going to compromise on speaking up and getting my point across. But yes, if it takes me just smiling my way through a lot of problems and politely escalating what I want to say, that's what I would do.

Mary Killelea: That's funny because I've only had women managers. I've had several. I mean, multiple, multiple while I've been at Intel.

Shalivi Wakhlu: That's interesting.

Mary Killelea: You have spoken over at 100 global conferences and coached hundreds of individuals. What have been some of the most rewarding aspects of sharing your knowledge with others?

Shalivi Wakhlu: I think it’s so wonderful when you hear back from real people, even if you may have met them many years ago. I think when people share about how what you said or something you highlighted positively affected their life. I think that’s such a wonderful gift. So, that has been super rewarding for me when people share individual stories. In some cases, people didn’t know they were stuck and then they happen to hear me. And the next day they went to work and implemented some the strategies you shared. I think those stories are amazing. I recently had a coaching client that said she was ready to quit her job until she decided to follow my playbook for seeking a promotion. It took a few months, but she got what she wanted out of that situation. I just think it's so heartwarming to actually hear that. Because yes, I may have talked to hundreds of people over the years, but it's a very small fraction that actually share what the impact of the situation actually was.

Mary Killelea: That's huge. That is why you are one of the women I really do admire because of what you're doing for other women out there and helping them leverage your path forward. I think that's amazing. Let's talk about your book Self Advocacy. It's a bestseller. What inspired you to write it and what do you hope readers take away from it and any highlights from it?

Shalivi Wakhlu: Yeah, I've genuinely been amazed and very, very grateful for how well the topic has been received. This book began as a talk. I gave this talk almost five years ago at a conference. It was cutely titled, How to hashtag Humblebrag Effectively. It ended up doing really well. I just kept speaking about it more. I used to mostly do data talks at that time, but then I started splitting my time between data and self-advocacy. And eventually, enough people asked me, do you also have a book that goes along with this? I said, yes. I have a book that goes along with it. Eventually, enough people asked me, do you also have a book that goes along with this? Maybe I should write that down.

What I really hope that people take away from it is I think it's divided into people who have not really actively thought about self-advocacy and they look at the book and they're like, this is my prompt to think about it. There are other people who have been thinking about it and they just don't know what to do next. So I hope both of those groups can find something of value, you know, of reiterating why it's important for them to build that skill. And hopefully when they're convinced to actually have very specific things that they can practice starting, you know, the next day on how they can get better at their self-advocacy skills.

Mary Killelea: In your book, you also discuss the importance of effective negotiation. Can you share a negotiation strategy that's been particularly successful for you?

Shalivi Wakhlu: Yeah, I, you know, I am big on sort of research. I'm big on data, like, you know, comes as a hazard of the profession, but I think it's really helpful to do your research, you know, to see like what is the market at and to also sort of research your own motivations. I think knowing you're having self-awareness about what is truly important to you, I think, I think goes a really long way in an effective negotiation, because then you're not just asking for something because you think that's what you're supposed to do. You're focusing on the things that you care about.

You know, for example, like in one of my past job offers, I was really very motivated to aim for a higher title. And I told the company that, hey, like, everything you're offering is great, but I want a higher title. You know, you don't have to give me more money, but the title is something that I really, really care about. And it was a very interesting negotiation, because I knew exactly like, you know, what the situation was, I knew how long they'd been looking for somebody to fill that role. Like, I had done my research about what was the, what was the cost of me asking for something. And, you know, again, in retrospect, like, of course, there was a there was a scenario in which I would have, I would have potentially walked if they didn't, if they didn't do the title change, and maybe lived to have regretted it later. But that's not what ended up happening. Like, they met my expectations with the title, and then they even threw in extra money. So that was a very happy bonus that ended up coming out of it.

Mary Killelea: And that's such good advice. Because for whatever reasons you had the title, it was important to you. And, and I'm assuming gaining that title, because I see other women who do that, who do go after the title, then from that point on, you're almost playing at a different level.

Shalivi Wakhlu: 100%. 100%. You know, you get anchored at a completely different career point. It was so interesting that even with that company, like, you know, they were initially like, okay, they weren't super gung ho about giving me the title. And eventually they did. But it was so funny that two months later, after I joined, they were already having conversations about my path to the next title. So amazed. I was like, wow, like two months ago, you know, you were still debating whether I deserved a higher title. And here we are today.

Mary Killelea: And you talk about creating a customized career plan in your book as well. Can you give us a glimpse into how someone might start building one?

Shalivi Wakhlu: Yeah, so this is this is something that I think I had worked with an executive coach a long time back. And she introduced me to this concept. And I absolutely loved it. But I think focusing on your career values, you know, this is something that I think people can Google and they will come up with a little bit of a list of what potential career values might be. And I really recommend that people force themselves to stack rank that list to the point where it says, you know, will you give up A for B of sorts. And because what I would hate is for people to be on autopilot, where they're just going after, you know, like, just to pick up, pick an example, like, you know, if a if a higher title is not of importance to someone, you shouldn't be gunning for that, like you should be going after something else that you care about more. Maybe it is work life balance. Maybe it is the recognition for your work or something like that.

But I really think that when people focus on those career values, they are in a better position to design the career plan that works for them. You know, it's not their neighbor's career plan. It's not their high school friend's career plan. It is their career plan. And I think it serves them so much better when it's customized to their own needs.

Mary Killelea: That's great advice. And one thing that I think I personally have struggled with over the years is when someone talks to me about wanting to help me get to the next, you know, point, I don't know what I have in the past, not known where I wanted to get either because I didn't see it, didn't know it. And so, I felt almost just frozen with I'm not sure how you can help, which did me, you know, horrible harm. Right. And so that's, again, I think part of the reason I do this podcast is to introduce different pathways. So what do you recommend for people who are in roles who don't know the pathway?

Shalivi Wakhlu: Yeah, I think, I think it's, it's maybe easier for people who have, again, you know, like, if it's a if it's a career path that many people have gone through before them, then it's easier to sort of figure out. And, you know, like you said, like, I think, I think, I think podcasts are honestly a great way to really hear the stories of individuals. I think there's so many people who are willing to share and answer questions and really kind of showcase, you know, a version, and maybe it's not going to be exactly your version, but a version of what of what that success on that career path look like.

But I think for careers that are more formalized, there's a lot more sort of information out there. I think those things, it is easier to find those examples, like, you know, for example, yesterday I met somebody who was the head of engineering at a pretty decent sized company. And, like, I could have almost predicted what their path might have been, because it is it is it is common for people to have gotten to that level. And, you know, when I looked at their LinkedIn, it was it was easy to see all this all the things that they did that led to that. And of course, there's no guarantee there's no guarantee that, okay, you do the exact same things, and you will land up with the same outcome. But there are definitely things that you can, you can see people who have been successful in their fields, and then try to triangulate from that, like, what are the patterns that you can try to repeat, that you can try to incorporate into your next steps. And hopefully, if you are in a company that is really big, you know, they sometimes have an actual career ladders, or something like a promotion documentation or something that actually shows how is progression measured. And companies that have that documentation available, of course, it's a lot easier to just say that, okay, these are the things that I'm lacking that would showcase that I'm moving forward in my in my career growth.

Mary Killelea: I think those are so valuable for companies to have to help their employees, because career growth, or the vision or visibility into that is one of the biggest reasons people leave their companies.

Shalivi Wakhlu: Absolutely. Yes.

Mary Killelea: Okay, so one thing that you also mentioned that I want to circle back on, was your work life balance, you know, if that's important to people, how have you been able to manage work life balance over the years?

Shalivi Wakhlu: Yeah, I think I think it is something that I consciously focus on. You know, I'm very ambitious about my career. My husband, we've been together for a long time, and he's very ambitious about his career. But I think, I think both of us have a focus where we also want to make sure to prioritize time with each other, you know, take regular breaks and vacations. And I think that commitment can be translated into goals that you set for yourself. I, for example, have a lot of startups in Silicon Valley, have the concept of an unlimited vacation, you know, it sounds really fun, like, Oh, unlimited. It is really never unlimited. Like, that's not a that's not a thing. And yeah, like they are banking on the fact that just by saying unlimited, some people will not take the regular amount of vacation that you that you usually get.

And so in my case, you know, that was that was like step one, I'm like, okay, a regular job typically gives me 20 days of vacation. So, I want to make sure that I actively take that like, I'm not going to be one of those people who will end up with five vacation days the whole year, like that's not me. So, I think when you start actually, you know, tracking those type of things, like, I want to go swimming three times a week, I want to be able to have healthy food, and, you know, at least cook a certain number of times a week. So, I think I think those things when you start putting focus on them, that's when you turn it into a muscle that you no longer have to think about that you no longer have to negotiate with your with your job, because it is it is just a base baseline that you are that you are focusing on.

Mary Killelea: That's great advice. What does to be bolder mean to you?

Shalivi Wakhlu: For me, I think it means just not being afraid, you know, just going after what you want. And I often I often say this sometimes even to my coaching clients that it can be really scary to ask for something and then get rejected. Oftentimes, it's even scarier if you ask for something and get exactly what you want. Because then you have to actually close the loop, like, you asked for something and you got it. And now you have to do what you said you do if you got it. o yeah, that's what it means to me.

Mary Killelea: I love it. What advice would you give your younger self?

Shalivi Wakhlu: I would definitely tell my younger self to improve my self-awareness. I think so many times we fall into the trap of just not being able to tune out the noise of what everyone around you wants. And then you just start mimicking those patterns. And sometimes it's too late when you suddenly realize you've been leading someone else's life or, you know, you have the career that someone else wanted and it's not it's not the life or career that you wanted. So, I think just improving your self-awareness, it really goes a really long way in in getting you what you want.

Mary Killelea: What is next for you?

Shalivi Wakhlu: You know, I think there's there's always so many so many things. I'm a I'm a polymath. I have lots of interests. I have lots of things that I'm excited about. But I would say one specific thing that's come up recently, which got me excited was, I have a client who wants me to run a workshop on self-advocacy, but not just for individuals, which is what I typically do, but for their leadership team. So, sort of the what and how of like, what happens when leaders intentionally try to encourage self-advocacy skills on their team. So, I'm super grateful when I find partners who see the value of this as a business benefit and not just something for individuals. So that's something that I'm that I'm looking forward to.

Mary Killelea: I am going to make sure that I include a link to your website and your profile on LinkedIn and a link to your book before I let you go. I like to do a little fun, quick question thing to get to know you. So winter or summer?

Shalivi Wakhlu: Summer.

Mary Killelea: Coffee or tea?

Shalivi Wakhlu: Oh, tea.

Mary Killelea: Dogs or cats?

Shalivi Wakhlu: Can I get both?

Mary Killelea: Pizza or pasta?

Shalivi Wakhlu: Pizza.

Mary Killelea: Chocolate or vanilla?

Shalivi Wakhlu: Oh, chocolate any day. Vanilla is just a waste of calories.

Mary Killelea: It has been so fun meeting with you, getting to know you. I am a big fan. So thank you so much for being here and for all that you do for women.

Shalivi Wakhlu: Thank you so much, Mary. I am such a huge fan of yours. So, I'm just really grateful to be included in your show. And thank you so much for a very, very thoughtful conversation.

Mary Killelea: Thanks for listening to the episode today. It was really fun chatting with my guest. If you liked our show, please like it and share it with your friends. If you want to learn what we're up to, please go check out our website at 2bbolder.com. That's the number 2 little bbolder.com.