10 Leadership Tips for Women in Data

A round-up of some of top favourite themes and key takeaways from women leaders in data
Last updated
May 2, 2024

And just like that, we’re 10 episodes deep into Women Lead Data–what a ride it has been so far! I’ve had such a wonderful time chatting with our guests. I’ve learned so much about leadership paths in data, what it’s like to become a founder/CEO of a data company, and how to navigate different social aspects that are affecting women in tech.

With International Women’s Day on March 8th, I thought–what better time to summarize these valuable learnings from our guests so far?

So, here is it–a round-up of some of my favourite themes and key takeaways from the first ten episodes of Women Lead Data.

1) Starting a company pushes you way out of your comfort zone–but this is a good thing

This may be one of the least surprising things I learned–but possibly the most important piece of advice. Even after speaking to many founders and CEOs, I’m confident that I still don’t fully grasp how far out of your comfort zone the experience of starting a company truly feels.

I’m sure that many potential founders have great ideas for businesses, but the comfort zone barrier feels too high to push through (“What if it’s a failure?”). If you’re someone considering starting your own company, but feeling like this is holding you back, here are a few soundbites worth considering:

“I think for failed founders, it's not a ding on your resume, at all. If anything, it's a huge plus–regardless of where you interview. So, you know, other than the short-term struggle, I think overall, it ends up being quite rewarding.”–Jenny Sui, Craft Ventures

“I was so wrong with so many of my assumptions when I started the business, which I guess probably all entrepreneurs experience this, but this is why it's important to make hypotheses and then test them.”–Nicole Janeway Bills,CEO and Founder of Data Strategy Professionals

2) There’s no specific skill set or experience to become a Founder/CEO–almost everyone has to grow in the role

Similar to becoming a first-time parent (of a child or a pet!), most first-time founders and CEOs are just figuring it out as they go–learning the skill sets required to be a CEO on the job. While there are certainly many beneficial skills you can take with you into a founder or CEO role, the role is so varied every day, and so dependent on the company you’re running–that almost everyone will have to learn this role on the job. This is both a blessing and a massive challenge for people stepping into these roles for the first time.

I loved these discussions with Jacqueline Cheong of Artie, and Sarah Nagy of Seek AI, where they both summarized the initial experience and growth process of stepping into the CEO role:

“The development and self-development has to be the best part of being a founder. You learn so much and get to meet so many smart, motivated people to surround yourself with. Sometimes I feel like I’m almost cheating because it's my job to just become a better version of myself. For example, I'm working with a sales coach now, and it's like I'm just learning how to become a better salesperson, how to communicate better, and how to read body language or understand that when someone says something, their underlying intention is not always what they tell you. And just becoming a better version of myself is obviously a plus for the company, but it's also just great learning that you can bring with you forever. // But then overall, I think you just grow up a lot emotionally and mentally. So it's really cool. The better I become, the better it is for the company. It's amazing.”–Jacqueline Cheong, Co-founder and CEO of Artie

“I'd also worked at a couple of startups and watched those CEOs, and kind of felt a little bit like, okay, maybe I could do that. But in the very beginning, I had no idea what I was doing for sure. I didn't even know what a letter of intent was, or a MSA. I had to learn pretty much a hundred percent of things on the job. So, looking back, it was actually pretty fun, just learning so much, but that was definitely a memorable experience.”–Sarah Nagy, CEO/Co-founder of Seek AI

3) Networking and relationship-building are critical to success

Whether you want to start your own business, move into leadership roles, or become a C-level executive one day, networking and strong relationships can be a significant driver towards your success. And the earlier you start networking and relationship building in your career, the more impact this can potentially have on your overall career trajectory.

Especially for folk stepping into the founder and CEO role, building a network of peers and potential mentors can be a tremendous help when you have that feeling– “I have no idea what I’m doing”.

In my episodes with Sarah and Jerrie, they shared more about how to build relationships when you’re just starting with networking:

“I didn't have a huge network when I was starting out, but I was definitely a big fan of Y Combinator. I had already read a lot of their library before I started Seek, so I found their library to be a really great resource, and it's free. I joined a community on Discord actually, that helped me out a lot. It was this community called Founders Cafe; it's just this Discord where a bunch of founders, mostly first-timers, come together to kind of give each other support. // And then, out of the network I did have, something that helped me a lot was I eventually was introduced to this mentor, Pat Headley. She has this great Ted Talk called ‘Meet 100 People’. She says, if you're trying to do something and you're trying to build your network, don't say no to meetings, just try to meet a hundred people. If you can meet a hundred people, whatever it is you're trying to get done, you'll get done. So I adopted that philosophy pretty early on, fortunately. And it was one of the best pieces of advice I've ever gotten. So that's how I was able to grow my network.”–Sarah Nagy, CEO/Co-founder of Seek AI

“I think when you first hear about networking, a lot of people wrestle with the concept. They're just like, "I don't like it. I don't like the term. It seems very formal and like you expect something out of this relationship." And that is how I first thought of networking, meaning I thought it was this rigid way of engaging with someone to get something specific out of them. And that doesn't work for me in general. I'm very much a people person, very much about connecting in a genuine way. So I had to reframe networking as something more about building relationships with individuals that you admire, want to learn from, or feel like you have a connection with.”–Jerrie Kumalah of dbt Labs

4) Unsolicited advice is directly related to workplace power dynamics–consider how you want to navigate it

The topic of unsolicited advice has come up in several of the episodes of Women Lead Data, and I anticipate that I will continue to hear these kinds of stories. I dug into this topic a bit more as I was working on this blog post, and found quite a bit of research that shows, unfortunately, unsolicited advice is something many women deal with regularly–especially women in tech and those moving up in leadership roles.

At best, it’s an unwanted annoyance or distraction. At worst, it can chip away at your confidence, and make you question yourself. Researchers have also found that offering advice makes one perceive influence over others and power within themselves–which points to the power dynamics and politics that workplace advice can create.

Given this aspect of power and politics, navigating advice in the workplace is a skill that everyone (especially women) should learn–anticipating and identifying when an advice-giving situation has arisen will allow you to proactively decide how you want to respond, and how you will let it affect you. Here are some soundbites from guests who have experienced unsolicited advice:

“One concrete example of this was when I left my job at Deloitte. The person who actually had helped me get that job, because it is an old boys club, made a comment as I was leaving. I was doing the courtesy calls, like 'hey, thank you so much, and here's my new email.' And this guy was like, 'you really don't seem like somebody who would want to work in data or who would be interested in data.' And I was like, 'are you saying I'm incapable of logic?' I just couldn't understand why he thought it was acceptable to say something like that, and he said it twice.//

Imagine if you were on the fence, and then you get those kinds of comments that just make you question your decisions. That's kind of disheartening. And I think in those moments, like when those types of things happen, sometimes it kind of takes you by surprise. And then it's not until later that you realize how much it affected you.”–Nicole Janeway Bills,CEO and Founder of Data Strategy Professionals

“One thing I always talk to people about is like, you don't have to take every piece of advice you get, right? If you have advice you want to disagree with, or somebody's onboarding you and they're like, "I really want you to do this," and that's not what you thought you signed up for, say it right. Be like, "Oh, that's not really what I'm—let's talk about that." Right? Like, is that what your expectation is?”–Colleen Tartow, Field CTO and Head of Strategy at VAST Data

I found the research around this topic particularly intriguing, and if you’re also interested, you can read more about this below:

5) Bad behaviour still happens–every day–speaking up in these situations can benefit yourself and others

Unsolicited advice is a particular type of bad behaviour, but other types of negative behaviours come up frequently for women in the workplace–especially in tech and the data industry. Some of these can include:

  • Being ignored
  • Being spoken over
  • Having someone take credit for your ideas

These can be very frustrating, overwhelming, and confusing situations when they arise. In my episode with Celina Wong, CEO of Data Culture, she shared her thoughts on how to deal with these types of situations and how to turn them into opportunities for yourself and others:

“I had a meeting where I remember sharing my opinion and then being spoken over, and the next person delivered the same exact thought I had, but with different words. In that moment, something just clicked for me. I thought to myself, if you don't speak up now, you're just going to let this keep happening to you. So, I channelled the energy of taking up space and speaking up for myself. I stopped the meeting and asked the participants, "What did I just say in the last five minutes that wasn't said when you're repeating after me?" I was so livid that they were repeating exactly what I said and got praised for it, wasting another five to ten minutes saying the same thing. Everyone stopped, likely shocked that they were being called out. I realized I needed to hold up a mirror to this behaviour because if I'm not going to do it, who else will? This is a moment of encouragement. If you're feeling moments like that, I challenge you to hold up that mirror to that behaviour. There are so many people out there who may think they're an ally but don't realize that their behaviour is actually contributing to what we perceive as toxic behaviour. // And if you're fortunate enough where you haven't had to deal with that, but you witnessed that happening to someone else, a great thing to do is to pause the conversation and say, "Hey, I think so-and-so just tried to speak up. What was your thought or your opinion?" Because you can usually tell someone wants to jump in, but the conversation is just so dominated by other folks that the person who may have some of the smartest ideas doesn't get to chime in, and oftentimes it's a woman.”–Celina Wong, CEO of Data Culture

6) Asking for what you want, and “just going for it”

In most episodes, I’ve tried to ask guests, how did you make the jump from X to Y? Whether that be into a C-level role, becoming a founder, or moving into more senior roles. The most common responses I’ve gotten have been:

  1. Ask for what you want
  2. Just go for it

Asking for what you want means being very clear with your direct manager or leadership team about the direction you want to go, instead of waiting for them to present opportunities to you. Being able to ask for what you want means truly understanding what that is–doing some self-reflection and development work to understand and set those goals for yourself. No one else can tell you what to do with your career, it’s up to you to own it. Taking ownership of your career ensures you stay in the driver's seat, rather than passively waiting for opportunities to come to you. Sometimes having the courage to speak up and ask for what you want can take your career on a new path:

“And I was like, ‘OK, so how do I get more involved in this data? I want to be involved in this”. So basically, I just asked my manager to be put on more of those projects. And that kind of started my career in data.”–Monica Kay Royal, Founder of nerdnourishment

And sometimes, making big leaps into the next level or a new role means “just going for it”–even if you don’t feel 100% ready. I loved this discussion with Colleen about her experience making big leaps:

“My husband will probably laugh if he can hear this, but every single job I've taken, I've freaked out beforehand. Like a week before I'm like, "I don't think I can do this. This is a terrible idea. What if this role is an awful fit? I'm going to suck at this." And he just laughs and he's like, "Okay, we've known each other for quite some time now. You do this every time. Can you please just try to remember this?" And every time, like a week later, I'm like, "Oh yeah, what was I freaking out about? This is great."–Colleen Tartow, Field CTO and Head of Strategy at VAST Data

Colleen also referenced a great quote from the movie, The Princess Diaries:

“Courage is not the absence of fear, but rather the judgment that something is more important than fear. The brave may not live forever, but the cautious do not live at all.”

7) Resiliency is key to leadership success

Another theme I continue to hear from most guests is this concept of building resilience–whether that be in the face of rejection, or managing through feelings of self-doubt and imposter syndrome. Resilience is critical to help you persevere through difficult times, and make it through to see the impact and success you’re having.

“It was definitely really, really hard at the beginning to get rejected. But, fortunately, my brother-in-law is a salesperson, and he kept telling me, "Look, it's just a numbers game. You're going to get rejected this many times, and this percent of the time, maybe you'll make it to the next level." And I heard that from other people too, from Founders Cafe or my network. I think that's something that, now, I would say my skin has gotten much thicker. It's rare that things really get to me.”–Sarah Nagy, CEO/Co-founder of Seek AI

“Over time, I've learned how to compartmentalize because, in the beginning, things would be said about me on platforms like Reddit or Twitter, and I couldn't resist wanting to respond to it or wanting to read other people's comments on it. However, having support from others who have gone through the same thing, like some of my data creator friends, and leaning on them, asking, "What should I do in this situation?" has been really helpful. // Having a support system of people who have been through it themselves helps me deal with the haters who care so much about what I have to say. But regardless, in the grand scheme, if you are consistent in putting out your content and establishing yourself as a thought leader consistently, those things are just a blip in the grand scheme of what you're trying to do.”–Megan Lieu, Data Advocate at Deepnote

8) Career paths are rarely a straight line–most people just figure it out as they go

The options for career paths in data, and what it means to be a “leader”, are consistently growing and changing. Becoming a leader doesn’t mean you have to follow a typical management career track or even a typical role. There are so many examples of people merging their passions with emerging roles. In our episode, Megan shared some great advice about how to think about your career path as constantly evolving:

“I was on this panel with people who had been at their companies ever since they graduated from college. Their advice to college students was to find a good culture, like find your cultural fit in a company, plant your roots, and just grow there. That's a lot of pressure for 22-year-olds to figure out their life and be like, "Hey, yeah, just stick with that, and you'll be good to go." So, I was that one dissenting voice on the panel where I was like, "You don't have to have it figured out when you're 22, because I definitely did not. And I still don't have it figured out now. And that's OK. Like, I will figure it out year by year, month by month." And I think that narrative doesn't get pushed up as often.”–Megan Lieu, Data Advocate at Deepnote

9) The Importance of Role Models and Giving Back

The importance of role models for women in typically male-dominated industries is sometimes questioned–”Why can’t women look at any leader and see themselves in that role?”. 

Well, based on my own experience, and the feedback from some of my guests, I continue to believe that role models play a major role in helping improve the lack of gender diversity in certain fields–especially in data. Here are some of my favourite soundbites from episodes where role models came up:

“This woman (Vigdís Finnbogadóttir) I mean the president, she was president for some years–enough years so that the crazy interesting thing about this is that in Iceland, there was a generation that grew up thinking you have to be a woman to be president. I love that. It's so powerful. We have all of these conversations all the time in life or the general conversation about ‘How do we fix the gender bias in tech and startups and finance and venture capital and everywhere?’. We always have this discussion about what role do role models play in that? I’ve had numerous conversations with people where they're like, ‘It doesn't really matter that much, aren't people just able to find role models in whoever?’ And sure, I'm sure that's true. I know that people can do whatever they want in life, but I think this example just says so much.–Stefania Olafsdóttir, CEO and Co-founder of Avo

“Since I was little, when thinking about what's driven me in the past, I remember being four or five years old. Growing up in New York, I recall driving past women in business suits and thinking, "That's going to be me one day, right? I'm going to be a CEO.//

Reflecting back on when I was a junior and starting my career in banking and finance, I remember trying to find a role model in a field where there weren't many folks I could look up to and see myself in. However, there was one person in particular who stood out to me, and to this day, I still remember her. I looked up to her because I watched her walk into the office, dressed in a way that was authentically herself, complete with flashy earrings. It left a lasting impression on me, and I remember thinking about how she represented a role model for me in that environment.”–Celina Wong, CEO of Data Culture

Both of these examples demonstrate how role models can inspire people to reach new heights, and also provide permission to be yourself.

10) It’s possible to find balance and synergy between an ambitious career and home life

For many women, the societal expectations at home are significantly more demanding. This means it can be difficult to maintain a fast-paced and ambitious career, and balance this with the demands you’re met with at home. Women who already have children, or are planning to start having children, face the societal impacts of the Motherhood Penalty:

  • Research into the motherhood penalty found that the hourly wages of mothers are approximately 5% lower (per child) than the wages of non-mothers, and mothers are less likely to get hired than non-mothers.
  • Relative to other kinds of applicants, mothers were rated as less competent, less committed, less suitable for hire, promotion, and management training, and deserving of lower salaries.

While these kinds of stats are both infuriating and demotivating to hear–after speaking with some of my guests, there seem to be some critical pieces of the puzzle women need to leverage to set themselves up for success in balancing the demands of ambitious careers and family life:

“I would say, more than helps me be successful, it's just a prerequisite having a good partner at home and having a good partner in their startup or the company is really important. Neither would work without it.”–Stefania Olafsdóttir, CEO and Co-founder of Avo

“Oftentimes you hear women talk about this after they've made it, right? They're already at the top of the game. They're CEOs, or they're directors, or they're leading their efforts and very visible. And it seems like they figured it out. The part that I don't often hear about, and that is very real, is like those of us who are still at the beginning, meaning starting families. You have these ambitions, and you haven't nailed down the balance. What does balance look like? And I don't remember who said this, but I was listening in at a conference, and she, the leader, said, "You can have it all, but not at the same time."–Jerrie Kumalah of dbt Labs

I think these soundbites from Stef and Jerrie are so impactful, because they create a framework for balance. Oftentimes, expectations on women are incredibly unrealistic, and as a society, we don’t talk enough about how this, which leads to feelings of isolation and “I’m not as good as other mothers”. I hope that we see this dialogue opening up more, and that more companies are supportive of women making the transition into motherhood.

So to wrap up this blog post, I want to share our guests and I encourage you to follow them so you can continue to learn from their experiences:

Women Leaders You Should Follow

If you’re a leader in data and are interested in being on the show, or have suggestions of guests I should bring on, please add me to LinkedIn and let’s have a chat!

You can check out all the episodes here on Spotify or Apple.

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