Unfiltered: #ChooseToChallenge with Lisandra Rickards

Okay, let's get going. Hi, Cloudflare TV. Before I go any further, I want to make sure that everybody understands we're going to have a chat here, myself and Lisandra Rickards, we're going to have a chat, but we invite you to join us.

So please feel free, as you notice at the bottom, we've got the live studio at Cloudflare TV.

If you have questions, feel free to submit them in that email alias, and then we'll pick them up as we go.

But just stepping back, it's happy Women's Empowerment Month.

It's a phenomenal month. We're doing some cool stuff. As many of you may know, I'm Jen Taylor.

I'm the Chief Product Officer at Cloudflare. We're excited to be doing this Choose to Challenge series on Cloudflare TV, which is brought to you by our Womenflare group, which is our Cloudflare employees resource group focused on women and their allies.

And then in celebration of this month, we're hosting a series of episodes on unfiltered throughout March, where we'll be celebrating and chatting with inspiring women in our lives and in our world and gathering their insights and experiences and sharing how they forge a more inclusive and equitable world.

So enough from me. Without further ado, I'd like to introduce you to my guest, Lisandra Rickards.

Lisandra, if you could actually just go ahead, please introduce yourself to the group here.

Sure. I am founder and CEO of Soul Career, which is an online course and coaching company that helps professionals, executives and entrepreneurs find their life's work that matches their personality, lead authentically and build powerful legacies.

And I came to this to this work through my experience coming out of business school, going into corporate America and finding that I wasn't a good fit for the role or the hierarchy or the structure of corporate America.

And so I had a very circuitous route to get to where I am today.

Well, and you and I were actually just chatting before we kicked off about the importance of really the fit of who you are and the work and the environment in which you'll thrive.

And, you know, we talked a little bit as we were sort of getting to know each other before the series about sort of how so how so much of who we are when we're young and the experiences we have when we're young are really formative to who we become.

So I guess just stepping back, you know, people who see me interview people on Cloudflare TV know that I always like, you know, when I'm talking to a superhero, I always like to go back to the origin story.

So tell me a little bit about your younger self. What was your first big dream?

Yeah. So my first big dream was to be a journalist. I wanted to go be dropped into countries all over the world and learn about what was happening there and write about my experiences and share them with the world.

That dream got kind of knocked out of me because, you know, society, my peers, my parents told me that you're not going to make money doing that.

You have to find something that makes money.

And in growing up in Jamaica in high school here, if you're bright, if you get good grades in school, you're funneled into doctor, lawyer, engineer and maybe banker.

But nothing else counts in terms of building a career.

And so I was being very heavily pressured into going into the sciences and becoming a doctor because I got good grades.

But I took some classes on economics and I found myself really loving understanding the world through the lens of scarcity and supply and demand.

And I was 14 or 15 in Jamaica at the time. And there were gas riots going on outside of school because the government had raised taxes on gas prices overnight and people weren't able to afford driving their cars.

And so there were riots in the streets and learning about what was happening outside school in class in economics really made transformed my interest from journalism into economics, which ended up being my career path through college.

And that's how I ended up in business school.

OK, so so you talk a little bit, you know, that kind of the question I always have is kind of how does how does that dream and that dream transform sort of turn into to that career?

You know, you sort of just got us to the narrative of sort of getting to business school, which is a phenomenal accomplishment and stuff like that.

Tell me a little bit about the journey from from kind of pre-business school, business school to really being, you know, focusing on your entrepreneurship.

Sure. So I actually decided in that period in my life in high school that I wanted to be minister of finance for Jamaica and save our economy and stop making terrible economic decisions.

I wanted our country to be a place that people wanted to stay in and raise family.

I didn't want my my friends to move all over the world and raise their families there.

I wanted us all to kind of stay and raise families together and be friends forever, you know.

And what ended up happening.

So the Caribbean is a very migratory place or we don't have generations of people living in the Caribbean.

People have come from China, India, Europe and Africa to the Caribbean.

And we tend to also migrate out.

So the dream of many people in high school is to migrate to the US or the UK, go to school there and get a job there and stay there.

And that was my trajectory as someone who got good grades.

So I ended up studying economics in undergrad. And then my I worked in economics out of undergrad with Steve Levitt, who is the author of Freakonomics.

He was my professor at the University of Chicago. And I was on a Ph .D.

track. So I ended up doing statistical programming in status, statistical software, regressions, residual analysis, Monte Carlos, all that stuff that I purged from my mind.

That was my life, learning how to be an academic. And he was the one who said to me, Lisandra, your personality is too big for you to be stuck as an academic behind a screen.

You need to go into business. You need to be a CEO. You're too much of a people person.

I'm going to write you a recommendation for Harvard Business School.

And I actually felt at the time that I was a failure as an academic for him to give me this advice that all the other research assistants were doing the GRE, getting into Ph.D.

programs. And I was being funneled into into business school, which was not as good as a Ph.D.

program. But I took I took his advice and he wrote me a great recommendation.

And I ended up at Harvard Business School or joint alma mater.

And while I was there, then there is this whole wealth, wealth creation.

There's a whole different life that I was introduced to at HBS of jet setting and travel and wealth and legacy and and the expectation that coming out of HBS, we're all going to be wealthy masters of the universe.

And I was coming from wanting a government job and wanting to be an academic.

And so it was a very I got caught up in that whole environment and ended up in management consulting at Bain and Company in New York City.

And that's where I really saw how disconnected I had become from myself.

I had gotten to this place. I was in the private equity group on track to make a lot of money coming out of business school.

And I felt like I was living somebody else's dream. That wasn't my dream.

And I felt like I didn't know who I was anymore. And it felt very empty, that work that was so detached from helping people.

It was more about solving problems for hedge funds, for example.

I felt that it was very empty and I lost a sense of self and didn't know who I was anymore at that point.

So then what happened? Like you've got me on a cliff here.

I'm like, and then what happened? Like she's just realized she's miserable and now she's in front of us incredibly successful.

Like what happened there?

How do you transform that sort of moment of like, oh no, into energy?

Right. So when you feel at a crisis point, when you feel like you don't belong, which many women and many women of color feel in corporate America, you have to come back to really reintroducing yourself to yourself.

So I went on this journey of countless psychometric tests to really understand how did I end up in a place that was so different from who I was?

And what they showed me was that I wasn't this heavy quant person that I thought I was.

I mean, statistical programming, that whole shebang.

I actually was a heavy people person who scored very high on influence and on creative production and on strategic thinking and not very low on quant.

So I had actually been living somebody else's life, which is why I got so burnt out.

I got really burnt out at that point. My brain had been pushed to the limit.

And so I decided to leave America completely and go back to Jamaica to really just figure out who I was and what I liked doing.

I took three jobs in three years and I hated every job.

And I was like, well, maybe I just hate working, period.

Maybe I knew I had lived in Spain during my junior year in college, and I was like, well, I'm going to move back to Spain and be a travel blogger and bartend my way through Europe.

Forget HBS, forget work, forget all of that.

I'm just going to live a bohemian life that's meant for me. That was my plan.

And I got thwarted from that plan. Let me leave on another cliffhanger there, Jen.

Okay, so hold on a second. I'm with you. I'm like, oh, now we're back to the initial dream of like writing and exploring and kind of going back to that sort of, to some degree, a journalistic instinct or a storytelling instinct you had when you were young.

Exactly, exactly. You're not a travel blogger, so. So what happened was I had moved back to Jamaica after graduating from HBS, after being all of that, I moved back to Jamaica, back into my parents' house, back into the same exact room I lived in at 17 years old to find myself.

And I felt like a complete failure.

And I took three jobs in three years, quit them all until I decided, you know, I'm going to save up some money because at this point I just have a lot of HBS debt and very little income.

And so I needed some income to buy my plane ticket to go to Spain and live my bohemian dream.

And I ended up attracting through my network, through the Harvard community in Jamaica, a job at the Richard Branson Center of Entrepreneurship.

So it was going to be part-time. Richard lives in the Caribbean.

He has completely relocated from the UK. We have great weather, you know, great lifestyle.

So he set up an organization to help entrepreneurs thrive in the region and to grow and scale and become like Silicon Valley entrepreneurs.

And so the role that I was offered was part-time, three days a week, training entrepreneurs in business principles that I'd learned at HBS.

I was like, I can do this for six months and I will write my book in the meantime and plan my move to Spain.

And I ended up staying there for seven years. And in the final three years, I was CEO of the organization.

That's amazing. Okay. So let's go back to this for a minute though, because like I'm thinking about this, you know, and one of the things we talk a lot about in the U.S.

and we should talk about what it's like in Jamaica and other cultures, because I think that will be interesting as well.

But, you know, so much of what we end up wrestling with and driving us is really the experiences and the expectations that are set for us from when we're very young, you know, and I'm really struck in this conversation we're having, which is, you know, you demonstrated very quickly when you were young, an affinity for something kind of quantitative and analytical, and that threw you down a trajectory that it wasn't until later in your life where you're actually able to step back.

There was this whole phenomenal sort of differentiated skill set for you that was just sort of off the map when you were a kid.

Why do you think that is? And what do you think we could be doing differently there?

Yeah. So I think that's because when you are getting good grades in school and you're in a country like Jamaica where getting to a U.S.

university is the key to upward mobility, especially for coming from a lower middle class, middle income family, right?

That's the key to success. So you need to do the things that will get you into a top tier university.

Being a journalist is not going to do that.

And so I was pressured by my teachers, by my parents into more quantitative and I was good at it.

And so I got so my thought on what should be different and the whole basis of the company that my brother, who is a strategic CSM, he's my co-founder, he's here at Cloudflare, big up to my brother Warren.

The whole thinking behind that is that we should be matching our careers to our personality type and to these internal interests and internal motivators that are innate in us rather than this external thought of status or money alone.

Money is important and all of our clients make out more money coming out of our program than they did before.

But before you can even get there, you have to be leveraging your strengths and taking a strengths based and an interest based approach rather than an external approach.

So we discussed before this call, Jen, on Myers Briggs, I'm an ENFP, which is the most free spirited, bohemian personality type of all the personalities in Myers Briggs.

And for people with P at the end of their type, dynamic, constantly changing environments that are unpredictable is where we thrive.

Put us in a structured hierarchical organization, any corporate organization, and we don't thrive in that environment.

For you, you shared with me that you're an ENTJ, which is perfect for a structured environment that is built on process and procedure and results.

And that is a perfect fit for that kind of environment.

So for me, we should always be matching the personality to the role.

And if I could just add, Jen, Virgin, the Virgin group was the first organization that decided where to place me in organization based on my psychometric test results.

And that's why I stayed there for seven years. Every job I had before that, I was there for less than a year.

Yeah. Well, because it was sort of like, what shape peg are you?

Let's figure out where in the organization you'll thrive.

And it's important to note not to cancel or reject a candidate based on psychometrics, but to see talent, oh my gosh, this is a talented person.

We want them in the organization.

Let's put them where they can thrive in the organization. I think about that a lot as we hire and as we mentor, manage, and grow people, it's really this sort of assessment of like, okay, hold on a second.

Who am I? Who are you?

What are your personal goals? And then how does that fit with what we're trying to go on?

How do you basically put somebody in a place where they would excel?

Yes. Except that often people don't even know who they really are. There's a split between who we think we are and who we really are underneath.

I thought I was heavy quant person and I got the shock of my life when these tests showed me that I was a people person.

I knew that to some extent. Yeah. So kind of given where you are now, kind of this journey that you've been on, if you could go back and have a cup of coffee or a tea or a soda with your 14-year-old self, what would you say to that person?

Oh, this is a hard one, Jen, because I don't think I would have done all the things I did with Richard Branson and the Virgin Group if I didn't have that quant background, even though it was such a divergence from my innate interests and skills.

So what I would have told that person was my younger self to have more fun.

Don't be so laser focused on the future to the extent that you're not enjoying and really living in the present, especially in college.

Gosh, I worked really...

I did not have fun in college. I wish I had fun in college. That's what you're supposed to do in college.

I worked so hard. So I would definitely say explore more, have more fun, take other things, take more art, more culture, do more.

The first time I did that was when I lived in Spain.

It was the first time I gave myself permission to get off the achievement treadmill and just live a little bit.

I wish I had done that earlier.

Yeah. It's sort of like the sayings that it's the journey, not the destination, or sometimes when you're lost, you actually are the most found.

The opportunity to have that unfocused or unfiltered time to sort of get in touch with the kind of serendipity of what might come here.

So I think a little bit about maybe some of the women or the allies of women that are maybe listening with us today.

And obviously, Women's Empowerment Month is a time when we really step back and reflect on sort of how do we encourage women to grow.

And as we were chatting beforehand, you shared with me the role of women in Jamaica is pretty different.

And I was completely uneducated about this. And I'm imagining some other people might be as well.

So tell me a little bit about what it means to be a woman in Jamaica and the role of women in the Jamaican economy.

Right. So in most countries in the world, you have a masculine dominated workplace, but actually the World Economic Forum put out a report a few years ago that showed that Jamaica was number one in terms of percentage of women in managerial roles in the workplace.

And in fact, the top three countries were all Caribbean countries. And for the percentage of women in senior roles, board director or CEO positions, Dominican Republic was number one.

So the Caribbean flips the status quo on its head, where women are in most of the leadership positions in the Caribbean.

Women tend to be the primary breadwinners in many of the families in the Caribbean.

And so it's a very different experience.

However, we still engage with toxic masculinity in the workplace, even with women dominating managerial positions.

And that comes from ego.

We have a very, you know, macho culture, still more traditional, you know, more conservative culture here.

And so there are still microaggressions that women face in the workplace here that also exist in the U.S.

Similarly, you know, we live in a majority black society here, but in the U.S., black women, black men have a very different experience in the workplace than you would have here.

So there are some similarities that transfer, but there's also large differences working here versus working in corporate America.

Yeah. What are some of the factors that you think might contribute to those differences?

What do you think may be unique or happening in those cultures, your culture?

Yeah. It's hard to pinpoint.

There is a lot of studies being done here to understand why, because we actually have a crisis for men in this country, because coming out of college, I didn't go to college here.

I went to college in the U.S., but colleges in Jamaica, 80 percent of the graduates are women.

Eighty percent. Wow. Twenty percent men.

Yeah. So migration has a lot to do with that. So a lot of our top quality guys go overseas.

But also how men and women are cultured in their home environment.

So girls are told, read your books and get good grades. And boys are told, go and play and be free and explore.

So there's much more rigid, kind of strict upbringing for girls than for boys in the Caribbean, which has led to these outcomes.

But that's more anecdotal. But that's kind of where we're leaning towards as an answer to that question.

It's interesting because it's a little bit beforehand, but, you know, a lot of people think about sort of what are some of the things we could do to kind of shift some of the dynamics that we see within.

I'm just going to take a very U.S.-centric point of view.

You know, what we could do to kind of help shift the role of women in the workplace and women in leadership.

And it's kind of, you know, I'm curious to just think about, like, you know, what can we be learning from some of those models?

Sure. So most of our clients at Seoul Korea are actually American or European.

So UK, Denmark, Sweden, we have Japanese and North America, Canada and the U.S.

And what I see over and over again that bears talking about is this perfectionism in women in these societies that I cannot go for the things that I want unless I am perfect, unless I have every credential possible, unless I meet every criteria on the job description.

And if there is one thing that's off, there's waves of self -doubt and the confidence that is needed to go for what you want is really there's just a lot of self-criticism in women.

And I felt that myself as well.

And I also questioned myself leaving Virgin and my great, amazing job to be an entrepreneur.

So I think across the board, women have this social pressure to live up to this perfect standard that we ourselves are putting on ourselves.

Society is putting on us. There's this internal and external dialogue and we have to shift our belief system and cultivate more confidence to go after what we want.

If men meet 60 percent of the job criteria, they're going to go for the job.

Right. Women have to meet 90 to 100 percent of the criteria to go for it.

Yeah, that's that's been interesting. I do a lot of mentoring and it's one of my favorite things to do.

And I have that conversation with with women all the time where they're like, well, I read the job description and I'm not blank, blank, blank.

And it's like the workshop, the workshop test. Can we can we shift the perspective?

Can you can you actually see that the ones that you do match and sort of the encouragement and the hope there?

Exactly. So, you know, I think also we haven't had a chance to talk much about about the work that you're doing today.

But, you know, one of the things I think a lot about as a woman in leadership is really reflecting on how important my mentors and my allies have been sort of men, both men and women throughout sort of my my career.

As you think about the your your your experience in your career and then also sort of some of the clients that you work with, what advice would you give somebody who wants to to be an ally and help women help women grow?

Sure. Well, I think first about men who have a lot of access to my first mentor was the author of Freakonomics, Steve Levin, and he wrote a book and he opened the door to Harvard Business School for me.

It wasn't even on my radar before he opened that door.

So men with a lot of access in spaces that are predominantly male dominated like finance, tech, business school.

When I went to business school, I think it was 60, 65 percent men.

Right. Should make sure that they're opening the doors for women, opening the eyes of women first and opening the doors to enable us to access some of the opportunities that have been traditionally been closed to us.

The second thing I think about is my current mentor is the chief partnerships officer at a global nonprofit acumen.

And she is a white woman that sat next to me at dinner at a conference in Virginia.

And we were just connected.

And she offered to to mentor me. This was right when I got the information that I was going to be the next CEO of the Brancisanto.

And I was stepping into this role that I'd never had before.

And she offered to mentor me in that role from her position as bringing in multiple millions of dollars for a large global nonprofit.

Then I have allies who are similar demographics as me who have made it to the top.

The first CEO of the Brancisanto, a woman of color, Lisa Lake, who matched me to a role that was perfect for me and allowed me to come alive in the organization.

So when I think about allies, this runs the gamut. Right. So all of us should be looking back to to who is coming up behind us and who can we open the door for that has traditionally been underrepresented, marginalized, and that feels like they don't belong in these spaces.

How can we encourage them to know that they belong there because the diversity of perspectives always leads to a better end result?

Completely. And I think about that, the notion of opening doors.

And I think so much of what you've touched on today and so much of my own experience has been not only the importance of opening doors, but also just opening my eyes.

You know, I mean, I think if you know, when I think about like my own, like starting it, like I would have been a chief product officer when I was five, like I was not doing that in the sandbox, like that was not, you know, I'm an ENTJ, so I was organizing what was happening in that sandbox.

You better ruthlessly prioritize the sandbox.

But just the importance of having some different perspectives and having people offer you those insights, I think it's been it's been transformational in my career.

And it sounds like it's something that is similar for you.

Absolutely. Absolutely. I would never have ended up at HBS, which changed my entire trajectory.

I would never have ended up there had it not been for Steve Levitt.

Yeah, that's just these kind of happenstance moments. So we've got just a little over two minutes left.

And so, you know, just to kind of close this out, I could keep talking to you forever.

I think we've got we've got so much we could cover here.

But just to kind of close this out, you know, the theme right now for Women's Empowerment Month right now is really Choose to Challenge.

And, you know, for me, you know, when we did a Q&A kind of panel internally, you know, my Choose to Challenge call to people was to in the next 24 hours from listening to this, you know, seek mentorship and offer mentorship to sort of foster that kind of allyship that we were talking about.

Sort of when you think about that theme of Choose to Challenge, what does it mean to you and what are some of the things you might do or you might encourage other people watching to do?

Sure. So personally, it means to me to speak up about things that you observe but that you would normally be silent about.

That's really important for me because I'm very diplomatic and I tend to self edit a lot, especially coming out of a role that was in a really large brand where the brand is very important.

So becoming a little more controversial and speaking out, it's a real boundary that I have to try to push through myself and that's what I'm challenging myself to do.

But in terms of challenging the status quo, something that's been on my mind a lot recently is this concept of status and ego and winning at the expense of someone else, which it's the ego and how it interacts in different work environments and different personalities and how they receive that versus not.

And trying to speak up about different ways of approaching work that can still lead to a phenomenal outcome but may not be aligned with or traditional concept of what a high -performing person looks like.

And I have three investors that are all men who've stepped up to support me in this business.

I have my brother who's been my number one cheerleader in this business, who's also a guy.

I went to women to invest in the business and they weren't as comfortable putting money into a high-risk endeavor as the men that invested more.

And so I want to challenge that as well, like challenge us to take more risk with capital as women but also challenge the men to understand and support my way of working, which is still very effective and it might be different from their way of working.

Perfect. What a great way to leave it. Thank you so much, Lisandra, for taking the time.

I've learned a lot in this conversation and I hope we get to continue it again soon.

Thank you so much for having me.

Thank you.