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Women in Leadership – Olympia De Castro

Our company is filled with extraordinary women. And our Women in Leadership spotlight aims to highlight the brilliant women who hold leadership positions here at Datacubed Health. This article is focused on our CFO, Olympia De Castro.  

What are the challenges women leaders face? 

I would say one of our main challenges lay in how we show up at the table. How we communicate and support each other. For some years, we have lived in a society where business acumen and success are tied to ‘male traits.’ This has built on itself, creating implicit bias about what we associate with success or leadership. It is not a surprise that studies show women who have historically mirrored male behavior often achieve success. 

Yet, I believe this paradigm is changing. We have an opportunity and a responsibility to bring the female voice and traits to the table. Personality studies, including the ‘Gender Differences in Personality Traits Across Cultures: Robust and Surprising Findings,’ have found that women reported themselves to be more anxious and risk-averse (down to earth) and agreeable and warm (empathetic). At the same time, men were higher in assertiveness (tough) and openness to ideas (conceptual/imaginative). (Costa, Terracciano & McCrae, 2001).

However, how do we lead with our innate, authentic traits? 

There is a great advantage to being a woman and thus leading as a woman. We are better at being personal oriented more capable of telling it how it is when necessary because we do so from a place of compassion, empathy, and collaborative success. 

However, the challenge is that we have few and far between role models of what it looks like to be a female leader with ‘female traits,’ making it feel like uncharted territory. This feeds into what effective communication and leadership look like. The world is adjusting to a new voice and approach to leadership. Often, I look at Madeline Albright as a model for what female leadership looks like. One of the significant points she makes is when she came forward in her delegation and said, “Well, I feel we should do something about this,” to which the other men at the table responded, “What do you mean you feel?” 

Given leadership with female qualities is still a new phenomenon, it can take a moment for all of us to adjust. Soon after, her delegation heard another female leader, the now prime minister of Finland, use the same tone and language. “That’s when the men understood,” she says. It will take more than one woman to normalize the change.

Crisis and change

The 2008 crisis served as one of the many catalysts for companies and countries to recognize the need to include the female voice in leadership scenarios. Countries and companies with women in leadership fared better during these challenging times. The same was true during COVID-19.

Similarly, the corporate world has recognized the need for female qualities in leadership. In “Leaders Eat Last: Why Some Teams Pull Together, and Others Don’t,” author Simon Sinek proposes a concept of leadership that has little to do with authority, management acumen, or even being in charge. True leadership, Sinek says, is about empowering others to achieve things they didn’t think possible. Exceptional organizations, he says, “Prioritize the well-being of their people and, in return, their people give everything they’ve got to protect and advance the well-being of one another and the organization.” (Levitt, 2017).

Finally, I would argue beyond just corporations; capitalism is evolving to a more collaborative and inclusive approach. Without balance in a leadership team, we gradually find ourselves in a short-term-oriented system of the Milton Friedman shareholder primacy days. This has shifted to long-term goals and a broader set of stakeholders, best exemplified by the Business Roundtable’s new Statement of the Purpose of a Corporation signed by 181 CEOs; Corporations should benefit customers, employees, suppliers, communities, and shareholders. 

What factors influence a woman’s ability to lead?

We have all seen the pendulum swing significantly in favor of having women in leadership. However, we must be cautious not to drive this movement in a way that isolates and antagonizes our fellow men. In my career, I have come across many men who recognize the challenges we face as women and who, as a result, have supported many women in their career growth.

There is now an open and broad recognition of the challenges women face. However, the goal is not to replace the men or make them feel so uncomfortable and threatened that progress comes to a standstill. This is about engaging in change together. A Harvard Kennedy School Women and Policy Program study found that business teams with an equal number of women and men perform better in terms of sales and profits than male-dominated teams (Hoogendoorn, Oosterbeck, & van Pragg, 2013). The key is having the proper collection of people with the whole sleeve of leadership qualities needed to help an organization succeed.

Quoting Albright again, “When there are more women, the tone and goals of the conversation changes … when there are more women at the table there is an attempt to develop some understanding… empathy, collaboration, putting ourselves in the other guy’s shoes. But it doesn’t mean the whole world would be a lot better if run by women… if you think that, you have forgotten high school!” 

Is there a woman leader you admire?

We know there is a shortage of women in leadership and thus a lack of what it means to lead with female traits. Per Harvard Business Review, there were more large US companies CEOs called John or even David than there were female CEOs. But we are beginning to see a rebalance. 

The COVID-19 crisis saw the emergence of a cadre of female political leaders come together with more successful responses in their countries. Coined the ‘super seven’ of the ‘Nordic quartet’ this included Erna Solberg of Norway, Sanna Marin of Finland, Mette Frederiksen of Denmark, and Katrin Jakobsdottir of Iceland, together with New Zealand’s Jacinda Ardern and Taiwan’s Tsai Ing-wen, rounded off with the G20 member Angela Merkel of Germany. The approaches of these women encompassed a range of stereotypical female traits, caring, empathy and collaboration, listening to diverse views, and communicating effectively. These traits led to building trust, transparency, and accountability at a time when the world was in a panic.

Beyond admiration, to personal connections

I admire these women, but even more so, I have found that I have collected a group of incredible female friendships throughout my life. Some are single working moms like myself, others are stay-at-home moms, or just simply great women. Be they working professionals or not, I am fortunate to be surrounded by a group of exceptional, confident, kind, and unwaveringly supportive women and friends. They are my village. They inspire me with their strength; they are great sounding boards for advice and are incredibly generous. I salute you, ladies, here and extend my deepest gratitude and admiration. 

Finally, as I look for other woman role models, I believe there are many women leaders whose stories are yet to be told. I am currently reading “Hidden Figures” by Margot Lee Shetterly, and I love that she gave up her career in investment banking because of this calling to tell the stories of the many exceptional women mathematicians who helped the US win the space race.

What advice would you give the next generation of female leaders?

Speak in a voice that is natural to you. Show up with confidence and authenticity. Your voice, knowledge, and input are integral to your company’s success. The diversity of views and approaches will help drive better decision-making and collaboration. And this applies to ALL employees, not just women.

Finally, make sure to bring other women with you to your success. As Albright said, “there is a special place in hell for women who don’t help each other.” We have faced enough challenges to break through the glass ceiling; we need to recognize we are stronger when we stand together, unified, and there is space and the need for all of us. Remember, ultimately, your career advancement is changing the paradigm of female leadership. Never give up the effort to try and make things easier for our next generation of women and girls. Change takes time. And as Shirley Chisholm, the first African-American woman elected to the US Congress was quoted as saying, “If they don’t give you a seat at the table, bring a folding chair.”

We thank Olympia for her contributions to our company, and we’re so lucky to have her as one of our woman leaders at Datacubed Health. Be on the lookout for another Women in Leadership article next quarter.

Works Cited:

Costa, P. T., Jr., Terracciano, A., & McCrae, R. R. (2001). Gender differences in personality traits across cultures: Robust and surprising findings. Journal of Personality and Social Psychology, 81(2), 322–331.

Sinek, Simon. “Leaders Eat Last by Simon Sinek: Book Summary by Paul Minors.” Paul Minors, 12 Jan. 2020,

Hoogendoorn, S., Oosterbeek, H., & van Praag, M. (2013). The impact of gender diversity on the performance of business teams: Evidence from a field experiment. Management Science, 59(7), 1514–1528.