Authenticity Makes a Difference

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Who is Carolyn Herzog?

Carolyn Herzog, Chief Legal Officer at Elastic

Carolyn Herzog’s journey into legal leadership has been filled with a lot of twist and turns, but there “ain’t no mountain high enough” to prevent her from overcoming obstacles and coming up top. She might not have been able to fulfil her childhood dream of being a singer like Diana Ross, but she has certainly made a significant difference in the legal profession.

"In the future, there are no female leaders. There will only be leaders."

- Sheryl Sandberg, former chief operating officer of meta platforms (formerly facebook)

In the past few months, I have had the pleasure of being a part of Herzog’s legal team at Elastic, an NYSE-listed technology company, where she holds the role of chief legal officer leading an international team of diversified individuals.

Herzog is not new to leadership roles. She previously served as the general counsel at Arm Ltd and has held several senior legal leadership roles at Symantec Corporation including VP and Head of EMEA, based in London and deputy general counsel, based in their California HQ, supporting their commercial, services, product, litigation and support teams, as well as leading their compliance office. She is also a board member of ACC and a charter member of TechGC.

Notwithstanding the number of senior leadership titles she’s had in front of her name, Herzog remains humble, authentic, and continues to strive to make a difference. Her journey started out with a job in the World Bank as the project administrator for health and education programs in the francophone regions of Africa. During her four years with the World Bank, Herzog had the opportunity to work with a couple of managers who gave her the idea of going to law school. It was around the time the European Union formed, and she spent summers in Paris studying international law with the ultimate goal of wanting to make a difference. After all, she had gone to law school not to be a corporate lawyer but to make an impact in the world. Her father jokes that she must be one of the only few people who made less money after law school than before it.

While she was working for the nonprofit, International Law Institute, she met a lecturer who was doing a program on transfer of technology, and he was extremely passionate about his job. He mentioned to Herzog that AXENT Technologies (which was later acquired by Symantec) was looking to hire a legal counsel. Though she was still young and did not know a single thing about a license agreement, she went for the interview and gave it her best shot. The rest is history.

Showing hints of vulnerability, Herzog shared her biggest challenge of being a general counsel is “to have your own moral compass.”

Overcoming obstacles

Elastic is a multinational, dual headquartered company, and with it comes its own challenges of having myriad laws and legal regulations that the company has to follow. As CLO, she has had to make tough decisions. As the ultimate legal decision maker, Herzog has to help her company, her team, and fellow colleagues come to the decision on the right thing; she does not believe in forcing what is right on others.

She has to be prepared to put everything on the line when making a decision. For instance, any difficult decision which may affect a commercial contract, beyond what Elastic is usually happy to agree to, may require Herzog’s input. To avoid prolonging commercial negotiations, which would not be easily accepted by the sales team, it is important that Herzog is in constant communication with various key stakeholders including but not limited to Elastic’s chief sales officer and other stakeholders to ensure she has their buy-in.

While it should not be difficult to guide people to make the right decision, it has not always been easy. Herzog is thankful that it has not been very difficult to have people aligned at Elastic as Elasticians (yes, we coined the term and are proud of it) want to do the right thing.

Learning to lead in the right way, at the right time

Adding to her list of challenges is her gender — it should not be an issue, but it is. Reflecting on her journey as a female leader, Herzog shares that there have been times when people draw the wrong conclusions because they assumed the female in the room was not the decision maker. She took this in her stride and used their underestimation of her to her advantage. Herzog is petite, and people are usually surprised when they meet her in person for the first time. They may not comprehend that someone small in stature could pack a big punch and could actually be the one calling the shots. Learning when and how to assert yourself in the right way and at the right time, and when to simply listen, is one of the most important lessons she has learned.

Female executive leading a meeting with colleagues.
Learning how to be confident with your presence in the workplace is key to upholding a high position and gaining respect from other colleagues. Monkey Business Images /

When asked if she has experienced resistance when leading men, Herzog shared that she experienced resistance regardless of gender, as women adjust differently to being managed and led by women. As a woman myself, I found myself nodding when she shared that women generally have a hard time asserting themselves in a group regardless of gender.

We discussed tokenism and agreed that quotas — alone — can backfire. Relying just on quotas may diminish the underlying value of why quotas were created in the first place. Nobody wants to be the token female or the token diversified figure on the board. We should instead look at the gap, the system process, targets, and quotas as a holistic package — whether we are looking to increase female representation, LGBTQ+ representation, or another group, we would have to go behind the system, create a process that is transparent, and work to remove any unconscious bias within the system.

Diversity drives innovation. It is important for companies to create and maintain a diversified workplace. The voice of the corporation has changed; people are demanding that companies they work for stand for certain values. Leadership matters; it is not just about connecting people to the jobs that they are hired to perform but how these jobs connect to the companies’ larger purpose.

Leadership matters; it is not just about connecting people to the jobs that they are hired to perform but how these jobs connect to the companies’ larger purpose.

Diversity is more than just gender diversity; we need to create an environment and a comfortable system for everyone to co-exist. Working in this wonderfully distributed world and working in a distributed company such as Elastic requires us to collaborate across silos, across countries, across cultures. Leaders need to create a safe space, an open space for people to co-exist which would in turn drive innovation.

Group of diverse business people in a meeting with gears.
Employees from all different backgrounds should feel comfortable to coincide together, making it easier to work together as a team. /

Leaders need to create a safe space, an open space for people to co-exist which would in turn drive innovation.

The difference in gender-specific challenges were starker when Herzog first started working and the world had changed to be more receptive of female leaders. While she believes that there is little gender-specific differences in terms of leadership skills, analytical abilities, empathy, etc. Herzog shares that she would probably be able to talk about DEI (diversity, equity, and inclusion) related issues with more ease. DEI related issues are of critical importance to her — as well as the key importance of belonging. While she has been a DEI advocate for years, she admits that, having LGBTQ+ children have taught her how little she knows. And, in that moment, I see a mother opening up about the challenges she has faced living through COVID as a parent; I see a sister who experienced a sibling tragedy; I see a leader who is not afraid to be more open about the emotional side of leadership. It is truly admirable.

Self-doubt and imposter syndrome

And to illustrate her emotional side of leadership, Herzog shares that she has never not felt imposter syndrome. As much as she has confidence in her abilities, she lives with imposter syndrome all the time. She shares an anecdote of an incredibly competent mother who is not able to bake cookies nor make costumes for the school play, and she can never imagine herself doing so; she shares yet another anecdote of how she has sat in meetings where she simply did not understand a thing that a presenter had shared.

Herzog shares her tips on how she deals with it: She stays confident in her ability that she is able to bring something else to the table, and she is not afraid to ask someone else for help. It is important to be able to speak openly and feel comfortable with that gift of feedback so that we can keep growing. Curiosity is a tremendous skill, and we should learn to be comfortable in the unknown.

Smiling curious young businesswoman raising hand at group meeting.
It is important to build emotional intelligence, you will constantly learn and acquire knowledge by staying engaged and being curious. fizkes /

It is important to be able to speak openly and feel comfortable with that gift of feedback so that we can keep growing. Curiosity is a tremendous skill, and we should learn to be comfortable in the unknown.

It takes courage for one to be able to admit when we do not know something and to ask for help. Allowing me a look into her younger days, Herzog shared a story of how her female high school teacher had told her that she would not be able to succeed in science simply because her hair was pulled back too tight. It convinced her that she could not excel at science when in fact she could and did.

Oftentimes, we have an easier time believing the negative comments that others give us instead of the positive feedback. As a leader, Herzog believes that it is important to give positive feedback. It is important for people to know where they stand and to build on what makes them great should they want to get to that next level of greatness.

It is important for people to know where they stand and to build on what makes them great should they want to get to that next level of greatness.

As the role of the in-house counsel changes over time to include the responsibility of being a business advisor, it is self-limiting if we were to only discuss the law. After all, lawyers have more to offer than just law. In-house counsel have the ability to help business partners come to the right decisions and grow in business partnering. Herzog demonstrates this best in her business partnership with the Elastic senior leadership team, proving that legal has more to offer, and she relies on the specific expertise of each leader at Elastic to share their expertise so that she can be their best legal partner. We cannot work in silos, and it is important to find partnerships both within the workplace and outside of the workplace.

In order to be the business’ best legal partner, it is important to understand and accept that there will be differences amongst us, and it is important that we find a compromise and a common ground in spite of our differences. Herzog shares a story about her hero, the late US Supreme Court Justice Ruth Bader Ginsburg, was best friends with someone who had opposing views. To be able to push for systemic change, we would need to gain advocacy and to do so, we need to be able to understand what exactly we are fighting for, what is the outcome that we would like to achieve. Is there a way we can reach our outcome and build our advocacy through it. Herzog said it best, “Sometimes lawyers are so busy being right that we forget about being human.” At the end of the day, we are all humans, and we all have something in common. The onus is on us to find that common ground and utilize that to find a way forward, and in that process, we may be surprised to comprehend that what we thought were important aren’t actually as important. We could be debating about surface issues when there are other ways in which we could get to the same outcome.

Nuggets of wisdom

As the interview comes to a close, Herzog imparts her nuggets of wisdom on how:

  • Leaders need to make time and create a safe space;
  • Leaders need to step up and be sponsors for all types of diversity;
  • We need to think inclusively and not in terms of male/female — not black and white.
  • Leaders need to put the ladder out there and bring up another person by creating development and professional opportunities. Herzog shared about how she has helped many people including other women to get GC roles, and she is absolutely thrilled that she could help “ladder up” someone else.
  • As a leader, we should also look inwards and call ourselves out when we are not being as supportive as we should be. We need to make time and create the space for networking and support each other whether in the workplace or outside of it.

Advice to the next generation of female leaders

“Be your authentic self,” Herzog advised. “Don’t try to be anyone but yourself and stay curious.” While there is nothing wrong with being in awe of others, we should also be a little in awe of ourselves. We may constantly be in self-doubt, and we may forget how brilliant we are. So, we should build a posse of people around us that remind us of how great we are.

Female empowering other colleagues in workplace.
Having a support system can and will enhance a positive self-image and within yourself. /

Driving ambition

We ended the interview with Herzog sharing about the Elastic value, the Elastic source code that she resonates most with:

Progress, SIMPLE Perfection. In Elastic, we believe that “perfection is not a destination. Color inside the lines or color outside the lines. Just pick a color. It’s as simple as 2048. An Elastic that moves is an Elastic that survives, thrives, and stands the test of time.”

Herzog shares that it is a privilege for her to work in a profession where people come to ask for our advice daily. This is an honor, and as lawyers, we need to learn how to be better at providing the legal advice on the how. We are here to help define how to balance risk and make a judgment call on risk and progress. In-house counsel are here to help the company progress, legally and soundly, but we cannot be perfect all the time. And, in order to make progress, we need to be able to balance the risk. Leaders need to create the safe space to provide coverage for the team to allow the team to make reasonable mistakes, and to learn from these mistakes, to trust and rely on colleagues, ask questions, and pivot when they make reasonable mistakes but ultimately, to seek progress above all.

Growing up in a patriarchal environment, I was not exposed to many strong capable female leaders. And, it is “hard to be what we cannot see” (Anonymous is a Woman).

I am innately drawn towards capable female leaders because they embody who I aspire to be. Like me, I am certain that there are many others who would love to see a more diversified group of leaders taking the helm in global corporations and  on the world stage. Role models, representing diversified groups, be it LGBTQ+, people of color, Asian representation, or others gives people a chance to be inspired. When we can see people who resemble us rising, on their terms, it spurs our ambitions.