Most lawyers are trained to spot what could go wrong.
That skill matters. It always will. But in a world shaped by AI disruption, geopolitical instability, nonstop regulatory shifts, and businesses demanding faster decisions, Carolyn Herzog believes something else matters too: optimism.
Not blind optimism. Not corporate positivity. Operational optimism.
The kind that allows leaders to move through uncertainty without freezing their organizations in place.
In a recent conversation on “Notes to My (Legal) Self,” Carolyn Herzog, chief legal officer and company secretary at Elastic, reflected on what it means to lead legal teams amid continuous turbulence. The discussion moved from AI governance to COVID to trust, resilience, contracts, and the future of in-house practice. What emerged was not a theory of leadership. It was a survival framework for modern legal teams.
And notably, it came from someone who has spent decades operating inside global technology companies where uncertainty is not episodic. It is structural.
Carolyn Herzog Never Planned To Become A Lawyer
One of the most interesting legal leaders is often the one who did not follow the traditional script. Carolyn Herzog is one of them.
“I’m one of those lawyers who actually never intended to be a lawyer,” she said early in our conversation.
Before law school, she studied French and music, then worked at the World Bank in the African department. What pulled her forward was not doctrine. It was curiosity, international work, and people.
“I’ve worked with people who saw things in me that maybe I didn’t see in myself.”
That perspective matters because it shaped how she approaches leadership today. Carolyn has never worked at a law firm. Her entire career has been in-house. That changes how you think about legal work. It changes how you think about relationships, accountability, speed, and business partnerships.
It also changes how you experience transformation.
AI And COVID Changed Legal Leadership Forever
When asked about the most significant changes she has led organizations through, Carolyn did not hesitate. Two moments immediately came to mind: COVID and AI.
The comparison was revealing.
COVID forced vulnerability into the legal profession. It disrupted the illusion that lawyers could always operate through control, precision, and endurance. It exposed the human side of leadership.
“It made us all vulnerable at the same time, regardless of what profession we were in.”
For many legal teams, COVID permanently changed expectations around work, flexibility, empathy, and communication. It also accelerated another realization: legal departments were no longer supporting the business from the sidelines. They were helping organizations navigate existential uncertainty in real time.
Now AI is forcing another transformation.
But unlike prior technological shifts, Carolyn pointed out that generative AI did not arrive gradually enough for organizations to prepare comfortably.
“It happened yesterday.”
That sentence captures why so many legal departments feel disoriented right now. AI adoption is not waiting for governance structures to mature. Businesses are moving. Employees are experimenting. Boards expect strategy. Regulators are still evolving.
The old legal instinct to pause, assess, and draw hard boundaries no longer works.
“We would’ve tried to draw a hard line until we understood what the impact was. We would’ve just said no. That’s not possible with artificial intelligence.”
That shift may be one of the most important mindset changes happening inside legal departments today.
The New Legal Skill Is Not Caution. It Is Controlled Adaptability.
One of the strongest themes throughout our conversation was the distinction between pessimism and preparedness.
Carolyn put it bluntly: “Pessimism doesn’t really serve you to achieve things.”
Lawyers still need skepticism. They still need to think through downside scenarios, regulatory exposure, cybersecurity threats, and operational failures. But legal leaders who only operate from fear become blockers instead of strategic advisors.
The real challenge is learning how to combine optimism with disciplined risk analysis.
“I think we have to have a pretty healthy sense of paranoia,” Carolyn explained. “At the same time, when you’re encouraging people to follow a vision, it’s really important to be optimistic about that vision.”
That tension defines modern in-house leadership.
The legal department cannot merely identify risk anymore. It must help organizations move through risk intelligently and quickly.
That requires adaptability. It requires clarity. And increasingly, it requires legal teams to become technologically fluent.
AI Governance Is Becoming a Leadership Problem, Not A Technology Problem
Many discussions about AI governance focus narrowly on compliance frameworks. Carolyn approached it differently.
She framed AI implementation as an organizational leadership challenge.
How do companies move with velocity while still creating guardrails?
How do legal teams guide behavior instead of trying to prohibit technology?
How do organizations distinguish between low-risk automation and high-risk decision-making?
That distinction became particularly important during our discussion about human oversight.
For low-risk processes like self-service NDAs, automation makes complete sense. But for high-risk decisions involving hiring, compliance, or major legal judgment calls, human accountability still matters deeply.
“If the risk is high, you need to make sure you have a human in the loop.”
That sentence sounds obvious until you realize how rapidly organizations are normalizing AI-assisted workflows without fully understanding where assistance ends and autonomous decision-making begins.
Legal departments are now being asked to answer that question in real time.
Contracts Are Absorbing The Anxiety Of The Modern Economy
One of the most interesting moments in our conversation centered on contracts.
Over the past several years, major disruptions have reshaped contractual expectations. COVID changed force majeure clauses. AI is reshaping governance obligations, audit rights, data handling provisions, and liability frameworks.
And geopolitical instability is beginning to influence sovereignty, localization, and control over information flows.
Carolyn sees this clearly.
“We are seeing more of a push towards how do I control that information, how do I bring it back to keep it only in my environment, only in my private cloud, only in my country.”
That trend matters because contracts are often the first operational layer where uncertainty becomes tangible.
Businesses may debate AI strategy in executive meetings, but those fears eventually manifest in vendor agreements, procurement terms, compliance obligations, and data restrictions.
The result is a growing tension inside contracting itself. Companies are trying to protect themselves against future uncertainty that nobody fully understands yet.
“Many companies are saying, I want to be protective against the future.”
That instinct is understandable. It is also producing contractual demands that many counterparties realistically cannot satisfy.
Trust Is Becoming The Competitive Advantage
For all the discussion about AI, risk, governance, and transformation, Carolyn repeatedly returned to one word: trust.
Not efficiency. Not scale. Not automation.
Trust.
“If you start with the premise that we want to be trusted, and then you think about how do you build and retain trust …”
That framing matters because trust changes how legal departments operate internally and externally.
Inside organizations, trust allows legal teams to move faster because business partners believe legal is helping them succeed, not simply blocking exposure.
Externally, trust shapes vendor relationships, negotiations, and long-term commercial durability.
In periods of uncertainty, trust becomes operational infrastructure.
And increasingly, that trust depends on transparency, adaptability, and responsiveness.
The Future In-House Lawyer Looks Different
Toward the end of our conversation, Carolyn described how she would design a legal department today.
One answer stood out immediately: legal operations.
“Legal operations has become a critical part of how we run the legal team.”
That observation reflects a broader reality. The modern legal department is becoming more data-driven, technology-enabled, and operationally integrated than ever before.
The future legal team will not succeed purely through technical legal excellence. It will succeed through systems thinking, process design, technological fluency, and the ability to manage information velocity.
And perhaps most importantly, curiosity.
“I think the more curious you are as a leader, the more you think about what is potentially a better way to do this.”
That may ultimately be the defining trait of resilient legal leaders in the AI era. Not certainty. Not perfection.
Curiosity strong enough to keep adapting.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics.She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.
The post Carolyn Herzog On Why Legal Leaders Need Optimism, Not Certainty appeared first on Above the Law.
Most lawyers are trained to spot what could go wrong.
That skill matters. It always will. But in a world shaped by AI disruption, geopolitical instability, nonstop regulatory shifts, and businesses demanding faster decisions, Carolyn Herzog believes something else matters too: optimism.
Not blind optimism. Not corporate positivity. Operational optimism.
The kind that allows leaders to move through uncertainty without freezing their organizations in place.
In a recent conversation on “Notes to My (Legal) Self,” Carolyn Herzog, chief legal officer and company secretary at Elastic, reflected on what it means to lead legal teams amid continuous turbulence. The discussion moved from AI governance to COVID to trust, resilience, contracts, and the future of in-house practice. What emerged was not a theory of leadership. It was a survival framework for modern legal teams.
And notably, it came from someone who has spent decades operating inside global technology companies where uncertainty is not episodic. It is structural.
Carolyn Herzog Never Planned To Become A Lawyer
One of the most interesting legal leaders is often the one who did not follow the traditional script. Carolyn Herzog is one of them.
“I’m one of those lawyers who actually never intended to be a lawyer,” she said early in our conversation.
Before law school, she studied French and music, then worked at the World Bank in the African department. What pulled her forward was not doctrine. It was curiosity, international work, and people.
“I’ve worked with people who saw things in me that maybe I didn’t see in myself.”
That perspective matters because it shaped how she approaches leadership today. Carolyn has never worked at a law firm. Her entire career has been in-house. That changes how you think about legal work. It changes how you think about relationships, accountability, speed, and business partnerships.
It also changes how you experience transformation.
AI And COVID Changed Legal Leadership Forever
When asked about the most significant changes she has led organizations through, Carolyn did not hesitate. Two moments immediately came to mind: COVID and AI.
The comparison was revealing.
COVID forced vulnerability into the legal profession. It disrupted the illusion that lawyers could always operate through control, precision, and endurance. It exposed the human side of leadership.
“It made us all vulnerable at the same time, regardless of what profession we were in.”
For many legal teams, COVID permanently changed expectations around work, flexibility, empathy, and communication. It also accelerated another realization: legal departments were no longer supporting the business from the sidelines. They were helping organizations navigate existential uncertainty in real time.
Now AI is forcing another transformation.
But unlike prior technological shifts, Carolyn pointed out that generative AI did not arrive gradually enough for organizations to prepare comfortably.
“It happened yesterday.”
That sentence captures why so many legal departments feel disoriented right now. AI adoption is not waiting for governance structures to mature. Businesses are moving. Employees are experimenting. Boards expect strategy. Regulators are still evolving.
The old legal instinct to pause, assess, and draw hard boundaries no longer works.
“We would’ve tried to draw a hard line until we understood what the impact was. We would’ve just said no. That’s not possible with artificial intelligence.”
That shift may be one of the most important mindset changes happening inside legal departments today.
The New Legal Skill Is Not Caution. It Is Controlled Adaptability.
One of the strongest themes throughout our conversation was the distinction between pessimism and preparedness.
Carolyn put it bluntly: “Pessimism doesn’t really serve you to achieve things.”
Lawyers still need skepticism. They still need to think through downside scenarios, regulatory exposure, cybersecurity threats, and operational failures. But legal leaders who only operate from fear become blockers instead of strategic advisors.
The real challenge is learning how to combine optimism with disciplined risk analysis.
“I think we have to have a pretty healthy sense of paranoia,” Carolyn explained. “At the same time, when you’re encouraging people to follow a vision, it’s really important to be optimistic about that vision.”
That tension defines modern in-house leadership.
The legal department cannot merely identify risk anymore. It must help organizations move through risk intelligently and quickly.
That requires adaptability. It requires clarity. And increasingly, it requires legal teams to become technologically fluent.
AI Governance Is Becoming a Leadership Problem, Not A Technology Problem
Many discussions about AI governance focus narrowly on compliance frameworks. Carolyn approached it differently.
She framed AI implementation as an organizational leadership challenge.
How do companies move with velocity while still creating guardrails?
How do legal teams guide behavior instead of trying to prohibit technology?
How do organizations distinguish between low-risk automation and high-risk decision-making?
That distinction became particularly important during our discussion about human oversight.
For low-risk processes like self-service NDAs, automation makes complete sense. But for high-risk decisions involving hiring, compliance, or major legal judgment calls, human accountability still matters deeply.
“If the risk is high, you need to make sure you have a human in the loop.”
That sentence sounds obvious until you realize how rapidly organizations are normalizing AI-assisted workflows without fully understanding where assistance ends and autonomous decision-making begins.
Legal departments are now being asked to answer that question in real time.
Contracts Are Absorbing The Anxiety Of The Modern Economy
One of the most interesting moments in our conversation centered on contracts.
Over the past several years, major disruptions have reshaped contractual expectations. COVID changed force majeure clauses. AI is reshaping governance obligations, audit rights, data handling provisions, and liability frameworks.
And geopolitical instability is beginning to influence sovereignty, localization, and control over information flows.
Carolyn sees this clearly.
“We are seeing more of a push towards how do I control that information, how do I bring it back to keep it only in my environment, only in my private cloud, only in my country.”
That trend matters because contracts are often the first operational layer where uncertainty becomes tangible.
Businesses may debate AI strategy in executive meetings, but those fears eventually manifest in vendor agreements, procurement terms, compliance obligations, and data restrictions.
The result is a growing tension inside contracting itself. Companies are trying to protect themselves against future uncertainty that nobody fully understands yet.
“Many companies are saying, I want to be protective against the future.”
That instinct is understandable. It is also producing contractual demands that many counterparties realistically cannot satisfy.
Trust Is Becoming The Competitive Advantage
For all the discussion about AI, risk, governance, and transformation, Carolyn repeatedly returned to one word: trust.
Not efficiency. Not scale. Not automation.
Trust.
“If you start with the premise that we want to be trusted, and then you think about how do you build and retain trust …”
That framing matters because trust changes how legal departments operate internally and externally.
Inside organizations, trust allows legal teams to move faster because business partners believe legal is helping them succeed, not simply blocking exposure.
Externally, trust shapes vendor relationships, negotiations, and long-term commercial durability.
In periods of uncertainty, trust becomes operational infrastructure.
And increasingly, that trust depends on transparency, adaptability, and responsiveness.
The Future In-House Lawyer Looks Different
Toward the end of our conversation, Carolyn described how she would design a legal department today.
One answer stood out immediately: legal operations.
“Legal operations has become a critical part of how we run the legal team.”
That observation reflects a broader reality. The modern legal department is becoming more data-driven, technology-enabled, and operationally integrated than ever before.
The future legal team will not succeed purely through technical legal excellence. It will succeed through systems thinking, process design, technological fluency, and the ability to manage information velocity.
And perhaps most importantly, curiosity.
“I think the more curious you are as a leader, the more you think about what is potentially a better way to do this.”
That may ultimately be the defining trait of resilient legal leaders in the AI era. Not certainty. Not perfection.
Curiosity strong enough to keep adapting.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics.She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.
The post Carolyn Herzog On Why Legal Leaders Need Optimism, Not Certainty appeared first on Above the Law.
