Carolyn Herzog, chief legal officer and company secretary at Elastic, is calling on legal leaders to rethink one of their most deeply ingrained professional habits.
Most lawyers are trained to identify risk, anticipate failure, and stress-test every decision before it is made, a disposition that has long defined the profession.
But Herzog believes that in today’s environment of AI disruption, geopolitical instability, and relentless regulatory change, that instinct alone is no longer sufficient for effective leadership.
Speaking on the podcast “Notes to My (Legal) Self,” Herzog argued that what legal leaders need now is what she calls operational optimism, not blind positivity, but a mindset that allows organisations to move through uncertainty rather than freeze inside it.
She was direct about the limitations of a purely defensive outlook, stating: “Pessimism doesn’t really serve you to achieve things.”
That does not mean abandoning rigour or ignoring downside scenarios, and Herzog was clear that a degree of vigilance remains essential for any serious legal leader.
“I think we have to have a pretty healthy sense of paranoia,” she 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 between caution and forward momentum is emerging as one of the central challenges facing in-house legal teams as businesses demand faster, more strategically integrated counsel.
Herzog pointed to generative AI as a particularly sharp example of how the old instinct to pause, assess, and impose hard boundaries has become untenable in practice.
Unlike previous technological shifts that arrived gradually enough for governance structures to keep pace, AI adoption has outrun the ability of most organisations to build frameworks around it.
“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,” Herzog said, describing the change in approach.
Boards are demanding AI strategy, employees are already experimenting with the tools, and regulators are still working out their own positions, leaving legal departments caught in a rapidly moving current.
The implication is significant: controlled adaptability, rather than caution, is now the skill that separates effective legal leaders from those who inadvertently become blockers to their own organisations.
Herzog also addressed how she would structure a legal department built for this environment, pointing immediately to legal operations as a critical and often underestimated function.
“Legal operations has become a critical part of how we run the legal team,” she said, reflecting a wider industry shift toward data-driven, technology-enabled legal functions.
The modern in-house team, in her view, will not succeed through technical legal excellence alone but through systems thinking, process design, and the ability to manage high volumes of fast-moving information.
Above all, Herzog identified curiosity as a defining trait of resilient legal leadership, noting: “I think the more curious you are as a leader, the more you think about what is potentially a better way to do this.”
Her message to the legal profession is pointed and timely: the leaders best positioned for what comes next are not those who demand certainty before acting, but those who have learned to lead credibly without it.