Senior Leadership Workshop on Dragonfly Thinking: Institutional Strategies for Balancing Risks, Rewards, and Resiliency in a VUCA World

Insight April 16, 2024

On April 2, 2024, the Center on the Legal Profession hosted an invitation-only, Senior Leadership Workshop, “Dragonfly Thinking: Institutional Strategies for Balancing Risks, Rewards, and Resiliency in a VUCA World” at Harvard Law School. This workshop examined one of the most important questions facing every organization today: how to deal with challenges such as ESG, geopolitical risk, and the use and misuse of AI and other similar technologies in a world that is increasingly VUCA (volatile, uncertain, complex, and ambiguous).

The workshop was co-led by Professor David B. Wilkins, faculty director of the Center on the Legal Profession, and Anthea Roberts, professor at the School of Regulation and Global Governance at the Australian National University (ANU) and a visiting professor at Harvard Law School. Attendees included the chief legal officers/general counsel of leading companies, including Blackstone, Thermofisher Scientific, AIG, Citizens Bank, Vanguard, BlackRock, eBay, Cummings, Wayfair, Bridgewater, Maersk, IAC as well as the managing partners of major law firms, such as Morgan Lewis, Orrick, McGuireWoods, Holland & Knight, and Vinge.

After an introduction from Professor Wilkins on why VUCA issues are increasingly landing on the desks of lawyers, Professor Roberts lead participants through an interactive discussion on how to operationalize an analytical method—a mindset—that she has developed to help make sense of complex decision making: what she calls a Risks, Rewards, and Resiliency (Triple R) Framework. Drawing on her extensive experience working with the Australian government, NGOs, and business leaders, the Triple R Framework, she says, can help individuals map complex problems in a VUCA landscape. While identifying risks and rewards alone is common in business and policymaking, Professor Roberts challenged participants to add a third lens—resilience—to help break out of binary thinking. (You can read more on the framework from a 2023 Foreign Affairs article by Professor Roberts, entitled “From Risk to Resilience”). Additionally, taking lessons from psychology, economics, law, and international relations, Professor Roberts illustrated the linkages between the framework and the need for what she calls “dragonfly thinking.” Drawing inspiration from the unique visual strategies of dragonflies, Roberts explained that “Dragonfly Thinking™ involves synthesizing a multitude of points, counterpoints, and counter-counterpoints so that the integrated whole is more valuable than the sum of its parts.”

In the second half of the workshop, Professor Roberts demoed how the Triple R Framework and Dragonfly Thinking might be supplemented with new AI tools. She noted during the workshop, because complexity often means defaulting back to one’s preexisting, narrow methodologies, AI allows humans to more easily maintain a dragonfly mindset and integrate and hold more perspectives in tension at once. Deploying a number of case studies (ranging from starting a blueberry farm to opening significant new operations in China) Professor Roberts demonstrated how the Triple R framework, combined with AI, can provide a user-friendly model for thinking through complex decision points, whether at the individual, organizational, national, or global level.

Following the workshop, participants took part in the Center’s 2024 Annual Awards Dinner with a theme of Complex Decision Marking in a VUCA World. At the dinner, the Center was proud to present Anne-Marie Slaughter, CEO of New America, with its Award for Global Leadership.

All photos by Martha Stewart.