The Future Of Less Work Why AI Makes Leadership Harder with Dr. Kirsti Samuels
What happens when AI doesn’t just do our work—but starts shaping how we think?
In this episode of The Future of Less Work, host Nirit Cohen sits down with Dr. Kirsti Samuels—founder and CEO of KS Insight and Adjunct Professor at Columbia University—to unpack the overlooked risks AI poses to leadership and culture. From standardized thinking to conflict avoidance, the conversation challenges the idea that AI is an innovation partner—and asks what we lose when tools reward consensus, speed, and surface-level answers.
Drawing on her work with heads of state, rebel leaders, and Fortune 500 executives, Kirsti explains why the best leaders create “pressure cookers” where discomfort leads to insight, and why psychological safety is no longer enough without dissent, disagreement, and deliberate resistance to vanilla answers. Together, they explore how to lead through change, why answers are cheap but good questions are rare, and why the real threat isn’t that AI replaces people—but that it teaches leaders to avoid being human.
If you’ve ever wondered what leadership should look like in an AI-driven world—or what skills organizations must urgently develop—this conversation is your starting point.
Guest Information:
Dr. Kirsti Samuels is the founder and CEO of KS Insight, a leadership and strategy consultancy based in New York City. She is also an Adjunct Professor at Columbia University, where she teaches Leadership and Management in Moments of Adversity and Opportunity to Master’s students at the School of International and Public Affairs.
As an entrepreneur and strategist with 25 years of experience, Kirsti specializes in tackling complex problems with innovative approaches. Her clients have included the President of the Comoros Islands, the leadership of the Sudan People’s Liberation Movement, the U.S. Department of State, the Clinton Global Initiative, the United Nations, the World Bank, the American Hospital Association, and the Broad Institute of Harvard and MIT.
Kirsti holds a Doctorate in Law from Oxford University, a Master’s in Public Administration from the Harvard Kennedy School, and a Bachelor of Science and Law from Sydney University
Links:
Chapters:
00:00 — What Happens When AI Shapes How We Think?
03:10 — Why AI Makes Everything Sound the Same
07:30 — Can Leaders Train AI to Challenge Them?
10:00 — The Real Skill Behind Innovation: Tolerating Discomfort
12:00 — What High-Stakes Leaders Do Differently
14:45 — Leadership Skills for a Volatile AI Era
17:30 — How to Lead Change Without Breaking People
20:00 — Why AI’s Warmth May Weaken Us
22:00 — The Marshmallow Challenge: When Having the Answer Kills Innovation
24:00 — How Social Discomfort Blocks Better Ideas
26:30 — Can We Still Spark Innovation Without Face-to-Face?
29:00 — Building Cultures That Welcome Pushback
31:00 — Why Human Feedback Still Matters More Than AI
33:00 — The Question We Should Be Asking About Leadership
35:00 — The Deeply Human Skills AI Can’t Replace