Some conversations stay with you. This was one of them.

Kirsti Samuels is a leadership strategist, founder and CEO of KS Insight, and an adjunct professor at Columbia University’s School of International and Public Affairs, where she teaches leadership in some of its most demanding forms. She holds a doctorate in law from Oxford, a master’s from the Harvard Kennedy School, and has spent over 25 years working with executive teams, senior country leadership, and yes, armed rebel groups.

She also launched the Women Igniting Leadership Lab (WILL) the year she turned 51 — after catching herself, credentials and all, still waiting for permission she never needed.

We went well over time. I’m not sorry.

“We are so entrenched in our lived experience as humans that it’s very hard for us to see ourselves. It’s just really hard.”

Watch the Replay above. Here is a small clip

What This Conversation Is About

Kirsti Samuels brings the kind of depth you rarely encounter in a 45-minute conversation. A leadership strategist with over 25 years working in some of the most high-stakes environments imaginable — including active conflict zones — she has spent her career studying a deceptively simple question: can leadership actually be learned?

The answer, she’s found, is yes. But only if you stop waiting for someone to give you permission.

That realization hit her personally at 51, when she caught herself — a woman with every credential imaginable — still waiting for someone to greenlight the women’s leadership program she’d been advocating for inside corporations for years. That clarity sparked WILL, built on the premise that women leaders can’t afford to learn leadership by fumbling through it in real time. The system judges them too harshly for that. Instead, WILL creates a safe but intense training space — the flight hours before the flight.

The conversation moved between Kirsti’s personal leadership journey, including a candid account of her first leadership role being a genuine disaster, the two-bucket framework she uses — diagnostic skills and self-management skills — and how she’s now integrating AI into leadership training. Not as a shortcut, but as a practice partner. She’s built custom, principle-driven AI tools that let leaders run difficult scenarios repeatedly, get debriefs, and retrain ingrained behavioral patterns between lab sessions.

She and I found deep alignment on what AI should and shouldn’t be: not faster and cheaper, but deeper and better.

“You cannot hope women who haven’t had the flight hours are going to be able to learn on the job in the same way... the system judges you really harshly.”

Three Things Worth Listening For

Why the lab exists — and why “winging it” isn’t an option for women leaders Kirsti made a point that landed hard: women in leadership roles cannot afford the learning curve that comes with being thrown in and figuring it out. The system watches more closely, judges more harshly, and gives less room to recover. WILL was built to solve for that — creating the equivalent of flight simulator hours so leaders arrive at high-stakes moments already trained, not hoping instinct kicks in.

The moment her own tool turned the mirror on her One of the most disarming moments in this conversation came when Kirsti described taking the pattern-recognition diagnostic she’d helped design — and discovering it reflected back something she hadn’t seen in herself. Despite her extraordinary career, she still hesitated to use her authority in moments that might upset others. She traced it to a single interaction in her 30s when a senior leader pulled her aside after a meeting and told her that speaking up had been inappropriate. That one moment shaped how she showed up as a leader for two decades. It’s exactly why she does this work.

AI as practice partner, not shortcut Kirsti’s perspective on AI in leadership development is one of the most sophisticated you’ll hear. She’s not anti-AI — she’s built custom tools with 50 pages of guiding principles to create structured, scenario-based practice for WILL participants. But she’s pointed in her critique of how most people are using it: asking how to do things faster and cheaper instead of how to do them better and deeper.

About Kirsti

Kirsti Samuels is the founder and CEO of KS Insight, a leadership and strategy consultancy based in New York City. She also served as the Executive Director of the Adaptive Leadership Network in its start-up years, and is an Adjunct Professor at Columbia University, where she teaches Leadership in Action, Leading and Managing in Moments of Adversity and Opportunity, and Managing Yourself as a Leader: Skills and Practices for High Stakes Moments to Master’s students at the School of International and Public Affairs. Kirsti specialized in tackling complex problems with innovative approaches, and her work has spanned executive teams, senior country leadership, and even armed rebel groups. 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.

Connect with Kirsti

Have a question for Kirsti? Drop it in the comments — I’ll make sure she sees it. And come back next Wednesday at noon ET, we have interviews booked months in advance.

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The Real 50 over 50-Meet Kirsti Samuels