Caroline Webb is a leadership coach, economist, and author of How to Have a Good Day and the forthcoming Leadership Intelligence. She has been named one of the top fifty executive coaches in the world by Thinkers50, and one of the top fifty leadership and management thinkers by Inc. magazine. She is a senior advisor to McKinsey & Company, where she was previously a partner. Her work has been featured in The Wall Street Journal, The New York Times, Harvard Business Review, Financial Times, The Economist, The Guardian, and Fortune. She lives in New York.
Her new book, Leadership Intelligence, distills decades of research across neuroscience, psychology, and behavioral economics into practical tools for making better decisions, motivating teams, and navigating difficult moments.
As AI becomes increasingly capable, Caroline argues that the leadership advantage will not come from competing with machines. It will come from understanding what humans uniquely bring to the table — and knowing how to bring out the best in that intelligence. “The best leaders, I think, are going to be those who understand how to make the most of human intelligence alongside AI,” she said.
At the heart of Caroline’s approach are three capabilities: deliberate wisdom, intrinsic inspiration, and reasoned resilience. Together, they offer a practical framework for thinking more clearly, helping people perform at their best, and navigating the inevitable challenges of leadership.
One of the biggest challenges facing leaders is not a lack of information. It is that our brains simply cannot process everything in front of us. Caroline demonstrated this with a simple exercise: participants were shown an image for five seconds and asked to count the circles. Most people were confident in their answers. But when she asked how many triangles they had seen, confidence quickly disappeared.
The exercise illustrated a fundamental truth about attention: we don't see everything we are looking at. Our brains are constantly filtering information, deciding what deserves our attention and what can be ignored. And that filtering is influenced by what is already on our minds.
Caroline calls this the “top of mind effect.” If you enter a meeting already convinced that you know what the problem is, you are more likely to notice information that confirms your assumption. If you are worried about a particular issue, your attention will naturally gravitate toward evidence related to it. The result is that leaders can miss important information without ever realizing they are missing it.
The antidote is to become more intentional about directing attention. Before an important conversation or decision, Caroline recommends asking yourself: What am I missing? What would be a different way of seeing this? These questions create an opportunity to step outside the mental frame you have already created and consider what else might be true.
This becomes even more important when leaders are overloaded. Constant notifications, multitasking, and the pressure to remain perpetually available all consume cognitive capacity. Caroline shared the example of a CEO who was spending much of her day monitoring Slack, believing that staying constantly connected would make her more effective. Instead, it was leaving her frazzled and making it harder to think. By limiting Slack to specific times rather than remaining in a constant stream of messages, she created more space for deeper work.
The broader lesson is one Caroline returns to repeatedly: widen your perspective where it matters, and lighten the cognitive load everywhere else.
Caroline's second capability, intrinsic inspiration, is rooted in a deceptively simple question: what makes people want to do their best work?
During the session, Caroline demonstrated the power of belonging through a game of catch. Participants were assigned to one of three players, but one player was repeatedly left out. Those assigned to that player quickly experienced feelings of frustration and exclusion. The exercise was a reminder that the brain's reward system responds not only to external incentives, but to our fundamental psychological needs.
At work, we often think about motivation in terms of compensation, bonuses, and promotions. Those things matter, but they are not the whole story. Caroline identified two powerful sources of intrinsic motivation: competence and connection.
Competence is the feeling that I am capable. It comes from learning, improving, mastering something, and having enough autonomy to exercise your abilities. Micromanagement can undermine that feeling by communicating, intentionally or not, that someone else doesn't trust you to do the job yourself.
Connection is the feeling that I matter. It comes from being useful to others, feeling respected and included, understanding the impact of your work, and feeling part of something larger than yourself.
For leaders, creating these conditions does not require grand gestures. It can be as simple as recognizing someone's contribution, giving feedback that emphasizes learning and growth, or helping an employee see the impact their work is having. Caroline also encouraged leaders to resist the instinct to immediately solve every problem brought to them. Instead of saying, “Here's what you should do,” ask, “How are you thinking about this?” or “What have you tried so far?”
That small change gives people the opportunity to develop their own judgment and reinforces their sense of competence. At the same time, creating opportunities for people to build relationships, share stories, and understand one another strengthens connection. The result is not simply a happier team. These psychological conditions are directly connected to motivation, engagement, and performance.
The third capability, reasoned resilience, is about understanding what happens when people are under stress — and using that understanding to help them move through it.
Caroline illustrated this with a familiar scenario: a delayed flight. Seeing the word “Delayed” on an airport board immediately creates uncertainty and frustration. But if the board then tells you that your flight will leave at 12:30, the situation becomes more manageable because you have information and can make a plan. If someone then explains that bad weather caused the delay and acknowledges the inconvenience, the experience becomes more human.
The flight hasn't changed. What has changed is how much control, clarity, and connection you feel.
Caroline explained that negative stress tends to emerge when a situation feels demanding, uncontrollable, and unpleasant. Under threat, the brain becomes more vigilant and focused on immediate concerns, while our capacity for careful, reflective thinking decreases. That means that when people are under significant pressure, they can actually become less capable of the creative and thoughtful problem-solving that leaders need from them.
The goal, therefore, is not to pretend that difficult situations are easy. It is to reduce the sense of threat wherever possible. Leaders can provide information, clarify what is happening, help people identify what they can control, and create plans for different scenarios. They can also reconnect people with purpose and create moments of warmth and camaraderie.
Sometimes resilience is not about removing the difficult experience. It is about making people feel more capable of navigating it.
These ideas become especially relevant as AI changes the way leaders and organizations work. Caroline is not advocating for leaders to step away from AI. Instead, she believes we need to become more intentional about where humans enter the process.
One of the most important human capabilities is the ability to make a decision when there is no obvious right answer — and to take responsibility for that decision. That is where Caroline's approach to AI comes in: keep humans in the first mile and the last mile.
Before turning to AI, do some of the thinking yourself. Define the problem. Decide what matters. Establish your criteria for success. This protects what Caroline calls intellectual sovereignty and prevents AI's first answer from becoming an anchor for your own thinking.
From there, AI can be incredibly useful. Use it to research, challenge assumptions, test ideas, identify holes, and surface perspectives you might not have considered. Caroline's favorite application is to give AI something she has already written or thought through and ask it to critique her: Where am I wrong? What are the holes? How could I make this stronger?
Then take the thinking back.
The point isn't to use AI less. It is to use it in a way that makes human judgment stronger. In fact, one of the most valuable questions to ask AI may be the same question Caroline recommends asking ourselves: What am I missing?
That instinct — to stay curious rather than assume you already have the answer — also sits at the center of psychological safety.
Caroline pointed to the work of thinkers including Daniel Kahneman and Amy Edmondson, emphasizing that leaders cannot make good decisions if people are afraid to tell them what is actually happening. Simply telling a team that you have an “open door” is not necessarily enough. People may still hesitate to tell their boss that something isn't working.
The leader has to demonstrate that they genuinely want to know.
That starts with asking better questions. Instead of “Any concerns?” Caroline suggests questions like “Tell me what you think is really going on here,” or “What's going better than anyone realizes that we should know about?” Instead of immediately offering a solution, ask, “What's your hypothesis on what's driving that?”
These questions create space for people to think, rather than simply waiting for the leader to tell them what to do.
That can be particularly challenging for experienced leaders. Pattern recognition and decisiveness are valuable leadership skills, but they can also become liabilities when they cause us to jump to conclusions too quickly. Sometimes the most effective thing a leader can do is pause long enough to hear what someone else is seeing.
For Caroline, leadership intelligence also means being deliberate about where you spend your time.
Her framework is simple: Yes, Grow, No.
Start with “yes”: the things you are uniquely positioned to do. Ask yourself, If nobody else does this, what happens? and What will I be proud of accomplishing a year or five years from now? These questions help separate the work that truly requires your attention from everything that simply happens to land in front of you.
Then comes “grow.” Leaders often hold onto tasks because they can do them faster themselves. But doing so can prevent other people from developing. Delegating well means creating opportunities for others to build capability and judgment, even when it may initially take longer.
And then there is “no.”
Caroline shared a framework for what she calls the positive no: begin with warmth and appreciation, lead with the positive priority behind the decision, give a clear no, and end with warmth again. Saying no is not simply about protecting your calendar. It is about protecting the things that matter most.
Caroline's message is ultimately not about choosing humans over AI. It is about understanding how the two can work together — and recognizing that the more capable AI becomes, the more important human intelligence becomes, too.
The leaders of the future will need to know how to see what others miss, make thoughtful choices under uncertainty, create the conditions for people to do their best work, and help teams navigate difficult moments without losing sight of purpose.
They will need to think from first principles, challenge their own assumptions, ask better questions, and create enough space for other people to think.
Most importantly, they will need to understand that leadership is not simply about having the answers. It is about creating the conditions for better answers to emerge.
As Caroline put it, “We need leaders who know how to think things through from first principles and know how to check perspectives and not fall into thinking traps.”
In an age of increasingly powerful AI, that may be the new leadership edge: not knowing more than the machine, but knowing how to make the most of the intelligence in the room.
