At AI Speed, Can Positive Leaders Still Lead with Heart?

At some point in the last few years, most leaders have asked themselves a version of the same question: Am I still the one making the decisions, or am I just approving what the machine already chose?

Few people are better placed to address it than Jean-Philippe Courtois. With over 40 years at Microsoft, leading global sales and operations across 124 countries, he was at the helm when Satya Nadella transformed the company from a 'know-it-all' into a 'learn-it-all' culture – a shift that took cloud revenue from 0.5% to nearly 50% of total turnover. Today, through his Positive Leadership podcast and the Live for Good foundation, he champions young social entrepreneurs from underrepresented backgrounds.

In a recent HEC Paris masterclass with Professor Ilona Boniwell, Academic Director of the Global Executive Coaching programs, Courtois laid out what AI exposes in leaders: the traps it sets, the competencies it cannot replace, and what it means to remain genuinely human at the helm when the pace of everything around you has stopped being negotiable.

Courtois describes himself as “a cautious optimist” when it comes to AI. For him, being cautious means recognizing the vulnerabilities that often get overlooked when adopting new technologies. He points out three key traps for leaders.

The first is what he calls the authority trap. Leadership has always had a tendency to gravitate toward certainty: the urge to be the smartest person in the room. AI can amplify this instinct. A leader who relies solely on AI-generated insights risks shutting themselves off from the humility that good judgment demands.

The second trap is more subtle: the trust trap. Every leader operates within a value system, whether it’s explicit or implicit, that influences decision-making when things go awry. The pressing question AI raises is how much of that system can be handed off. An AI model can be trained on a company’s principles, but it can’t replace the leader who embodies those principles when they’re being challenged from all sides.

The third vulnerability is what Courtois calls the empathy deficit. He believes that empathy isn’t just a trait we possess; it’s something we actively practice.  

The trend he observes is reminiscent of what we've seen with social media: while our consumption increases, our innate ability to connect with others seems to quietly diminish. For leaders who are not only managing individual relationships but also shaping the emotional atmosphere of entire organizations, this decline can have significant consequences, both ethically and relationally.

In Silicon Valley, the people working on AI don’t stick to the typical quarterly schedules or product timelines. “They’re all about what’s being developed and launched as a new AI product in the coming week,” Courtois points out. The pace of it all, as he describes, is “out of this world.” This is a huge cognitive challenge for leaders.

To understand what’s at stake here, let's look at Daniel Kahneman's framework, which distinguishes between fast thinking and slow thinking. System one is all about pattern recognition: it’s automatic, efficient, and reliable for the countless decisions we make daily, like brushing our teeth, driving, or navigating familiar situations. 

But then there’s system two, which is a different beast altogether. It’s slow, deliberate, and requires effort. This is where critical thinking happens, where we weigh our experiences and make ethical judgments. And here, speed is a risk.

As an example, Courtois references a war game simulation he came across in one of Reid Hoffman's podcasts – founder of LinkedIn and a well-known Silicon Valley investor. The scenario involves a large-scale AI simulation based on historical nuclear crises, including real-life instances in which human commanders chose to step back from the brink. In one notable case, a Soviet officer, interpreting signals that suggested an incoming US strike, decided against retaliation. His reasoning stemmed from a profound understanding of the other side’s mindset and what they would or wouldn’t do. He believed it couldn’t be true, and he was right. However, when researchers fed the same scenario into an AI system, it opted to launch an attack.

The responsibility of leadership, then, is to sort things out. To know exactly which decisions fall under system one, where AI can speed things up without any drawbacks, and which ones belong to system two, where relying on machines is more about shirking responsibility than being efficient. 

Back in 2014, Microsoft was riding high financially but felt a bit lost strategically. They had missed the boat on smartphones, tablets, and were late to the cloud party. When Satya Nadella stepped in as the company's third CEO, he realized the real issue was the culture: how people thought, collaborated, and embraced new ideas.

However, just rolling out a new mission statement doesn’t magically change how 120,000 employees act in meetings. Nadella and his leadership team accurately labeled the old Microsoft culture as “know-it-all.” Engineers and executives would stroll into meetings eager to showcase what they already knew rather than explore what they didn’t. Meetings were more about impressing others than learning. Feedback was seen as a threat rather than a chance to grow. 

To shift this mindset, they needed to dig deeper than just tweaking processes or strategies. Carol Dweck's work on growth mindset (psychologist and author of Mindset) became essential reading for the senior leadership team, while a session with Brené Brown (researcher and author known for her work on vulnerability and courage) pushed each executive to confront a deeper question: why are you here, and what choices have you made about your role? 

Courtois had the important job of turning that cultural vision into a tangible reality, leading a salesforce of 35,000 people across various subsidiaries from Japan to Mexico to Kuwait. His approach was refreshingly straightforward: “If I want to change the mindset of 35,000 people, I've got to start with myself.” So, he retrained as a coach and then went on to train his 3,500 managers to adopt the same mindset. His methodology was built on three key principles, each one flipping the script on how high-performing corporate cultures usually function.

The first principle is curiosity, treated as a discipline. “You need to peel the onion”, Courtois explains. Simply asking someone what their problem is and jumping straight to a solution isn’t true management. Genuine curiosity involves lingering in the question long enough to grasp what’s really going on, beyond just the numbers on a scorecard or the issues on the agenda.

The second principle, being lazy, is about not rushing in to solve your team’s problems. The urge to step in, fix things, and move on can feel rewarding. It boosts your sense of competence and creates momentum, but it also stifles growth. A manager who solves every issue becomes a bottleneck, while one who digs deeper with questions allows their team to discover their own solutions, fostering scalability.

The third aspect is ritualization. Coaching should flow naturally, woven into the everyday fabric of work life, sparked by genuine moments instead of just scheduled times.

This shift was reflected in the structural swap of “business reviews” for what Courtois calls “business connects.” Business reviews were all about scrutiny: going through numbers line by line that everyone already had, justifying positions, and clarifying discrepancies. In contrast, business connects focused on collective learning: what insights does the top-performing market have that others might be missing? What’s the story behind the results, not just the numbers themselves? “We transitioned from inspection to insights,” he notes.

The commercial results are now a matter of public record. Back in 2014, Microsoft's cloud revenue was just 0.5% of total revenue. Fast forward to 2024, and it’s nearing 50%, which is about $120 billion. Courtois is careful not to attribute a decade of transformation to a single factor. However, he’s clear about what fueled the change on a human level: 35,000 individuals adapting their work styles because 3,500 managers first learned to lead in a new way.

It's tough to predict where AI will be in a decade, and Courtois is the first to admit that. However, he’s ready to tackle what leadership will demand in that future, highlighting four key skills he believes no machine can replicate.

First up is self-awareness.

He views self-awareness as an active, relational process: being curious about your actions, genuinely seeking feedback from others, and being open to discovering uncomfortable truths about yourself.

Next is critical thinking. Courtois makes an important distinction here. Critical thinking isn’t a binary trait you either possess or lack; it’s a skill that needs to be taught, learned and practiced. The ability to assess AI-generated content, challenge seemingly credible frameworks, and inquire about what’s missing instead of just accepting what’s given. These are skills that must be cultivated.

The third competency is rooted in Daniel Goleman's (psychologist and author of Emotional Intelligence) insights. Goleman identifies three types of empathy: cognitive empathy, which involves grasping what someone is saying; emotional empathy, where you actually feel what they’re going through; and empathetic concern, which is the genuine desire to help. It’s this third type, going beyond just understanding and feeling to actually caring enough to take action. “As a leader, you really need to cultivate this more than ever”, he emphasizes, “because it’s not just about one-on-one interactions; it’s about one-to-many.” 

This “one-to-many” dynamic is about to become much more intricate. With AI agents entering the workforce, future leaders will need to manage a hybrid team of humans and machines working side by side. They’ll also be responsible for shaping the overall atmosphere that arises from this blend. The emotional weight of this challenge is something we haven’t seen before in management discussions.

The fourth competency revolves around trust. Specifically, Courtois refers to the trust architecture that a leader constructs and nurtures over time. This is not about being likeable or consistent in calm waters, but rather how a leader behaves when the system is genuinely under pressure. When results don’t meet expectations, when errors occur, and when tough choices must be made.

There’s one more signal that Courtois highlights, which is a bit trickier to measure but definitely can’t be overlooked. It’s all about the kind of energy a leader gives off. “You know those people you leave a meeting with feeling totally energized, pumped up, and excited?” he explains. “Then there are others who just drain your energy, leaving you feeling toxic”. As we navigate a more hybrid work environment, where face-to-face interactions are less frequent and often more structured than before, this exchange of energy (or the lack thereof) becomes even more significant. It might just be the clearest indicator of whether genuine positive leadership is taking place.

For the last decade, Courtois has been balancing his corporate advisory role with running Live for Good, an NGO he started with his family. This organization is all about empowering young people from diverse backgrounds to create social enterprises that tackle real-world issues. We're talking about everything from environmental degradation and the circular economy to sexual harassment and access to education and healthcare. Each nine-month cohort revolves around one pivotal question: why are you here, and what do you want to achieve in life? What Courtois sees in these young entrepreneurs is something that many seasoned executives seem to have lost along the way.

First off, they possess a clear and personal “why.” Every project in the Live for Good program kicks off with a story, often a formative experience that makes a specific problem feel urgent and personal. “They all have a story, and that story is actually determining in a sense that they picked a project, a social cause, because of who they are and what they've gone through”, Courtois explains.

Secondly, there's an unwavering focus on impact. These young founders aren't just aiming for an exit; they're striving for tangible results: tons of plastic recycled, hundreds of people with disabilities employed, communities uplifted. “Their mantra is to have the biggest impact”, Courtois notes. While the economic model needs to be viable, it’s all in service of something much bigger. “I would tell you I find it actually harder and more exciting to work on such issues because you have to harmonize the economic model with social and environmental results”, he reflects.

Third is community. The one that’s tight-knit, aligned in values, and built to last. Even years after their program wraps up, the alumni of Live for Good stay connected, support one another, and collaborate on new ventures. They are not networking in a transactional way, but building a true community, where people share a common mission and hold each other accountable.

Finally, when Ilona Boniwell asks Courtois to sum up four decades of leadership, 130 podcast chats, and ten years of mentoring young social entrepreneurs into one piece of advice for those feeling overwhelmed by today’s complexities, his response bridges both worlds. 

This doesn’t just mean starting a business. It’s about taking ownership of your life. So, can positive leaders still lead with heart at AI speed? Courtois's answer is yes, but with a condition. You can lead with heart at AI speed, but it is going to take treating heart as something you build, not something you have. The curiosity to know yourself. The ability to think slowly when the world is compelling you to decide fast. A willingness to remain present with people when it would be easier for you if a tool could do it instead. None of that is natural. All of it is learnable.

“Your health and your time are your most valuable resources”, Courtois concludes. “How will you use them?” In a world where so much can be delegated, automated, or sped up with AI, deciding what you won’t relinquish – your purpose, your values, your presence – might just be the most significant act of leadership there is.