Leadership: 'Lead with Empathy' Experiment

Michael Rispoli, a CTO and co-founder of the New York product studio Cause of a Kind, posted a simple leadership prompt on X: start with the question “how would I like to be led?” Then act from there. The point was not softness for its own sake. It was speed. He argued that teams move faster when leaders stop performing certainty and start making it easier for people to learn in public. That idea lands because it cuts against one of tech’s oldest habits. Managers are often expected to sound like the person with the map, even when the ground is shifting under everyone’s feet. Rispoli’s experiment rejects that pose. On his own site, he describes a career that spans product, design, and engineering, and a role that includes serving as a fractional CTO and CPO. In earlier writing, he has returned to the same theme from different angles: shared context beats top-down guesswork, and habits beat heroics. That gives the post more weight than a stray bit of social-media wisdom. You can see the pattern in how he has described running software teams. In a 2022 essay on delivery problems, Rispoli wrote that his agency had to stop looking for perfect experts and instead build “great habits” that let ordinary teams improve through iteration. He said the real shift came when they stopped treating projects like fixed blueprints and started treating them as journeys with clients. That meant shorter loops, more feedback, and less pretending that anyone could foresee everything at the start. The same logic shows up in his writing about code review. He argued that reviews were not most valuable as bug hunts. Tests and QA should do that work. The deeper value was organizational learning. Reviews helped people see how other engineers thought, where they were stuck, and what the team was actually building. That is an empathy argument in disguise. It treats feedback as a way to understand another person’s context, not just a way to correct them. He pushed the idea further in another essay about developers and business context. There, the problem was not incompetence. It was blindness. Engineers were being asked to build from polished designs without understanding the business behind them. Once his team began using story mapping earlier in the process, developers, designers, and stakeholders could make tradeoffs together instead of lobbing revisions back and forth. Empathy, in this frame, is not emotional ornament. It is a method for reducing wasted motion. Research has been catching up to that intuition. A 2025 systematic review in *Management Review Quarterly* examined 42 studies on empathy in leadership and found effects across performance, well-being, interpersonal relationships, attitudes, and leadership practice. That does not mean empathy is magic. The literature on leadership is full of fuzzy claims. But it does mean the basic premise of Rispoli’s post is sturdier than it first appears. Empathy is not the opposite of execution. In many settings, it is part of execution. That is why the most interesting line in the post is not the call to be kind. It is the refusal to fake expertise. Plenty of managers know how to sound decisive. Fewer know how to say, in effect, I may not have the answer, but I can help create the conditions where the team finds it faster. Rispoli has been writing versions of that lesson for years. This time he compressed it into a leadership experiment small enough to fit inside a single question: how would I like to be led?