Most people assume the fastest route to winning their manager’s favor involves a combination of enthusiasm, agreement, and a willingness to never push back. Amazon CEO Andy Jassy says that approach is not only wrong but actually counterproductive. According to Jassy, who has led the company since 2021, the habit of constantly nodding along and telling leadership what they want to hear is a skill that many workers fundamentally misunderstand, and one that quietly works against them over time. Real trust, he argues, is built through a very different set of behaviors.
Jassy has identified three qualities he believes are essential for any employee who wants to earn genuine respect from those above them: honesty, authenticity, and directness. The way he frames it, building a strong and cohesive team depends on people’s willingness to truly listen to one another while also being comfortable enough to respectfully push back when they disagree. “Employees should be honest, authentic, and direct,” he said, adding that the ability to challenge ideas with care and reasoning is not a threat to team dynamics but a foundation of them.
The willingness to speak up extends beyond disagreements on strategy. Jassy has been emphatic that employees should feel empowered to raise concerns when they believe something is being done wrong, whether for customers or for the business as a whole. “If you think we’re doing something wrong for customers or for the business, say so,” he said plainly. Equally important to him is how people handle failure. Rather than deflecting or downplaying mistakes, he expects employees to own them directly: “If you’ve taken something on and it’s not going well, take responsibility.” In Jassy’s view, accountability is not a weakness to be avoided but a signal of trustworthiness.
Crucially, Jassy is not placing these expectations solely on employees. He has been equally clear that leaders must hold themselves to the same standard, emphasizing that strong managers need to be “loudly self-critical, even when it’s uncomfortable or embarrassing.” This mirrors one of the more demanding aspects of Amazon’s well-known leadership culture, which has long prized a willingness to surface problems and own failures rather than bury them. Performance also matters enormously in this framework. Jassy stressed that claims and commitments need to be backed up with concrete evidence and data, not just good intentions, as a way of demonstrating that a person’s word can be relied upon.
To illustrate these principles, Jassy reached back to an early career experience that shaped how he thinks about accountability. While leading Amazon’s marketing team in the early 2000s, he was presenting a 220-slide deck during an operational review when company founder Jeff Bezos interrupted him at the tenth slide to point out that his numbers were wrong. Rather than becoming defensive or rattled, Jassy quickly recognized that Bezos was correct. He chose to acknowledge the error immediately and take responsibility for it on the spot — and in doing so, he says he actually gained more credibility with his boss, not less.
That moment proved to be a turning point. Jassy went on to become one of Bezos’s most trusted advisors, and in 2020 Bezos named him as his successor to lead the company. Jassy credits that trajectory directly to the culture of accountability and honest self-criticism he embraced throughout his career at Amazon. The same values that guided him in that early conference room eventually helped steer an organization that, as of 2026, ranks as the largest company in the world by revenue, with annual sales exceeding $717 billion and a global workforce of 1.5 million people.
Amazon’s internal culture has long been studied by business schools and management consultants alike, and its famous 14 Leadership Principles — which Bezos began developing in the 1990s — explicitly include “Are Right, A Lot” and “Have Backbone; Disagree and Commit,” both of which align closely with what Jassy describes. Research in organizational psychology consistently finds that teams with high psychological safety, where members feel comfortable admitting mistakes and challenging each other, outperform those where conformity is rewarded, which gives Jassy’s advice a strong empirical grounding beyond his own experience. It is also worth noting that Bezos himself has said some of his best decisions at Amazon came from employees who pushed back on his instincts.
Do you think more workplaces should actively encourage employees to challenge leadership, or does it depend on the culture? Share your thoughts in the comments.
