Building a strong working relationship with your boss can be tricky, but the CEO of Amazon says that trying to win them over with constant agreement isn’t the way to do it.
Instead, he argues that real credibility comes from being willing to push back when it matters.
In a YouTube video, Andy Jassy, 58, shared the three qualities he believes consistently earn a manager’s respect.
He said many people misunderstand what it takes to build trust at work, especially when they focus on pleasing a leader rather than engaging honestly.
“I won’t challenge you if you don’t challenge me or this person isn’t trustworthy because they challenged me in a group of people.”
According to Jassy, trust is built by consistently demonstrating three core traits.
“Employees should be honest, authentic, straightforward,” he said, adding that ‘listening intently, but challenging respectfully if you disagree’ is essential for keeping teams aligned and effective.
“If you think we’re doing something wrong for customers of the business, speak up,” he added. “If you own something, and it’s not going well, own it.”
Jassy also emphasized that this isn’t just an employee responsibility. Leaders, he said, need to model the same behavior—especially by being openly willing to critique their own performance, even when it’s uncomfortable.
He noted that how you communicate matters too: if you’re going to challenge someone, it helps to come prepared with facts, data, and clear reasoning that show your concerns are grounded.
To illustrate the point, Jassy recalled an experience from the early 2000s, when he was running Amazon’s marketing team.
During an operating meeting, he presented a 220-slide PowerPoint, but Amazon founder Jeff Bezos repeatedly stopped him—interrupting on 10 different slides—to say the figures were incorrect.
Jassy said he was surprised initially, but quickly understood Bezos was right.
Rather than letting the moment derail him, he chose to acknowledge the mistake, raise his hands, and take responsibility—something he believes strengthened the trust between them.
That approach appeared to serve him well: he later became one of Bezos’ key advisors and eventually took over as CEO in 2020.
Jassy said the trust he gained came from ‘owning it’—being candid about errors, being willing to scrutinize his own work, and then making improvements.
He also pointed to the broader impact of that kind of trust-based culture, suggesting it helps explain how the tech giant grew into a retail force, surpassing Walmart and reaching more than $717 billion in annual sales.
As on 2026, Amazon, which employs 1.5 million people across the globe, was ranked the world’s largest company by revenue.