Self-made billionaire Ray Dalio is the founder and co-Chief Investment Officer of the world's largest hedge fund, Bridgewater Associates, which manages about $150 billion.
Consider this email that a colleague sent to Dalio after a meeting with an important potential client:
Ray — you deserve a "D-" for your performance today … you rambled for 50 minutes … It was obvious to all of us that you did not prepare at all because there is no way you could have and been that disorganized at the outset if you had prepared … today was really bad … we can't let this happen again.
"At a typical company, sending an email this critical of a boss would be career suicide," writes Grant, who interviewed Dalio, among other highly successful non-conformists for his book. But at Bridgewater, employees are expected to critique each other and are evaluated on whether they speak up.
In fact, "they can be fired for failing to challenge the status quo," Grant notes.
It's an expectation that is set from day one, Grant says: "During training, when employees learn the principles, they're constantly asked: Do you agree?"
Ultimately, Dalio wants employees who will think for themselves and challenge standards when necessary. "Don't let 'loyalty' stand in the way of truth and openness," the billionaire writes in Bridgewater's principles. "No one has the right to hold a critical opinion without speaking up about it."