The world's most successful investor insists on brutal honesty from employees. Could you survive?

A few days before our interview, Ray Dalio’s team said Ray would like to talk. While I’m happy to meet before an interview, the Influencers usually don’t request a pre-brief. These are professionals who are supremely confident in their ability to manage any situation. But it wasn’t a problem; a typical pre-brief is short and glossy — a discussion of the topics and a review of logistics.

This call didn’t go quite so smoothly.

“I don’t think you’re very well prepared,” Dalio told me. I put the phone on mute and turned to my colleague to ask if I’d heard what I thought I’d heard.

Dalio and I had been talking for only a few minutes and I’d barely covered the first of the topics I was hoping to discuss about his company’s unique culture. Dalio founded and is co-CEO of the largest hedge fund firm in the world, Bridgewater Associates, with $152 billion under management. Since starting the firm in 1975, Dalio has returned more money to investors — $45 billion in gains, according to one estimate — than any other manager in hedge fund history, topping even George Soros.

But in the finance world, Bridgewater, based in Westport, Conn., is known as much for its remarkable track record as the remarkably unusual way it runs itself. The firm's 1,500 employees have committed themselves to a doctrine of radical transparency and brutal honesty. Nearly every meeting large or small is taped and anyone relevant to the discussion is allowed to go back and watch the meeting. Confrontation and open debates are mandatory and hard-edged. James Comey, the head of the FBI who was formerly Bridgewater's general counsel, said that getting "probed" — or questioned — at Bridgewater was harder than arguing in front of the Supreme Court or briefing the President.

While modern management thinking argues that it’s best to focus on building your strengths, Dalio preaches the opposite. Employees must write down their weaknesses and the weaknesses of others — and then be logical and unemotional as they get mercilessly critiqued by colleagues.

“Identifying who made mistakes is essential to learning. It is also a test of whether a person will put improvement ahead of ego and whether he will fit into the Bridgewater culture,” Dalio writes in the 106-page culture bible provided to recruits and employees. It’s called simply Principles. “A common error is to say, ‘We didn’t handle this well,’ rather than, ‘Harry didn’t handle this well.’ This occurs when people are uncomfortable connecting specific mistakes to specific people because of ego sensitivities. This creates dysfunctional and dishonest organizations.” In another section, he offers this simple formula:

Pain + Reflection = Progress.

Not surprisingly, about 35% of new hires quit or are let go within their first 18 months. Those who stick around are said to have “made it through to the other side.” Getting to the other side often comes with the realization that you can never work at another company because you can never operate somewhere where you can’t be completely honest. You are free, says Dalio, to stop pretending.

When I talked to Dalio on the phone that first time, I wasn’t through to the other side yet. Heck, I wasn’t even looking toward the light. My goal was to assuage any concerns he and his team had and get back to work. But Dalio wasn’t interested in a get-to-know-you. He told me that it was clear I hadn’t read an essential Harvard Business Review article about his company or watched his 2014 interview with the New York Times’ Andrew Ross Sorkin. Not doing so meant I was wasting his time, mine and the time of readers/viewers/the crew, etc. He said the only reason he was sitting down with LinkedIn was because he was 66 and felt an urgency to pass on his cultural learnings to the business world. He also told me that a few of my general questions were terrible.

The call was my first taste of Bridgewater total honesty. I wish I could say that I followed Dalio’s Principles and reveled in the rich understanding coming from being in a “position of pain.” Nope. Not at all. I was pissed. This call wasn’t supposed to be a quiz, it was supposed to be a ground setter. My research would be done and my questions honed before the interview started; no one had ever doubted my preparation before. Who was this guy?

“You can convert the 'pain' of seeing your mistakes and weaknesses into pleasure,” Dalio writes.“Embracing your failures is the first step toward genuine improvement; it is also why 'confession' precedes forgiveness in many societies.”

A few hours later, I started to process the meeting a little bit differently. I realized that Dalio had provided me a gift. He had opened the doors to the kind of discussion that might put others ill-at-ease. In most interviews, you want to walk a fine line: pressing but not hammering; asking but not attacking. Dalio demanded honesty of himself just as much as of those around him. He had opened the door to an interview where we could skip the niceties and get right to the tough questions.

And I had plenty. Even after doing all of the research and talking with people who had been recruited by Bridgewater, I had real doubt about his belief that his principles were evolutionary — that we’d all be working like Bridgewater some day.

Didn’t a culture that accepted double-digit attrition mean that some of the best minds weren’t weighing in with investing ideas simply because they couldn't make the cultural leap? Why weren't other investment firms copying him, if his success was a result of the culture? Dalio is halfway through a 10-year transition plan that has played out partially in the press, with a co-CEO losing his title and a new co-CEO, former Apple exec Jon Rubinstein, about to join. How would he handle it if Rubinstein, a Steve Jobs acolyte, couldn't cope? But even more generally: In a workplace that demands conflict, how do you make room for introverts or people for whom English isn't a first language? How do you accept grey areas, where there is no one right answer? And is radical honesty from the start such a great thing when opinions and ideas often take time to form? 

True to his beliefs, Dalio didn't try to sidestep any of the questions. The video above is 10 minutes of our nearly 40-minute talk. By the end, after some great sparring, I felt like I got a glimpse of life on the “other side.” There's something to be said for the Bridgewater world.

But if we're going to be honest, brutally honest, here? I could never work in it.

Read Ray Dalio's piece here.