Blackstone's Jon Gray is a master of sticking with decisions when the world thinks you're wrong. Here's how he does it.

"You have to stay calm, and you have to recognize these things are cyclical, they're not secular."

When Jon Gray invested an additional $800 million in Hilton Hotels in 2009, it looked to the world like a gambler doubling down on an already bad bet. He'd orchestrated a buyout of the company two years earlier and it was problematic from the beginning. Now the economy was making it worse: The world was still reeling from the financial crisis. Hotel demand had plummeted. Most investors were fleeing real estate.

But Jon had conviction. And, as you can probably guess now that Jon is COO of investing giant Blackstone one and one of the best-known figures on Wall Street, it worked out well. I'll get it into it more below.

But the reason I wanted Jon on This is Working wasn’t to talk about investing advice, but management: With something like Hilton, how do you get people to keep believing in a theory that the world is telling you is a mistake. How do you get signals from your team or from the outside to make the calls that might be counter to conventional wisdom?

As AI and geopolitics upends how we work and how we manage, learning how to clearly see a path in the chaos is going to be a skill everyone needs to hone.

In today’s conversation, Jon talks about how he's built a culture at Blackstone that can separate cyclical noise from secular trends (including why he asks the youngest person in investment meetings to speak up first). He also revealed how leaders unconsciously shape behavior—and why being direct with difficult feedback is actually "throwing [people] a lifeline."

Check out the video for our fascinating conversation about decision-making in uncertainty. Oh, and be sure to follow Jon, whose running videos shot on business trips around the world alone are fun to catch in your feed!

The lobbies are empty, but they won't always be

Blackstone's acquisition of Hilton Hotels remains one of the most instructive deals in private equity history—not because it went smoothly, but because it didn't. When Blackstone committed to buy Hilton for $26 billion in July 2007, they were buying at the absolute peak of the market. By the time they closed in October, the financial crisis was taking down companies and economies.

"We found ourselves highly levered with EBITDA cashflow down 40%," Jon recalls. "We wrote the investment down by almost three quarters on an unrealized basis. So you can imagine the investor meetings I was having at that point."

But rather than cutting losses, Jon and his team made a contrarian bet. In 2009, as the world economy teetered, they made that $800 million re-up. The reasoning? "We fundamentally believe[d] travel was a secular growth industry that a branded hotel company was particularly special. And we separated the noise and we said, look, the downturn in demand for hotel rooms, that's cyclical in nature, that's going to come back."

That decision ultimately generated $14 billion in profits for Blackstone's investors when they took Hilton public and broke it into three companies. More importantly, it crystallized Jon's philosophy about crisis leadership: "You have to stay calm, and you have to recognize these things are cyclical, they're not secular."

When the youngest voice matters

Jon's approach to decision-making reveals something counterintuitive about running a $1.2 trillion asset manager: the best ideas don't always come from the top.

"We'll oftentimes in investment committees ask the youngest person on the deal team, 'Hey, what do you think of that?'" Jon says. "You need people who are challenging the status quo."

This isn't just democratic leadership—it's strategic. In a world changing as rapidly as today's, experience can become a liability if it creates blind spots. "A great investment organization is constantly challenging itself. It doesn't have a view that one person knows best," Jon says. "When the world's changing as fast as it is today, you need people who are challenging the status quo, who are saying, 'I've studied this, and no, no, no, your assumptions are wrong.'"

The key is balancing wisdom with fresh perspective. "Oftentimes older people have more experience. They've seen some things, and that's very valuable, that judgment, because you've been through cycles, you have some pattern recognition. But... if you just have this sort of top down, ‘we know all the answers,’ I think that's very dangerous."

The blue shirt revelation

And sometimes, you don’t even need to verbalize that this is coming top down for people on your teams to feel it. Jon shared a story about realizing the unconscious influence he was having on the org. A colleague once pointed out to him that all the men at Blackstone were wearing blue shirts and blue ties. When she asked if he knew why, Jon realized: "Oh, I guess because I wear blue shirts and blue ties."

The lesson hit him hard: "You begin to realize an organization, they take their cues from the leader."

But the deeper insight here isn't just about influence—it's about authenticity under a microscope. Jon's wardrobe was simply his personal preference. Yet it became the unofficial dress code for an entire organization. This reveals something profound about leadership: There's no such thing as a "private" moment when you're in charge.

"What matters in leadership... you can put up a lot of great slogans on the wall, but it's so often about who you hire, who you promote, and who you fire because that sends a signal. So if you're promoting the brilliant jerk who puts points on the board but treats everybody badly, then that sends a signal to the organization."

It's a reminder that leadership happens in the details—and that every decision, from hiring to what you wear, is being watched and modeled.

The lifeline of direct feedback

Perhaps Jon's most practical leadership insight involves feedback. Too many managers, he believes, avoid difficult conversations to spare feelings—but this actually hurts the people they're trying to protect.

"People would come in and they'd say, 'I've lost my job. I'm in shock.' And I'd say to them, 'Hey, Dan, you were the lowest scored XYZ person for the last three years.' And they'd be like, 'I've no idea. I didn't know.'"

"One of the best things you can do is deliver a tough message to people, and by you being direct, you're actually throwing them a lifeline for them to course correct."

His solution is radically simple: be direct. "One of the best things you can do is deliver a tough message to people, and by you being direct, you're actually throwing them a lifeline for them to course correct."

The key is combining honesty with respect. "You don't have to be difficult. You can say, please and thank you. You can be appreciative of hard work."

There's a lot more in our conversation...

...including why Jon has stayed at Blackstone for 33 years. But one thought to leave you with is the power of conviction, something I've heard from others on Wall Street is one of Jon's greatest strengths.

Jon acknowledged as much. He lives by a simple but difficult principle: "There's a lot of deliberation and work to get to a decision, but once you make a decision, it's total commitment." It's also evident in his advice to young professionals: "If you don't love what you do, I think it's very hard to give 110% to it."

In an era of constant change and uncertainty, Jon's approach offers a template: stay curious, stay calm, and when you find conviction, don't hesitate to act on it.

And be sure to check out the This is Working podcast (Apple | Spotify) for the full conversation!

On LinkedIn’s video series, This is Working, I sit down with top figures from the world of business and beyond to surface what they've learned about solving difficult problems. See more from Ralph Lauren CEO Patrice Louvet, JPMorgan Chase CEO Jamie Dimon, Savannah Bananas owner Jesse Cole, Google CMO Lorraine Twohill, Taco Bell CEO Sean Tresvant, Slutty Vegan founder Pinky Cole, Delta Air Lines CEO Ed Bastian, Cisco CEO Chuck Robbins, Mattel CEO Ynon Kreiz, former US President Barack Obama, filmmaker Spike Lee, Virgin founder Sir Richard Branson, IMF chief Kristalina Georgieva, cosmetics legend Bobbi Brown, F1’s Toto Wolff, and many more.