I've worked with a lot of big egos, narcissists, liars, and people who just take up space the second they enter the room.
They all share one thing in common. They hate being told no, and they hate being told their ideas suck.
And that is where everything goes wrong for them.
If you look back at history and you analyze so-called "bad decisions," many of them can be traced to the fact that nobody stood up in the room and said, "This is a really bad idea, and we shouldn't do this."
When Nobody Says Stop
A few years ago, when the five-person submarine spontaneously collapsed while going to visit the Titanic remains, everyone later agreed that they shouldn't have gone on that mission. If just one person would have raised their hand and said, "nope, this is an awful idea, you're all going to die, and we shouldn't do this," then there is a chance those five people are still on this earth today. Unfortunately, the CEO of the company didn't like to be told no, and his ego got him into some trouble.
One of my favorites is when Netflix approached Blockbuster in the year 2000. Now, if you rewind back to the early 2000s, Blockbuster was still dominating, and Netflix was a little-known startup that was mailing out DVDs via the post office. Netflix was struggling and thought they were going to ultimately collapse, so it approached Blockbuster about buying it out for $50 million. The CEO of Blockbuster all but laughed at Netflix at the time, and the team around him didn't tell him that was the wrong thing to do. Today, Blockbuster is a relic of the past, and Netflix has a market cap of almost $400 billion.
Just this last week, Meta announced they were shutting down the Metaverse. If you're not familiar with the Metaverse, it was a project that Facebook went all in on during the pandemic, thinking that our future was going to be focused on living "in the meta." Zuckerberg went on a rampage, changing the company's name and sinking over $80 billion into the project. It failed, and after spending all that money, we learned that Zuckerberg has no guardrails around him to say something like, "Hey Mark, maybe we shouldn't spend all that money on something of the sort."
The Courage to Be the First Domino
The list goes on. Epic failures from world leaders, tech company CEOs, and everyone in between are usually a by-product of people being surrounded by yes men and women, and not having enough systems, processes, and people with guts in place to say, "Hey, that idea sucks, we shouldn't do that."
The difference is in the leader having the intelligence and the humility to look around the room and see who is keeping them in check.
If you're going to make a bad decision, so be it, but at least do it knowing that a whole committee of people actually thought it was a great idea, and stress-test it repeatedly before going forward. Bad decisions by bad leaders are usually the result of no one being empowered enough to have the free will to even raise their hand to stop them.
You don't have to be the CEO to change the outcome of a room. You just have to be the one willing to get uncomfortable first. The one willing to risk the awkward silence, the side eye, the shift in energy when you say the thing everyone else is quietly thinking but hoping someone else will carry. Most people aren't lacking awareness in these moments — they're lacking the courage to be the first domino.
I've sat in those rooms. You can feel it. There's a subtle tension that creeps in when something doesn't quite add up, when the plan sounds good on the surface but falls apart the second you apply a little pressure to it. People glance around, waiting for someone more senior, more tenured, more "qualified" to step in. And when no one does, the room collectively agrees to move forward, not because it's right, but because it's easier.
Strong leaders don't just tolerate pushback — they demand it. They build rooms where disagreement isn't seen as disrespect; it's seen as responsibility. Because if you're the smartest person in the room and no one ever challenges you, you're not leading, you're performing. And eventually, that performance becomes a blind spot big enough to drive a billion-dollar mistake straight through.
So the next time you feel that hesitation creeping in, that little voice telling you to stay quiet and not rock the boat, I want you to pause and ask yourself one simple question. If this goes wrong, am I going to be okay knowing I saw it coming and said nothing? Because careers are built on action, but they're also defined by the moments you choose to speak when it would have been easier to stay quiet.
And more importantly, take a look around. Who are you surrounded by? Do they both cheer you on and hold you back? If yes, good. Honest, direct, and transparent people who can look at you and say, "Don't do that, that's a dumb idea," are just as important to have around you as the people who say, "Go faster!"