Why public figures keep hiring yes-men, even when honesty would save them

One of the strangest meetings I've ever sat in wasn't particularly dramatic. Nobody shouted. Nobody stormed out. Nobody threw a phone across the room. In fact, if you'd walked into the room halfway through, you probably wouldn't have noticed anything unusual at all.

A public figure was discussing a project they were convinced was going to be successful. Around the table sat various advisors, managers and consultants. As the conversation continued, I became increasingly aware that almost everyone seemed to share the same private concern. The idea wasn't very good. It wasn't catastrophic, and it certainly wasn't career-ending, but it wasn't particularly strong either. The problem was that nobody wanted to be the first person to say so.

What followed was fascinating. Rather than challenging the idea directly, people began dancing around it. They asked gentle questions. They suggested small tweaks. They proposed adjustments around the edges. What nobody did was state the obvious. Eventually the meeting ended, the project went ahead, and unsurprisingly many of the concerns everyone had privately discussed afterwards turned out to be completely correct.

I've seen versions of that meeting countless times throughout my career. Sometimes it's a celebrity launching something nobody around them seems particularly enthusiastic about. Sometimes it's a business owner pursuing a strategy that stopped working months ago. Sometimes it's a politician becoming convinced that public opinion is firmly on their side despite every available sign suggesting otherwise. The details change, but the pattern remains remarkably consistent. The more successful somebody becomes, the harder it often becomes for the people around them to tell them the truth.

Most people assume success gives you access to better advice. On paper, that makes perfect sense. A successful person can afford experienced lawyers, managers, consultants, advisors and publicists. They have access to people who have spent decades navigating complicated situations. Compared to the average person, they should theoretically be making better decisions because they have more expertise available to them.

What I've often found, however, is that success doesn't simply attract expertise. It changes the incentives of the people providing that expertise.

The term "yes-man" is perhaps slightly misleading because it suggests something deliberate. We tend to imagine somebody enthusiastically agreeing with every terrible idea in order to stay in someone's good books. In reality, most yes-men don't realise they're becoming yes-men. The process is usually far more gradual than that.

Imagine you're managing a famous musician, actor or broadcaster. One day you push back on an idea and the reaction isn't particularly positive. Nobody shouts at you. Nobody threatens your job. The atmosphere simply becomes awkward. A few weeks later, somebody else enthusiastically supports a different idea and their opinion seems to carry more weight. A few months after that, you notice certain conversations are easier than others. Before long, you don't consciously decide to stop being honest. You simply begin softening criticism, choosing your words more carefully and deciding some battles aren't worth fighting.

Human beings are remarkably good at adapting to social environments. Most people learn very quickly which opinions create harmony and which opinions create friction. When money, access, status or career progression become involved, that instinct only becomes stronger. The result isn't necessarily a room full of dishonest people. More often, it's a room full of intelligent professionals who have gradually started editing themselves without realising it.

This is one of the reasons I've always found fame so psychologically fascinating. Most people spend their lives receiving a fairly healthy amount of feedback, whether they want it or not. Friends tell us when we're being unreasonable. Family members point out our flaws, often with alarming enthusiasm. Colleagues challenge our ideas. If all else fails, the internet is usually more than willing to humble us. There are constant reminders that we are not the centre of the universe.

Fame disrupts that process.

When somebody becomes famous enough, wealthy enough or influential enough, they gradually become surrounded by people who have reasons to keep them happy. Sometimes those reasons are financial. Sometimes they're professional. Sometimes they're social. Whatever the motivation, the outcome is often surprisingly similar. Difficult conversations start happening less frequently. Criticism becomes more carefully packaged. Honest feedback arrives wrapped in several layers of bubble wrap.

What's particularly interesting is that this rarely happens because somebody at the centre demands it. In fact, many public figures are completely unaware it's occurring. The people around them simply adapt. Nobody wakes up and decides to build an echo chamber. It emerges naturally through hundreds of tiny interactions. One person avoids an uncomfortable conversation. Another decides not to raise a concern. Somebody else chooses diplomacy over honesty. None of these moments seem significant on their own, but eventually the person at the centre ends up living in a version of reality that has been softened, filtered and edited by everyone around them.

This is one reason I've always found the Meghan Markle conversation fascinating from a PR perspective. Whatever somebody's personal opinion of Meghan may be, many of the controversies surrounding her don't strike me as examples of somebody making obviously terrible decisions. They often feel more like examples of somebody who may not have enough people around her willing to challenge decisions before they happen.

Take the now infamous gift basket signed "The Duchess of Sussex." I don't believe the intention behind it was arrogance. If anything, I suspect the intention was warmth. A thoughtful gesture. Something personal. The issue wasn't the gift itself. The issue was that nobody appears to have asked the obvious question about how it might be received by people outside the room.

Sometimes the most valuable person in a meeting isn't the person generating ideas. It's the person willing to say, "I understand why we're doing this, but have we considered how this might look from the outside?"

I've had similar thoughts watching various celebrity documentaries over the years. Often, what stands out isn't the celebrity. It's the people around them. Everybody appears incredibly supportive. Everybody appears encouraging. Everybody appears enthusiastic. On the surface, that sounds lovely. Who wouldn't want to be surrounded by positivity?

The problem is that support and honesty aren't always the same thing.

One of the reasons I find Los Angeles culture so fascinating is because it often takes this dynamic to an extreme. This isn't true of everyone, obviously, but there is a particular kind of professional positivity that exists in certain entertainment circles. Everyone loves everything. Every project is amazing. Every idea is incredible. Every meeting is inspiring. Every opportunity is exciting. After a while, it becomes genuinely difficult to tell the difference between authentic enthusiasm and social performance.

I've occasionally sat in rooms where everybody appeared delighted by an idea, only to hear the exact same people criticising it privately afterwards. The contrast can be quite startling. It creates an environment where public agreement becomes the norm and genuine feedback becomes increasingly rare.

Ironically, some of the easiest people I've ever worked with have been genuinely famous.

This completely contradicts what most people expect.

There's a popular belief that the bigger somebody becomes, the bigger their ego becomes. Sometimes that's true. But I've also found that many highly successful people have already developed a level of confidence that allows them to hear criticism without feeling threatened by it.

Some of the most famous individuals I've encountered actively encourage disagreement. They ask questions. They challenge assumptions. They invite debate. They understand that surrounding yourself with people who constantly reassure you is incredibly comforting in the short term but potentially disastrous in the long term.

Interestingly, I've often found emerging talent far harder to advise.

That isn't because they're bad people. It's because everything feels more personal when you're still trying to prove yourself. Every project feels important. Every idea feels precious. Every criticism feels bigger than it actually is. Once somebody has spent twenty years succeeding at the highest level, they're often far less emotionally attached to any single idea. If something isn't working, they're more willing to move on.

Social media has only made this entire phenomenon more complicated.

Twenty years ago, public figures were largely dependent on the people around them for feedback. Today they can open Instagram and find thousands of comments telling them they're brilliant before they've even had breakfast. They can post an idea and receive immediate validation from an audience that already likes them.

The psychological effect of this is enormous.

One of the biggest mistakes people make is assuming that audience approval and public opinion are the same thing. They're not. A loyal audience is a specific group of people who have chosen to follow you. The wider public includes everyone else. I've seen countless situations where somebody becomes convinced that because their followers love something, everybody must love it. Unfortunately, the world rarely works like that.

In crisis PR, this distinction comes up constantly. Sometimes I find myself explaining that the people commenting beneath your Instagram post are not necessarily representative of the people reading newspaper coverage, discussing you at work, or forming opinions about you from a distance. The internet has an extraordinary ability to create the illusion of consensus.

What fascinates me most about all of this is that success doesn't necessarily make people arrogant. If anything, I think it often makes them isolated.

The strange irony is that many public figures spend years building teams, brands and careers designed to protect them from problems, only to discover they've accidentally protected themselves from reality as well. The very systems designed to support them can sometimes become the thing preventing them from seeing situations clearly.

I've watched people spend years surrounded by reassurance before suddenly finding themselves in a reputational crisis that appeared obvious to everyone outside the room. When that happens, the conversation is rarely about a single bad decision. More often, it's the result of dozens of small moments where nobody wanted to ask an uncomfortable question.

One of the most valuable things any advisor can do is risk being unpopular for five minutes.

Not because they enjoy conflict. Not because they want to be difficult. Not because they think they're smarter than everyone else.

Because sometimes the most useful sentence in the room is also the one nobody wants to hear.

"I think we're getting this wrong."

The people willing to say that aren't always the easiest people to work with. They can be frustrating. They can be inconvenient. They can occasionally ruin a perfectly pleasant meeting.

They're also often the people who save you from making a very expensive mistake six months later.