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Protect the Devil's Advocate

#businesstips #culturematters #drivingchange #highperformancehabits #innovation #leadershiptips #leadingchange #workshopfacilitator May 26, 2026
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If you have ever been at one of my talks, you’ll hear me speak about an office archetype I coin ‘Harry, the Seagull.’

 

Harry flies around the office and poops on ideas.

 

He is quick to point out why it won’t work, what’s wrong with the plan or what we inadvertently overlooked . . . usually with a sarcastic comment. Most of us assume that excluding someone like Harry is the key to building strong teams. After all, isn't unity the goal?

 

I want you to rethink this perspective.

 

The Romans understood something we have forgotten: The moment everyone agrees too quickly, danger has entered the room. So, the Romans institutionalized conflict. Before major military or political decisions, Roman leaders appointed an advocatus diaboli — literally, an advocate for the devil. One person whose job was to attack the plan—publicly, aggressively and without consequence.

Imagine introducing that policy at your next leadership meeting. “Before we move forward, Harry has been assigned to explain why this strategy will fail.”

 

Ancient Rome understood something modern leadership has forgotten: Smooth meetings often produce fragile outcomes. In high-performing teams, disagreement is not rebellion. It’s quality control.

 

Today, most organizations reward going with the flow and avoid the hard, challenging conversations. In the world of psychology, we call this bias the ‘fluency heuristic.’

If an idea sounds smooth, polished, confident and easy to understand, people assume it must also be the best idea. Our brains mistake familiarity and ease for truth. It’s why the loudest person in the room often wins. It’s why beautifully designed slide decks sometimes evade scrutiny they deserve. It’s why leaders often confuse confidence with competence; and, it’s why entire organizations nod at strategies nobody truly believes in.

 

The human brain loves cognitive ease. It burns fewer calories. Critical thinking, on the other hand, is exhausting. So, teams drift toward social harmony instead of intellectual honesty and curiosity. This is a hidden danger of team cohesion: the stronger the social bonds, the harder it becomes to challenge bad thinking.

 

Research from Stanford found that groups with a designated contrarian made dramatically fewer decision-making errors than groups left to ‘naturally’ reach consensus. Why? Dissent reactivates analytical thinking. It interrupts what neuroscientists call coherence bias — the brain’s tendency to stop searching for flaws once social agreement appears.

In plain English: The moment everyone nods, your brain starts getting lazy. One dissenting voice wakes the system back up. That’s why some of the best leaders I’ve ever worked with intentionally create discomfort in meetings--not toxic discomfort--intellectual discomfort.

There’s a difference.

 

Toxic leaders punish disagreement because they see dissent as disrespect.

 

Strong leaders invite civil disagreement because they see it as protection.

 

There is an old story out there that Jeff Bezos required Amazon teams to write six-page memos arguing against their own proposals before moving forward. The question wasn’t: “Why will this work?” The question was: “Why might this fail?”

 

High performing teams must learn how to challenge each other in a way that brings out the best in each other. We can do this in a safe, respectful way without breaking down trust and psychological safety. Many organizations that claim to value psychological safety inadvertently create intellectual fragility by forgetting to protect space for dissenters or challengers.

 

They confuse comfort with safety.

 

If your culture protects people from tension, challenge, friction and disagreement, you do not have psychological safety. Real psychological safety means: “I can disagree with you without being punished.” That’s different.

One creates growth. The other preserves politeness, and polite organizations make catastrophic decisions all the time. You see it in corporate scandals, failed mergers, tone-deaf marketing campaigns, sports dynasties that collapse and universities chasing trends they don’t fully understand. Over time, leaders begin hearing only echoes of themselves. That’s not alignment. The irony is that most leaders say they want honesty--until honesty arrives with consequences attached to it.

 

Here’s the uncomfortable truth: If people stop disagreeing with you, it may not mean you’re right. It may mean the cost of challenging you has become too high.

 

Once that happens, failure becomes inevitable — only now it arrives silently. The best teams I’ve ever been around — in sport, business, and leadership — were not the teams with the least conflict. They were the teams where conflict was routine. Where someone could say: “I think this is a terrible idea.” and nobody lost status for saying it. It’s not dysfunction. That’s organizational maturity. Roman generals understood this 2,000 years ago. Modern leadership teams, somehow, are still learning it.

 

So, here’s the challenge:

 

At your next meeting, before the final decision is made, ask one question: “Who sees this differently?”

 

Then do something radical. Don’t defend the plan. Just listen because the smartest person in the room may not be the one presenting the strategy. It may be the one brave enough to challenge it. 

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