The Devil's Advocate Protocol: How to Systematize Dissent The Catholic Church invented a job to argue against sainthood. Your team needs the same thing. For nearly 400 years, the Catholic Church employed someone whose entire job was to argue *against* sainthood. When a candidate was proposed for canonization, the Church appointed an official — the *advocatus diaboli,* the Devil's Advocate — to build the strongest possible case against. Find the flaws. Challenge the miracles. Poke every hole. Only if the case survived that assault did it proceed. It's one of history's smartest institutional ideas, and almost no team uses its lesson: if you want a decision to be good, you have to assign someone to attack it. Why you can't just "hope someone speaks up" We just saw why dissent dries up — power, conformity, the fear of being the difficult one. The problem is that all of those pressures push the *same* direction: toward silence. Waiting for objections to surface naturally is waiting for the one thing the system is built to suppress. The fix is to stop relying on courage and start relying on *role.* When disagreeing is someone's assigned job, every reason not to speak up evaporates. They're not being negative — they're doing the task. They can't be punished for it, because you gave it to them. That single move — turning dissent from a personal risk into an assigned duty — is what makes the Devil's Advocate so powerful. How to actually run it The protocol is simple, but the details matter: 1. Assign the role explicitly, out loud. "For this decision, you're the Devil's Advocate. Your job is to make the strongest case against what we're leaning toward." Naming it is what makes it safe. 2. Rotate it. If the same person always dissents, they become "the negative one" and get tuned out. Rotate the role so everyone takes a turn — and everyone learns to do it. 3. Demand a *steelman,* not nitpicks. The advocate's job isn't to find typos. It's to build the best possible case for the opposite decision. Weak objections are worse than none — they inoculate the group against the real ones. 4. Protect them completely. The decider must visibly thank the advocate, *especially* when it's annoying. The moment dissent gets punished once, the role becomes theater forever. 5. Make the team answer it. The point isn't to hear the objection and move on. It's to *strengthen the plan* against it — or change course. A warning Devil's advocacy has a failure mode: done lazily, it becomes a ritual that makes groups *more* confident in bad decisions. "We considered the other side" — when you didn't, really — is worse than never pretending to. The fix is the steelman standard. A real Devil's Advocate makes the room genuinely uncomfortable, because they've built a case good enough that, for a moment, people aren't sure anymore. If nobody flinched, it wasn't done right. Why this is the spine of a good decision Step back and notice what the Devil's Advocate actually guarantees: that the *strongest argument on the other side gets made,* even when everyone in the room would rather it didn't. That's the whole game. A decision is only as good as the best argument against it that it survived. Without a Devil's Advocate, the best counter-argument often never gets spoken — it just shows up later, in reality, as the problem nobody raised. The protocol drags it into the room *while you can still do something about it.* The Church understood something most modern teams don't: the case against is too important to leave to chance. --- For the next real decision your team makes — who would you appoint as Devil's Advocate, and what's the strongest case against the thing you're leaning toward? Reply and make that case in one line. Steelman it.

The More Senior You Get, the Less Truth You Hear Power comes with a hidden tax: the people around you quietly stop telling you when you're wrong. Here's a strange thing that happens as you climb. Early in your career, people tell you when your idea is bad. Peers push back. Bosses correct you. The feedback is constant, sometimes brutal, and it keeps you sharp. Then you get promoted. And promoted again. And somewhere along the way, the pushback… stops. Meetings get smoother. People nod more. Your ideas suddenly sound great to everyone. It feels like you got smarter. You didn't. You got powerful — and **power quietly surrounds you with people who've stopped telling you the truth.** Why the truth dries up It's not that people suddenly respect you more. It's that disagreeing with you got *expensive,* and they're doing the math: - You control their outcomes. Their raise, their project, their standing — you touch all of it. Contradicting you is now a risk with their name on it. - They assume you've decided. Senior people radiate certainty. Once you lean a direction, everyone reads it as settled and falls in line. (This is the HiPPO effect — the Highest Paid Person's Opinion anchors the room.) - Nobody wants to be "the difficult one." Going along is easy and invisible. Pushing back is effortful and memorable — and not in a way that feels safe. So people edit. They soften the bad news, bury the objection, and hand you a slightly nicer version of reality. Not because they're cowards — because they're responding rationally to the incentives *you* now represent. The trap this creates Put it together and you get something genuinely dangerous: the more authority you have, the worse your information gets — exactly when your decisions matter most. You end up in a bubble of agreement, mistaking the silence of people-who-won't-disagree for the confidence of people-who-think-you're-right. It's the emperor's new clothes, replayed in every leadership team in the world. The higher you rise, the fewer people are willing to be the child who says the emperor is naked — so you're the last to know. History is littered with powerful people who walked confidently into disaster, surrounded by advisors who knew better and said nothing. You have to engineer the truth back in Here's the hard part: this won't fix itself. Left alone, the natural drift of power is *toward* the bubble, not away from it. If you want the truth, you have to build systems that drag it back in — because it will not arrive on its own. That means doing unnatural things on purpose: - Reward the person who disagrees — visibly, so everyone sees that pushback is safe and valued, not career-limiting. - Ask for the case *against* your idea before the case for it — and don't accept "looks good to me." - Make dissent structural, not optional — assign someone to argue the other side, gather input before you reveal your own view, let people weigh in anonymously so rank stops deciding. - Speak last. The moment you go first, you've anchored the room and the truth gets quieter. Notice what all of these have in common: they're *structure.* You can't rely on courage to surface the dissent, because you've made dissent costly. You have to build a process where the best argument can win even when it contradicts the most powerful person in the room — *especially* then. The leaders who stay sharp aren't the ones with the best instincts. They're the ones who never let their power buy them silence. --- When did you last hold back a real objection because of who was in the room? And if you're the senior one — when did someone last genuinely tell you that you were wrong? Reply and tell me. The second question is the more uncomfortable one.