We know you have a full plate these days, so we’ll get straight to the point. You need to up your recruiting game. 

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Not for enlisting souls to the dark side, per se—you’ve reportedly been devoted to that mission since time immemorial. No, we’re hoping you can persuade more of our earthly professionals to take on a role that’s become more necessary than ever. We need more devil’s advocates.

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You know the role well, because you created the job in the age of Job. In tirelessly testing that poor guy’s faith—with the endorsement of the Big Guy, no less!—you turned the question “What if?” into an art form. And while Job ended up sticking to his guns, you made a lasting point: any opinion can be clarified and strengthened when confronted with sharp opposition.

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Of course, you can’t be personally available to provide a dissenting view for every human idea. But your terrestrial advocates can, and must. In an era where organizations prize consensus and minimize risk—and their people rely on safe choices rather than stand out or offend—we need more voices that dare challenge the status quo. Not simply for the sport of debate, but to make ideas better.

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While it may seem heretical to say so—up here, anyway—your advocates can make companies stronger too. When a corporate culture signals that dissent isn’t just tolerated but truly valued, it doubles down on real creativity and innovation. That commitment extends beyond the lip service of DEI boilerplate and promotes actual diversity of thinking. It lets the strongest ideas rise to the top, not just the easiest ones.

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Having more of your advocates around is good for individuals as well. When forced to defend our opinions, we become better critical thinkers—examining our motivations, rooting out our biases, and considering alternatives we might otherwise dismiss. Over time, the presence of dissenters makes us anticipate counterarguments and come to the table better prepared. Muscles need resistance to become stronger.

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While many organizations might bristle at the inherent discomfort of a devil’s advocate, resilient systems do not. The legal system embraces an adversarial process to air opposing viewpoints and ensure a fair trial. Military strategists deploy “red teams” to find defensive vulnerabilities and hedge against groupthink. Most recently, tech leaders pursuing tomorrow’s AI are hiring thousands to detect ways their products might be misused or violate their users’ intentions. As recent highlights have shown, the devil truly is in those details.

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Yes, you’ve been demonized for millennia. But when it comes to the art of persuasion, we’ll give you your due—you know this stuff better than anyone. 

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In your early serpentine days, your shenanigans may have gotten Adam and Eve kicked out of paradise, but you also provided the foundation of human free will. Sure, you tempted Faust down a dark path in your Mephistopheles phase, but you pushed him to confront the limitations of human knowledge. In Milton’s telling of Paradise Lost, your eloquence provided a powerful argument against blind obedience. Your wit is sharper than the fork on your tail, and your rhetorical chops would make Socrates blush right into your favorite color.

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That said, we don’t need your new advocates to be villains, but catalysts. Encourage them not only to point out the flaw in an argument, but propose a better alternative. Drive them toward directness and away from personal barbs—they’re here to attack the idea, not the ideator. And be sure the calculated risks they advise are backed by solid reasoning and, when possible, compelling data. Let them shake the tree, but know which branch they’re aiming for.

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Every great advancement starts with someone daring to challenge the status quo. While your own past is more than checkered, with the right approach, your advocates can become proud heirs to your tradition of skepticism. “Yes, and” is fine for improv comedy, but “Yes, but” is better for business.

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And should it prove too difficult recruiting provocateurs inside of organizations, don’t forget. You’ll always have a willing audience among outside consultants.

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Indelibly yours,

Matt, Jeff, Mike and Thom