In the pursuit of better governance, boards are increasingly turning to an old debating tactic: assigning a devil’s advocate. The idea is simple—someone is tasked with challenging the prevailing opinion, not necessarily because they disagree, but because the act of structured dissent can uncover weaknesses in reasoning and improve decision-making.
But while the intention is good, the execution matters.
“It’s important that it not be the same person every time,” said Paul DeNicola of PwC’s Governance Insights Center. “You certainly don’t want that person to become known as sort of the chronic dissenter.”
Instead, rotating the role and tying it to specific strategic discussions—such as a major pivot or a controversial investment—can help normalize disagreement as a healthy part of board deliberation. “You empower someone and it gives them license to look for” areas of risk or challenge, DeNicola said. “At least it’s part of the process.”
But used too much, it can become a kind of crutch. Rich Fields, a board advisor with Russell Reynolds Associates, urges boards not to rely too heavily on formal mechanisms like assigning dissenters. “I don’t think most decisions necessarily need someone to be appointed as the devil’s advocate,” he said. “I think it can sometimes be a lot simpler to just say… does anyone have any questions or different perspectives that we haven’t heard yet?”
For both Fields and DeNicola, the ultimate goal is to cultivate a board culture where dissent is natural—not something that needs to be assigned or manufactured. “The most important thing is just, again, to establish that culture,” Fields noted.
Making It Work
If your board does choose to implement this strategy, a few best practices can help it land well:
Rotate the role: Ensure different directors play the part over time to spread ownership of healthy skepticism.
This prevents one person from becoming typecast as the contrarian and encourages broader participation in critical thinking. It also allows directors with different expertise to challenge proposals from varied angles, enriching the discussion.
Contextualize the ask: Let the board know why the role is being used—e.g., “This is a critical decision, and we want to surface all possible risks.” Framing the role as a shared effort to pressure-test ideas helps remove stigma and keeps the conversation focused. It reminds everyone that the goal is improvement, not obstruction or confrontation.
Debrief afterward: After the meeting, reflect on what emerged from the discussion. Did it reveal anything overlooked? Was it handled respectfully? This step reinforces the value of dissent and encourages learning from the process itself, not just the outcome. It also allows leadership to make adjustments in tone or facilitation if needed for future sessions.
Protect the voice: Make sure the devil’s advocate is heard and not marginalized as simply playing a role.
Validate their contributions in the moment and ensure follow-up if their concerns raise substantive questions.
If they’re dismissed out of hand, it defeats the purpose and can chill future expressions of dissent.
“You’re not going to prevent groupthink entirely,” DeNicola said, “but you can set up a structure where someone is empowered to ask: ‘What are the risks we’re not seeing here?’” And in a world where strategic missteps can be costly, boards can’t afford to ignore the value of a well-placed challenge.
