Coaching practices for Devil S Advocate Thinking
Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For Devil S Advocate Thinking, these are the strongest matches in the current practice library.
Does this sound like the set of challenges you might be facing?
- I’ve settled on my position and I can feel how much I want it to be right, which is exactly why I don’t trust it yet
- Nobody around me will actually push back
- We’ve all fallen in love with this plan and the room’s gone warm and agreeable, and now it feels almost rude to be the one raising what could go wrong
- In our meetings everyone just nods along and the doubts only come out in private afterward, because being the one who pushes back makes you look like you’re not a team player
- I keep giving the same person the benefit of the doubt
Practices that may help
- Ask what alternative perspectives would say
Deliberately steelman the strongest objection to your current position before treating it as settled.
Socratic Questioning - Invite an adversarial collaborator
Find someone whose genuine prior is the opposite of yours, and work together on the same evidence.
Confirmation Bias: Seeing What You Expect to See - Black hat: identify risks and why something could fail
Apply the most rigorous critical scrutiny to the idea — the black hat is the voice of caution and evidence-based pessimism.
Six Thinking Hats, Made Practical - Appoint an explicit devil’s advocate role
Give one person the formal job of arguing against the plan — making dissent structural, not personal.
Red Teaming: Stress-Testing Plans Before They Fail - Update your attribution when evidence warrants
Charitable interpretation is a starting point, not a final verdict — revise it when facts change.
Hanlon's Razor: Never Attribute to Malice What Stupidity Can Explain - Find the strongest version of the opposing view
If there are multiple ways to interpret a position, choose the most defensible one.
Steelmanning - Examine the evidence for and against
Systematically list what supports your interpretation and what doesn’t — like a fair-minded lawyer, not a prosecutor.
Check the Facts, Made Practical - Consider the opposite before finalizing a judgment
Deliberately generate the case for the conclusion you are not reaching.
Motivated Reasoning - Apply the double-standard check: would I accept this reasoning if it pointed the other way?
Test whether you are holding your team’s arguments to a lower bar than the other side’s.
The Scout Mindset - Separate steelmanning from endorsing
Accurately represent a view without implying you agree with it.
Steelmanning
Related concerns
- Devil S Advocate Critical Thinking
Apply the most rigorous critical scrutiny to the idea — the black hat is the voice of caution and evidence-based pessimism.
Black hat: identify risks and why something could fail
- Devil S Advocate Role
Give one person the formal job of arguing against the plan — making dissent structural, not personal.
Appoint an explicit devil’s advocate role
- Devil Advocate Vs Real Opponent
Find someone whose genuine prior is the opposite of yours, and work together on the same evidence.
Invite an adversarial collaborator
- Steelman Vs Endorse
Charitably interpreting a position is not the same as agreeing with it, refusing to disagree, or softening your critique to avoid conflict.
Distinguish steelmanning from sycophancy
- Steelman Vs Sycophancy
Charitably interpreting a position is not the same as agreeing with it, refusing to disagree, or softening your critique to avoid conflict.
- When Scout Mindset The Double Standard Check
Test whether you are holding your team’s arguments to a lower bar than the other side’s.
Apply the double-standard check: would I accept this reasoning if it pointed the other way?
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