Playing Devil's Advocate at Work: When It Helps and How to Do It

A room where everyone agrees has not necessarily thought things through. A devil’s advocate is someone who argues against a proposal, often one they do not personally oppose, so the group has to test its reasoning before it commits. At work, playing devil’s advocate is a deliberate way to find the flaws in a plan while there is still time to fix them. It is not a license to be difficult.

That distinction is the whole game. Maybe you have been asked to take the role, or you have a doubt about a plan and wonder whether to raise it as “just playing devil’s advocate.” Either way, the question is how to make the challenge land as a contribution rather than as contrarianism, especially while you are still new. The answer depends less on how sharp your objections are than on which kind of devil’s advocate you are being.

What playing devil’s advocate actually means

The phrase started as a job title. In the Catholic Church, the advocatus diaboli argued against making a candidate a saint, looking for character flaws or evidence that had been presented too favorably. Pope Sixtus V established the office in 1587, and it stayed part of the canonization process until Pope John Paul II streamlined it in 1983. The modern meaning keeps the core of the original: an appointed skeptic whose task is to find the holes in a case everyone else would like to accept.

In everyday use, playing devil’s advocate means arguing a position you do not necessarily hold, either for the sake of debate or to push an idea further with sound reasoning. The defining feature is the gap between what you argue and what you actually think. That gap is why people usually announce the role before they start. The announcement tells the room that you are testing the plan, not attacking it or the person who proposed it.

Seen this way, “devil’s advocate” is not one thing. It covers several different ways of bringing disagreement into a decision, and they do not work equally well.

Four kinds of devil’s advocate

The assigned devil’s advocate

As a formal decision-making technique, devil’s advocacy means the group selects one person, or a small subgroup, to act as the critic of a proposed decision. The role is given, not volunteered, and that is its strength. Because everyone knows the critique is expected, the critic can press hard on weak assumptions without the challenge being read as a personal stance. If a manager or project lead hands you this role, you have been given permission to be thorough, and you should use it.

The self-announced devil’s advocate

This is the version most people mean in meetings: someone says “let me play devil’s advocate for a second” and argues the other side. Here the speaker makes the gap between the argued position and their own view explicit, and that label does a lot of work. It signals that the objection is a test, not a verdict. It also has a cost, which the fourth type below makes clear: a challenge everyone knows is pretend is easier to wave away.

Dialectical inquiry: bringing an alternative

In dialectical inquiry, the challenger does more than list what is wrong with the proposal. They also put forward a worked-out counterposition, so the group weighs two real options instead of one plan and a pile of objections. Devil’s advocacy and dialectical inquiry have been studied side by side as two techniques for bringing constructive conflict into decisions, and a meta-analysis in Organizational Behavior and Human Decision Processes examined the effects of both. The practical difference for you is simple. Arriving with objections only makes you the critic. Arriving with objections and an alternative makes you a contributor to the decision.

Authentic dissent

Authentic dissent is what happens when a colleague genuinely holds the opposing view and argues for it. According to research by Charlan Nemeth and colleagues, published in the European Journal of Social Psychology in 2001, this is where the real benefit lies. When groups faced a role-played devil’s advocate, people mostly came up with more reasons to support the view they already held. When they faced someone who actually disagreed, they generated the most thoughts, and those thoughts were their own rather than paraphrases of the case material or of other people’s points. The reason is credibility. Everyone knows the devil’s advocate is pretending, so the objection is easier to set aside.

This finding has a practical consequence. If you have a real doubt about a plan, say it as your own view. Dressing a genuine concern up as “just playing devil’s advocate” gives the group an easy reason to dismiss it. Keep the devil’s advocate label for when you really are testing an idea you might support.

Why devil’s advocacy matters in group decisions

The case for the role rests on groupthink. The psychologist Irving L. Janis described three symptoms of groups caught in it: they overestimate the group, they become closed-minded, and they put pressure on members to conform. Janis supported devil’s advocacy as a counterweight. A designated critic makes dissent legitimate, so doubts that people would otherwise keep to themselves get said out loud before the decision is made, not afterward in the hallway.

Timing decides whether that works. Devil’s advocacy is most useful close to a decision point, once a proposal is developed enough that there is something concrete to test and a choice actually has to be made. Raised too early, while an idea is still forming, the same objections can shut it down before it has had a chance.

How to play devil’s advocate without seeming difficult

The goal is to find the flaws in an argument so the problems do not appear later. It is not to make anyone feel bad. That aim shows in how you do it:

• Announce the role. A short signal that you are testing the plan keeps the challenge on the idea, not on its owner.
• Aim at the idea, never the person. “What happens to the timeline if the supplier is late?” invites thinking. “You haven’t thought about the supplier” invites defending.
• Do your homework. A challenge built on real understanding of the topic is heard as help. A challenge from someone who has not read the proposal is heard as noise.
• Name what is strong. Acknowledging the merits of the plan shows you are improving it, not trying to sink it.
• Bring an alternative when you can. That turns a critique into a second option the group can weigh.
• Stop once you have been heard. The role has done its job when the risk is on the table. Pressing it again and again, or on every idea, is when devil’s advocacy starts to read as negativity.

Being new adds a layer. You may see things that look wrong precisely because you are new, and not know whether it is your place to say so. One of the young people we interviewed about starting work described the dilemma like this:

One of the difficult things when you are new is that you often start by learning all the official best practices — the way things are supposed to be done.

But then you gradually realize that what is written down and what people actually do in practice are not always the same thing. That can leave you caught in the middle, wondering how you are supposed to respond.

Do you keep being the new person who raises your hand and says, ‘Actually, we’re doing this wrong — we’re supposed to do it this way’?

I think a lot of it comes down to learning where that line is: when is it appropriate to challenge the way things are done, suggest a better approach, and say, ‘Couldn’t we improve this or make this process more efficient?’

He does not resolve it, and there is no rule that resolves it for you. What helps is choosing the moment rather than challenging by reflex. Hold your devil’s advocate questions for decisions that are actually about to be made, phrase them as questions about the plan, and pick the one or two that matter most instead of raising all of them. Most people also find they lean one way by default, either staying quiet when they disagree or pushing back harder than the moment needs. Neither default is fixed, and it is worth seeing how you handle disagreement now, while the habits are still easy to adjust.

When a colleague always plays devil’s advocate

Sometimes you are on the other side: a colleague who greets every idea with “just to play devil’s advocate.” The most useful response is to treat the challenge as material, not as an attack. Take the strongest version of their objection seriously and answer it on the merits. Then use the types above. Ask whether they have an alternative in mind, which turns criticism into dialectical inquiry. Ask whether this is a real concern for them, because if it is, it deserves more weight as authentic dissent. If the challenges keep coming before ideas have had time to develop, suggest saving the stress test for the point where the group is ready to decide. None of this requires you to take the habit personally. It only requires steering it toward the moment when it helps.

The skills that make a challenge worth hearing

Look back at what separates a useful devil’s advocate from a draining one. It is rarely the objection itself. It is how the challenge fits into the decision, how it is said, and what happens to the working relationship afterward.

Decision-Making. Playing devil’s advocate is one of several ways to make better decisions with others. It sits alongside recruiting differing opinions, gathering input independently before discussing, and asking the quiet people in the room. Its purpose is to counter confirmation bias and overconfidence in a group that already likes its answer. Knowing that turns the role from a quirk into a tool you choose deliberately, for the right decision, at the right point.

Communication. Expressing disagreement is one of the trickier things to say well at work. Being clear and direct, stating your main point first, and keeping the framing positive are what make an objection sound like help rather than an attack. How you open, whether “let me test this for a minute” or “that won’t work,” often decides whether anyone listens to what follows.

Teamwork. Devil’s advocacy only helps if trust survives it. That means keeping the disagreement on topic, never letting it turn personal, and noticing when a colleague has started to feel attacked so you can reset. It also means knowing how to finish: argue the other side fully, then commit to what the team decides and help make it work.

The Job Skills Test measures these three, along with nine other workplace skills, and shows which of them would give you the most room to challenge ideas with confidence. Each one is learnable through practice, so it is worth measuring these three skills before the next big decision lands on the table.

Where you fit in this

Parts of this may already feel familiar. Perhaps you are the one who asks the awkward question, or the one who waits until after the meeting to share a doubt. If you have ever held back a concern in a meeting and then watched that exact problem surface weeks later, you already understand what the role is for. What remains is building the habits that let you raise it at the right moment and in the right way. Those habits can be learned, and learning them does not require you to become more combative or more agreeable than you are.

The decisions you are part of will get bigger, and the people in the room more senior. The ability to challenge a plan well tends to count for more as that happens, and the skills behind it can be built one conversation at a time, starting with the next one.

Find out how you handle a challenge

All that is left is to see where you are starting from.

The Job Skills Test is a free self-assessment of your work skills. It asks how you actually behave at work, not what you know. In 7 minutes it shows where you stand across all twelve skills, including Decision-Making, Communication and Teamwork, and which ones would make the biggest difference to how you contribute when a group has a decision to make.

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