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Devil's Advocate – Break it until you make it!

By Chiara Lamacchia.

During my law studies, there was a special exercise I quite liked. It consisted in reviewing the details of testimony and trying to anticipate questions which would have arisen from the counterpart during a trial. You cross-examine your witnesses as much as you can, grilling and attaching their statements, pressing on every piece of existing evidence, and confronting them with tough questions. The more you can spot and review upfront, the better you can reduce setbacks and complications.

This is called playing the Devil's Advocate and it is an intriguing practice that might come in handy in many situations.

In this article, I will look at the Devil's Advocate beyond its strategic feature of the lawyer's craft to explore the approach and understand how to use it both in personal and business life.

The Advocatus Diaboli

It was quite a job title in the Catholic Church, between 1587 and 1983: the Advocatus Diaboli [1] had the role to present counter-evidence to whoever was proposed as a candidate for sainthood. Quite a rigid door policy but we cannot be all saints, after all!

Taken out of context, the role of a Devil's Advocate can be generalised as "someone who pretends, in an argument or discussion, to be against an idea or plan that a lot of people support, in order to make people discuss and consider it in more detail" [2]. Thus, the goal is to test an idea and expose it to a thorough examination.

It is true that this approach does not always enjoy a good reputation: it is tendentially stymied, as we often confuse the Devil's Advocate with a merely evil one, who is silencing opinions, derailing from fostering a conversation or test a concept.

Instead, it is about engaging in a healthy critical debate: be incisive but never disrespectful; avoiding frictions; remember you are challenging ideas not attacking others personally; be objective and reasonable and never have a personal agenda; always test an opinion on multiples levels, examine whatever comes out: literally everything and its opposite.

You embody the antagonist to the idea of someone else. If they successfully defend it, we conclude the idea is successfully tested. If they struggle, there is space to investigate more and learn (please note: when there is no apparent defence to your objection, you should try to find a defensive argument, actually going against your own objections: I warned you that this is about testing everything and its opposite!).

Having the ability to test ideas and uncover possible logical or practical weaknesses can have impressive implications in many contexts, both professional and personal.

Dealing with the Devil

From start-ups to settled companies, failure is more common than success when launching a new product or service. Certainly, failure is complex and needs to be framed and contextualised. Many reasons can cause fiascos: market demand misreading, pricing mismatching, competitors misesteeming, customer experience misdesigning, product mistiming, success miscalculation, etc.

We usually "mis-do" when we do not have all elements at our disposal to "properly do". In business, this might be due to specific approaches or group dynamics that prevent us from even delving into those elements. I have compiled just a couple of cases I encountered till now.

  • I-have-a-great-idea. This dynamic is often based on the wrong logic that "I like it, therefore they will like it". If the person stating an idea is quite influential, due to status or charisma, it will be difficult for the group members to challenge it, either they do not dare to oppose it or because they are bought in.

  • Let's-go-with-the-flow. This approach is typical of those organisations with cult-like company culture, which infuse the team with so much emotive attachment that the people tend to support ideas on the emotional wave or sense of belongings, becoming excessively in line with whatever the majority is supporting.

  • They-know-their-stuff. This is the classic situation where a statement is given for granted, although it appears odd, solely because the person stating it is an expert. This induces the group to believe that an idea would work, based on certain non-challenged assumptions.

  • They-told-me-so. This is often a consequence of bad decision-making. However, I experienced it way too often not to name it as a factor in bad decision-making. Inputs usually come from random sources: a meeting with a client, who asks us to solve a problem but then suggests to us how to solve it; a chat with an old friend, who probably does not know anything about our core business and targets; a once-a-year dinner with that uncle who still thinks we live in two-cities-ago. Whatever the source: it suddenly happens that a single individual input is lifted up as an absolute assumption, the great foundation of our next strategic step.

You might see that these cases are leading to making sub-optimal decisions. At this point, getting a Devil's Advocate to do the dirty job of confronting your idea with its demons pays off immeasurably.

In some industries, this is a common practice. For instance, in the software security field, companies test their systems by letting hackers find a way to break into their security maze. This ensures a high level of quality in security before it is released to the public, saving millions in lost income in the event of a security breach. Another example is the automotive industry, where the car crash test is the ultimate Devil's Advocate: all automobile prototypes must pass destructive testing to check the safety standards in case of a crash.

The bottom line is the same: whenever you are not testing your idea or input you receive, your decision-making is likely to be partial, resulting in a guessing game rather than an optimal step. We need to start from the principle that every time we are not able to defend and back up our ideas or opinions, there is something wrong. When we can logically and tangibly hold up against criticism, conflicting scenarios, alternatives and objections then we have fewer chances to fail. To do so, we need to be ready to shake our certainties. Playing the Devil's Advocate challenges stagnant thinking and the status quo, forcing a more intense level of analysis and reducing the risk to overlook roadblocks.

We take more sound decisions, and when confronted with other inputs, we can better discern which input is worth exploring further and which to disregard.

Breakfast at the Devil’s

Who did say that this approach is exclusive to business purposes? I would argue we can use it for almost everything in life.

I admit I probably abuse it – as soon as someone states a fact, my mind always tries to look at the opposite side. Sometimes, it results in a dead-end street. Some other times, it creates powerful moments to enrich the conversation, unveiling and integrating perspectives otherwise not taken into account.

I do it almost automatically, perhaps to remind myself that we mostly have only a partial view: whatever we think, we believe, we support – there is always another side of the story we are yet to discover. Almost everything is relative.

As humans, we tend to be surrounded by a homogenous environment, preferring people with whom we share at least, by and large, the same principles. Although physiological, this is narrowing our possibilities to get to see the other side of the coin. To worsen this situation, nowadays, all external inputs we receive tend to be indexed around what we like or prefer. Ads, news, captions, images, videos, songs: everything revolves around our tastes. We live in a world where all is dangerously targeted on our profile.

Gone are those times when we were exposed to many different and disparate opinions, ideas or products. This was silently enriching us, providing a smattering of this and that, independently from our preferences. These general notions granted us to make potentially more complex and richer reasoning, detaching ourselves from our niche of reference and, above all, being exposed to new opportunities. Of course, we were more or less sensitive to one topic rather than another, but at least we were exposed to different universes.

From my experience, playing Devil's Advocate is handful whenever we need to take decisions under emotional circumstances or stress, where we tend to focus on validating rather than criticising our idea, fear or issue. Most probably we are more irrational, unreasonable and short-sighted than usual. In fact, in such circumstances, we are pressured by the urgency to find a solution or follow what is expected of us. We become resistant to new or dissenting ideas and substantially blind to foresee problems – we cannot see past our own noses. What is coming next? Bad decisions.

That is when your Devil's Advocate can support us: take your opinion and try to smash it, pretending to be against your own idea, secretly aiming at uncovering any flaws or mistakes. Your only purpose is to find out whether there are weaknesses or not.

The added value is the capacity of bringing different perspectives into the picture. We stretch our brains to find a convincing counter-argument.

Again, it can bring nothing other than taking our decision stronger. It can also lead to exploring other possibilities, creating a stimulating environment for personal reflection and growth. Either way, it will force us to think harder.

In some cases, it is also powerful when confronting others, to gather insights into their point of view and underpinning reasons. This then helps us to play with an angle when presenting our opinion, making it understandable and digestible.

To take a sound decision, we need diverse perspectives, experiences, points of view, and styles. I have to be honest: it takes a lot of effort to bring up counter-evidence and opposite perspective against our own opinions. By all means, it is arduous to argue with yourself. Pretending to support something against something we strongly believe in is almost impossible as we inevitably sabotage the overall operation to draw water to our own mill. Still, it is worth trying – you could become the best ally to yourself.

On another note, this can be an evening saviour when you need to spice up a dinner with friends: try to be Devil's Advocate just for the sake of it. You might need to do some explaining at the end, but I assure you this is the best way to enhance the debate and have a deeper conversation. The result might be surprising.

How to do it in practice

Where and how could we start to put it into practice? I listed some tricks and tips that are useful to experience it.

  1. Turn a statement into a question. This is a terrific place where to start. Put your statement on the spot by transforming it into a question, over and over again, never allowing the same answer twice. Nothing is taken for granted, as soon as you are questioning it. Once confronted with a question, our minds will naturally be on the lookout for an answer.

  2. Say "yes, but…" out loud. Whatever the idea on the table, initiate the "yes, but…" conversation. The instant we say it, we feel stimulated to find the end of the sentence, with an objection, a contradictory example or a small remote concern.

  3. Ask incisive questions. Chase the statement closely with a chain of questions (e.g., How can you be sure? Is it really feasible? Are we biased? Is this misrepresented? Who is disadvantaged by this? Does it apply to all situations? Is there any exception? What do you mean when you say …? How would you define the word "…"? Why do you think so? Are there examples that support this? Is this relevant for…?)

  4. Consider the opposite perspective. As humans, we are much more inclined on finding problems than solutions. There is a technique that I found very powerful to come up with new ideas: reverse brainstorming, where you identify the problem, reverse it, collect ideas, reverse ideas, analyse them and find solutions. In the same way, we can apply it when we play the Devil's Advocate.

  5. Find exceptions. Think about specific cases or scenarios where that certain statement, belief or opinion would not work. If you find it difficult to find exceptions, try to find hidden assumptions and place them in another situation or context. If you still cannot find suitable exceptions, use reductio ad absurdum: think of extreme scenarios and push the arguments to their logical limits. In any case, as soon as you find an exception, you offer a seat for doubts, leading to more questions and more answers.

  6. Look for alternatives. The quickest way to achieve it is to give for granted that the statement is unquestionably wrong, unavailable or unfeasible. This will push the debate towards possible alternatives.

  7. Think of the downsides. Anything in life has its pros & cons. If we focus on the downsides, we create a powerful space to enrich the idea even more.

I also have a final tip. Like any other skill, this one requires considerable practice. I would advise you to start with yourself in your daily life. When you are too convinced of something, try to break the logic behind and look at the other side. If you pass the hardest task – i.e., challenging your own opinions and beliefs – the rest will be a piece of cake.


Getting a Devil's Advocate on board is an enriching move. Being it in business in your daily life, it is worth taking a look at the other side of things. We are exposed less and less to beliefs, tastes, opinions, and customs that are different from our own.

On a professional level, we should get our new ideas, strategies and tactics crash-tested. In this way, we come up with a stronger idea, a better product, a more far-sighted strategy, or more innovative solution. We discuss better, exchange better, learn other ways of thinking, resolve conflicts and reach compromises.

On a personal level, we should take the healthy habit of questioning or testing our opinions or beliefs. Break our own ideas can help us grow, enrich our universe, and take sounder decisions.

There are some techniques to try and give it a go: at the end of the day, it is all about questioning and creating space for doubts, curiosity, and analysis. If you cannot find anything against an idea – then you have it there: the idea might be the one you should go with!

What is the worst that can happen anyway? We can always agree to disagree.



[1] All That's Interesting. (2018). The Origin Of The Term 'Devil's Advocate' Is More Literal Than You Think.

[2] Definition of devil's advocate from the Cambridge Advanced Learner's Dictionary & Thesaurus © Cambridge University Press

Further readings

Vv.Aa. (2017). The Devil's Advocate approach: An interview technique for assessing consistency among deceptive and truth-telling pairs of suspects. Legal and Criminological Psychology. 23.

Schlitz, I. (2018). Stop Playing Devil's Advocate, and Other Advice for Better Decision Making. Behavioral Scientist.


About the Author

Chiara Lamacchia is a consultant in legal, marketing & legal forecasting, working in corporate strategy for global organisations across different sectors, after an LL.M. from Bocconi University (Milan, Italy) and an MSc in Marketing from Edinburgh Napier University (UK). Chiara is the Founder of and, promoting the adoption of ground-breaking ways of using the law for innovation and competitive advantage.

Besides, among other things, she authored and published the book "Lawrketing – What Business Never Realised About Law", introducing a new concept, lawrketing, combining law, business, marketing and innovation.

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