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This post is part of a series on practical methods for stress-testing your ideas (and ultimately validating your sparks of inspiration). Missed the introduction? Check it out here.
You’ve probably heard the phrase ‘playing devil’s advocate’ before, perhaps in the context of having an intellectual discussion or a debate with a friend. This is sometimes also described as contrarianism—taking an opposing viewpoint for the sake of enriching a discussion. Or to “stir the pot”, in the case of some people.
One of the fastest, cheapest ways to test your idea is to try and tear it down—before someone else does. That’s where the contrarian method comes in. Also known as “playing devil’s advocate,” this is a deliberate attempt to challenge your own thinking with the help of a trusted critic. Done right, it’s an excellent stress test that can save you time, money, and heartache.
To play devil’s advocate in a way that helps you validate your sparks of inspiration :
What You’ll Need
A quiet space, conducive to discussion without distraction;
A devil’s advocate (a person whom you trust and can converse freely with about ideas);
A scribe (a person or AI assistant who can take notes / transcribe the exercise so that you and the devil’s advocate can focus your mental energy on the discussion without breaking character to write down notes).
What You’ll Do
Think through how you would present your idea to someone who knew nothing about it, or the topic, and jot down some notes to refer to while engaging another person or persons;
Round up a trusted confidant and set aside some time with them to run through the exercise with as the devil’s advocate. Importantly:
Remove yourself from environmental distractions (if you work in a busy office, go off-site);
Block off sufficient time to focus on the exercise and engage in rich discussion (depending on the scale and complexity of the idea, it might need an hour… or it might need the better part of a day);
Remove any technology distractions (laptops closed, smartphones set to silent unless either is essential to communicating the idea—in which case, shut them off when finished);
Before beginning the exercise, set (or reiterate) the basic ground rules with your devil’s advocate:
Their role is to think critically about the presented idea, and explore it through question and criticism with the objective of invalidating the spark (removing confidence that it could work);
They can ask questions or for clarification wherever needed in the discussion in order to better understand the idea and highlight points of weakness in it (often for further discussion);
Though their immediate objective in the exercise is to weaken the spark (idea), the ultimate goal is to refine a shared understanding of under what conditions the idea could work;
They should feel free to be highly critical of the spark (idea), but it’s important that the criticism should always be focused on the idea and never the people involved with it. Playing devil’s advocate is not an adversarial, hostile role—it’s an inquisitive one;
There should be no fear of repercussion from you or other leaders toward the devil’s advocate if you don’t like what they have to say. The purpose of the devil’s advocate is to strengthen an idea by attempting to tear it down.
Ask the scribe to begin recording or taking notes for the session;
Begin by presenting the idea to the devil’s advocate, who should make every effort to allow you to finish before asking questions (unless a clarification allowing them to understand what you’re saying is needed);
After the idea presentation is complete, kick of the inquisition by the devil’s advocate by asking them, “Why won’t this work?”
The devil’s advocate should respond by making sound statements and ultimately asking questions with the intent of poking holes in the idea and highlighting problems with it and your underlying assumptions.
You can respond to these questions in a manner which is conversational—there’s no set structure to this part of the exercise. Simply, you should debate freely with the devil’s advocate. Your goal is to refine the idea and build confidence in it. The devil’s advocate’s role is refine their understanding of the idea and undermine confidence in it.
When the session concludes, the scribe should summarize their notes for everyone involved including a list of takeaways or action points that arise from it.
It can be useful to have whiteboards or notepads for sketching present for use by you and/or the devil’s advocate. The devil’s advocate also doesn’t have to be a single person—a small group of people with diverse expertise can collectively play the devil’s advocate drawing from their own backgrounds. Though having more than one person “gang up” on your idea can feel more mentally draining, this approach often does yield more useful results.
Pros of this Method
Very little advance planning required;
Very little investment of time required, relative to other methods;
Can serve as a fantastic ‘first step’ in a deeper process of validation (you can use more than one of these methods in sequence if desired);
Forces you to strengthen the underlying assumptions behind your spark;
Cons of this Method
Finding the right devil’s advocate can be difficult (they criticize the idea, not the person, and they have strong critical thinking skills);
The devil’s advocate will have their own inherent biases and motivations, no matter how hard they work to suppress them for the purposes of the exercise;
A robust criticism of the spark (which is the point) may discourage you from pursuing the idea further, even if it could be viable under certain conditions;
This method feels robust and can lull you into a false sense of security—remember that it’s not a substitution for market feedback. Never pull the trigger on substantial investments due to the outcome of this exercise alone.
Notes on Using AI
You might also find it useful to engage in devil’s advocate with an LLM-based AI tool playing the part of devil’s advocate. This can be more comfortable for some people, and less time-consuming. However, there are some very important things to remember if you choose to use generative AI in this way:
Despite the marketing by leading-edge model developers, LLM systems do not reason in the same way which humans do—they simply predict what text is statistically most likely to be what the user wants in response to their query.
LLM systems score very poorly on assessments of critical thinking skills for the same reason—don’t expect an AI tool to reason deeply and factor in the nuance behind your underlying idea.
LLM systems hallucinate. They lack the ability to strictly ground their text outputs in fact, and to do their own fact-checking (for now, at least).
As such, I suggest only considering using an AI system as the devil’s advocate to sharpen your own skills in advocating for your spark or for very simple ideas that don’t require a lot of context or understanding of the specific nuances of your business or industry.
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