A Case For Playing Devil’s Advocate

Content was originally published on Inc.com on April 2, 2019.

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I recently shared the idea of the business coaching concept of the six hats from the Late Dr. de Bono with our readership and I wanted to go into more detail about the third hat in the series: The Black Hat. This hat is often one that doesn’t go over very well in meetings. It’s the one that plays the devil’s advocate and asks the questions that no one else wants to ask.

What Is A Hat?

A “hat” is not a physical piece of clothing, but a state of mind. It is a tool that can be used to push the boundaries of thinking and help you grow as a group and as leaders. You can think of a hat discussion as a movement, NOT an argument. It’s not about asking questions like: “Is this correct?  Do I agree/disagree?” Instead ask yourself:  “Where does this idea take us?”

Black Hat:  Your Protective Counterpoint

A lot of successful people get so used to thinking positively that they often do not see problems in advance. This leaves them vulnerable to difficulties that may arise. When you wear your black hat during meetings or mastermind groups your job is to focus exclusively on what is wrong or could go wrong.  This is the hat that deals with cautious risk assessment and wants to protect you from pain.  It cares most about survival and keeping you safe by looking for what’s wrong.  This is the “traditional” western critical thinker.  It anticipates obstacles and kills bad ideas before they get you into trouble.

A word of caution here: wear this hat for very short spurts of time. There is a fine line between killing ideas or good ideas that have simply not been fully flushed out.

How to Use the Black Hat:

  • Look at a decision’s potentially negative outcomes.
  • Look at it cautiously and defensively.
  • Try to see why it might not work.

Questions to Ask While Wearing the Black Hat:

  • What is wrong here?
  • What could go wrong?
  • How could this come back to haunt you?
  • What are risks here?
  • How would a skeptical thinker see this proposal?
  • Why should we say no?

Key Descriptive Phrases To Help With the Process:

  • Skeptical skeptic
  • Applying the brakes
  • Devil’s advocate

Why Should You Wear The Black Hat?

In most cases playing the Devil’s advocate isn’t a popular choice during meetings and mastermind sessions. Which is exactly why it’s so important to fuel future growth. A few minutes of a black hat session can help you in several ways.

  • Prevent you from doing something stupid or costly or painful…
  • Highlight the weak points in a plan.
  • Layout the landmines and pitfalls onto the map so that you can plan to avoid them
  • Help to make your plans “tougher” and more resilient.
  • Push you to come up with even better solutions and clearer thinking
  • Fight your own confirmation bias.
  • Allow everyone, including the person who proposed an idea, to be critical and find potential pitfalls

Important Things To Remember About The Black Hat

The most important thing about the black hat is that you wear it consciously. When playing Devil’s advocate during a business meeting, it’s important to remember that it’s not about winning an argument or having an excuse to argue. The goal is to pinpoint areas of weakness to allow yourself to plan for all possible outcomes. Wear the hat for a few minutes at a time, and then move onto other thought exercises. Spending too much time thinking of all the negative things that could happen can quickly change the tone of your meeting if you aren’t careful. Always be logical and not emotional (otherwise it’s under the red hat).

Model Black Hat Thinkers:

  • An attorney you are consulting with
  • A police officer on patrol
  • The captain of the guard
  • Warf
  • Chief of staff

In black hat thinking, parallel thinking becomes critical… when people bring up conflicting black hat ideas, simply put them both down and move forward in your thinking.  Only choose between the two if you absolutely have to, and usually you don’t, at least not during the black hat part of your thinking.


A Case For Playing Devil's Advocate
Article Name
A Case For Playing Devil's Advocate
A little critical thinking goes a long way....
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Maui Mastermind Business Coaching
Business David is a Wall Street Journal and Business Week bestselling author of 11 business and financial books. A syndicated columnist for Inc.com and HuffingtonPost.com, David’s articles have appeared in over 6,500 publications. As the founder and CEO of Maui Mastermind®, David has worked with 100,000+ business coaching clients and community members to buy, build, and sell over $5 billion of businesses.