Looking for the other side of the story may not always be easy or fashionable. However, sometimes looking for the other side of the story can lead to breakthroughs and insights that may have otherwise been overlooked. Taking a look at the opposite side of something is one aspect of taking a contrarian point of view.

There is more to just looking for the other side of the story to being a true contrarian. However, there are skills and tips you can use in your everyday interactions that have contrarian elements. Below I have shared three ideas for thinking like a contrarian. Before getting into them let’s talk about what it means to be a contrarian and to highlight a few famous contrarians.

Being a Contrarian

What does it mean to be a contrarian? The definition of a contrarian is below.

A contrarian is a person who takes up a position opposed to that of the majority, regardless of how unpopular it may be.

There are times when it is very difficult to be a contrarian. By definition a contrarian takes the opposing view. Beware: Contrarian styles of argument and disagreement have historically been associated with radicalism and dissent. (source: Wikipedia).

Even though thinking and acting like a contrarian can be controversial there are benefits to you and your efforts to make good decisions. I personally think that being able to hold a conversation from a contrarian point of view will help your career — including your interviewing skills, your ability to make an impact in meetings, and your ability to help your business grow.

Famous Contrarians

Three Tips for Thinking like a Contrarian

Below are three ideas for starting (or perhaps ending) a conversation. I hope these three tips will be used to spawn conversations and not end them. However, don’t be surprised if people and groups jump on the person that brings up these points. The first one is a little more aggressive and the second is a little less so. The last one is seeking a positive outcome. I suggest you try one of them — pick the level of controversy you are up for and start asking:

So what?

Someone I work with often says “So What?” when listening to ideas and plans.

Not because he wants to be confrontational. It’s because he wants to make sure you have thought about your idea and thought through the possibilities.

What If?

You can play devil’s advocate. Again, not to be confrontational. Rather to think about the other side of the issue. Assign yourself or ask someone else to play the role of the contrarian and to try and poke holes in your argument.


This is one of my favorites. It’s not purely a contrarian thing. It’s almost the opposite of a contrarian point of view in that it’s looking for the optimistic side of things.  SBO is what I call “Step Back Optimism” and I use it to do just what it says. Take a step back — literally or figuratively (or both) — to evaluate a given situation. The intent is to look for the optimistic end result.

So what? What if? and SBO — Three Tips to Consider when you want to ask questions like a Contrarian

Try them all. Do what works for you. Sometimes one will work better than the others. Sometimes all three can be used together.

The point is to consider other options and other possibilities. The goal is to make better decisions. The result should be faster decision cycles and the ability to create a process for evaluating ideas. Whether they are solo decisions or decisions where a group is involved.

What do you think?

  • Are you naturally a contrarian?
  • Do you include contrarianism in your decision making processes?
  • Will you consider adding contrarianism to your decision cycles?

Drop a comment here. I’d like to hear your thoughts.


Jeff  is a veteran in the Enterprise Content Management industry. Over the past 20 years he has worked with customers and partners to design, develop and deploy solutions around the world. Jeff is currently the Director of Strategic Alliances at Winshuttle. He has worked for Microsoft, FileNet (IBM), K2, Captaris, Open Text, Kofax and Kodak. He speaks and blogs about ECM and the Intersection between Social, Mobile and Cloud Computing.