Having a ‘devils advocate’ around you is one of the most productive relationships you can have in a complicated enterprise. Such a relationship enables the stripping of any position held back to its core, removing the bias, preconceptions, and power of the status quo, but leaving room for intuition born of domain knowledge, experience, and most importantly, data.

You should seek out and nurture such relationships.

The most successful commercial relationship I have had was with a bloke to whom I reported for a long time, in two different businesses. Vigorous ‘conversations’ took place as a natural part of determining the best course of action to take, the best allocation of limited resources, with each testing the positions taken by the other.

The eventual outcome was more often than not, one that would not have emerged without such a process, although we both knew who held the power of veto, and from time to time, it was used.

I was reminded of this relationship recently in a conversation with a client who had reached a conclusion I thought was absolutely wrong. It was based on flimsy information, the opinion of someone whose opinion in this matter was in my view skewed by some unfortunate and irrelevant bias, and a reverence for the status quo which appears to me to be destructive.

I went through my standard list of  ‘Devils questions’ to no avail. Tell me what questions I should have asked on top of those below in an effort to help him consider the real merits of the decision he was about to make.

  • What is the source of the data you are quoting? Without a reliable, robust and repeatable data source that stands up to scrutiny, an ‘insight’ based on it is just another opinion.
  • How did you get from the ‘data’ quoted to the ‘insight’ you appear committed to? I like to see logic chains, definable cause and effect, when gathering insights from data, and am wary of leaps of faith that do not have the authority of logic and experience.
  • What biases have you have built in from your background and experience? Nobody is immune from some level of built in bias, a good devils advocate holds up a mirror to them.
  • What other options could there be based on the same data? In most situations, there is more than one way to interpret and leverage data, opinion, experience, and outside knowledge. Playing the ‘options game’ as a part of a conversation is a very useful tool.
  • How do we test the insight without betting the farm? These days the ability to test has been multiplied a thousand fold by the digitisation of everything, it is no longer wise (if it ever was) to bet the farm. The scientific method rules!
  • What will you do if you are wrong? Learning from mistakes, and applying the learning is the basis of improvement, and without an inclination to learn from mistakes, you will be destined to repeat  them, usually for  the same reason they were made in the first place.  In addition, answering this question almost inevitably opens up other options for consideration that may not have been adequately considered, or completely missed in the conversation.

Devils can be very helpful when used well, but they also have the power to be destructive, so be careful with whom you dance.