Leadership: Questioning the Foregone Conclusion

Playing the devil’s advocate.

I had not expected the emotional response I received to those four words when I raised them a few weeks ago. Exasperated, the woman across from me stated how she despised people wasting her time by playing the devil’s advocate. I was surprised to say the least as I had always thought it to be a very constructive technique. One which I’ve employed successfully throughout my career.

So, before I go on, let’s clear things up. According to Merriam-Webster, the devil’s advocate is:

1.   a Roman Catholic official whose duty is to examine critically the evidence on which a demand for beatification or canonization rests

2.   a person who champions the less accepted cause for the sake of argument

Well then. What I’ve been doing is obviously not related to the first definition, nor am I arguing for the sake of argument. In my glass half-full view, I see it as a little of both.

I don’t have a better name to describe a conscious, critical review of all options at the time when one idea appears to be favoured over all others. (This clarification is important, as this form of assessing options is long past the point of brainstorming, it occurs only when one idea becomes the clear choice.) All it takes is one brave person to find their voice around the boardroom table, the watercooler or wherever ideas are conceived at your workplace. Below are some of the reasons why they are helpful to you as a leader.

3 Benefits to Having a Devil’s Advocate

1.      Trap: group think. This is especially true if you hold a position of influence in the organization or are a subject matter expert. Other contributors may feel intimidated to speak up and question your suggestions for fear of reprisals or to avoid looking incompetent. As smart as we all think we are, the whole point of bringing a group together to resolve an issue is to hear contrary viewpoints and develop the best solution possible.

Escape: ‘What options are we overlooking?’, ‘What have we not thought of?’ If you realize you are at risk of group think, challenge the group to come up with the best alternative to your idea. Give them the freedom to do so until they become comfortable enough around you to understand they will not be reprimanded and that sometimes the subject matter expert could benefit from a 30,000-foot viewpoint. The secondary trap that awaits you is how to address subsequent options if they clearly fall short of the main solution being considered. Being too quick to dismiss an alternative may result in that person never raising their voice again, so spend time exploring the opportunities you are presented as a group and be prepared to moderate.

2.      Trap: the perfect solution. We’ve all been here. That one-size fits all solution materializes to solve not only your website needs but it will also cure acne, force your teenager to do their homework and create world peace! You’d be a fool to not move forward. Sure, there are some unknowns to be dealt with but we can address them as the come, right? 

Escape: ‘This is the solution we are looking at, tell me why it won’t work.’ Think of it as a mini-thesis defense. Ask those around you to figure out why it won’t work. Certainly, you will have thought of some of their responses, but you might be surprised but what they come up with. I highly encourage you to not only ask people with deep understanding of the issue you are trying to resolve, but also those that do not. Climbing out of the weeds can result in a reset of your perspective and some creative idea generation.

3.      Trap: not seeing the forest for the trees. Your idea makes sense technically, fiscally and/or logically. It is sound. Nothing has been overlooked. You will create a new procedure manual with every step defined and then on Monday it will be rolled out to the effected staff (insert face palm emoji).  

Escape: ‘How will this impact people directly involved? Indirectly involved?’, ‘Have we considered the optics of implementing this idea? Will it cause problems for other departments/teams?’  It is surprising how many snap decisions are made that involve people and yet their response is either not considered or is a complete shock to the decision makers. This trap is particularly destructive to team dynamics and is often a key to unsuccessful change management initiatives. 

As a leader, when your words carry more weight, it is important to create a culture that respectfully questions your ideas so you can avoid these traps. Being the devil’s advocate opened a lot of doors for me early in my career and allowed me to learn a great deal more about the businesses I worked for. It can take a lot of courage to speak up in front of peers and the higher ups though. By trying out some of these escape questions/clauses, you can foster that ability to respectfully question ideas within your teams. 

Do you have any experience successfully playing the devil’s advocate or creating a culture of respectful questioning? What I have I left out? Please tell me about it in the comments.