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Hi Reader,

I once had a colleague who was always contrary in team meetings. She would constantly bring up potential problems and issues with whatever we talked about.

Yet, she did it with a smile and a mischievous glint in her eye.

At first I thought she just liked being difficult, but over time I realized she was doing us a huge favour. She was spotting risks we might have overlooked, and in her own playful way, she had become our team’s very own Devil’s Advocate.

History of the Devil's Advocate

The Devil’s advocate actually began as a real job in the Catholic Church. The official title was “Promoter of the Faith,” and their role was to argue against someone becoming appointed a saint.

They were supposed to be skeptical, question the candidate’s character, the evidence, and argue that the supposed miracle was fake. Can you imagine being hired to say, “Well yes, they were holy, but what about that one time when they did this?”

Nowadays, when someone is playing devil’s advocate, they are usually taking a side they do not necessarily believe in, just to see if an argument can hold up. It is not about committing to the other view so much as stirring the pot to get everyone thinking.

Devil’s Advocates fit into the broader conversation about team personalities, something I’ve touched on before, especially in this past article. A Devil’s Advocate can also be an extrovert, ambivert, or introvert, and brings a unique perspective to a team.

Stirring the pot

My colleague loved pot stirring and she did it quite well.

There was a time when we were co-leading a major initiative and working closely with a new partner. Everything seemed to be going smoothly until, in the middle of an important meeting, she asked what we would do if the partner pulled out. I brushed it off, pointing out that the contracts were solid and there was no way that would happen.

With that mischievous glint in her eye, she pressed, “But what if it did?”

You can probably guess where this story is headed. Sure enough, the partner pulled out, and we were left with nothing to show for all our work.

Luckily, because this exact scenario had been brought up ahead of time, we had already talked through what we would do, raised the risk with our superiors, and even lined up a potential backup partner.

So when the worst actually happened, we were ready. We got the new partnership running quickly, and in the end it did not impact our timelines.

Who's your Devil's Advocate?

You only need one Devil’s Advocate on your team. The real trick is recognizing who that person is. Often, it’s the one who speaks up with the unpopular opinion or challenges the group’s assumptions.

Instead of shutting them down for being “too difficult,” invite them in. Give their perspective space, and let the team hear them out. What might feel like contrariness is often exactly what keeps a project moving forward smoothly.

Sometimes the person who asks the toughest questions is the one who saves you from the toughest problems.

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