11 Ways to Handle Your Devil’s Advocate Without Getting Burned

I was struck hard by this cartoon honoring superstar children’s author Maurice Sendak, who passed away recently.

Sendak was a fearlessly innovative storyteller, who introduced previously taboo topics and tone into his work beginning with Where the Wild Things Are. It’s no surprise that the childrens’ publishing establishment didn’t welcome his innovations with open arms, but Sendak persisted with game-changing results.

“When it was published in 1963, the book was hated by critics and banned in libraries. Wild ideas always attract naysayers. But wild ideas are the ones that make a dent. Where the Wild Things Are is one of the most awarded and influential children’s books in history. But too often wild ideas are smothered or diluted before they’ve really had a chance,” says Marketoonist Tom Fishburne.

Friend or Foe?

“Design great Tom Kelley once called the devil’s advocate the single greatest threat to innovation,” says Fishburne, “because a devil’s advocate encourages idea wreckers to assume the most negative possible perspective. Once those floodgates open, they can drown a new initiative in negativity.”

It’s true. Your devil’s advocate will introduce a bump or two into the smooth path of your fundraising and marketing groupthink.

But I’d argue that those bumps can be hugely important., and I’m in good company here. “Decisions…are made well only if based on conflicting views, the dialogue between different points of view, the choice between different judgments,”  wrote management guru Peter Drucker in The Effective Executive.

You’ll find a striking model in Toyota’s ramp up of a devil’s advocate strategy after recalls across models and production plants deflated its previously golden reputation.

Shift Your Devil’s Advocate from Foe to Friend

You face the occasional devil’s advocate as you move fundraising and marketing agendas forward, just as I do. Here’s the approach that works best when a devil’s advocate surfaces in one of our client organization teams:

1. Open your arms, and your mind: Despite the pain of facing a devil’s advocate, the product of the mash-up is frequently better than the original idea.

Be proactive: Look back on previous sparring for the useful takeaways, and keep that value add in mind, even when you feel like screaming in frustration.

“The devil’s advocate is your the most powerful ally in getting an idea across the line. I include that person early in the idea stage because they help produce a robust result. They also become the greatest sales person for the idea as they see the other sides better than those who are just hesitant, “ says nonprofit consultant Doug Watson.

2. Acknowledge the downside of conformity: You want to move quickly and smoothly to implement your idea or program, just like I do. But you’ve seen that rushing to approval or release ends up a complete disaster or, at the very least, generates diminished results.

The squeaky wheel can be your most valuable advisor. Listen up!

3. Encourage debate: Dissent doesn’t always come when you want it, but your openness to other ideas will shape the environment as one that’s productive, rather than acrimonious.

4. Pick your battles. You’ll lose ugly and often when you go head-to-head on every pushback. Focus on the fights (a.k.a. discussions) that really matter.

5. Depersonalize the difference of opinion, maintaining focus on the project goal. Avoid personal pronouns.

6. Leave your fear at the door, staying calm and confident. Devil’s advocates tend to pounce when they see weakness.

7. The power of three: Ensure that it’s not just you and the devil’s advocate slugging it out. That’s the quickest path to an ugly stand off.

An odd number of discussion participants (three or more) eases decision making. Three (or five or…) is a balanced tripod, rather than a tug of war.

8. Embrace co-creation with a thank you. You have it, whether you want it or not. Thank the devil’s advocate for testing the feasibility of your idea.

9. Have proof points ready—models from competitive and colleague organization, stats, stories from peers in the field. Validation trumps opinion every time.

“A couple of years ago I was invited to be on a panel about social media at a managers’ retreat with our HR and IT folks, both of whom were very wary of this “new” thing.”

The week before I had attended a wonderful workshop with Shel Holtz, focused on why organizations should allow employees access to social media on the job. I came to our retreat armed with objective, specific stats and stories (versus my colleagues’ vague worries) that opened their minds and built their confidence. I blew them out of the water,” says Bobbie Lewis, Director, Communications, Lutheran Social Services of Michigan.

10. Redirect: Ask the devil’s advocate for his alternative solution to the problem he voices.

It’s far easier to punch holes in someone else’s idea than to come up with a good one of your own, but he might come up with something great, and you’ve fulfilled your responsibility to listen.

11. Turn devil’s advocacy on its head—Assign someone to ask the tough questions in all major decision making.

Dissenters are frequently hated, squashed or ignored. So share the wealth.

Rotate the role of taking an opposing point of view to a different team member each time you face a significant decision. But skip those individuals who aren’t likely to push back on groupthink.

Have fun with this—to depersonalize and add a laugh—by having the devil of the day wear a wacky hat.

Follow this 11-step path to turn your devil’s advocate into a productive partner. Let me know how it goes!
What about you? How do you handle your devil’s advocates? What are your techniques for shifting them from foes to friends? Please share your stories here.