Does Your Business Need a Devil’s Advocate? How It Can Benefit Your Team

There are four things every business leader should do to help increase their success. The first three involve understanding the downside of your organization’s strengths, studying history, and allowing for imperfection. But the fourth one — having a devil’s advocate on your team — is probably the most important.

We all know about “yes” people, but do you have “no” people? This is a person (or a group of people) you can trust to help you step out of your own head and clearly examine the situation objectively. These are people who will not only tell you where weak spots might be, but help you actively see them on your own by being able to clearly communicate in a way that resonates.

This is advice every leadership book and business coach in the world gives:

• Don’t hire people who are going to tell you what you want to hear.
• Hire people who are smarter than you.
• Create a team of people who are going to push back and play devil’s advocate.

Having a devil’s advocate on your team isn’t easy

It’s incredibly challenging to have a devil’s advocate. We all have enough of an ego that it’s hard to hear when we’re wrong or someone disagrees with us.

When you start a business from the ground up, put all of your sweat, tears, heart, and money into it, and have your entire life wrapped into it, it’s really hard to hear your baby is ugly.

And that is exactly what a devil's advocate does. They tell you your baby is ugly … and then help you figure out how to make it pretty.

You waffle between wondering why things have to change when it’s been working great all along, and wondering why you didn’t make the suggested changes (or think of them yourself) a zillion years ago.

Sometimes a devil’s advocate wants to make change for change’s sake, and sometimes they want to make change because it’s the right thing to do.

As the leader, you have to figure out the difference and either push back or set your ego aside and listen. Really listen. And then take action.

5 steps to responding to feedback from your devil’s advocate

So how do you decipher between change for change’s sake and change that will make a difference?

First, put your ego aside. It’s not easy. But you can do it, I promise.

You may cry. You may get really frustrated. You may get angry. You may have to drown your sorrows in a bottle of wine (not that, you know, I’ve ever done that).

Then you’ll put on your grown-up pants and follow these steps:

• Listen. This is the hardest part because you’ll listen and you’ll feel yourself getting defensive. You cannot do this. You have to listen without formulating your response. You have to listen without interruption. You have to listen and then think. Sometimes you may have to go away for a day or two before you respond.
• Back up your position. If you disagree with the devil’s advocate, back up your position. Tell them why. Perhaps you have knowledge about the business they do not have. Perhaps you’ve tried their suggestions in the past and they didn’t work. Begin a conversation about it and let them tell you why they think it will work this time.
• Ask yourself, “Does it go to our vision?” Sometimes the devil’s advocate will suggest things that are really great ideas, but take you away from your vision. Restate the vision and get them on board. But if it does go to the vision, it’s probably a good thing to consider.
• Use “Yes, and …” I learned this trick from reading Tina Fey’s Bossypants (which is a great book if you haven’t read it). It’s a trick they teach you in improv. Rather than saying “no” or “but,” agree with the suggestion and add your two cents. This creates a collaborative discussion instead of a defensive and frustrating one.
• Concede defeat. There are going to be times—more times than you’re probably willing to admit—that you’ll have to concede defeat. The devil’s advocate will have won and you have to give them their gold medal.

Being the big boss is more about conceding control, motivating people to succeed, and coaching them to be their very best. If you can’t do that because your ego is in the way, no one will win.

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