Field Manual: Entry # 2 – Distinguishing the Devil from the Devil’s Advocate

Building a team is an essential stepping stone in the progress of a project or enterprise.

As we learned in the last field manual entry, being the leader can be lonely and even damn right despairing.

Being bombarded left and right with comments, doubts and skepticism comes with the job. The question now is, does it make sense to have that atmosphere internally?

A devil’s advocate can be an asset. Showing you a perspective that you didn’t see or addressing concerns that a possible consumer might bring up. But, you need to be sure your so-called devil’s advocate is not the devil in disguise.

The “devil” can rip your organization apart from the inside. 

Here are some questions that you can use as guide to help distinguish the Devil from the Devil’s Advocate (be reminded, friends, family and significant others are NOT exempt):

1. Is the person listening for failure or listening for success?

It may seem like a semantic conundrum but there is a major difference.

When one listens for failure, they will give a comment for the sake of shooting an idea down (and usually for no other purpose). 

Anyone who’s been in a college defense or murder board, knows that it may give you a few insights and train you take a few blows but it will usually end up with you feeling like shit (unless you’ve gone numb – which is an entirely different problem altogether).

On the other hand, listening for success is a delicate process of giving comments of a constructive nature. The person has your back and is looking at what’s best for the endeavor. Almost as if the person was a gardener nurturing a small seed.

So, how can you tell one from the other (aside from whether or not you feel like shit or strangling someone)?

A concrete indicator is when all you seem to hear is criticism/comments and no concrete action points. Or, when they shoot it down and they try to absolve themselves by saying some version of “But, don’t get me wrong, I’m here for you.” Kind of like saying, “You’re ugly… just kidding. But, I wouldn’t date you.”

In situations like that, I stand my ground and I say something like, “I got your concerns. But you’re not helping. Give me a real suggestion or shut up.” Paraphrase depending on your patience levels. Or, I simply cut them off. No, really, I cut them off…

The Devil listens for your failure (consciously or unconsciously). The Devil’s Advocate listens for success; pulling the team and your vision forward.

And, what question do you ask to know if the devil pulls you down?

2. Will the person’s pessimism and negativity pull down the team?

Negativity, like drama, is contagious. 

I’m not being figurative or relying on the observations of philosophers like Seneca. Studies have suggested that it’s a real phenomenon. Negative opinions catch on in a group.

Weigh your options. If you think having this person on the team will be more detrimental to the success of your project than having their skills, talents or opinions, maybe it’s better to move on and cut your loses.

I have intentionally avoided people with great skills and experience on my team simply because of their negative attitude.

You get enough negativity externally, why pollute the water with something toxic? Because before you know it, you may have more than one devil in the mix. Then you have a whole team doubting what’s possible. Plus, you may have a workplace where you produced a result but you all hate working with each other. In the end, it’s not sustainable.

Negative people can “help out” all they want but remember you may need to manage their negativity if you keep them on board.

Which brings us to the last question…

3. Will you be spending more time managing this person’s concerns rather than working on your mission and vision?

I can’t stress this more… balance.

Again, weigh your options. Will the person’s skills and contributions outweigh the time and effort it will take you to appease them?

In connection with question number 2, ask yourself, is it worth it?

Remember that their ever-growing concerns (whether warranted or unwarranted), may catch on. If you have a group of people who constantly doubt your decisions, you may start doubting your own choices. Moreover, you will end up explaining everything you plan to do rather than acting on what really matters. 

A little doubt is good. A lot of it is destructive.

And, ultimately, this may hinder innovation, disruptive thinking and action within your team. Analysis paralysis. If you’re a start-up, you usually won’t have the time to deal with all of that in the initial stages.

Simply put, you’ve got better things to do. Like running your project or enterprise.

So ask these questions. Get clear on who you’re working with.

Having a Devil’s Advocate, listening for success, can produce amazing results. Dealing with the Devil, who listens for failure, is toxic and unproductive.

Field Manual is a series of instructional insight-driven posts designed for founders, entrepreneurs and changemakers.