Leading Contrarians

Contrarians, relax. This leadership lesson isn’t here to pick you apart. My aim is to help leaders bring out the best in you and help you bring your best to the teams you serve. I believe being wired as a contrarian is a superpower when it’s used for good. But in my experience, only one out of ten actually knows how to leverage that gift. I hope this teaching helps close that gap.

Let’s get clear on definitions. A contrarian is someone who instinctively and often immediately challenges ideas, assumptions, or plans, to test their strength. Studies show that 10 to 15 percent of people are naturally wired this way.

This is Part 2. Be sure to read Part 1: “Navigating Negative People."

Chronically negative people are terrible for team culture and default to criticism without curiosity. They offer no constructive alternative, and drain the room's energy rather than sharpen the idea.

Contrarians, on the other hand, are wired to push back first, but it is out of curiosity, risk awareness, or problem-solving impulse.

The key distinction is simple. Contrarians refine. Chronically negative people erode.

REVEALING THEMSELVES

Unskilled contrarians often come across as chronically negative, even though they're not.

Here’s how:

They challenge ideas and plans in a tone that comes across as superior. “Sure, if we’re not worried about the obvious problems.” The jab sounds like they assume the team is either blind or careless.

They often confuse skepticism with insight. “I’m not saying it’s wrong, I’m just not sold,” making it sound thoughtful, but they are not doing anything to move the idea forward.

They sometimes treat every discussion like a debate to win, not a plan to improve. That shows up when they keep dragging up the same objection long after it’s been addressed and the team has already moved on.

And my biggest peeve? When an unskilled contrarian plays their part in the meeting, then turns around in the hallway and uses snarkiness as a punchline. What they’re really doing is undercutting the team. Sarcasm and snarkiness can make great jokes, but when used to make points, they’re corrosive.

Salvador Dali is my favorite artist. My wife and I had the chance to see many of his original works at the National Museum in Madrid. I thought of those paintings while writing this section, because when an unskilled contrarian is in a team meeting, the whiteboard feels like a clock in a Salvador Dali painting... warped, drooping, and with skewed perspectives.

SKILLS CONTRARIANS CAN BUILD

Let’s briefly explore a few skills I coach contrarians on to develop their gift to make more full use of this untapped superpower.

Start with curiosity, not combat.
You don’t have to come in swinging with “This is a disaster waiting to happen” or “Are we seriously considering this?” Sure, those statements sound an alarm, but they also drown out any real conversation. But if you’re truly curious, people listen with interest. Try this instead: “Help me understand…” It signals you’re acknowledging the idea and genuinely testing its strength, not just shutting it down with attitude.

Don’t just spot the hole, offer a patch.
Saying, “That won’t work,” or “That’s going to backfire,” is just lobbing grenades. It might feel smart in the moment, but it leaves the team ducking for cover. Skilled contrarians say things like, “What if we flipped this piece and tried it this way?” Now you’re collaborating to build a better plan.

Check your tone.
You might be analyzing, but if it sounds like you’re doubting everything, people will hear it as negativity. A flat “That’s a stretch” or “I don’t buy it” might feel like you’re just thinking out loud, but to the team, it sounds like you’re shooting things down. It doesn’t take much… an eye roll, a heavy sigh, a “Good luck with that,” and suddenly your tone buries your point.

Clarify your intent out loud.
“I’m not against this, I’m just exploring a few potential issues we should look at.” That one sentence can change how the whole room hears you. It makes it clear to us that you want to sharpen the idea. Because when you sit there with your arms crossed and your face doing whatever your contrarian brain makes your face do… let’s be honest… your body language reads as if you think you’re some kind of brooding genius. So tell us you’re trying to help the idea become as strong as possible.

Know when to stop "contrary-ing."
There’s a time to speak up and a time to stop prodding and move forward. Once the team has made the call, let it go. If you keep circling back to the same point after a decision, you start to look like my dog when he won’t drop a sock. That’s not idea testing anymore, that’s your ego overshadowing the team’s decision.

LEADING CONTRARIANS

Now, leaders, unskilled contrarians are often a pain in the posterior because they present as a chronically negative person (again, see last week’s article linked here). But if you write them off as just difficult, you’ll miss their gift. The trick is learning how to pull the good out of them while helping them to see the difference.

Ask early for “the risks we’re not seeing.”
“Before we get too far, what landmines might we be missing?” That question permits contrarians to voice their concerns without making them sound negative. Don’t wait until the end of the meeting. That’s when a contrarian’s objections hit us like wet bread. Instead, invite them into the discussion early. Set them up to be a contributor and not just a critic.

Redirect when they drift from analysis into negativity.
Sometimes they’ll start sharp and useful. Then they slowly shift to negativity.

I hear it in their words. “Here’s the risk” starts slipping into “That will never work” or “This is doomed.” That’s your cue to steer it back on course.

As a leader, you can say something like, “Well, we want what we decide… to work. So, how do we solve the challenges you see?” That way, you’re not shushing them. You’re pointing them back toward solutions.

Keep conversations task-focused.
If they say, “This isn’t sustainable,” don’t clap back with, “Why are you always so negative?” Instead, ask, “Okay, what specifically is not, why, and what adjustments would make it sustainable?” Don’t make it about how they said it. Keep pulling it back to the substance.

Tell them when they strengthen a plan.
“That pushback made this better.”
“You spotted a risk I hadn’t seen.”
“You really helped us dodge a bullet.”

That kind of affirmation wires them to stay in the game productively. It also signals to the whole team that thoughtful challenges aren't just tolerated. They’re needed.

LET’S BUILD BETTER TEAMS TOGETHER

Yes, unskilled contrarians can be exhausting. But when they’re coached well and brought into the process correctly, they’re often the very ones who save the team from blind spots, groupthink, or charging ahead with a half-baked plan.

So contrarians, sharpen your gift. Don’t settle for being the one who turns the team whiteboard into a melting Salvador Dali painting. Stay curious. Be constructive. Learn when to push and when to let the idea breathe. Your voice can make things stronger, but only when it’s constructive will it actually be heard.

And leaders, develop them. Call out their value. When a contrarian is skilled and trusted, the team gets the full benefit of their superpower.

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