The Courage to Disagree

I’ve been thinking about disagreeable people lately (myself definitely included), although probably not in the way you would think.

I’m not talking about people who are rude, combative, spiteful, or who simply enjoy arguing for the sake of arguing. I have no particular interest in that kind of disagreeableness. What interests me is something I’ll call productive disagreeableness: the willingness to challenge an idea, question an assumption, say no when necessary, and stand up for something you believe, even when your position isn’t particularly popular or welcome.

The more I think about it, the more I believe this is an enormously valuable trait, particularly in business. We spend a lot of time teaching people how to collaborate, build consensus, listen to others, and work well in teams. All of those things matter. But there are moments when maintaining harmony and getting to the right answer are simply not the same thing. In those moments, somebody has to be willing to create a little friction.

Jordan Peterson got me thinking about this through his discussions of the Big Five personality traits. One of those traits is agreeableness. Highly agreeable people tend to be compassionate, cooperative, accommodating, and sensitive to others' needs and feelings. Those are obviously valuable qualities, and they make agreeable people pleasant colleagues, friends, spouses, and neighbors.

But every strength has a point at which it can become a weakness. If maintaining harmony becomes overly important, you may begin to avoid necessary conflict. You may recognize that something is wrong but decide not to say it. You may accept a mediocre piece of work because you don’t want to hurt the person who produced it. You may accept a bad deal because negotiating harder feels uncomfortable. You may sit through another meeting because declining the invitation feels rude. And perhaps most dangerously, you may find yourself supporting the consensus simply because challenging ten other people in a room requires more courage than going along with them.

At some point, being agreeable can become more important than being right.

What makes this particularly interesting is that agreeableness and intelligence are different things. A highly intelligent person can also be highly agreeable. In fact, that person may understand perfectly well that the group is heading in the wrong direction and still remain quiet because speaking up comes with a social cost.

Imagine ten smart people sitting around a conference table. Nine of them believe X. The tenth person believes X is completely wrong. That tenth person may be the most important person in the room, but only if they are willing to speak.

Intelligence may help you see something other people don’t see. Productive disagreeableness helps you say it when other people don’t agree.

Peter Thiel has a wonderful way of testing for something very close to this. One of his famous interview questions is: “What important truth do very few people agree with you on?”

I’ve always loved that question because it tests something beyond intelligence. It asks whether you have thought independently enough to arrive at a conclusion that differs from the prevailing consensus. More importantly, it asks whether you are willing to own that conclusion. Thiel makes the point beautifully when he writes that “Brilliant thinking is rare, but courage is in even shorter supply than genius.”

That gets to the heart of productive disagreeableness. You might be smart enough to recognize something that everyone else has missed, but are you willing to say it out loud? Are you willing to defend it? Are you willing to have everyone else in the room look at you as though you are the one who has lost the plot?

Over my life and career, I have spent countless hours thinking deeply about productive disagreeableness as the willingness to tolerate social friction in pursuit of a better outcome.

Once you define it that way, you begin to see it everywhere. A good negotiator has to be willing to say that the deal isn’t good enough and perhaps walk away. A good manager has to be willing to tell someone that their work doesn’t meet the standard. A good investor occasionally has to believe that the market is wrong. An entrepreneur, almost by definition, has to believe that there is a better way to do something that thousands of other people have somehow failed to see. A leader sometimes has to make a decision that people dislike today because they believe it will produce a better outcome tomorrow.

And then there is one of the simplest and hardest forms of productive disagreeableness: saying no.

I’ve spent a lot of time thinking about Big Rocks and the 80/20 principle. We talk about prioritization as though the difficult part is figuring out what matters. Sometimes it is, but I don’t think that’s usually the hardest part. The hard part comes after you know what matters.

The hard part is everything you have to stop doing.

If you decide that one or two things are genuinely your Big Rocks for the week, then dozens of other things cannot be. Every meaningful yes creates a collection of noes. No to the meeting. No to the interesting side project. No to someone’s request. No to something worthwhile that simply isn’t worthwhile enough. Sometimes it means saying no to someone you genuinely like and would genuinely like to help.

That requires a certain amount of productive disagreeableness. If you are unwilling to disappoint anyone, you will eventually end up with twenty priorities. And twenty priorities are no priorities at all.

There’s another idea I’ve written about before that I think fits perfectly with this one: strong opinions, loosely held.

Productive disagreeableness supplies the first half. You need enough conviction to put a stake in the ground and say, “This is what I believe, and here is why I believe it.” But loosely held supplies the essential counterweight. You also need enough humility to listen to the argument on the other side and pull that stake right back out of the ground when the evidence tells you that you were wrong.

Without that second part, productive disagreeableness simply becomes stubbornness. The point isn’t to win arguments. The point isn’t to be the contrarian in every meeting or to build an identity around being the person who always disagrees. In fact, disagreeing simply for the sake of disagreeing is probably just another form of conformity.

The point is to get closer to the truth and, ultimately, to a better outcome.

I think this is especially important in organizations because they naturally drift toward agreement. People want to get along. Projects acquire supporters. Nobody particularly enjoys telling a colleague that their favorite idea should be killed. Nobody wants to tell the CEO that his idea is terrible. Meetings get added much more easily than they get removed. Initiatives multiply. Standards gradually soften because making an exception today is easier than having an uncomfortable conversation.

A little productive disagreeableness can act as an antidote to all of that.

The more I think about it, the less interested I am in whether someone is fundamentally “agreeable” or “disagreeable.” What I want—in myself and in the people around me—is a particular combination: warm personally, disagreeable intellectually, demanding about standards, and willing to be proven wrong.

You can respect someone deeply and still think their idea is completely wrong. You can care about someone and still tell them that their work isn’t good enough. You can passionately defend an idea on Monday and abandon it on Tuesday because somebody showed you evidence you hadn’t considered.

In fact, that may be one of the healthiest cultures an organization can create: one where people are kind to each other but hard on ideas.

So perhaps the lesson isn’t that we should all become more disagreeable. It’s that we should become more willing to disagree when disagreement matters.

Don’t confuse agreement with truth. Don’t confuse disagreement with conflict. And don’t assume that because everyone around the table agrees, everyone around the table is right. The clock should never run out for a valid Socratic question that starts with “Why”

Sometimes the most valuable person in the room is simply the one willing to ask a question that starts with “I don’t get it, can you tell me what makes you so sure?”