8 tips on being a productive skeptic in your workplace

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There’s a fine line between being a team player at work and being a pain in your boss’s neck. Those who walk the line gracefully are what we might call “productive skeptics.” They are willing to openly question the premise or logic or value of an idea, and they somehow manage to do this without building a reputation for being a naysayer or difficult to work with.

How can you be a productive skeptic in your own workplace? The better question might be how you become one—because it is a process, requiring intentionality on the part of the would-be critic.

In our Quartz at Work (from home) workshop on Feb. 4, Jim Detert, a professor at the University of Virginia Darden Graduate School of Business and author of the forthcoming book Choosing Courage: The Everyday Guide to Being Brave at Work, offered a host of advice on how to marshal the pluck and goodwill that every skeptic needs to be successful.

Click the image above for the complete video playback. For a recap of his top tips, read on.

Stop equating courageous acts with martyrdom

Yes, that whistleblower who lost everything, the one you read about in the paper, represents an important type of courage we need in the world’s workplaces, Detert said. But just as vital are the everyday behaviors that keep companies from going off track. Courage, he said, is simply the choice to do “a worthy act despite the risks.”

Develop your skill at this

Plenty of us might be described as born skeptics, but not many of us naturally understand how to steer the energy productively. It’s something that you can work on, though.

When you start feeling like you might be ready to confront something that makes you sweat, “sitting at home in an armchair with a drink just thinking about how you’ll act is not going to be enough.” Try your best to practice under the same sort of pressure-filled conditions you are sure to face in the moment. At Detert’s leadership lab, he sometimes brings in actors from a local improv theater to sit around the table with a student who is instructed to try to sell them an idea. As the actors put the students through their paces, Detert’s lab measures the students’ heart rate and other physiological responses. You might not go to such lengths, but you can do better than just daydreaming about what you would say if given the chance.

Choose your battles

This means knowing yourself well enough to know what’s genuinely important to you, “versus what’s a trigger that happens to make you angry or passionate,” Detert advised. Picking the right battles also comes down to timing. Is there momentum in the organization that suggests your idea can get traction? Have you recently cashed in other chips, which might suggest you hold off for a bit before taking another turn at playing the skeptic role?

Remember to follow through

If you successfully articulated your point at a meeting, please understand that it’s still unlikely you secured the real commitments you need to pull off whatever it was you were suggesting, Detert said. If you need another meeting to sort out the logistics, organize one. If you need certain resources to put behind your idea, ask for them.

Try to smooth any ruffled feathers

If your skepticism struck a sour note and your critique has offended a colleague, Detert said, “[d]o you take what might feel like a second courageous act and go talk to them and try to make things better?” Yes, reader, you do.

Before you take the courageous stand, make sure you can do so credibly

Two things successful skeptics usually have in abundance are warmth and competence. Their colleagues already see them as engaged, trustworthy people who have the organization’s best interests at heart. And they have put in the work to make sure their opinions are respected. This can take patience. Detert recounted the stories of executives who spent years biding their time and building up their credibility so that when opportunities to make big changes presented themselves, they were able to be effective advocates.

Be aware, biases abound. People from traditionally marginalized groups might find it harder to get credit for warmth or competence. Women, for example, often face a double bind, Detert said: If they act warm, they are frequently better liked but also misconstrued as being too soft; if they take charge, they might be viewed as competent but they’re also more likely to be disliked, whereas men exhibiting the same behaviors might be viewed as decisive and appropriately assertive.

Try building a “courage ladder”

Detert encourages would-be skeptics to make a list of actions they would like to take in the workplace, putting important but overwhelming ideas at the top and smaller, more manageable goals at the bottom. Then, work your way up the ladder. Each success will train you to better handle the next situation, whether in terms of your ability to articulate a problem, offer a clarifying solution, convince others, or do the necessary follow-up work.

If you’re a leader, consider an alternative to encouraging courage

“It’s become fashionable to say as a company that we as a company want to encourage courage,” Detert notes. Why is this problematic?

“When our strategy is to encourage courage, we are implicitly acknowledging that this is a scary place, because courage is only seen as necessary when people are afraid,” Detert said. “One of the ways I think leaders can themselves be courageous is to dedicate themselves to creating the conditions” where people can speak freely without feeling they need to summon courage to do it.