How to Constructively Disagree with Your Boss

In the fourth season of The Office, sales rep Jim Halpert voices some concerns about a new company website project, led by temp-turned-executive Ryan Howard, to David Wallace, the company’s head of finance—and Ryan’s boss.

 Shortly after, Ryan calls Jim into a boardroom to issue a formal warning, ostensibly about Jim’s overall job performance.

“Is this because I talked to Wallace about your website? Because I really didn’t mean to go over your head,” Jim says, blindsided.

“This has nothing to do with that. I always appreciate constructive criticism,” Ryan replies evenly—and totally unconvincingly. “I thrive on it.”

The scene taps a nerve for anyone who’s ever been in a similarly awkward situation. Messy things can happen when you disagree with your boss.

In 2025, many in business understand that organizations tend to function better when employees are empowered to voice their thoughts—including critical ones. Many also get that groupthink (in which often-mediocre ideas go unchallenged) can hinder performance, and that cultures of silence (in which people don’t feel safe speaking up) can damage organizational resilience.

But none of this is particularly comforting when you find yourself at odds with the person who signs off on your performance review. In fact, voicing dissent to a superior can feel pretty perilous if you’re the subordinate in the situation. What if your boss lashes out? What if they retaliate—immediately, or down the line? What if feelings of resentment of betrayal poison a previously harmonious relationship?

These are real risks, even if your boss is usually enlightened and supportive—and even if they, like Ryan Howard, profess to welcome criticism. “Leaders are human beings, like everyone else,” says Smith PhD alum Kyle Brykman, PhD’18, an associate professor of management at the University of Windsor’s Odette School of Business, whose research interests include employee voice, resilience and conflict in the workplace. “When their ideas are challenged, it can feel like a threat to their image, or their ego.”

While experts like Brykman say it is absolutely possible to disagree with your boss without sabotaging your career, they do recommend taking a thoughtful approach to the endeavour. Here’s what that can look like.

Assess the risks

When your boss says, does or decides something you disagree with, experts agree it’s generally best to take a beat to assess whether it’s worth opening your mouth about it. Even—perhaps especially—if it’s something that sparks a visceral response in you.

“You have to determine the risk of speaking up—and how beneficial it might be also,” Brykman says. “How risky is it to say something? How much trouble might you get into? How much do you care if you do get in trouble?”

A set of more pointed questions can help you triage the situation.

First: How much does it matter to you? Is it something that feels contrary to your principles—or is does it simply feel annoyingly misguided or short-sighted? “If it’s a matter where personal values don’t align with what the organization is doing, that can be a deal-breaker,” Brykman says.

Second: How much does it matter to your boss? The situation you take issue with may be extremely important to your boss. “It could be a sacred cow for them,” Brykman says. Perhaps it’s a file they’ve invested a lot of time into, or an issue that holds deep importance. “If it’s something they really value, it’s not a stretch to say that they’d feel their identity is on the line,” he points out. “And when that’s the case, they’re often just not going to take any criticism of that.”

Third: Do others share your dissent? There’s an emerging body of research into the value of vetting ideas with colleagues before you move them up the chain—including a 2023 paper Brykman co-authored with the Smith School of Business’s Jana Raver—and the principle is especially useful in instances of discord. A quick “Hey, do you think X is the right call?” posed inconspicuously to someone you trust can stress-test whether you’re missing context and whether you’ve misread anything. “We all get locked into our own biases,” Brykman points out. And it can also up your confidence that the battle is worth fighting: “As advanced as we are as societies, we still often act based on principles of reinforcement.”

And finally: Will you be heard? “You really have to read the room,” Brykman says. Because here’s the hard truth: Not every boss has the temperament or tendency to take on well-thought-through criticism.

Understand up

Count Smith MBA alum David Lahey, MBA’99, as a leader who definitively gets the value of constructive criticism. “I’m the CEO of a company that is growing fast,” he reasons, speaking of his role at Predictive Success Corp., a management consultancy that helps organization optimize their talent mix, leveraging technology and tools like the Predictive Index. “I want to know if we’re making a mistake. If people are worried that they can’t bring that information forward, that can cost us a lot of money.”

As someone who spends his days working with business leaders, and who wrote a whole book on better management, Lahey believes most bosses, deep down, are like him: They really do want to hear tough talk when it’s warranted. But he also understands why most employees are apprehensive to offer it. In his view, bridging that gap comes down to looking beyond your boss’s title or clout, to register what wires and drives them as a person: “You have to understand the personality and communication processes of the person you’re trying to influence to be successful,” he says.

No two bosses are exactly alike. Some only want topline information, while others need nitty-gritty details. Some like at least 10 minutes of chatter about the Blue Jays or the latest Netflix hit before any substantive conversation, while others prefer you to get right to the point. Some thrive on being challenged; others can’t stand it.

Before you voice your complaint, spend a bit of time observing what your boss does—how they tend to react in certain circumstances, or what makes them shut things down.  Technology can help speed this process along: As one example, Predictive Success offers AI-enabled software that draws on organizational analytics to give users, essentially, a recipe on how to better meet the individual communication needs of colleagues—including bosses. “When you understand the personality of your boss you can say what you need to say a lot faster, and a lot more effectively,” Lahey says. “It gives you a road map to navigate the disagreement. And that means a lot less stress and drama for everyone.”

Proceed with care

At the 2024 Super Bowl, star tight end Travis Kelce made headlines for reasons unrelated to his celebrity girlfriend, or even the eventual win of his team, the Kansas City Chiefs. During the first half, with the Chiefs down, he chose to ambush his coach, Andy Reid, jostling and screaming in frustration as the cameras rolled. Kelce apologized for the incident almost immediately, but the lesson lingers: Even if you have a valid beef, and even if you know how your boss will receive it, impulsivity is rarely the right move.

Kate Rowbotham likes to use the story of the Kelce meltdown because it’s easy for most people to relate to both parties: the angry football player and the blindsided coach. “No one likes to feel like their authority is being challenged,” says Rowbotham, who is an adjunct assistant professor and Distinguished Teaching Fellow of Organizational Behaviour at the Smith School of Business, where she is also assistant dean of teaching and learning. “That rarely leads to productive conversations.”

When you’re ready to make your case, Rowbotham recommends asking your boss for a meeting—ideally not surrounded by masses of people—to share some feedback about the matter in question. In that meeting, start by confirming your alignment with the organization’s overall goals. “This reminds your boss that you both want what’s best for the for the company and the team, and that’s the reason you’re there.”

From there, articulate your concerns as rationally and carefully as you can. Think: Less declarative statements (such as “This will be a disaster”), more conversational questioning (such as “This is how I see things playing out—what am I missing?”) Rowbotham says this approach can lower defenses and position the interaction as a constructive dialogue instead of an airing of grievances. And it can allow you to demonstrate both character and competence, which Harvard Business School professor Linda Hill considers the foundation of trust. “The way you say it really does matter,” Rowbotham says.

She also recommends you rehearse what you want to say with a friend or colleague in advance. Doing so might seem like overkill (or even a bit silly), but it can give you confidence in your message—and keep you from tripping up if nerves kick in. “The more you practice hard conversations, the more you’ll feel equipped can handle them.”

None of this guarantees success. The conversation may still go badly. Your boss may ignore your feedback, or dismiss it, or hold your dissent against you. Your differences may prove to be irreconcilable. But by taking a measured and prepared approach, experts say you’ll increase your odds of addressing the matter with your head held high. “You don’t have control over how people will perceive you, or the outcome of disagreeing with them,” Rowbotham explains. “But you do have control over how you demonstrate your competence and your character.”