There's little that's more stressful than trying to make important strategic decisions when you're not sure exactly who or what you're up against.
One of my favorite comedians, Ron White (who you may remember from the Blue Collar Comedy Tour), a proud Texan, tells a story about when he got physically thrown out of a bar in New York City.
Seeing multiple enormous bouncers follow him into the back alley, he recalled dryly:
“Now, I didn't know how many of them it would take to kick my a**,
But I knew how many they were going to USE.
And that there's useful information!”
Ron gained that critical intel before the first punch landed.
Unfortunately, the rest of us usually have to decide whether to speak before we know exactly what we're walking into.
We all find ourselves needing to initiate some sort of confrontation from time to time, like when we need to disagree with our boss or other key stakeholders who outrank us.
We certainly don't want to do it in a way that ends up being counterproductive, coming across as disrespectful or embarrassing, or otherwise causing defensiveness and doubling-down rather than open-mindedness. So we’re faced with the key question at the crossroads:
Do You Speak Up or Stay Silent?
Do we speak up or stay silent? Either can have potentially negative consequences. Is there a right and wrong way to do it?
One way or another, it's really hard to make smart decisions on things like timing and approach if we lack key information, especially when you factor in the intercultural/international complexity of today's global workplace.
The short answer: you can usually disagree with someone more powerful than you without damaging the relationship — as long as you:
- tie your objection to a goal you both already share,
- ask permission before making your case, and
- keep the focus on the problem rather than the person.
What the Research Says About Disagreeing With Someone More Powerful
I recently stumbled upon a 2016 HBR article from Amy Gallo, How to Disagree with Someone More Powerful Than You, and it's every bit as relevant now as it was when first published. (Some good advice never gets old!)
Gallo talks with Joseph Grenny, the coauthor of Crucial Conversations, and Holly Weeks, the author of Failure to Communicate (both highly recommended), and drew 9 key considerations when deciding how and when to voice your concerns in a way that will more likely get the attention and consideration they deserve while strengthening your relationships, reputation and leadership image. Below is a summary of those nine keys.
9 Keys to Disagreeing With Someone More Powerful Than You
(HBR, March 2016)
1. Be realistic about the risks. We reliably overestimate what happens if we object, and rarely price the other side. Grenny's move is to run the ledger both directions: what does it cost if you don't say it — the project going sideways, the team quietly deciding you don't push back — against what actually tends to happen when you do, which is usually a moment of friction and not much else.
2. Decide whether to wait. Sometimes the right call is to hold. Weeks names the tells: your own reasoning isn't finished, the topic blindsided you, or you can't yet read the room. If others likely share the concern, talk to them first — you may pick up information that sharpens the case. And setting counts as much as timing. A concern raised privately costs the powerful person nothing publicly, which is exactly why it lands better.
3. Identify a shared goal. Figure out what the person is actually protecting — their team's credibility, a delivery date, a promise they made upstairs — and connect your objection to it out loud. Don't assume the link is visible. Named explicitly, you're a colleague working the same problem; left implicit, you're a subordinate being difficult. Weeks's image for the difference is worth stealing: it turns the exchange into something “more like a chess game than a boxing match.”
4. Ask permission to disagree. It sounds excessively deferential, but it isn't. (Laura's note: as long as you don't apologize for disagreeing…*ahem* — ladies?!) It hands the other person control at the exact moment they're bracing to lose some. Something like: “Before we lock this in, I have a concern about the timeline. Can I walk you through my thinking?” They opt in out loud, which changes the conversation from an ambush to an invitation, and you speak with more authority because you were asked to.
5. Stay calm. As I reinforced throughout Speaking to Influence, make sure your verbal, vocal and visual (a.k.a. words, voice and body language) are congruent in projecting calm confidence, even if your heart races and palms sweat. Breathe. Grenny also confirms that panic makes us louder and faster, so consciously slow the pace and hold an even tone — not a whisper, just measured. It steadies them and it steadies you, and it reads as confidence whether or not you feel any. (If this is a challenge for you, you'll want to check out the section on speed and pausing in chapter 4 of Speaking to Influence!)
6. Validate the original point. Once you have the opening, state their position in your own words — and state it well, ideally sharper than they did. It closes off the argument nobody wins, the one about whether you actually understood. The bar: they should be thinking she gets it before they hear a word of your objection.
7. Don't make judgments. Watch the vocabulary; stay objective and non-judgmental. Grenny flags loaded words like short-sighted, foolish, or hasty, and recommends cutting the adjectives entirely, because any of them can be received as a personal verdict rather than a professional one. Deal in evidence. Not “that deadline is naïve” but “we've run four projects at this scale; two landed in that window, and both had conditions we don't have here.” Same objection, no character assessment attached. It's the people-versus-problem distinction, applied at the level of word choice.
8. Stay humble. What you're offering is a view, not, in Grenny's words, “gospel truth” — however well researched it is. He advises you to “talk tentatively and slightly understate your confidence.” (Laura's reminder: Again, ladies especially, do not apologize for raising a legitimate red flag; no walking stereotypes allowed!) Weeks recommends salting the conversation with “guiding phrases” like “I'm thinking aloud here” to keep the door open. Then, invite them to take it apart, e.g., “Have I missed something here?”
9. Acknowledge their authority. The decision is almost certainly theirs, so name that: “I know you'll make the call here. This is up to you.” It signals that you understand the hierarchy while reminding them they have options. What it shouldn't become is retreat or flattery. As Weeks puts it, you want to show respect to the person while maintaining your own self-respect.
The 10th Move: Say Why You're Speaking Up, Not Just What's Wrong
When you're not sure how a concern will land, say out loud why you're raising it. You're answering the question they are thinking but haven't asked yet — “Why are you making this harder?”
It's safest and easiest to explicitly state your rationale for speaking up, e.g.
“I realize that this may take more time to address, which is not ideal, but I'd rather take responsibility for bringing it up proactively to ensure that we've covered all our bases, than stay quiet about it and have it create massive problems, knowing that we could have prevented it.”
The Other Half of This Skill: Admitting What You Don't Know
Disagreeing upward and admitting a gap are the same muscle. Both are moments when you're exposed in front of someone with more power than you, and the reflex is to go quiet. And in both cases, what you say next either builds your credibility or spends it.
That's exactly what I got into with Kevin Price on The Price of Business: why “I don't know” is not a complete sentence.
Using a widely covered political stumble as the case study, I break down the difference between blanking and giving up — and give you the three-part move to use instead:
- Anchor on what you stand for and what you know for certain.
- Name the gap in a single clause. One. Not a paragraph of apology.
- Commit to closing it by a specific date.
🎧 Listen to the episode → (also on SoundCloud)
And if you're ready to make sure that the hardest conversations you have are the ones that build your leadership image rather than chip away at it, let's talk.
Frequently Asked Questions About Disagreeing With Your Boss
Is it ever appropriate to disagree with your boss? Yes — and the risk of staying silent is routinely underestimated. A derailed project or a team that quietly concludes you won't push back is a real cost, and it rarely gets weighed against the far milder discomfort of raising your hand.
How do you disagree with your boss without sounding disrespectful? Connect your objection to something they already care about, ask permission before you make your case, restate their position accurately first, and strip the judgment words out of your language. Deal in evidence, not adjectives.
Should you disagree with your boss in a meeting or in private? Private, in most cases. A concern raised one-on-one costs the other person nothing publicly, so they can consider it on the merits instead of managing how it looks in front of an audience.
What if your boss makes the final call anyway? Name their authority explicitly — the decision is theirs — without retreating from your position or resorting to flattery. Showing respect to the person and maintaining your own self-respect are not in conflict.
How do you disagree with someone more powerful across cultures? Directness norms vary widely, so calibrate the packaging, not the substance. Asking permission to raise a concern travels well almost everywhere, because it hands control back to the more senior person before the disagreement begins.
