By Steven Matthew Leonard
As we sat in the general’s office, the conversation carried the typical banter we’d come to expect. The general had a habit of talking out new concepts until he was sure he fully understood them and could articulate them clearly.
We were there to help him frame his thoughts, sort of like speech prep for big ideas.
That particular day, we’d brought in a major from a subordinate headquarters to give us a hand as we worked to make sense of a white paper he’d written. The topic wasn’t particularly difficult to grasp, but the writing was a little thick, so we thought it best to make him part of the process. Everything seemed to be progressing normally, until the junior officer’s tone changed sharply.
“No. That’s stupid. That’s not how it works,” the major blurted.
“You’re wrong.” The major pushed his chair back and crossed his arms in front of him. “I wrote it, I know.”
“Okay, let’s dial this back a bit,” the general answered. “Remember who you’re talking to.”
“You want a debate? I’ll debate you,” the major replied, pointing his finger at the general. “Right now. You’ll lose.”
The aide-de-camp and I looked at one another, totally dumbstruck. Try as we might, we couldn’t intervene quickly enough. The general didn’t have much of a temper, but the major had pushed his buttons to a point we hadn’t previously seen. The aide distracted the boss—whose face was rapidly approaching a disturbing shade of purple—as I pulled the major outside and away from the general’s office.
“He’s afraid to debate me,” the major said confidently. “He knows I’d win.”
“That’s not the point,” I explained. “If he’s wrong, you’re here to help him understand, not to piss him off. Not to argue with him. Not to tell him he’s stupid.”
“Nobody can beat me in a debate on this,” he said. “I know more about it than anyone. That’s why I wrote the white paper.”
I pushed the major out the door and down the hall, still in disbelief. Words like blunt, tactless, and caustic came to mind. I’d seen people disagree vehemently before, but never in quite so spectacular a fashion, and never with someone so senior to them. I shook my head as I watched the officer walk away, shoulders back and head held high. There was no doubt he believed he’d just achieved a major victory, oblivious to the fact that he’d probably just written the epitaph on his next evaluation.
When Trying to be Right is Really Wrong
It’s not unusual to want to disagree with your boss: A new project proposal you don’t think will solve anything, a timeline that isn’t realistic, or an initiative that will cost more than it’s worth. Disagreeing with the boss elevates speaking truth to power to new heights. This isn’t just about providing unsolicited feedback or sharing knowledge of a problem. It’s about telling someone you think they are wrong. And not just anyone—someone senior to you who could just be in a position to influence your future. For a lot of people, this situation triggers a fight-or-flight response, and they choose survival over disagreement.
The truth is you can disagree with someone without fearing for your livelihood. It requires a delicate blend of timing and social intelligence, but it can be done.
First, weigh the risks. Is the matter at hand so important that you want to take a stand? These are what I often call silver bullet moments. You only get so many silver bullets; don’t waste them on squirrels.
Second, acknowledge their authority. A little respect goes a long way if you’re planning to disagree. The decision is usually theirs to make, so acknowledge that. Your role is simply to help them make an informed decision, not to make the decision for them.
Third, ask permission to disagree. This is one area where it’s far better to ask permission now than to beg forgiveness later. Often, all this requires is a statement like, “If you don’t mind, I’d like to offer some thoughts.” This allows your boss to invite you into the discussion instead of you barging in like the Kool-Aid Man.
Fourth, validate their position. This is a simple, yet essential step in disagreeing with your boss. Acknowledge their position, even if you think it’s completely wrong: “I think that’s a great point. Maybe we could also…” If you allow disagreement to turn into debate, you’ve already lost.
Fifth, keep your emotions in check. Sometimes, our passions are our undoing. If you feel particularly strong about an issue, this can be a true challenge. Always remember facts, not emotions. This might also save you from using judgmental terms, such as “stupid,” “short-sighted,” or “wrong,” or inadvertently telling someone senior to you to do something that might be anatomically impossible.
Finally, stay humble. You’re not the authority figure in the room and it’s not your decision to make. Don’t pout if you don’t get your way and don’t gloat if you do. Keep things in perspective.
You can disagree with your boss without committing career seppuku. Be smart about it.