Telling your boss that he/she made a poor decision doesn’t have to be a stupid career move—but you’d better approach this conversation in a smart way. Get it wrong, and your boss could see you as an impediment or even an adversary, and that’s a battle you’re unlikely to win. But if you get it right, it actually could boost your career—smart employers value employees who say what needs to be said even when that’s difficult. The key is how you handle the disagreement…

Scenario 1: Disagreeing About a New Plan

Say your boss lays out a plan or voices his opinion, and you immediately spot a potential problem.

Your inclination might be to hold your tongue for the moment—perhaps you’re in a meeting and don’t want to disagree with your boss in front of a group…or perhaps you hope something will change your boss’s mind without your having to step in. But waiting usually is a mistake. If you say nothing now and disagree later, your boss might wonder why you didn’t speak up sooner—before time was lost and resources were committed to the original idea. And psychologically, the longer he believes in an idea, the less open he is likely to be to alternatives.

Exceptions: It usually is a bad idea to disagree with a boss in front of a client, and it often is prudent not to disagree in front of your boss’s boss either—unless you can do so in such a way that your boss does not lose face.

A three-step plan for minimizing the ruffled feathers when you disagree with a boss about a new idea…

1. Align your intentions with a greater good. If your boss views your disagreement as a me-versus-you confrontation and becomes defensive, it could harm your career. To greatly reduce this risk, frame what you are about to say as an attempt to help your boss or company achieve a greater goal. Ask yourself, What is my boss under pressure to achieve, and how could the idea he just presented make it more difficult to achieve that?

Example: Your boss says that he intends to switch to a supplier that ­charges lower prices but that you know to be unreliable. Before saying that you disagree with the decision, frame what you are about to say in terms of this cost-cutting goal. “The company has put an emphasis on cutting costs lately. When I hear that supplier’s name, my concern is that when we’ve used it in the past, we ended up paying much more than we expected because of its mistakes and missed deadlines despite its low price quotes.”

2. State the facts on which you are basing your disagreement before stating your conclusion. When people disagree, each may say what he thinks and then double back to explain how he came to that conclusion. But if you do that, your boss (and anyone else present who holds an opposing viewpoint) might feel in opposition to you as soon as he hears your position. Then, rather than objectively weigh your facts and reasoning, he might look for ways to shoot them down. Instead, state your conclusion after you present your ­evidence.

Example: In talking about an unreliable supplier, you might say, “We’ve ordered from that supplier twice. One time it sent the wrong parts, and one time it missed the delivery date. We had to place last-minute rush orders with other companies to get what we needed—and those rush orders were very expensive.” Only then state your position that a different supplier would be a better choice…or that this supplier should be used only when there is no looming deadline.

3. Transform the disagreement into a dialog if other people are present. After you disagree with the idea your boss has presented, invite comment about the alternative that you just raised. Whether other people agree with you or not, this reduces the odds that your boss will see the situation as a me-versus-you challenge and increases the odds that it becomes a let’s-hash-this-out-as-a-team cooperative situation.

Example: After presenting your position, you say, “I’m wondering whether others feel the same or differently.”

Scenario #2: Disagreeing About an Existing Decision

Say you didn’t speak up the first time your boss said something that you disagreed with—perhaps you were not even present when the decision was presented—but the situation does not seem likely to improve on its own and you cannot stay silent any longer. To disagree with your boss about a decision that he might think is no longer even in debate…

1. Schedule time with your boss. If you plop your disagreement on your boss without any warning, he might justifiably wonder, Why am I hearing this just now? If you do so in front of a group, he even might suspect that he is being intentionally sandbagged. Asking for a one-on-one meeting to “raise a potential concern” can lead to a better result because it gives the boss a chance to mentally prepare for unwelcome news, so it doesn’t feel out of left field (or threatening) when it arrives.

2. Before this meeting, consider why a reasonable person would have made the decision your boss made. The longer you allow a decision that you think is wrong to remain unchallenged, the greater the odds that you will start to imagine nefarious motives that might not really exist. Why did the boss do this? can transform into How dare the boss do this to me!

The odds of career-damaging conflict increase if you have this perceived negative motive in mind when you speak with your boss about the decision. So before your meeting, think through how a reasonable, well-meaning person could have reached the boss’s decision.

Example: Your boss alters the department’s bonus plan in a way that reduces the amount you are likely to ­receive. Could he have done this not with the intention of slashing your compensation but rather with the intention of rewarding different results?

3. Open the meeting by framing your purpose in a noncombative way. Say something such as, “There’s a potential issue that I think should be considered.” This is much more likely to lead to a productive conversation than opening with something negative such as, “I think you made a mistake.” Quickly provide a key fact or two to support your position…and then propose a solution, ideally one that your boss can accept without having to admit that his original idea was completely wrong. Try to distill all of this down to just a few sentences, if possible.

4. Dial down potential anger by clarifying your intentions in a way that casts you as an ally. If your boss tends to react angrily when he feels challenged or you notice signs of anger as you present your position—hands balled into fists, for example—use don’t/do statements about your intentions to stress that you actually are on your boss’s side.

Example: “I certainly don’t want to cause trouble for you—that’s the last thing I would ever want to do—but I would like to get a handle on how this will work so that I can help you implement your decision successfully.”

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