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Exactly What Your Boss Is Thinking When You Disagree With Them

First, the good news: Unless you do something extreme, they probably aren’t considering firing you.

Exactly What Your Boss Is Thinking When You Disagree With Them
[Photo: Max Newhall]

People often fear that if they disagree with their boss they’ll get fired. But as a manager, let me reassure you that unless you do something extreme (like use NSFW language or publish a blog about what an idiot I am), odds are you won’t be let go for the sheer act of saying you see things differently.

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In fact, the most common complaint I hear from managers I work with—and have felt myself—is quite the opposite. We want feedback from our employees. We hired you because we believe in you and your ideas, so keeping them a secret isn’t helping either of us.


Related: How To Calculate How Valuable You Are To Your Boss 


Now, to be fair, you want to push back in a way that makes you look helpful and thoughtful—and not like a know-it-all.

And I know what you might be thinking now, is that possible? Yes, especially if you know the four most common thoughts managers have when you disagree with them.

1. “I Wish You’d Done Your Homework—First”

Give me the benefit of the doubt when you learn about something that sounds wrong to you. Ask yourself, “What are the valid reasons my boss may’ve made this decision?” before building a case to argue with me.

Before correcting me, put yourself in my shoes for just a minute. If I feel like you’ve considered why I might think or feel the way I do, it’s easier for me to listen to your ideas.

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Disagreeing with me is the easy part, recommending a better solution is the hard part.

This means that before you get to the constructive criticism, mention the merits of your boss’s approach. For example: “I can see where this would help us make our process more efficient, but I’m concerned about having enough time to do good work, so what if we adjusted [different] part of process?”

2. “Why Didn’t You Tell Me This Earlier?”

Frankly, I hear complaints and observations about my job all the time—including from my boss and our customers.

I most appreciate hearing from you when I’ve made a decision you don’t like that applies directly to your job. In fact, don’t wait to be asked. If my decision impacts you on a daily basis, let me know immediately. While I may stand by my decision even if you disagree with it, I want to know how you feel.

With that said, it’s helpful to remember that everyone has something they’d do differently if they were the boss. So share feedback that’ll help you do your job better (or be happier), but keep thoughts on nitpicky things that don’t impact you to yourself.

3. “Please Mind Our Surroundings”

It could be that our one-on-one check-ins are characterized by robust discussion and occasional disagreement—and that’s great. However, that doesn’t mean that you can always take that approach when voicing a differing opinion.

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Related: Two Ways To Handle A Hopelessly Indecisive Boss 


If it’s during a staff meeting, remember that your colleagues are watching and set an example for them about how to challenge me. If we are with a client, I’ll be the most sensitive to you publicly disagreeing with me—not because my ego can’t take it, but because I don’t want the customer to lose faith in our organization. So if you’re not sure how the client will react when you correcting me, hold off on doing so until we are alone.

4. “If I Stick To My Decision, I Expect You To Support It”

If I hear you out but stick to the original plan, it doesn’t mean I wasn’t listening. More often than not, it means I’m considering factors that are external to your role, and that you may not be aware of—for all you know, my boss’s boss told me to do it this way.

I’m not looking for a team of “yes” people who never speak up. But I am looking for employees who trust me enough that if I push back on feedback, it’s for a good reason—and if they don’t support the plan, they’ll support me by going along with it anyhow.

The final thing I’ll confess is that sometimes I’d just like my employees to do what I’ve asked. It’s exhausting (for both of us!) if I have to defend every single decision, plus it makes me feel like you have no faith in my judgment.

If you’re still unsure whether it’s a good battle to pick, ask me. Say: “Are you open to a different opinion on this?” and give me the choice of opening it up for discussion. I’ll tell you whether it’s a good time to share a differing opinion, or if, this time, it’s better to let it go.

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