The safest way to disagree with your boss on behalf of your team (or yourself)

One of the trickiest parts of management is advocating for your employees in critical situations. Employees are rarely in the room when key decisions are made that directly affect them, so your task is to stand-in on their behalf.

This responsibility is put to the test when company executives rearrange the company organizational chart, create or discontinue lines of business, or change compensation structure. These choices have consequences that are either unforeseen or under-considered and can often appear woefully out-of-touch from what you and your team experience at the front lines.

So what are your options? Many of us avoid speaking truth to power because of how risky these conversations can be. None of us want to come off as combative or “not a team player”. You don’t want to rock the boat with senior leadership. Remember, all leaders (and especially senior leaders) often underestimate the unintended consequences of their decisions/actions. They may not even be aware of the legitimate concerns people have about decisions that are being made. They think they’re the good guys. That’s because so few in middle management have the willingness to broach these discussions and offer productive pushback to help evolve the conversation.

It’s important that you find a way to express your concerns and thoughts in a way that is constructive, sensitive to context you may not have, and allows you to show that you stood up for your team.

Ask if the topic is open to discussion

First, when broaching a potentially controversial or divisive topic, it’s best to ask if it’s even open for discussion. Send an email to your boss or ask them in passing.

“Hey, I was hoping we could talk about [controversial topic] in the near future. I have some questions and wanted to get more context. Is that okay?”

Most leaders are going to be curious about what you have to say. But be prepared, there’s always the chance you get a response that’s something like: “Honestly, it’s not something that’s open to discussion right now”. If that’s the case, at least you’ll know and can act accordingly.

Restate your interpretation of the reasoning behind the decision

When opening the discussion, state your understanding of the topic from your boss’s perspective. This is essential. One of the worst things you can do is state your case when there’s a chance you don’t fully understand senior leadership’s perspective. This not only makes you look foolish but can create conflict where none exists.

Ask for your boss to fill in any gaps in your understanding. Be sure to listen to understand as best you can, not just to respond. The better you understand, the better you’ll be able to articulate your concerns and questions.

See if they’re willing to hear an outside perspective

Next, ask if they’re open to hearing a counter-perspective on this issue. There’s a chance that your boss isn’t going to want to hear any dissent, and that’s their choice. But more often than not, curiosity is going to get the better of them and they’re going to want to hear what you have to say. If your boss gives you explicit permission to challenge their thinking then it decreases the likelihood of them getting defensive and shutting down the dialogue.

Give your perspective

State your case clearly and calmly. Be direct, but don’t be aggressive or antagonistic. Again, your boss thinks they’re the good guy. Be honest about where your concerns are and what you see that they don’t. Avoid becoming emotional about the topic if you can. Getting too emotionally engaged can give the impression that the emotion is what’s driving your concern. It’s an unfortunate truth that when bringing a potentially unpopular perspective, the bar will be set high for how you deliver your talking points. No one wants to be disagreed with, so people implicitly look for ways to discredit the person that’s challenging them. That’s life.

Ask for reasonable concessions

This is the most important step. Ask if any concessions can be made to the decision. Can it be rolled out in phases? Can the timeline be moved back. See if there’s any room to negotiate. Is there any room for negotiation? Have a clear idea in your mind of what a good outcome would be for your employees, and start from there. If your boss gets defensive or shuts down, then simply ask, “is there any room for flexibility here?”

The higher the stakes, the more you need to let your boss sit and think about the discussion. They are going to need time to consider what you said and think everything through. If you press too hard now, you’re more likely to get pushback and fewer concessions. If you give them time to think on everything (and appreciate your oh-so tactful approach) then they’re more likely to offer an olive branch.

Senior leaders want you to be happy. If you make a thoughtful argument, they’re going to give it serious consideration. All leaders want to be liked; they want to feel like they have the loyalty of their team. If you make them aware of unforeseen or unconsidered negative consequences, they’re going to want to soften the blow.

Surprisingly few leaders take the time to approach upper management when decisions that negatively affect their team get announced. Many of us aren’t sure it’s our place to involve ourselves. Never forget, your job is not to “just follow orders”. You’re an advocate for your employees. It’s essential that you engage in this sort of dialogue as much as possible around key topics that your employees care about. The better you are at having these conversations with your boss and senior leadership the better you can speak to your team about these decisions, the better you can understand your business, and the better senior leaders an understand a counter perspective to these issues. Good luck out there.

-Patrick

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