Managing disagreements: How to handle diverging points-of-view with your boss

Six leadership tips on what to do when you disagree with your boss (or another senior leader at the company)

It’s inevitable: You’re going to disagree with your boss. No two people on the planet agree with each other on everything, 100% of the time.

That’s a terrible idea,” you think to yourself, after listening to your boss share a decision she’s come to. “She strongly needs to consider an alternate option.

Yet, managing disagreements at work is tricky — made only trickier if the person you disagree with is your boss. Of all people, you don’t want that person to get defensive or misinterpret your disagreement as an attack. You want whatever thing you’re arguing for to be considered, and hopefully enacted.

The key is to share your opposing point-of-view respectfully — and effectively — so the outcome you’re looking has a higher likelihood of happening.

So, how do you do that? How do you disagree productively with your boss, or another senior leader on the team?

In The Watercooler, our online community for leaders, managers from all over the world suggested taking these five steps when you and your boss disagree:

Peel back the layers of “why”

Start with the assumption that people are reasonable and make rational decisions. Then, ask yourself, “Given that assumption, what would have to be true for them in order to cause them to make the decisions they did?” Are there other priorities they’re managing that you’re not aware of? Are there other stakeholders who have an interest in the outcome that you aren’t considering? Rigorously peel back the layers of their rationale to figure out what those underlying reasons are.

Emphasize the common destination, not the divergent paths.

You’re both on the same team. Remind them of this. While trying to explain your own view, extrapolate the assumptions, beliefs, and values you both have in common. For example, you both care about the team’s success, you both value speed over perfection, you both see X priority to be most critical. What you most-likely differ on is the approach: The strategy to execute, the timeline, the resources, etc. Highlighting the points of agreement re-centers the conversation: While the roads you mapped out are different, you both want to end up in the same place.

Show, don’t just tell.

Evidence is compelling. How can you show — and not just tell — that your recommendation or idea should be taken up? Is there anything that you can work on that directly contributes to the company primary goals and illustrates your point? For instance, one Watercooler member discussed how she started a project without many resources, and eventually recruited people who shared similar views to build her case. It worked — her boss implemented the idea.

Consider: What is the one thing you can fix right now?

When we see a lot of fires, our urge is often to build a brand new fire station. However, in reality, all we might need is to find the nearest fire hydrant to hook up to. If many things are broken and you think you know a better way, avoid the desire to solve everything at once. Focus on just one thing that can be a visible quick win. Connect to the fire hydrant, first. Then, you can better make the argument to build the fire station for the neighborhood.

Ask yourself, “Do we really disagree on core beliefs?”

Sometimes, the gap between the opinions of you and your boss isn’t just a crack — it’s a chasm. It’s much wider and deeper than you initially thought. This is important to pay attention to. If you disagree with a coworker on core beliefs, then the change will be an uphill battle. You’ll want to seriously consider if it’s worth the trouble. And, if it’s not, perhaps it’s not the right company for you to be at. Core principles that you want to be aligned on include: your beliefs around company culture, how managers see and respect employees, the ratio of autonomy vs. control, iteration process, team structure and long-term goals.

Look for an outside advisor or mentor.

A third party can bring objectivity to a disagreement. One Watercooler member recommended how this option is helpful when the conversation becomes circular and isn’t progressing in a positive direction. Having someone fresh can not only be useful to moderate the discussion, but provide new insights that you both may not have considered. However, when doing this, it’s important to set clear expectations, and decide on how to handle the outcome of the discussion. You don’t want the outcome to devolve into office gossip because you “brought someone from the outside in to help.”


These tips have helped orient my thinking around approaching differences of opinion within my own team. I hope they help you too.


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P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

Written by Claire Lew

CEO of Know Your Team. My mission in life is to help people become happier at work.

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