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How to disagree with your boss 👌

Disagreeing with *anyone* at work can be tough… but disagreeing with your boss? Now that feels a lot harder!

Just the other day I attended a meeting with a team where a junior associate disagreed with their superior.

Here’s how that played out:

The executive started out by giving a short overview of the product and who they believed the target audience to be. Then, with some trepidation, the junior coordinator said, “No offense to anyone, but I think we should define the audience differently.”

A few moments later the coordinator *again* said, “Not to step on anyone’s toes here…but I think it would be great if we could appeal to a broader audience.”

We could all feel how hard this junior colleague was working to modulate his words, “respect the hierarchy,” and not offend anyone.

What made this moment even more cringey is that no one on his team “caught the ball” or engaged this junior associate further! When I finally asked him to explain his position more, I got some awkward, unhappy looks from the group.

Oy. It was tough to watch.

How about you? Do you ever hesitate to speak up when *you disagree* with an authority figure? If so, you’re in good company.

Voicing a dissenting view is nerve-wracking stuff, especially when confronting a person in power. On one hand, you want your opinion or a good idea to be heard. On the other, you don’t want to come off as overstepping.

In either case, we all want to preserve a healthy working relationship and avoid resentment.

These tips will help you to confidently speak your mind with your boss and come to a resolution that satisfies everyone. Try them out and let me know your results!

Quick Confidence Tips for Sharing Your Opposing Views with Your Boss:

  1. Interpersonal. Make it an invitation. When we preface our disagreement or criticism with an invitation, it has a way of opening up people’s ears. That means instead of declaring, “This is the worst idea ever!” (Okay, maybe that’s an exaggeration of the exact phrasing any of us would use), you can ask, “Can I share an alternate viewpoint?” Similarly, you could say, “I have a different view on things. Would you like to hear it?” or “I don’t share that same line of thinking. Would you be open to hearing a different interpretation?” Making an invitation before launching into advice or input gives people a sense of what’s to come, in this case, a dissenting opinion. It also gives them some agency to choose what’s next – hopefully to open up the lines of communication further!

  2. Embodied. Show up at the right time and place. Even the most well-intentioned sentiments can offend someone when given at the wrong time and place. For example, it may not be the best time to keep ideating at a time when everyone needs to pitch in to make a project move forward! Or if you disagree about something sensitive or nuanced — say, an HR or morale issue — broaching it in a meeting could make your boss feel attacked in a room full of people. Instead of taking it upon yourself to guess the best time to raise the issue, collaborate with your boss. Consider sending an email that says, “I have some thoughts about X that I’d like to share with you. When and where would be a good time to chat?” It shows respect when you give people the opportunity to choose the right forum.

  3. Mindset: Be solution-minded. Think back to the days in school when you learned how to write argumentative essays. You most likely had to present evidence to support your point of view, right? The same goes here! Bringing documented evidence that supports your opinion will show that you’re looking out for everyone’s best interest — not just trying to get your way. In the same vein, it’s important to come with a solution or suggestion if you’re going to point out what’s not working. For example, if you think a Zoom meeting every Monday eats up too much time, explain why and suggest an alternative. For example, “I wanted to share that 90-minute Zoom meetings on Monday mornings prevent the team from getting any work done until 10:30 on those days. With mornings being our #1, busiest time at the IT helpdesk, and our strong track record for being responsive, I’d like to propose switching to Thursday afternoons instead. What do you think?” Backing up your point of view with supporting evidence and alternate solutions will also make it a lot harder for your boss to say “no”, don’t you think? 😉

And here’s a bonus piece of advice: if you tend to hesitate when bringing ideas to your boss, it helps to remind yourself of your own intentions.

Will your idea help your team accomplish its goals faster? Or maybe you like your job and your solution will ensure that you *continue* to like your job.

Whatever your reason, being clear on your intentions will ground you and give you the courage to say your piece.

Never forget that you have unique and valuable opinions that deserve to be heard.

It also helps to keep in mind that your boss will likely be grateful that you’re looking for ways to be as productive and efficient as possible. After all, they want your team and organization to succeed as much as you do!

I’d love to hear in the comments about a time when you shared a dissenting opinion with a superior despite feeling nervous. What was the outcome? Was it worth it?


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