How to Disagree with Your Boss—And Still Have a Good Relationship

How many times in your career have you totally and wholeheartedly disagreed with your boss? It’s a tricky situation. You don’t want to hurt the relationship, but you want to do right by the company, client or customer, and you’re compelled to say something.

So what’s the right approach? Here are some proven strategies I share with my coaching clients on how to disagree respectfully—and, in particular, how to disagree respectfully with someone who’s above you on the org chart.

Gather feedback. Before you approach your boss, get feedback from someone you trust about your idea and how you can be more persuasive. Encourage them to poke holes in your theory and ask questions like . . . well, like a boss.

Seek out expert opinions. Make sure you have advance contact with a subject-matter expert—someone recognized within your company or network for their knowledge of the topic. They’ll be able to provide you with a point of view you might not have thought of on your own.

Rehearse your ideas. Practice your pitch with a few people you trust. If you you can’t get them to see your point of view, either try a different approach or consider hanging it up for a while.

Be mindful. Once you’re ready to approach your boss, it’s important to be mindful. If the issue is something you feel strongly about, ask yourself whether it’s worth a fight if it comes to that. Remember, if you make everything combative you won’t have much to draw on when something truly important comes along. Make sure your opinions hold together logically; a clear-headed argument  is almost always better than a passionate one.

Leave emotion out of it. Pull together data, charts, spreadsheets and any other hard evidence you can to support your point of view. Stick to the facts and don’t make it emotional.

Listen to learn. Make it a point to listen to your boss, which is only respectful after your boss has listened to you. Most situations have something to teach everyone involved—maybe it will be you, maybe your boss, maybe both. In any case, you want to come across as someone who isn’t afraid to speak their mind but who’s driven by commitment to the organization.

Evaluate to review.  When it’s all over, review and evaluate how well things went. Ask yourself how your role in these conversations has grown through the years. And if it didn’t go well, ask yourself what can you do better next time.

Lead from within: Disagreeing with someone is not a bad thing. It’s how you disagree with that person, especially when it’s your boss, that matters.

standards for hard work and integrity.

Leadership may be hard to define and good leadership even harder, but if you can get people to follow you to the ends of the earth, rest assured—you are a great leader.

Lead from within: Before you become a leader success is all about growing yourself; after, it’s all about growing others.


N A T I O N A L   B E S T S E L L E R
The Leadership Gap: What Gets Between You and Your Greatness

After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR,, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

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