Difficult Conversation 2: Disagreeing With Your Boss

🙋‍♀️ Disagree but don’t oppose

When you have a different opinion, you want to be able to discuss it with your boss without things spiraling into a fight. So how do you say what matters to you, without personal conflict?

Leadership Coach Toby Sinclair has a 6-step approach that will help you turn disagreements into a vehicle for building trust.

👂 Show respect with a question

Help your boss feel secure by showing that their point of view is important to you. Start by asking:

What do you think about X?

Listen and consider. You might hear something surprising!

☝️ Ask for permission to challenge the situation

Next, ask permission to share your point of view. If you’re challenging their perspective, focus on the situation, not the person. You can say:

I’d love to pressure-test that idea.

What do you think would happen if we tried it this way?

This gives them a chance to consider your idea, without conflict.

🏆 Find shared goals

Let your boss know why you care so much, and link your idea to goals you have in common:

I really care about this because I think it will help the team accomplish X goal. What do you think?

You might have to collaborate and modify your idea, but that doesn’t mean giving up your ultimate goal. Stay open to creative solutions.

💡 Keep asking

After sharing your idea and why it matters to you, ask more questions:

What am I missing?

Is there a better way to do this?

How do you see it?

This will support collaboration and prevent an argument.

🤝 Summarize

If you’re listening, considering, and still don't agree, state it clearly and ask an open ended question about finding a solution together:

I understand, and I still don’t agree. How can we resolve that?

They may be willing to try things your way, or you may be asked to go ahead with their approach anyway.

💌 Better communication

Try to stay flexible and move forward with positivity. Even if you don’t “win” your case, you will have improved communication and built trust with your boss.

Now they know more about what matters to you, and the next conversation will be easier!