I was seething. The CEO had just asked my team to do something that I felt lacked integrity, was unprincipled, manipulative, and put our clients in a bad position. On top of all that, it involved an external stakeholder with whom I had my own separate relationship. There was no way I could face my friend in this circumstance. But how do you talk with your boss when you radically disagree?
He was the CEO, and I was a team leader. What could I do?
When we lead workshops to help leaders lead courageous cultures and have tough conversations at work, the question of how to talk with your boss always comes up.
Why It’s So Hard to Talk with Your Boss
On paper it shouldn’t be that tough—just have a conversation and share your concerns. But if you’re like most people, talking to an executive, senior leader, or Board member feels daunting.
Most of the time, when you fear to talk with your boss about an issue where you disagree, it’s because of the power they have over your employment. Self-preservation kicks in and you don’t want to do anything to jeopardize that paycheck. That’s normal for most people.
The problem is, when you don’t speak up, you’re not advocating for your people and it limits your influence and reputation as a strategic thinker. Speaking up can be a career-building move when you do it well.
The good news is that with a few tools and a little practice, you can address both concerns and have meaningful conversations with leaders at every level of your organization.
Talk to Yourself First
As upset as you might be, don’t charge into your boss’s office and unload your righteous anger. That may feel good for a moment, but that’s a career-limiting move.
The first conversation is one you have with yourself.
Come back to the Winning Well model: start with your own confidence and humility—confidence to stand up for what matters and humility to recognize you don’t know what you don’t know (and you’re not as perfect a leader as you might feel). Focus on results and relationships. How can you approach the conversation to build the relationship and achieve meaningful results?
For me, it begins with reminding myself that the person I’m upset with didn’t wake up intending to ruin my day. They’re doing what makes sense to them.
My CEO had his reasons for the way he had approached the situation. I didn’t like what I saw and believed it was wrong, but I knew him well enough to know that he wasn’t trying to be evil. Reminding yourself that there’s always another side to the conversation and that you don’t have all the information helps to lessen the grip of strong emotions.
Do Your Homework Before You Talk with Your Boss
What strategic objectives are at play? What data do you need to bring to the conversation? Learn as much as you can about the issue. You’re not complaining—you’re making a reasoned business case why your boss should consider another course of action.
Time to Talk with Your Boss
Create space for the conversation. If you have access to the person, schedule it. Catching them for three minutes in a hallway, overcoming interruptions, and distractions doesn’t give you the best chance to talk.
To start the conversation, be direct and respectful. One of the most powerful openings you can use is to frame your concerns in terms of outcomes you know they value.
For instance, when I approached my CEO, I knew that he prized the organization’s reputation in the community. To start the conversation, I thanked him for the meeting and said, “I am concerned that we aren’t putting our best foot forward regarding the event next month.”
When you’re able to start the conversation about a topic that matters to them, you have a greater chance to be heard. Often, the other party will follow up with a question—after all, you’ve let them know that something they care about is at stake. That question allows you to share what’s on your mind.
This approach also helps you overcome the most common fear about how to talk to your boss when you disagree. By putting the discussion in terms of something they value, you are approaching them as a strategic partner, not as a complainer or antagonist. Even if they don’t agree with your perspective, they know you were trying to help.
Time to Listen
As you finish sharing your concerns, invite them into the conversation. It takes humility to acknowledge that—as right as you may feel—you don’t have all the information and you don’t know their perspective.
For example: “Those are my concerns. I’ve got some thoughts about how we can do this differently, but I’m curious about how the situation looks from your perspective and what I might not see.”
As they share, actively listen. Try to reflect what you’re hearing in your own words. Eg: “So our number one goal is to acquire new customers before our competitor launches their product, even if we need to temporarily reduce our response times to existing customers? Do I understand that correctly?”
From there, you may propose solutions that meet both of your goals.
When I spoke with my CEO, I was young and didn’t know how to do this. He was the one that brought it up. He said, “I hear what you’re saying and, although I don’t see the ethical concerns the same way you do, I also don’t want us to do anything that violates your ethics. How can we do this event in a way that achieves the purpose and that you would feel good about?”
It’s a smart question. You’ll often find the best solutions in answer to “How can we do A and B” when A and B seem to be mutually exclusive. When he asked this question, I came up with a way to meet his goals and satisfy my values.
Results and Relationship—but Not Always In That Order
Let’s be real: just because you approach the conversation this way, it doesn’t mean you will get the change you want.
You may get some, you may get all, or you may get nothing. Regardless, you’ve built a relationship that will help you be more influential—and you’ve learned more about your business from a senior leader’s viewpoint. That can inform your work, your decisions, and future conversations.
It’s also possible that you’ll discover a massive clash in values: an irresolvable difference that you just can’t be part of.
It may not be comfortable, but it’s better to know. Now you can make a conscious decision about your future—whether you’d be better off in a different role, different department, or a different company. Either way, you’ve come out ahead because you had the conversation.
And it might surprise you at how much influence you have when you take the time to have the conversation.
When you can have a healthy talk with your boss about areas of disagreement, you build your influence, clarify values, and become a more valuable strategic partner.
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