Things Leaders Do

How to Disagree With Your Boss (Without Getting Fired)

• Colby Morris

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Ever felt stuck between speaking up to your boss and protecting your career? You're in a meeting, your boss makes a decision you know is wrong, but you stay silent—worried that disagreeing will make you look insubordinate or damage the relationship. Here's the truth: you're not alone. 76% of employees avoid workplace conflict, and nearly 24% of all workplace conflict happens between employees and their direct supervisors.

This episode tackles the biggest challenge middle managers face: how to disagree with your boss without getting fired. You'll learn practical strategies for managing up, navigating upward conflict, and advocating for your team while protecting your career.

What You'll Learn:

  • How to push back on decisions using clarification instead of confrontation
  • What to do when you're not getting support from your boss (it might be bandwidth, not neglect)
  • The critical documentation step when you fundamentally disagree with a decision
  • How to recognize when your boss is truly the problem—and when it's time to walk away
  • Real story from Colby's 20+ years in healthcare leadership about managing up during a budget crisis

Key Takeaways:

  • The "clarification approach" for disagreeing without seeming confrontational
  • Why coming with solutions (not just problems) changes everything
  • The follow-up email strategy that protects you when decisions go wrong
  • When to walk away from toxic leadership situations

Featured Statistics:

  • 76% of employees avoid workplace conflict whenever possible (Source: Zippia)
  • Nearly 24% of workplace conflict occurs specifically between employees and their direct supervisors (Source: CPP Global)

Perfect for: Middle managers, directors, VPs, and team leads who need to navigate upward conflict, manage up effectively, and advocate for their teams while working within organizational power dynamics.

Resources Mentioned:

Need Help Managing Upward Conflict in Your Organization? Colby works with leaders and teams through keynote speaking, executive coaching, and leadership training to build people-first cultures where difficult conversations lead to better outcomes, not damaged relationships.

For Executives: Want to create an environment where your leaders feel safe disagreeing with you? Let's talk about building that culture.

How to Support The Things Leaders Do:

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  • Share this episode with a leader who's stuck knowing their boss is wrong but not knowing what to do about it

Keep advocating for your team. Keep navigating with strategy. Keep protecting your integrity. Because those are the things that leaders do.

Related Topics: Managing up, upward management, how to disagree with your boss, workplace conflict resolution, difficult conversations with leadership, navigating power dynamics, middle management skills, leadership communication, managing upward conflict, when to leave a toxic boss

#TheThingsLeadersDo #PeopleFirstLeadership #LeadershipDevelopment #MiddleManagement #ManagingUp #UpwardManagement #DifficultConversations #WorkplaceConflict #LeadershipSkills #LeadershipPodcast #ConflictResolution #ProfessionalDevelopment


SPEAKER_00:

People first leadership. Actionable strategies, real results. This is Things Leaders Do with Colby Morris.

SPEAKER_01:

Hey leaders, this is Colby Morris, and this is the Things Leaders Do podcast. Hey, if you're listening on your commute, you're in the right place. This is the show where we skip the theory and just get straight to the practical tools that you can use today. No fluff, no corporate jargon, at least I try not to, just actionable strategies you can implement as soon as you walk into the office. So let's get to it. You know that feeling when you're sitting in a meeting and your boss says something or makes a decision or gives direction, and you just know it's wrong? Not in a, I prefer it a different way, wrong, but like this is actually going to hurt the team wrong. Or it contradicts what they said last week, or you've done the research and there's genuinely a better path forward and you're stuck. Because on one hand, you want to speak up, you want to advocate for your team, you want, you know, take the right approach for what you know will work better. But on the other hand, they're your boss. And there's this voice in your head going, if I push back, am I gonna look insubordinate? Am I gonna damage this relationship? Am I going to get fired? So you stay quiet and then you leave that meeting feeling frustrated, maybe a little resentful, and definitely wondering if you made the right call. Well, here's the thing: you're not alone. 76% of employees avoid workplace conflict whenever possible. And almost a quarter of all workplace conflict, okay, like 24%, happens specifically between employees and their direct supervisors. That means the struggle that you're feeling is not just you. It's not even unusual. It's one of the most common challenges leaders face today. So if that's you, this episode is for you. Today we're talking about upward conflict, how to disagree with your boss without torturing your career in the process. I want to be really clear from the start. This isn't about winning. It's not about proving you're smarter than your boss. It's about navigating power dynamics in a way that protects your team, protects your integrity, and keeps you employed. I'm going to walk you through four scenarios, four different situations where you might find yourself in conflict with your boss and give you practical approaches for each one. Because the reality is, not all upward conflicts is the same, and the way you handle it matters. So let's start with the first scenario. Your boss has made a decision or given you direction, and you genuinely think there's a better way forward. Maybe it contradicts something they said before. Maybe you've done research and found a more efficient approach. Maybe it's just not going to work the way they think it will. Your instinct might be to say, I disagree, or I think we should do it this way instead. But here's the reality that can land as confrontational, especially if your boss is already under pressure or feels defensive about their decision. So instead, you're going to do two things. Ask for clarification or reframe it as a problem-solving opportunity. Let's start with clarification. If your boss's request contradicts something they said previously, don't call that out directly. Instead, ask them to help you understand. It sounds like this. Hey, I want to make sure I'm understanding this correctly. Last week you mentioned we were prioritizing the website design, and now it sounds like we're shifting resources to the mobile app launch instead. Can you help me understand what changed or how these fit together? You're not saying you contradicting yourself. You're saying help me connect the dots. And nine times out of ten, one of those two things will happen. Either they realize the contradiction and they adjust, or they explain the context you were missing that actually makes the decision make sense. Now, if you've done research and found a genuinely better approach, this is where you reframe it as a problem-solving opportunity. You're not pushing back, you're offering an option. It sounds like this. I know you said you wanted us to move forward with the quarterly town halls. I did some research and it looks like we might have another opportunity here. If we shift to monthly team huddles instead, we could actually increase engagement and get real-time feedback, which might help us address the issues faster. Would it be worth exploring that, or do you want to stick with that quarterly format? Notice what you're doing here. You're acknowledging their direction. You're presenting your research, and then, and this is key, you're giving them the choice. You're not saying your way is wrong. You're saying here's another option. What do you think? This approach does two things. It shows you you're thinking critically and bringing solutions, not just problems. And it gives your boss a space to either adopt your idea or explain why their original plan still makes more sense, without feeling like you're challenging their authority. Again, the goal here is not to win, it's to make sure the best information is on the table so the best decision can be made. And most of the time, your boss will appreciate that you came with solutions, not just resistance. Now let's talk about the second scenario. You need something for your boss, like resources, clarity, support, a decision, and you're just not getting it. Projects are stalling, your team is stuck, and you're starting to feel frustrated or even neglected. Here's what is important to understand. This might not be about you at all. Your boss might be completely swamped. They might be dealing with their own upward pressures, finding fires you don't even know about, or juggling priorities that have nothing to do with your team. Let me give you a real example of this. I was in an executive role, and we were under massive pressure to cut the budget, specifically to do it without cutting labor, which meant I was drowning in spreadsheets and data requests. I was completely underwater. I was trying to figure out how to make the numbers work without losing people. Meanwhile, one of my leaders needed information from me to complete a big project they were working on. And of course, what did they need? Labor numbers. One thing I was actively trying to avoid dealing with at that exact moment. Here's what they did that made all the difference. They came to me with empathy and understanding. They said, Hey, I know you're slammed right now with budget stuff. I need some labor numbers to move this project forward. If you're underwater, can I go directly to the finance department? Or is there someone specific you recommend I talk to? That was such a relief. They weren't asking me to do the work. They weren't adding to my plate. They were just asking me to point them in the right direction. I could give them a name, connect them with the right person in finance, and know that they weren't waiting on me or that I wasn't becoming a bottleneck for their progress. That's the approach I'm talking about. When you go to your boss for support and they're not responding, don't just assume neglect. Assume bandwidth. And then make it easy as possible for them to help you without actually doing the actual work. It sounds like this. Hey, I know you're juggling a lot right now. I'm working on the budget approval for the new software system, and I've hit a roadblock with procurement. Is there someone you'd recommend I talk to who might be able to help me navigate that process? I'm happy to handle it directly. I just need to know who to go to. I was thinking maybe Barbara since she handles most of the tech procurement pieces, but if that's not the right person, just let me know. You see what you just did there? You didn't even make them stop to think about who the right person was. You came with a suggestion. Now all they have to do is, yes, Barbara, or no, actually talk to Mike in finance. Either way, you've given them the context they need to point you in the right direction without having to dig through their mental Rolodex while they're already drowning. And if it's a decision you need from them, don't just ask them to decide. Come with options that make it easy for them to choose. Something like this. I need your input on the training schedule for next quarter. I've pulled together three options. We could do it all in one week in January, spread it across four and a half days in February, or offer it on demand so people can complete it on their own timeline. Given everything else on your plate, which approach would work best from your perspective? You've done the research, you've narrowed it down. All they have to do is pick. You're making their job easier, not harder. The key here is this: be a problem solver, not a problem presenter. Your boss doesn't need another thing to do on their to-do list. They need someone who can take initiative, get unblocked with minimal involvement from them, and keep moving forward. And here's the truth: when you approach it this way, you're not just getting what you need, you're also showing your boss that you're resourceful, that you can think strategically, and that you're someone they can trust to handle things without constant oversight. That's the kind of leader they'll invest in when they do have the bandwidth. All right, now we're getting into trickier territory. This is the scenario where you and your boss have a fundamental disagreement about strategy, approach, or direction. You've presented your case, they've presented theirs, and you still think they're wrong. Here's the reality you have to accept. In the end, they're your leader. They get to make the call. That's just how hierarchy works. That doesn't mean you roll over without doing your due diligence. Your job is to make sure they have all the information they need to make the best decision possible, even if that decision isn't the one you would make. So here's what you do: present the strengths and opportunities of both approaches. Lay it out objectively. It may sound like this. I know we're deciding between launching the new product line in Q1 versus waiting until Q3. And here's what I'm seeing. If we go in Q1, we get first mover advantage and we capture the holiday momentum. The risk is we're working with a tighter timeline and less runway for testing. If we wait until Q3, we have more time to refine, get customer feedback, and launch with more confidence. The risk is a competitor might beat us to market. I still think Q3 gives us a stronger foundation, but I wanted to make sure you have the full picture of both options. Look, you're not being passive aggressive. You're not saying, I told you so in advance. You're being thorough. You're making sure your boss isn't missing something critical, and then you just let them decide. Here's the critical step that most people skip. After the meeting, send a follow-up email. Not a snarky one, not a cover your butt just in case, tone. A professional, straightforward recap. It looks like this. Hey Mary, thanks for the conversation today about the product launch timeline. Just wanted to confirm we're moving forward with the Q1 launch as you outlined. I'll get the team aligned on the accelerated timeline and keep you posted on our progress. Let me know if you need anything else from me to make this successful. This email does two things. First, it confirms alignment so there's no confusion later about what was decided. And second, and this is the part nobody likes to talk about, it documents the decision in case things go south. Look, I'm not saying go into this assuming your boss is going to fail. But if six months from now the Q1 launch didn't go as planned, leadership is asking questions, you have a clear record that shows you presented both sides, the decision was made, and you executed it professionally. This isn't about being right, it's about being responsible. You advocated for what you thought was best, you gave your boss the information they needed, and then you supported the decision they made, because that's what good leaders do. All right, let's talk about the scenario nobody wants to admit they're in. When your boss actually is the problem. Not, you know, we disagree on strategy or they're too busy to support me. I'm talking about when your boss is micromanaging to the point where you can't do your job, or they're undermining you in front of your team, or they're inconsistent, playing favorites, or creating a toxic environment that's affecting your health and your team's morale. You've tried the clarification approach. You've tried being a problem solver, you've documented decisions and stayed professional, and nothing is changing. Here's the question you have to ask yourself. Is this really where you want to work? Because here's the hard truth. If your boss is a problem and the culture supports that behavior or ignores it, then this might not be the leader you want to follow or the organization you want to be a part of. Now, I'm not saying bail at the first sign of trouble. Don't give up immediately. But if you've genuinely tried, if you've had direct conversations, if you've adjusted your approach, if you've given it time, and you're still exhausted by the effort, then it's time to start asking yourself some honest questions. Can you sustain this long term? Is this affecting your mental health, your performance, or your relationships outside of work? Are you dreading Monday mornings? Are you constantly venting to your partner or friends about your boss? Are you losing sleep over it? Those are signs that this isn't just a rough patch. This is a fundamental mismatch between you and the leadership you're under. And if that's where you are, it might be time to move on. I know that's not easy. I know it feels like giving up or admitting defeat, but leaving a bad leadership situation isn't failure. It's recognizing that your time, your energy, and your mental health are valuable. And this environment just isn't honoring that. Now here's what I will say. If you decide to leave, be honest in your exit interview, respectfully, okay, professionally, but honestly. Tell them what happened. Tell them what you tried. Tell them why it didn't work. Don't trash your boss, but don't sugarcoat it either. Say something like, I want to share some feedback that I hope will be helpful. I struggled with the leadership dynamic on my team. I tried addressing concerns directly. I adjusted my communication style. I sought support where I could. Ultimately, I didn't feel like I could be effective in that environment, which is why I made the decision to move on. I'm sharing this because I think there might be an opportunity for the organization to look at how leaders are supported and held accountable. And then maybe, just maybe, you'll start a conversation higher up the ladder that leads to change. Or maybe you won't, but at least you gave them the information. And then you move forward. You find a leader who values you, a culture that aligns with how you want to lead, and an environment where you can actually do your best work because that's what you deserve. All right, let's bring this home. Upward conflict is one of the hardest things you'll navigate as a leader. It really is. Because you're caught in this impossible spot. You want to advocate for your team, but you want to do the right thing. But you also have to work within a power structure that doesn't always make that easy. So here's what I want you to remember from today. When you need to push back on a decision, don't confront, clarify. Ask questions, reframe it as a problem solving. Give your boss the information and the choice. When you're not getting the support you need, recognize it might be bandwidth, not neglect. Be a problem solver. Make it easy for them to help you without adding to their plate. When you fundamentally disagree, present both sides. Make sure they have all the information, and then document the decision and move forward professionally, because in the end, they're the leader. And when your boss really is the problem, give it your best effort. But know when to walk away. Your mental health, your integrity, and your career are worth more than staying in a toxic situation. If your organization needs help navigating difficult conversation or building cultures where upward conflict is handled constructively, I'd love to help. I work with leaders and teams through keynote speaking, executive coaching, and leadership training to build people-first cultures that drive real results. And for executives listening, if you have the authority to create an environment where your leaders feel safe disagreeing with you, and you want to know how to do that effectively, reach out to me. Let's have that conversation. And hey, if this episode resonated with you, would you do me a favor? Subscribe to the show wherever you listen to podcasts and leave a review and share this episode with another leader who's been stuck in that impossible spot of knowing their boss is wrong but not knowing what to do about it. That's how we grow this community and how we get the word out to make a bigger impact on the workplace. Because the more leaders who get this stuff right, the better workplaces become for everyone. And remember, keep advocating for your team, keep navigating with strategy, and keep protecting your integrity. And you know why? Because those are the things that leaders do.

SPEAKER_00:

Thank you for listening to Things Leaders Do. If you're looking for more tips on how to be a better leader, be sure to subscribe to the podcast and listen to next week's episode. Until next time, keep working on being a better leader by doing the things that leaders do.