262: How to Disagree with Your Boss and Not Lose Your Job

Have you ever found yourself biting your tongue in a meeting, even when you know your boss is making the wrong call? You’re not alone. Disagreeing with leadership is one of the most intimidating things we do at work, but here’s the truth. Learning how to disagree with your boss without losing your job is one of the most valuable leadership communication skills you can develop. 

In today’s episode of Leading Women Tech, I’m going to be diving into how to push back at work professionally, strategically, and without damaging your credibility. Because when done right, healthy disagreement at work isn’t a threat, it’s a sign of maturity, trust, and even promotability. I’m going to cover how and when to speak up, scripts for disagreeing at work that are respectful and impactful, and how to recover if the conversation doesn’t go quite as planned. Whether you’re practicing psychological safety in teams or figuring out how to stand your ground,

You’re going to walk away from this episode with some clear steps to handle disagreement. Like the leader, I know you are. And if you missed the episode from two weeks ago, the art of being professionally blunt, go check it out. So that’s episode 260. It is the perfect foundation for the work we’re doing today. So if you’re ready to move beyond, just going to say those last two sentences. And if you missed the episode from two weeks ago, The Art of Being Professionally Blunt, that’s episode 260, go check it out. It’s the perfect foundation for the work we’re doing today. So if you’re ready to move beyond the yes culture and into the kind of leadership that drives impact, even when it’s uncomfortable, this one is for you. Let’s get into it.

For one of my clients, let’s call her Erin. Healthy disagreement that looked like a boss who wasn’t engaging with the sales team. She was watching revenue slide and morale drop. Subtle signals didn’t work, hints were ignored. So eventually my client did something bold. She told her boss directly, she told him that his lack of leadership was hurting the business. It was uncomfortable, it took weeks of coaching for her to get there because she was so nervous about it and it ruffled feathers, it did, but it also shifted the dynamic and ultimately helped her grow her influence and impact in the company. That moment of respectful dissent didn’t end her career, it elevated it. Now on the flip side, I’ve been the employee who got in trouble for pushing back. Early on in my leadership career, I disagreed with my boss on a major decision. I had facts, I had conviction, but I didn’t yet have the language for healthy disagreement or the situational awareness to frame it in and guess what? I paid the price. I got shouted down, literally shouted at for half an hour and honestly, possibly one of the most unpleasant experiences in my career. I learned a lot that day. I’m not saying my boss handled it well, he definitely did not and his behaviour was completely unacceptable but neither did I and the bit that I have control over is me.

and the bit you have control over is you. I share that not to scare you, but to be real, because disagreeing with leadership carries risks. Yes, it also holds incredible opportunity, and that’s the main point of today, especially when you have the right mindset, preparation, communication strategy. And for me, I couldn’t not disagree. The disagreement was fundamental to who I was. It was ethical, it was the right thing, it was important.

I was going to stand my ground. And so I want you to also learn how to push back without pushing people away the way I did. I’m going to share with you some scripts for disagreeing that keep conversational productivity. And most important, understanding that disagreement isn’t disloyalty, it’s actually leadership. So whether you’re afraid of damaging a relationship, getting labeled as difficult, or just don’t know where to start the conversation, I want you to leave today.

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with the tools, the confidence to do better. But let’s just bust my first myth here in workplace culture, that a good employee always says yes, and that a team player, and I put that in their quotes, never pushes back. That disagreeing with your boss is risky or worse, disloyal in some way is just completely untrue. Here’s the truth you do need to hear. Disagreeing at work professionally, especially upwards,

Isn’t it red flag? It’s a sign of a strong, engaged leader. Because when everyone’s just nodding along, innovation dies. Critical thinking disappears and costly mistakes go unchallenged. And on a personal note as well, keeping silent is a slow, insidious cause of burnout. When you know something needs to be said and you aren’t saying it, you create an internal misalignment. This alignment over time causes long-term stress. And unrevol-

And unresolved long-term stress is the ultimate cause of burnout. One thing is I actually do with a lot of new clients, not with all of them, but when they come in and somebody’s not quite right with their work or there’s a bit stress, we do something called sparkle planning. It’s a four to eight week process where we go through and figure out what makes somebody sparkle. And some of the most interesting results that come out of that are not necessarily who they want to be when they want to be in all that, which is kind of why I created this process.

But we do a lot of stuff around internal alignment, like what do you want, how do you want to speak up, what is a good day at work, what is a bad day at work. And most of the ones who are stressed, one of the reasons there’s this chronic underlying burnout is because of a lack of voice of work, a lack of ability to stand up and say this is what matters to me. And that is so damaging to our morale, to our ego. Ultimately, it causes burnout and it means you leave an organization before you

Should be, potentially. Psychological safety though, a term that you’ve heard thrown around a lot, depends on people being able to raise concerns. And I want you to have that ability yourself. I want people to be able to offer alternative perspectives and challenge status quo without that fear of punishment or retaliation. I want you to do it without spending half an hour in the bathroom afterwards like I did that day that it all went wrong for me.

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In fact, some of the best leaders I work with expect healthy disagreement. Now, they might be a self-selecting group, don’t get me wrong. They’ve come to work with a leadership coach like me. They know they don’t have all the answers and they are not that unusual. Most leaders know they don’t have all the answers. In fact, they’re drowning in, my gosh, I’ve got to make decisions and I don’t have the data. They want a team who speaks up, not the team that stays silent. But I also wanna be honest with you that there is another side because not every environment is psychologically safe.

Some of my clients come to me thinking they are the problem when in reality, the culture they’re in is toxic. They’re walking on eggshells, second guessing themselves, trying to survive a don’t rock the boat culture where respectful descent in the workplace isn’t welcome. So let’s start here. Ask yourself, what’s really going on? Is it a fear about the situation or about the self doubt?

Are you assuming your voice won’t be welcome or is there genuine evidence it truly won’t be welcome? And there’s a difference between not welcome and not something they’re paying attention to this time because sometimes you’ll get heard but then they say we’re going to do this anyway. That doesn’t mean your voice wasn’t welcome. If however, you are living in a place of fear, then I want you to know you need to look at what’s really going on there.

Is it fear based on facts? Because if it is, it’s time to get out. If your workplace is punishing you, treating you harshly and repeatedly doing so, might be time to reconsider if it’s the place for you. But if this is a fear that is not based on fact, that is not based on previous experience in that workplace, then this is an incredible opportunity for growth. Because when you learn how to navigate healthy disagreement at work with clarity, with confidence, you not only earn respect,

you become the kind of leader others want to follow. So let’s talk about how to prepare for those moments so you can try grounded, strategic, and most importantly, ready.

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Before you speak up, you need to check in with yourself because you need to show up in a disagreement and you need to shape it long before the conversation begins. So let’s start with why are you disagreeing? This is why disagreement takes some effort. Ask yourself, is this about the business, the team, or is it about your ego? Now don’t worry, I’m not here to tell you your ego is always bad.

Sometimes what we call ego is much deeper, like integrity, unmet needs, or feeling overlooked. For example, if you’re pushing back because you haven’t been promoted in three years and your ideas keep being ignored, that’s not just ego, that’s a flag that some things are well out of alignment. But clarity here matters. Before you push back at work, be sure you’re clear on why you’re pushing back, what matters, what the impact is, what outcome you actually want, and then do your homework.

Disagreeing with that preparation isn’t bold, it is risky. There are places for it in that you might be in a meeting and somebody says something and you’re like, something’s off here. You’ve got to work on the think on your feet activities then because you’ve got to have the facts and data, the evidence and an alternative before you speak up. So your preparation is precisely that, facts and data, not just feelings. Oh my God, my cat. Rose, piss off. I’m going to have to do a take two.

dear. Okay, I’m back. We dealt with the cat. There’s a pause button now. There didn’t used to be a pause button in Riverside, so that’s exciting. Here we go.

You need to go in with facts and data, not just your feelings. You need to go in with evidence of impact. What’s at stake if this decision goes unchallenged? And by that I mean not just to you, but to the organisation. And you need an alternative. Don’t just raise problems, come with solutions. Remember my mantra, be the solutions person, not the problem person. If you disagree with something and you just raised the problem, you are nine times out of 10 are just going to get shut down because they don’t know what else to do.

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So ask yourself, what does success look like for the team, not just for me? How can I frame this so it aligns with our shared goals? And here’s the big one. Are you ready to listen to, I’m going to say that differently.

And here’s the big one, are you also ready to listen? Because leisure communication skills aren’t just about speaking up, they’re about navigating disagreement with curiosity, adaptability, and openness. You might be wrong or partially right or uncover a better option together. That’s the magic I love being involved in is when the discussion, you pushing back your curiosity, blah, blah, didn’t say that.

That’s the magic I like being involved in. It’s when the pushback actually generates a whole new idea that nobody else was getting. That’s when it really becomes obvious why having a team outperforms the individual. You uncover a better option together. So when you do this prep work, it’s not about arming yourself for battle. It’s about building clarity and confidence. It’s how you move from reacting to responding, from defensiveness to presence.

Remember executive presence is everything here. And that’s how you lay the foundation for respectful descent in work and for a legit presence that gets you noticed. This is part of executive presence. Let me just recap, because this is possibly the most important thing. You want to go in with facts and data about the business, about the team, or about your ego, but facts and data, not just feelings. Evidence of impact. What’s at stake if this decision goes untalented?

and an alternative approach. So incredibly important. If you’re going to disagree, you need to go in with those three things. And that requires thinking. So now let’s talk about how to disagree upwards without losing your job. Because you’ve now done the homework. You’ve got the mindset in place, you’re prepped, you know you’re disagreeing on what you’re aiming to achieve, but what are the tactics you now need to use? Here’s how to disagree with your boss respectfully and still be seen as a team player.

Toni Collis (13:40.463)

Let’s start with language. I want you to use phrases that communicate clearly without triggering defensiveness. Try, I see it little differently. May I offer another perspective? Here’s what I’m noticing and here’s why I’m concerned. Can we, uh, mm-mm. Can we consider an alternative approach based on whi, I’m just going to start this again.

Let’s start with the language. Use phrases that communicate clearly without triggering defensiveness. Now this is something actually as women we tend to be very good at. We ended up downplaying ourselves. So I you to use phrases that are calm, not triggering, but at the same time hold your ground. Try things such as, I see it differently. May I offer an alternative perspective? Here’s what I’m noticing. Here’s why I’m concerned. Can we approach in…

can’t say this sentence at all. Can we consider an alternative approach based on what we’re seeing here from, and say your data, your team, your client feedback, whatever the thing is. What would success look like if we tried this path instead? These are high trust solution oriented phrases. They signal that you’re not attacking the person. And that’s so important because we tend to think it’s all about us. And it’s not just you thinking that, it’s everybody in the room.

Instead, you’re advancing the conversation. You’re showing respectful dissent in the workplace and it earns you more credibility, not less. And one of the most underrated tools, questions. If you’re unsure how to lead with disagreement, try asking, would you be open to another approach I’ve been thinking about? Can I share a concern I have around an impact, a risk, an outcome? What are you most focused on achieving with this decision?

Is this priority speed or long-term sustainability? Questions do two things. They show you’re engaged and thoughtful, and they give your boss a chance to clarify their reasoning, which might genuinely need doing before deciding how hard to push. Now, I want you to remember timing and time matter. If your boss just walked out of a high-pressure board meeting, this is not the time to challenge them. Wait, be intentional, book 15 minutes if needed,

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and come in with a calm, solution-oriented energy. your boss just walked out of a high pressure board meeting, it is not the time to challenge them. Wait, be intentional, book 15 minutes if needed and come in with a calm, solution-oriented energy. And by the way, actually doing it in one-on-one can be really powerful, particularly if you think the person you’re challenging, whether it’s your boss or someone else, is going to take it personally.

You can challenge in a big meeting when there is a healthy culture of that and it’s not about an individual. But when you are looking at how and when to challenge an individual, here’s a powerful reframe. You’re not disagreeing to win, you’re disagreeing to improve the outcome. And that’s leadership. Ask yourself, what kind of leader do I want to be known as? One who agrees to keep the peace or one who sees blind spots speaks up

and helps build something better. Your ability to push back at work with respect, empathy, and strategy is what helps you become the leader that really is able to speak up, see those blind spots. Ugh, I’m going to say that again. Your ability to push back at work with respect, empathy, and strategy is what helps you become the better leader, the one who sees those blind spots, who speaks up, and helps build something better.

And remember, when you’re bringing a new idea or perspective, it’s not about you. It’s about the impact on the business, the team, the customer. Talk about your ego, take it out of the equation. Now I’m going to say that all again.

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Take your ego out of the equation and then decide, do I still need to speak up? If the answer is yes, then bring your full self, clear, curious and confident. Because now we’re going to end, I’m not doing well today, right? I’m so sorry.

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I’m just going to go back a little bit. Your ability to push back at work with respect, empathy and strategy is what helps become the leader who is showing the blind spots up, speaks up and helps build something better. And remember, when you’re building a new idea or perspective, it’s not about you, it’s about the impact on the business, the team, the customer. Take your ego out of the equation and then decide, do you still need to speak up?

If the answer is yes, then bring your full self, clear, curious, and confident. Because now we’re going to talk about how to navigate the situation when your boss does get defensive, if the conversation takes an unexpected and maybe unpleasant turn. So let’s talk about this situation. You’re in the room or on a Zoom room. You’ve done your prep, you’ve started the conversation with clarity and care, and then your boss pushes back.

Maybe they get defensive, maybe they shut it down, maybe it gets tense. By the way, some of the tenseness is in you, not just in them. What now? This is the moment that separates those who collapse from those who lead. First, breathe. A bit of resistance does not mean you did it wrong. No, let’s say that again. A bit of resistance doesn’t mean you did it wrong. It means you’re in a real conversation.

Disagreement is uncomfortable, but discomfort is not dangerous. You are allowed to stay in the room. You are allowed to be uncomfortable. Your body is going to be fine. Your brain is going to be fine. You’ve got to breathe your way through this and bring down your fight or flight response. If your boss, if your boss pushes back, try. I hear you. I’d love to understand your thinking more deeply. That makes sense. Can I clarify what I was aiming for?

Thanks for being honest. Let me take a step back and rethink the framing. This isn’t backing down, it’s buying time. It’s demonstrating your emotional maturity for one, rather than just shutting down and shutting up or reacting negatively outside of that. You are showing that you’re not there to win, but to build with your boss. And yes, sometimes your boss will just say no. And that’s when you ask yourself, how far am I willing to push?

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Sometimes it’s worth gently reinforcing your point, other times. It’s time to move on and get on board, which we’re going to talk about in a few minutes. But then there are those rare cases where the issue is too big to let go. Maybe it’s an ethical red flag, maybe it’s a decision that will damage your team or customers. Maybe you’ve raised it before and you’re watching history repeat itself. In those cases, it might be time to stand your ground respectfully with clear articulation of the risk and your position.

That might look like, understand you’re cool and I’ll support your direction, but I want to go on the record that I have a serious concern about insert specific risk. If this path is set, I’ll move forward, but I’d be remiss not to flag what I’m seeing coming. These aren’t power plays, they’re leadership moments. And if emotions rise, even yours, it’s okay. You are human, we’re all human. Well, I hope we are. What matters is that you don’t burn the bridge, you repair it.

If the conversation gets heated, come back later. Thanks for staying with me in a hard conversation. I know it wasn’t easy and I appreciate the space to talk it through. Or I’ve had a chance to reflect, I stand by my concerns, but I want you to know I’m here to support the outcome of whatever it is. That’s how trust grows, even through conflict. Because respectful disagreement at work is about more than what you say in the moment, it’s about how you stay in that relationship afterwards.

So let’s now talk about how to get on board when a decision’s been made that you do disagree with and still keep that credibility, your influence and your peace of mind because this one is so key. So here’s the situation, your boss heard you, great, but didn’t take your advice and you’re thinking, not so great. The decision’s been made, the direction is set, now what do we do? This is where a lot of leaders, especially high performing women, get stuck.

We’ve spoken up, potentially we’ve built ourselves up to such a big thing about speaking up. It’s really hard to now come down from that fact that you’ve challenged something that really matters and now you’re left wondering, do I back down? Do I pretend to agree? Do I disengage entirely? Is this a battle just not worth fighting? I was actually told early in my career, choose your battles, Tony. And it was meant with good intent, but it meant that I thought whenever somebody disagree with me, I just shut down.

Toni Collis (22:46.797)

That wasn’t the point. The point my friend was making was a senior leader who was also a mentor and a kind of a friend. She just wasn’t in my direct line. The point she was trying to make to me is that sometimes you need to get on board because it really doesn’t matter that much to you. Other things hold your ground. So let’s be real. When somebody continues to disagree, when your ideas are not heard, when your caution is dismissed, it stings. It really, really does. I get it. I have felt it.

I don’t know anybody who hasn’t, who has spoken up. And I think it’s one of the reasons why we learn not to speak up. And what I’m trying to untrain in you is that fear of the sting. I think a lot of the time we don’t speak up because we remember that pain early on in our careers. like, I’m not going to go through that again. I’m just going to align with everybody. But how do you respond after a disagreement is as important as how you raised it in the first place. So.

Hopefully this is not necessary, but it’s going to be necessary at some point because bosses are different people from us, right? Our boss is who they are. They have different rationale. They have different criteria for making decisions. They often know things we do not and they can’t necessarily tell us, whether it’s because they can’t tell us because they can’t tell us or because they can’t articulate it. But often there’s a reason why. You just might not agree with it. Here’s the other side of this.

This is also a skill, if you learn how to do this with a boss now, if you’re ever CEO, which I hope some of you will be, this is a great skill for using downwards as well because it’s really respectful. It means you can show how to get on board with your team even when your initial idea has been taken off the table, which is a level of humility a lot of CEOs never figure out. So let’s reset your mindset first.

You weren’t ignored, you contributed is the first thing to understand. You did your job as a leader, you offered insight, you challenged assumptions, you advocated for what you believed would drive success. So now it’s time to get on board professionally, not because you’re backing down, but because great leaders know when to shift gears. One of my clients, let’s call her Catherine, deeply disagreed with a strategic pivot earlier this year in her company.

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She shared the data, she made her case. The leadership team said thanks and moved forward with their original plan. Here’s where Catherine stood out. Instead of stewing or subtly resisting, she got in the game. She asked, how do I make this work? She became the solutions person and her influence grew and grew and today it’s astonishing. Even though she didn’t win the argument, because here’s the truth. Disagreement doesn’t define your leadership.

Your response does. But just in case you think Catherine is superhuman, and let me let you into another secret. She wasn’t there immediately. She came to a coaching session with me, really upset, really annoyed, asking, how do I make them see this huge mistake? We had a long discussion and asking things such as, like, why does this really matter? Are you going to be able to change things? And until she realized that she was not going to be able to change things.

and by going in, focused on making them see the mistake, which is what she came to me with. I need to figure out how to make them see this. I was like, okay. But if she actually went forward into that conversation, she was going to be the problem person. They had decided there was a line that had been drawn in the sand and diagnosing that is what we did in the coaching session we had together. So we flipped the script and made her the solutions person.

And what it’s done is mean that those decision makers are now involving her more than ever before. They now listen to her more simply because she gave her concerns and she got on board with the decision anyway and she became the person who delivered. So now they invite her to the decision making table more often. So let’s talk about how to communicate after a disagreement. I want you to try phrases such as.

I appreciate the opportunity to share my perspective. I’m here to support the decision moving forward. While I had a different view, I’m fully on board with making the success. I’m going to say that again. I’m going to just go back to the beginning of that section.

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So let’s now talk about how to communicate alignment after a disagreement. I want you to try phrases like, I appreciate the opportunity to share my perspective. I’m here to support this decision moving forward. While I had a different view, I’m on board with making this successful. Now that we’ve chosen a direction, here’s where I think I can add the most value. This shows emotional intelligence, a leadership communication, and most important of all, maturity. It tells your boss and your peers,

that you’re not just in it for your ego, you’re here for the impact, which means next time you’re more likely to be heard about your concerns because people start to genuinely see you are there raising concerns because you care, not because of your ego. Guess what? This gets remembered, maybe not today, but six months from now when it’s time for promotions, raises, special projects, you’re the one who showed up with clarity, courage, and collaboration.

So now you’ve got the mindset, the strategy, the scripts. Let’s put this into action because knowing how to disagree with your boss is one thing. Doing it is what builds your confidence and shapes your leadership identity. So here are two quick steps to get you started. Number one, reflect what’s one disagreement you have been avoiding. Maybe it’s a small decision you quietly disagree with in last week’s meeting. Maybe it’s a bigger issue, a direction, a pattern, or even a culture shift you’re resisting.

Ask yourself, why haven’t you brought it up? Is it fear, doubt, timing? What would it take for me to speak up with clarity and respect? Write that down, sit with it, feel it, experience it, then decide if and how you want to act. And then number two, the challenge, because I love to challenge you on this podcast. In your next tough conversation, try using one of today’s scripts. Just one, it might be.

I see it a little differently. Would you be open to another perspective? Or here’s what I’m noticing and why I’m concerned. Or even what would success look like if we tried this instead? Start small, start where it’s safe. Practice the language. You’ll be surprised how quickly it becomes second nature. And if things don’t go perfectly, that’s okay. This is a skill. Every conversation is a rep.

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Every rep builds your presence, your resilience, and your ability to live with authenticity. Healthy disagreement at work isn’t about being right, it’s about being brave. You don’t need to fight every battle, but you do need to be willing to show up, speak clearly, and hold your ground when it really matters. Disagreeing with your boss isn’t just safe, it’s essential for great leadership because leaders who rise,

They’re the ones who don’t stay quiet. They’re the ones who know how to speak up with clarity, courage, and respect, especially when it’s uncomfortable. So as you head into your next meeting, I want you to remember, healthy disagreement is a mark of leadership, not rebellion. Done well, it builds trust, it earns you influence, and it shapes the culture around you for the better. If this one resonated with you and you want to dig in deeper,

into how to build a leadership presence, navigate tricky conversations, or step into more visibility without burning out. I’d love to support you directly. You can book a free strategy session with me at tonycollis.com forward slash let’s dash chat. This is your space to get clarity, ask questions, and start building a plan that actually works for your career. If you missed, like, like, mm-mm.

If you missed the episode from two weeks ago, The Art of Being Professionally Blunt, go give it a listen. It’s the perfect companion to today’s topic and such a powerful foundation for anyone wanting to lead more authentically. That’s it for this week. Keep showing up, keep leading with your heart and never underestimate the power of your voice, especially in the rooms that need it most.