How to Deliver Bad News to Your CEO (Without Losing Credibility)

In this episode of Executiveland, Elizabeth Freedman tackles a high-stakes challenge for senior leaders: rebuilding lost credibility in the C-Suite. She shares actionable strategies for navigating this, focusing specifically on how to deliver bad news to your CEO without escalating the damage.

Key takeaways include:

• How to leverage clear and concise communication when things go wrong, taking ownership and pivoting from excuses to actionable solutions
• Why "under-reacting" to tough feedback or unrealistic requests helps preserve trust and avoid escalating tension
• The reason the "Trust Me" trap fails, and how to earn confidence through demonstrated competence and consistent action instead
• Why strong judgment is critical and understanding what truly matters to the executive team and making decisions accordingly

If you're ready to learn how to regain trust and communicate more effectively at the executive level, tune in to this episode!

For more tools, insights, and strategies to lead with clarity and credibility, visit Elizabeth’s website, take the C-Suite Readiness Assessment, and subscribe to Executiveland on  Apple Podcasts and Spotify and so you never miss a new chapter of the unwritten playbook!

Registration for Spring 2026 E-Suite Impact is now open – register before March 31 for preferred early rates. For details and to sign up, please visit https://esuiteleader.com/impact-program

• Free C-Suite Readiness Assessment
• Website: https://esuiteleader.com/
• Forbes Column: https://www.forbes.com/sites/elizabethfreedman/
• LinkedIn: https://www.linkedin.com/in/elizabethfreedman
• Twitter X: @‌esuiteleader

Transcript

SPEAKER_00 0:05

Hi and welcome to Executive Land. I'm Elizabeth Friedman, and this is where top leaders go off script to share straight talk and the unwritten playbook about life in the C-Suite. For more ideas, visit ESuiteLeader.com. Now let's dive into today's episode. Hi, everybody. Welcome back to an episode of Executive Land. So glad you're here, and I want to thank you for listening, for being part of this podcast. If you like what you hear, I would be so grateful if you'd consider rating and reviewing the podcast. It's easy to do. If you just go wherever you are listening and downloading this podcast, if you can rate it, give a comment. It's so helpful and it helps others find this episode. Well, today I want to talk about a tough situation. What do you do when you've lost credibility with the C-suite? Or let me put it a different way. How do you deliver bad news to your CEO without making things worse? You know, this matters because I see a lot of really very strong leaders struggle in this area. And it's not because they're not smart or working hard. You know, I think we all just know that when you get to these senior levels inside organizations, it really isn't enough to be right or have good intentions, even to be doing good work. You must be trusted by the executive team and be trusted as a leader who really understands what matters to the company, what matters to the team. You're the kind of leader who's trusted to exercise good judgment, good critical thinking, who can handle pressure. I mean, I could go on. And I think the point here is that if you find you're struggling, if for whatever reason, um, perhaps you're not trusted in one of these ways, it gets difficult, doesn't it? And look, we know what this looks like. If you're not trusted, everything becomes more challenging. CEOs become more skeptical, maybe when they meet with you. So therefore, the questions get tougher. And then what do we do? We may feel a little more anxious or defensive or just less confident when we're interacting with them, then the interactions aren't as strong. And now we're kind of caught in this cycle. And so let's talk about this today. Whether you're thinking about ways to either grow trust, perhaps you feel something does need to be rebuilt, or maybe you're leading a team where you've observed the team is struggling to gain credibility with the executive team, the CEO, whatever the case may be. And let's start with this. Let's look at your explanations and your reactions. Okay, so something that I see, and it's an easy mistake, I think we can make, particularly when we're delivering bad news, which is listen, we spend too much time explaining why something went wrong, why something didn't happen. And so we might say things like, well, look, we have this bad situation. We missed a deadline because our resources have been constrained. We've laid off part of the organization that used to do this work. Uh, a large customer decided to move their business elsewhere. The market shifted, the other part of the business didn't deliver, and that impacted us. And I think anyone can relate to this in part because a lot of what I've just said could really be very true in your case. But, you know, we know how this goes to a CEO that can just land as an excuse. And so, fair or not, they may be thinking, I have heard that from you before. You know, I've been hearing you talk about these same excuses, these same things for months. So, what is a plan? What are you doing about it? And the other thing that we can assume is, you know, typically your CEO is probably as aware of these issues as you are. I mean, I would assume they would already know the environment is tough. They know about the constrained resources, the shift in customers. That's not going to be new to them. So, again, we come back to the questions they do want to know. What are you going to do about it? And so this is where we really want to think about coming from a position of strength. So it might sound like we did miss the number. Here are the two biggest drivers. Here's what we're doing now to correct it. Here's the change you can expect to see over the next 30 days. Here is where we may need support from you. Here's when I'm coming back to you with an update. I mean, you get the idea, but the point is it's a different type of tone and conversation. And the other thing you have to do, of course, is you do what you say you're gonna do. You come back when you've done that, you close that loop. I know this seems obvious, but too many leaders keep showing up month even after month with essentially the same types of issues or challenges, the same types of explanations, and there really is no visible resolution. That's where you see the frustration in the relationship. That's where you see the credibility really erode. Executives get so impatient, you know this, right? When they feel like nothing is moving ahead. You and I are the same way. And so you have to say what you're going to do. And again, this is where you can start to shift that dynamic. But let's say one other thing, because it can get tricky. Let's say a CEO, someone in the C-suite, asks you to do something that seems, from your perspective, entirely unrealistic, impossible within a given time frame, too difficult given the current environment. And so when you're asked to take something on like this, you might be thinking understandably, no, you might be thinking impossible, no way this could be done. We just can't take it on. What I want to say is this is a critical trust moment. It really is. It is essential to slow down when these types of requests come your way to really pause and do something very important. Underreact. Wait a beat. Don't immediately react. Don't immediately respond with no or offer a long explanation, show your frustration. Again, right or not, that will be seen as defensiveness, becoming overly emotional. And remember, your job in these difficult moments is to just stay credible, maintain that trust. It's just another moment in a very long career. And so, how do we engage without appearing resistant? Well, there are many ways to do this, but I would suggest instead of, for example, debating about the feasibility of something, one easy technique, just offer some trade-offs. A trade-off might sound like, well, we could pursue this in a few different ways. Option one certainly would get us some speed, but it might carry some more risk. You know, another option may require additional resources, um, but would be slower, et cetera, given that my recommendation would be you get the idea. And most reasonable CEOs and leaders, they expect you to raise concerns, surface constraints and choices versus just saying a yes or a no. Um, if something you're being asked to do feels incredibly unrealistic and you want to react, instead underreact. And perhaps you might say, um, you know, I think implementing this immediately may be difficult for us to do. We could run a 30-day pilot. Let's test, let's see what's possible, and then let us come back to you with some data. So again, what are you showing? You recognize what that executive wants to accomplish instead of resisting with a no, this won't work and no, this can't be done type of message. You're signaling we're committed. So all you're trying to do in these moments of reaction is pause. Pause, underreact. That's what allows you to protect that credibility and if needed, come back with a better answer. The second consideration when you have to share bad news, when you're in a tough situation and you want to avoid any kind of hit to your own credibility, avoid the trust me trap. What is the trust me trap? You know what I'm talking about. This is when someone says to you, trust me, trust me, it'll be fine. And I do see this a lot. For example, leader says, Trust me, trust me, we're gonna make the number, the client's gonna buy, trust me, right? We've got it handled. But you know, what is that CEO thinking? They're thinking, trust you, right? What am I trusting you on? Based on what? Especially if that team, that leader has missed before. You know, I was speaking with a business leader recently. He's dealing um with this exact problem. His team is saying to him, trust us, we're gonna make the quarter. But when the leader looks at the monthly plan, there is no evidence to suggest to him that the team's gonna meet the goal. So what's happening? The leader keeps asking for more data, more specifics, more reports. Leader wants to get a more visibility and line of sight into where are we this month? And meanwhile, the team is feeling frustrated. They're thinking, you know, my God, let us do our job. Stop micromanaging us, right? We always deliver for you. Why do you need so many reports? But you know, in a lot of companies, the fact that you've delivered before doesn't necessarily matter. You know, most senior executives they cannot afford or risk being surprised. And, you know, the truth is, I think we understand this. You know, imagine a delivery service says to you, you know, your package is going to arrive tomorrow, trust me. But they can't tell you, you know, where is the package? Did it get shipped? Is it left in the warehouse? You do not feel reassured. Show me the tracking, is what you're thinking. And of course, this is exactly what happens inside companies. When executives don't have enough visibility, transparency, a line of sight into how the work will get done. You and I saying, trust me, of course, that's not gonna work. Of course they will start digging, asking questions, asking for reports. They're gonna schedule more frequent check-ins. And so if trust is low, even if you're trying to grow trust with a leader, we cannot be asking for more patience or trust from them. We have to show them the math, show them the data, show them the actions that we're gonna be taking to create the kind of outcomes that we believe we will see. And this gets me to the third idea. When we're struggling to gain credibility or trust with an executive team, even when we have to deliver tough or difficult news, it's so important that you show you understand what really matters. Because, you know, I find when leaders are struggling to gain trust with a CEO, it's rarely an issue of purely communication or presentation skills. It is really about the judgment, the discernment, the critical thinking that we show. So, for example, let's say that a senior team is asking a CEO to support an initiative at the company. Now, on its own, in isolation, it could be a very smart initiative. But perhaps upon inspection, we realize it's going to require significant resources. It may ignore the fact that there are existing projects underway that are tackling related issues. In other words, the initiative was sort of built in a vacuum. Leaders didn't really talk to other leaders in the company. Um, no one really checked whether there's another region or part of the organization that may already be doing something similar. And so what's really being assessed, I find, by the CEO is not the value of the recommendation. It's really the judgment behind the idea. You know, the CEO or executive may be thinking, okay, so how does this connect to what we're trying to accomplish? Is this really where we should be investing resources? You know, where else are we doing this across the company? Rather than create something new, how can we leverage what we're already doing? Who else did you involve in this type of, you know, recommendation or decision? And so that critical thinking, that judgment is what becomes so important. How you know what to raise, when to raise it, how to frame it, and also how to manage your emotions when you get challenged and get things back on track when things start to go sideways. This becomes so important. So I'll give you another example of this. I recently saw a situation where a business president and his team were presenting their strategy to the CEO. The CEO started digging into an issue in one of the regions, started asking some tough questions, and the questions were really directed at one of the team members. And this team member really struggled. They couldn't answer the questions, they got defensive, they just kept digging themselves into a hole in the meeting. After the meeting, the CEO went to the president and started questioning why this leader is even in this role? Why did the president even let this leader present at the meeting? Should this leader even be at the company? That is how fast trust and credibility can erode. Now, in this case, the president stepped in quickly. President reassured the CEO this would be resolved. And then the president had to invest a significant amount of their time helping the leader understand just how much credibility had been lost and how intentional and quick that recovery would need to be. What do I mean by a simple recovery plan? I'm talking about just admitting the fact that we have a real trust and credibility issue going on, and then taking some simple steps that can really help you regain that trust. Now, one thing I want to point out here is that when credibility takes a hit with the C-suite, I do think sometimes our instinct is to fix the perception they have of us. Um let's influence executives that they're seeing this in essentially the wrong way. And you and I know that really rarely works. The far more productive path, like we just want to focus on getting better. We want to focus on getting better at handling those kinds of interactions. And really, when we can improve that, we can trust that trust will improve. So consider three simple steps in your simple recovery plan. And the first one starts with your own self-awareness. I mean, we just have to take an honest look at where we are. If we've been having difficult interactions with the C-suite or CEO, or we're not even able to get access to them because of maybe a perception they have around trust when it comes to us, we have to just be able to see that. Because, you know, particularly this kind of issue tends to raise emotions. And, you know, it's hard to see the situation we're in objectively. So this is where I just urge you to get feedback. Get feedback from people you trust who can really help you understand clearly why there's a struggle. Get input on, you know, what does it look like when I'm struggling? What was going on? What caught me off guard? What did I miss? What does the CEO say about how, for example, a meeting went with me? If you're able to learn that. And all you're trying to do here is get accurate input. You're getting the kind of information that can really help you make the right kinds of changes. Then we go to step two of this simple recovery plan. You've gotten some good input from trusted people. Now it's about preparing, really preparing for interactions differently. That's all we can do. And so what does that mean? It means really building in enough time before interactions with individuals where we have a credibility or a trust issue so that we can show up much, much better. What does that mean? Well, maybe we have to really think through the assumptions that we're making about an idea before that meeting. We've got to pressure test those. We have to anticipate the hardest questions. We've got to make the connections between what we are there to discuss and whatever priorities are most significant to the company, to that executive team. We've got to clarify that. We've got to tighten the story. We've got to tighten the logic behind what we're recommending. You know, we've got to have a game plan for how we will underreact when the difficult moments come. And again, it's not just about our communications, it's about the critical thinking and the judgment. That's part of our preparation process. The third and final step of the simple recovery plan, you rebuild trust through repetition. You know, if you're working to grow or regain trust and credibility, take some time. We know it may not come back overnight, but do not let that discourage you. It can come back. And the way it will, just like any situation where you and I are trying to grow trust, it's with just one better interaction after another. It's the one good meeting you have, that ability to answer tougher questions with um more confidence, more composure, whatever the case may be, over time those moments can compound. And when those things start to improve, because your own thinking, your preparation, the feedback you've gotten, all of that improves. And then your leadership can improve, of course, trust and credibility can also improve. Do not suffer here. Really improve. Improving trust and credibility can be done. I've worked with leaders in teams for over 20 years, some who have absolutely transformed their relationships with their CEOs, with their executive teams. You can learn this. And this is exactly what I teach in eSuite Impact. I teach an eight-week advanced course where we talk about this. The next spring cohort starts April 15th. So if you're interested, visit me online at essuiteleader.com and check it out. Because in the course, we break down why senior leaders can lose credibility with the C-suite, but more importantly, what to do about it. Because what I found is lots of good leaders, even very capable leaders, have not necessarily been shown what to do when you run into this. Even just the dynamic that changes at this level. And you know what? When you are getting a lot of pressure and meetings from executive team, it's natural to struggle. And what I find is most of the leaders I work with, they really want to be effective with this audience. They want to be considered and promoted into an executive role themselves in many instances. They want to be respected and recognized and valued for the contribution they make. And of course, all of that is possible. But what I find is if you want to make that kind of impact, if you want to make an impact as an executive, first you have to show you can make an impact with other executives. So if you're finding that your interactions with the C-suite are harder when they could be or should be, this is what I help leaders overcome. Thanks for being in Executive Land with me today, everyone. Join me next week. I'll see you next time. Take care. Well, that's all for today in Executive Land. Thanks for listening. And if you're looking for more, check out my website, eSweetleader.com, where you'll see all kinds of free resources and take the free Executive Readiness Assessment. It shows you exactly where you're strong and where to focus next in your own leadership. And don't forget, subscribe to this podcast so you never miss an episode. I'll see you next time in Executive Plan.