Courage in Action: When Things Don’t Go as Planned – Leading Through Setbacks

Welcome to the Courage of a Leader podcast. This is where you hear real-life stories of top leaders achieving extraordinary results, and you get practical advice and techniques you can immediately apply for your own success. This is where you will get inspired and take bold, courageous action. I'm so glad you can join us. I'm your host, Amy Riley. Now, are you ready to step into the full power of your leadership and achieve the results you care about most. Let's ignite the courage of a leader. Have you ever had one of those leadership moments where you thought this was supposed

to have gone very differently? Maybe you championed an idea that didn't work, or you made a decision that turned out to be the wrong one, or your team missed an important goal, a client was disappointed, you didn't get the promotion, or the initiative you spent months building got canceled, or something completely outside of your control changed, and suddenly the plan you were so confident about no longer made sense. Setbacks are a part of leadership, and I don't think we talk enough about what happens after them. We hear a lot of advice about failure. Learn from failure. Fail

fast. Turn setbacks into opportunities. That's all good advice. It can sound pretty straightforward when we talk about it in theory, yet it feels very different when you're actually in it. When you're disappointed, when your team is looking at you, when you're wondering whether you made the wrong call, or when you have to walk into a meeting and say this didn't work, that's when the real leadership begins, and that requires the courage of a leader, not because courageous leaders don't fail, not because they somehow become immune to disappointment, and definitely not because they always know

exactly what to do next. Courage shows up in how we respond. So in this episode, I want to tackle five hard questions about what we do when things do not go according to plan. What do I do when something I led doesn't go as planned? How do I know when to keep pushing and when it's time to change course? How do I take accountability without taking responsibility for everything? Question four: How do I help my team recover when we've experienced a setback? And finally, the fifth question I'll tackle is: How can I make sure a setback actually makes me a better leader? Because setbacks are

inevitable. What we do with them is leadership. So let's dive in. The first question: What do I do when something I led doesn't go as planned? First, resist the urge to immediately explain why it happened. This can be really hard, especially if you feel responsible. Something goes wrong, and our brains immediately start assembling the case. We didn't have enough time. The customer changed the requirements. I told them this might happen. We didn't get the resources we were promised. There were circumstances outside of our control, and some or all of those things may be true. Yet notice

what's happening. We're explaining before understanding, and sometimes we're defending ourselves before anyone has even accused us of anything. I see this with leaders at every level. The more visible the setback, the stronger the temptation can be to protect our credibility. This is one of those interesting leadership moments. We're trying too hard to protect your credibility can actually damage it, because your team probably doesn't need your defense first. They need your leadership. So I'd encourage you to slow the moment down, take a breath, start with what actually happened, not whose

fault was it, not even how are we gonna fix it? Not yet. First, ask what happened. What do we know? What don't we know? What outcome were we expecting? What outcome did we actually get? What can we learn from that gap? That difference matters because it moves us from reaction to curiosity. Imagine that your team has spent six months developing and launching a new process. Everyone has worked hard. You've talked about how much this is going to improve the customer experience. You launch it, and it doesn't. Maybe customer complaints actually increase. Now you're sitting in the first meeting

where everyone is. Looking at the results, you have choices about how you enter that conversation. You can start explaining. We knew there would be some bumps in the beginning. We didn't get the adoption we expected.

Operations didn't implement this exactly the way we designed it. Notice what happens if you start there. People start protecting themselves too. Now we're all explaining. We're all defending. We're all trying to make sure the failure doesn't land too close to us. Or you could say something like, "This isn't the result we wanted. I know how much work went into this, and I'm disappointed too. Let's understand what happened. That changes the conversation. You haven't blamed anyone. You haven't minimized the disappointment. You're not pretending to know the answer, and you haven't declared

the whole thing a failure. You've created space to learn. That takes courage because one of the hardest things for leaders to tolerate is the space between this didn't work and now I know what to do next. We want to close that gap quickly. We want the answer. We may feel like the team wants the answers from us, or our leader does. Sometimes the most responsible thing we can say is, "I don't know yet. Let's figure out what this is telling us. That doesn't make you look weak. What can weaken your leadership is pretending to have certainty that you don't have. There's another part of this that I

think is really important. Let yourself be disappointed. If you cared about the outcome, of course you're disappointed. If you worked hard on something and it didn't succeed. Of course, that can sting. If you made a decision and now realize it was the wrong one, you might feel embarrassed. Courage isn't pretending those emotions aren't there. It's making sure they don't make the next decision for you. You can say, "I'm really disappointed by this result, and then let's understand what happened. Both can be true. You don't have to manufacture optimism five minutes after something goes

wrong. In fact, your team may trust you more when you acknowledge the reality they're experiencing too. Then, once you understand what happened, you can start asking, "What does this require from me now? Maybe you need to own a mistake. Maybe you need to communicate upward. Maybe you need to change the plan. Maybe you need to protect the team from an overreaction. Maybe you need to have a difficult conversation. Maybe you simply need to give everyone a little time, gather more information and come back together tomorrow. Leadership after a setback isn't about having the perfect

response immediately. It's about responding intentionally rather than reflexively. So the next time something doesn't go as planned, before you explain it, defend it, fix it, move everyone past it, ask yourself what actually happened? What does this moment need for me as a leader? Your answer to those questions tell you a lot about where you need to demonstrate the courage of a leader next. Okay, the second question: How do I know when to keep pushing and when it's time to change course? This is one of the hardest questions after a setback, because we celebrate persistence in leaders.

Stay the course. Don't give up. Be resilient. Keep going when things get hard. And sometimes that is exactly what leadership requires. You believe in something before other people do. You encounter resistance. The first attempt doesn't work. Results take longer than expected. You need the courage to stay with it. Yet sometimes courage requires something different. Sometimes it's saying this isn't working. Our goal is right, but our approach isn't. That distinction is important because resilience does not mean stubbornly continuing down the same path no matter what. Resilience is our

ability to adapt, recover, keep moving towards what matters. And sometimes moving towards what matters means we have to change direction. Question two: How do I know when to keep pushing and when it's time to change course. This is one of the hardest questions after a setback, because we celebrate persistence in leaders. Stay the course. Don't give up. Be resilient. Keep going when things get hard. And sometimes that is exactly what leadership requires. You believe in something before other people do. You encounter resistance. The first attempt doesn't work. Results take longer than you

expected, and you need the courage to stay with it. Yet sometimes courage requires something different. Sometimes it's saying this isn't working, or the goal is right, our approach isn't. That indifference is incredibly important because resilience does not mean stubbornly continuing down the same path.

Resistance is our ability to adapt, recover, keep moving towards what matters, and sometimes that requires us to change direction. Imagine you're leading an organizational change. You've spent months developing the plan. You've communicated. You've trained. You've invested money, and three months in, you're not getting the results you expected. Now what? It's easy to say we just need to give it more time, and maybe you do. It's also easy to say this isn't working. We need to abandon it, and maybe you do. The challenge is figuring out which one is true. So I'd encourage you to separate two

the goal and the approach. Ask: Is the goal still right? Do we still believe this is an outcome worth pursuing? Has something changed that makes the goal less relevant or less valuable? If the goal is still right, then ask: Is our current approach getting us there? Sometimes leaders abandon an important goal because the first approach didn't work. Other times, we become so attached to our approach that we keep investing in it long after the evidence is telling us to do something different, and there's a very human reason for that. We've invested in it, time, money, energy, maybe our

reputation. Maybe we were the person who convinced everyone else this was the thing to do. Now changing course can feel like admitting I was wrong. That's where the courage of the leader comes in because the question can no longer be how do I prove this was the right decision. It needs to become given what we know now, what is the best decision? Those are very different questions. One protects the decision we already made; the other serves the outcome we're trying to create. So, if you're trying to decide whether to persist or pivot, here are a few questions I'd ask: What have we learned

that we didn't know when we started? What evidence tells us to keep going? What evidence suggests we need to change? Is the goal still right? Is there another approach that could get us there? And here's the uncomfortable 1am: I continuing because I still believe this is the best path, or because I don't want to admit that we need to change? Sit with that one for a minute. Persistence can require courage. Changing course requires courage too. The goal isn't to prove that your original plan was right. The goal is to keep making the best decisions you can with what you know now. That's

resilience. That's the courage of a leader. Okay, the third question I want to tackle: How do I take accountability without taking responsibility for everything. This is an important distinction, and before we get into it, I want to be clear that the questions I'm about to suggest are not necessarily questions you're asking your team in the moment. These are behind closed doors questions, a conversation that you have with yourself first before you explain what happened. Before you decide what you need to say to your team, your boss, your customer, or anyone else, you need to get honest

with yourself about what was actually mine to own. Because when we talk about strong leadership, we say things like "own it, "take responsibility. The buck stops here, and I agree with the spirit of that. We want leaders who take accountability. We want leaders who are willing to say, "Here is the part I played. Yet, taking accountability does not mean taking responsibility for every single thing that contributed to an outcome. Let's say your team misses an important target. Maybe you didn't communicate the priorities clearly enough. Maybe you waited too long to address the performance issue.

Maybe you underestimated the resources the team would need. Own that, and maybe at the same time, a key customer changed direction. A supplier missed a deadline. The market shifted. Two people unexpectedly left the team. Those things happen too. So in that private debrief with yourself, accountability isn't everything that went wrong is my fault. Accountability is being able to look at the situation clearly and ask, "What is mine to own? That Requires self-awareness, also requires discipline because leaders can fall into two traps here. The first is deflection. That wasn't my decision.

My team didn't execute. We didn't have the resources. Nobody told me. If that's the whole story we're telling ourselves, we may be protecting ourselves.

From having to look at our own contribution, the other trap is over ownership. This is all on me. I should have prevented all of this. I let everyone down. That may sound noble. It isn't necessarily useful, because if you take responsibility for things you generally could not control, you're not getting a clearer picture of what happened. You may actually prevent other people from taking accountability for their part. So when you have that conversation with yourself, ask: What did I control? What could I influence? What did I miss? What would I do differently, knowing what I know now?

And genuinely, what was outside of my control? I particularly like the question, "What did I miss? because it moves us beyond blame, beyond blaming ourselves, others, circumstances. Maybe I missed information. Maybe I missed the resistance from the team. Maybe I missed an early warning sign. Maybe I missed an opportunity to ask a better question. Maybe I made a reasonable decision with the information I had, and now I have different information. Not every disappointing outcome means that you made a bad decision. Sometimes you can make a thoughtful decision and still get a disappointing

result. Leadership isn't about somehow controlling every outcome; it's about being accountable for how you led. Once you have that honest assessment privately, then you're in a better position to decide what you need to say and own publicly. Maybe you need to say, "I wasn't clear enough about priorities, or "I saw that we were getting off track, and I waited too long to address it. Or, given what I knew at the time, I still understand why I made that decision, and now I can see what I missed. That's very different from either defending yourself or saying this is all my fault. So when

something goes wrong, before you explain yourself and before you put the whole thing on your shoulders, get quiet and get clear. What was mine? Own it. Say what needs to be said. Learn from it. Do something differently because of it, and let other people own what is theirs. To me, that's real accountability-not blame, not martyrdom, ownership-and starting with our own ownership. Okay, question four: How do I help my team recover when we've experienced a significant setback? This is where leadership gets visible because when a team has worked hard and something doesn't go the way they hoped,

people are watching you. Not only for the answer, they're watching to see how serious is this, how disappointed should I be? Are we blaming people here? Are we pretending this didn't happen? Are we moving on too quickly? Do we still believe in what we're doing, lots of questions can come up, and one of the biggest mistakes leaders can make in this moment is trying to get everyone to bounce back too quickly, right? We want to be resilient, we want to stay positive, we want to keep momentum, so we quickly say, "Okay, that didn't work. Here's what we're going to do next. Yet your team may still

be disappointed, or frustrated, or embarrassed, or exhausted. Maybe they gave everything they had to something that didn't work. Maybe they feel like they let you down. Maybe they're wondering if all that effort was wasted. Don't rush them past that. You don't have to turn the setback into a motivational speech five minutes after it happens. Sometimes the first thing your team needs is for you to acknowledge the reality of the moment. This is disappointing. I know how much went into this. This isn't the result we wanted. That doesn't make you negative. It makes you credible. You're naming what

everybody already knows. Then give people some room to process. Once you've done that, help the team shift from disappointment to learning. And tone here matters. There's a big difference between asking who dropped the ball, and asking what happened. There's a big difference between how did we let this happen, and what were we seeing at the time? What did we miss? What would we do differently? Those questions keep accountability in the room without immediately creating blame, and that's important because if people believe a setback is going to turn into a hunt for who messed up, they're

going to protect themselves. They're going to explain, defend, or withdraw. And now you've lost access to the very information you need in order to learn. So create an environment.

Where the team can be honest about what happened, then reconnect people to what is still true. Maybe the goal still matters. Maybe the customer still needs what you're trying to create. Maybe the team is still capable. Maybe the strategy needs to change. Maybe you've learned something incredibly valuable that will make the next attempt much stronger. Then help people see the next step, not necessarily the whole plan. The next step, because after disappointment, momentum matters. Momentum comes from clarity. What are we going to do now? Who owns what? What are we going to test? What are

we going to stop doing? What do we need to communicate? That gives people somewhere to put their energy. So, if your team has experienced a setback, I'd think about your role in four different parts: acknowledge what happened, create space to understand and learn, reconnect people to what still matters, and establish the next step. That's resilience as a team, not pretending the setback didn't hurt, not staying stuck in it, learning from it together, and helping people move forward with clarity-that's the courage of a leader. And our final question: How can I make sure a setback actually

makes me a better leader? I love this question because we say things like "failure makes you stronger, "adversity builds character, "we learn from our mistakes. Yes, but not automatically. You can go through something difficult and learn almost nothing from it. You can also go through something difficult and come out more defensive, more cautious, more controlling, more reluctant to take a risk again. Gosh, I think that rings true for many. The experience itself doesn't create the growth. What we do with it does, and that requires intentional reflection, not endless rumination, not replaying

the mistake over and over, instead, reflection, rumination sounds like I can't believe I did that. I should have known better. What must people think? Reflection sounds like what happened. What did I learn? What will I do differently? That's where growth starts. So after a setback, I'd encourage you to ask yourself a few questions. What did this experience teach me about myself? Maybe you discover that you get defensive faster than you realized. Maybe you avoid difficult conversations. Maybe you're more resilient than you knew. Maybe you've learned you can tolerate uncertainty. Maybe you've

learned you need input from people who think differently than you. Then ask, what did this teach me about how I lead other people? Did you communicate enough? Did you listen early enough? Did you give people enough ownership? Did you ask for bad news? Did you make it safe for someone to challenge you? Then, what assumption did this challenge? This is a powerful one. Maybe you assumed the customer wanted something they didn't actually want. Maybe you assumed the team understood the priority. Maybe you assumed silence meant agreement. Maybe you assumed a person wasn't ready for more

responsibility. Maybe you assumed your first idea was the best one. Setbacks have a way of exposing assumptions. If we're willing to look at them, that can be incredibly useful. Then we can ask ourselves, "What will I do differently? Here we turn insight into growth, because if my answer is, "I learned that I need to communicate more. Okay, what does that mean exactly? Am I adding a weekly check-in? Am I asking more questions before making a decision? Am I sharing context earlier? Am I inviting someone to challenge my thinking? Am I addressing performance issues sooner? Make the

learning behavioral. If nothing changes in how you lead, I'm not sure the lesson has really landed. And there's one more thing I'd add: don't become so afraid of repeating the setback that you stop taking meaningful risks. This happens. A leader takes a chance, it doesn't work, and the lesson they take away is never do that again. The better inquiry is, what would I do differently next time? Not how do I make sure I never feel this way again, because if the goal becomes avoiding disappointment, avoiding embarrassment, avoiding failure, we can make our leadership very small. Courage requires

us to learn without becoming afraid to act. So, if you want a setback to make you a better leader, you're not just asking yourself what went wrong. You're identifying how you want to lead differently because of what you learned. That's where adversity becomes growth, not because the setback happened.

Because you chose to do something with it, and demonstrate the courage of a leader. As I wrap this episode, I want to come back to one idea: setbacks are inevitable. What we do with them is leadership. Things will go wrong. A decision won't work. A plan will need to change. A team will be disappointed. You'll miss something. You'll make a mistake, and sometimes something completely outside of your control will change the outcome. The goal isn't to become a leader who never experiences setbacks. That's not realistic. The goal is to become the leader who knows how to respond when

they happen, to pause before defending, to get curious about what actually happened, to know when persistence is courage and when changing course is courage, to take accountability for what's yours without taking responsibility for everything, to help your team process disappointment and move forward, and to make sure the experience actually changes how you lead, because adversity itself doesn't make us better leaders. Reflection does. Accountability does. So I'd like to leave you with this question: What setback are you still carrying, and what is that trying to teach you, maybe there's

something you need to own, maybe there's something you need to let go of, maybe there's an approach you need to change, maybe there's a conversation you need to have, or maybe there's a lesson you've already learned and now it's time to act on it. The courage of a leader is not about getting everything right; it's about being willing to look clearly at what happened, learn from it, and keep moving forward with greater wisdom and intention. Thank you for spending time with me today. If this episode was helpful, please share it with another leader who may be navigating a setback right now. And

until next time, keep leading with the courage of a leader. Thank you for listening to the Courage of a Leader podcast. If you'd like to further explore this episode's topic, please reach out to me through the Courage of a Leader website at www.courageofaleader.com. I'd love to hear from you. Please take the time to leave a review on iTunes. That helps us expand our reach and get more people fully stepping into their leadership potential. Until next time, be bold and be brave because you've got the courage of a leader.