The higher we climb as leaders, the easier we expect decisions to become. Yet, the opposite is often true. Bigger responsibilities bring greater complexity, higher stakes, and more uncertainty. The strongest leaders aren't the ones who always know the right answer. They're the ones who have the courage to move forward without waiting for perfect certainty.

In this episode, we unpack the questions that surface most often when leaders are faced with difficult decisions. We explore why fear can disguise itself as caution, how pressure quietly changes the way we think, when to trust data, intuition, and values, and why the quality of our decision-making process matters more than chasing perfect outcomes. Along the way, we're reminded that every decision becomes an opportunity to build confidence, strengthen trust, and grow into the kind of leader others are willing to follow, even when the path ahead isn't perfectly clear.

Key Takeaways:

• Confidence Isn't the Starting Point – Why waiting to feel ready may be the very thing holding leaders back.
• The Process Behind Every Great Decision – Discover how a clear approach creates confidence when certainty isn't possible.
• The Cost of Waiting – See why the decisions we avoid often shape our teams more than the ones we make.
• When the Numbers Aren't Enough – How experienced leaders navigate the space between data, instinct, and values.
• What Every Tough Decision Leaves Behind – What happens after a decision often matters just as much as the decision itself.

Resources Mentioned

The Inspire Your Team to Greatness assessment (the Courage Assessment) - In less than 10 minutes, find out where you’re empowering and inadvertently kills productivity, and get a custom report that will tell you step by step what you need to have your team get more done. Get it here: https://courageofaleader.com/inspireyourteam/

You don't need to have all the answers to lead well. Get your copy of the Clarity Kit for just $17 to learn the five practices to bring more clarity, confidence and courage into your leadership - https://courageofaleader.com/the-clarity-kit/

About the Host:

Amy L. Riley is an internationally renowned speaker, author and consultant. She has over 2 decades of experience developing leaders at all levels. Her clients include Cisco Systems, Deloitte and Barclays.

As a trusted leadership coach and consultant, Amy has worked with hundreds of leaders one-on-one, and thousands more as part of a group, to fully step into their leadership, create amazing teams and achieve extraordinary results.

Amy’s most popular keynote speeches are:

• The Courage of a Leader: The Power of a Leadership Legacy
• The Courage of a Leader: Create a Competitive Advantage with Sustainable, Results-Producing Cross-System Collaboration
• The Courage of a Leader: Accelerate Trust with Your Team, Customers and Community
• The Courage of a Leader: How to Build a Happy and Successful Hybrid Team

Her new book is a #1 international best-seller and is entitled, The Courage of a Leader: How to Inspire, Engage and Get Extraordinary Results.

http://www.courageofaleader.com

https://www.linkedin.com/in/amyshoopriley

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Mentioned in this episode:

The Inspire Your Team to Greatness Assessment (The Courage Assessment)

https://courageofaleader.com/inspireyourteam/

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. One of the questions I've been hearing more and more from leaders lately is this: How can I become a better decision maker? What's interesting is that this question doesn't just come from new leaders. I hear it from experienced executives, VPs, CEOs, people who have been leading for 2030, years, because leadership never reaches a point where decisions become easy. In many ways, they become harder. The stakes get higher. More people are affected. There are more competing

priorities, more ambiguity, and often less time to think. Some decisions are straightforward; others feel like every option comes with risk. You're balancing people, business results, timing, budgets, customers, culture, and sometimes incomplete information. So, if you've ever questioned yourself before making a difficult decision, you are not alone. I've seen incredible, capable leaders wrestle with decisions because they care deeply about getting them right. Over the years, I've started taking notes on the questions leaders ask me most often in coaching conversations, leadership programs, and keynote sessions, and decision making comes up again and again. So today I want to talk through six of those most asked questions, not from a theoretical perspective, from what I've observed working with leaders for more than 25 years. My hope is that you'll hear something that changes how you think about decisions, gives you practical tools that you can immediately use, and reminds you

that becoming a better decision maker is something every leader can develop. Because the goal isn't to make perfect decisions; it's not possible. It's to make thoughtful decisions, communicate them clearly, learn from them, and keep moving forward. Let's dive in. So the first question is that: How can I become a better decision maker? This question comes up all the time, and I think that there's a misconception underneath it. Many people believe becoming a better decision maker means becoming smarter, or gathering more information, or finding the perfect framework. Those things can certainly help. Yet, after coaching leaders for more than a couple decades, I found that's rarely what separates strong decision makers from everyone else. The strongest decision makers aren't the ones who always have the right answer. They are the ones who are willing to make thoughtful decisions without waiting for perfect certainty. That's where the courage of a leader comes in. The one thing that

I've observed is that many leaders are looking for confidence before they decide. The leaders who continue to grow have learned something different. Confidence often comes after the decision, not before it. It comes from knowing you've done the work, you've gathered the information, you've involved the right people, you've thought through the implications, and then you made the best decision you could with what you knew at the time. It doesn't mean every decision works out perfectly. None of us get that luxury, unfortunately. It means you've developed confidence in your decision-making process, and I think that that's an important distinction. The goal isn't to become a leader who never questions a decision that you've made. The goal is to become an intentional decision maker. What do I mean by that? An intentional decision maker doesn't approach every decision the same way. They don't overanalyze every issue, and they don't make every decision quickly just to appear decisive.

Instead, they decide how they're going to decide. That's one of the biggest shifts I'd encourage you to make before you decide what to do. Decide. How you'll make this decision? Ask yourself: How significant is this decision? Who needs to provide input? What information do I truly need? By when does this decision need to be made? What values need to guide it? These questions immediately create structure. They keep you from reacting emotionally. They help you become intentional. I've also noticed that leaders sometimes treat every decision as if it's equally important. They're not. Some decisions deserve weeks of discussion. Others deserve 10 minutes.

Learning the difference is part of becoming a better leader. Here's a coaching question I'd encourage you to reflect on this week: Do I have a decision-making process I trust, or am I relying on hope that the right answer will simply become obvious? Strong decision makers don't wait for certainty; they build a process they can trust. Next question: How do leaders make difficult decisions when there's no perfect answer? Here's one of the biggest mindset shifts I'd encourage: Stop looking for the perfect answer. Start looking for the best available answer. There's a difference. One thing I've observed is that many leaders spend an enormous amount of energy trying to eliminate every possible risk before making a decision. The challenge is that leadership doesn't usually work that way. Many of the most important decisions you'll make involve competing priorities. Do we invest now or do we wait? Do we keep this person in the role or do we make a change? Do we standardize the process

or allow for flexibility? Do we move quickly or gather more input? Sometimes every option has advantages. Sometimes every option has consequences, and that's why I encourage leaders to decide how to decide. Instead of immediately debating the answer, ask yourself what's the best way to make this decision. Sometimes the answer is conversation. Sometimes it's data. Sometimes it's experience. Sometimes it's involving the team. Sometimes it's using a simple decision-making tool to bring clarity. Sometimes it's a mix of those. For example, if you're trying to decide where to focus limited time or resources, an impact effort analysis can be helpful. It helps you identify which initiatives will create the greatest impact relative to the effort required. If you're weighing two or three viable options, a cost-benefit comparison can help you think it through objectively about the trade-offs instead of relying on emotion. If everything feels urgent, a prioritization matrix can be

helpful, and when you're leading change, I often recommend a force field analysis. Instead of focusing only on what's preventing change, you identify both the forces that are supporting change and the forces resisting it. This often leads to a much more balanced conversation and better decision. Here's what I like about these tools: none of them make the decision for you. They simply help you think more clearly, and sometimes that's exactly what you need. I've seen leaders walk into a conversation convinced they knew the answer, then after putting the situation through one of these frameworks, they realize they were solving the wrong problem. That's another coaching conversation. But many leaders don't struggle because they can't make decisions. They struggle because they haven't slowed down long enough to define the real decision. For example, a leader may think they have a performance problem. The real issue is unclear expectations. They think they have a communication problem. The

real issue is a lack of trust. They think they need to reorganize the team. The real issue is unclear priorities. The quality of your decision depends on the quality of the question you're asking, your framing. So, before jumping to solutions, pause and ask, "What problem am I actually trying to solve here? That one question has changed the direction of countless coaching conversations I've had with leaders. Next question, question three. Why do we sometimes avoid making the decisions we know we need to make? I love this question because I think every leader can relate to it. If we're honest, we all have decisions we've carried around longer than we should have. Sometimes it's a difficult conversation. Sometimes it's a personnel decision. Sometimes it's saying no to something that no longer aligns with our priorities. Sometimes it's making a change that everyone knows is needed. So why do we avoid them? The one thing that I've noticed is that leaders rarely tell me that they're

afraid. Instead, they say things like, "I just need a little bit more information. I'd like to think about it a little bit longer. Let's see how this next part plays out. Now, sometimes those might be the right responses. Sometimes gathering more information is exactly what a leader should do. Yet, I've also seen those same phrases become a way to postpone a decision we already know needs to be made, because underneath those statements is often something else.

That's the fear of making the wrong decision, fear of disappointing someone, fear of conflict, fear of criticism, or simply the weight of knowing that whatever decision we make, it's gonna affect other people. I understand that. I empathize with that. If you're a thoughtful leader, decisions carry emotional weight. They should, because people matter. The challenge is that delaying a decision doesn't eliminate its impact; it often increases it. I've seen leaders postpone addressing performance issues for months, not because they didn't know what needed to happen, because they genuinely cared about the employee. And unfortunately, while they were trying to avoid hurting one person. The rest of the team was carrying the consequences. Morale declined. Frustration grew. High performers started asking themselves, "Does leadership see what's happening? That's one of the hardest parts of leadership. Sometimes avoiding short-term discomfort creates bigger long-term discomfort. Here's a

question I ask leaders often: If nothing changed over the next six months, would you be okay with that? If the answer is no, it's probably time to act. Another question I encourage leaders to ask themselves is: Am I waiting because more information will genuinely improve the decision, or because making the decision feels uncomfortable? Those are two very different things, and recognizing the difference is part of demonstrating the courage of a leader. Question four: How can leaders stay calm and clear-headed under pressure. I think we can have the wrong picture of calm leadership. People sometimes imagine calm leaders don't feel pressure. That is not what I've observed and heard. The strongest leaders I've worked with absolutely feel pressure. They worry because they care. They wrestle with difficult decisions. The difference is that they don't allow pressure to make the decision for them. That's an important distinction. Pressure naturally narrows our thinking. We become

more reactive. We become more defensive. We start looking for the quickest solution instead of the best one, that's why one of the most important leadership skills is learning to create space between the pressure and your response. Sometimes that space is only 30 seconds. Sometimes it's overnight. Sometimes it's asking for another meeting instead of making a decision in the heat of the moment. I've coached leaders who received an email that immediately made them angry. Their first instinct was to respond. I've been there. Instead, we talked about pausing, sleeping on it, walking into the conversation the next day with curiosity instead of emotion. Almost every one of them came back and said, "I'm so glad I didn't hit send. Here's another observation: When leaders feel pressure, they often start telling themselves stories, like "This is going to be a disaster. Everyone's going to be upset about this. If I make the wrong decision here, I'm really going to lose credibility. Those

are stories; they're not facts. One practice I found incredibly helpful is separating facts from assumptions. Ask yourself, what do I know for certain? What am I assuming? What information am I still missing? Immediately, your thinking becomes clearer. I also encourage leaders to have one or two people they trust enough to think out loud with, not people who will simply agree with them, people who will challenge their thinking, people who will ask questions like, "Have you considered this?" What assumptions might you be making? What would success look like a year from now? Those conversations have saved leaders from making rush decisions more times than I can count. And finally, remember this: your team is watching you. They're taking emotional cues from you. Now that doesn't mean that you need to pretend everything's okay. It means that they need to experience steadiness, healthy, steady leadership. Sounds like this is a difficult situation. We're still gathering information. Here's

what we know today. Here's what we're doing next. That kind of communication creates confidence without pretending you have certainty when you don't, and that's something I've seen great leaders do over and over again. Question five: How do you balance data, intuition, and values when making tough choices? I love this question because I think many leaders feel like they have to choose between data and intuition. I've heard leaders say things like, "My gut is telling me one thing, yet the numbers are telling me something else, or "I can't explain it. I just don't think this is the right direction. Here's what I've observed: the strongest leaders don't rely on just one of those things-intuition or data.

They learn how to bring together three important perspectives: the data, their intuition, and their values. Let's start with the data. Data is incredibly valuable because it helps us move beyond opinions. It helps us identify patterns. It gives us objective facts. It challenges assumptions. Yet data rarely tells the whole story. For example, imagine you're looking at engagement survey results. The scores may tell you engagement has declined. They might not tell you fully why, or maybe an employee's performance numbers are excellent. The data says they're succeeding, yet every time you walk into a meeting, you sense people shutting down around that person. The data tells part of the story. Your experience is telling you another part. That's where intuition comes in. I think intuition is often misunderstood. People sometimes think intuition is simply a feeling. I don't. I think intuition is our pattern recognition. It's everything you've learned through years of

experience that your brain processes before you can fully explain it-that doesn't mean intuition is always right. It isn't. Yet I also wouldn't ignore it. When experienced leaders tell me something doesn't feel right, I encourage them to get curious, not to immediately act on the feeling, yet not to dismiss it either. Ask yourself, what am I noticing that's creating this feeling? Sometimes your intuition is picking up on something your conscious mind hasn't fully processed and recognized yet. Then there are your values. This is where the courage of a leader often becomes very clear, because sometimes the easiest decision isn't the right decision. Sometimes the most profitable decision doesn't align with your values. Sometimes the fastest decision comes at the expense of trust. I've coached leaders who knew exactly what the numbers suggested they should do, yet they also knew that decision would violate the kind of culture they were trying to build. Those are not easy moments.

They define leadership. One practice I use myself is asking three simple questions: What is the data telling me? What is my experience and intuition telling me? And what decision best aligns with my values? Now, when all three point in the same direction, the decision usually becomes much easier. When they don't, that's often a signal to slow and explore the tension. One final thought here: data helps us understand the business, values help us protect what matters most, and intuition helps us notice what might otherwise be missed. The strongest leaders incorporate all three. Question six: What should leaders do when a decision turns out wrong? Oh, let's start by acknowledging something we don't talk about often enough. Every leader will make a decision they wish they could take back. Every. One of us. If you lead long enough, you'll hire the wrong person. You'll choose the wrong priority. You'll underestimate something. You'll overestimate something. You'll miss information. This

isn't a sign you're a poor leader. It's part of leadership. The question isn't whether you'll make a mistake. The question is, what will you do next? One thing I've noticed is that leaders often believe a mistake damages their credibility. I understand that. Yet, in my experience, that's rarely what damages trust. What damages trust is refusing to own it, defending it, blaming others, pretending it didn't happen. I've actually seen leaders gain credibility after a difficult decision because of how they handled it afterward. They said, based on what we knew at the time, this was the best decision we could make. Then they added, now we've learned something new, and we're going to adjust. There's strength in that. People get that. It tells people we're learning, we're paying attention, we're not letting our ego get in the way here. I think that's one of the biggest differences between confident leaders and insecure leaders. Confident leaders don't need to be right all the

time; they want to get it right. Those are very different things. I also encourage leaders to separate the quality of the decision from the outcome. Sometimes a thoughtful decision produces a poor outcome because circumstances change. That doesn't automatically make it a bad decision, and sometimes a careless decision produces a good outcome simply because we got lucky. Circumstances came together that doesn't automatically make it a good decision. Judge your decisions by the quality of your thinking, of your process, not only by the result. One practice I found incredibly valuable is conducting a simple debrief after an important decision.

Ask yourself, what worked well, what surprised us, what assumptions turned out to be wrong, what did we learn? What will we do differently next time? That's how good decision makers become great decision makers, not because they avoid mistakes, because they learn from every one of them. As I wrap up today, I'd like to leave you with one final thought: Leadership is full of decisions. Some are small. Some are life-changing. Some you'll make with confidence. Others you will make them while you're wishing you had just a little bit more information. That's a part of leadership. The goal isn't to make perfect decisions. The goal is to make thoughtful decisions, communicate them clearly, learn from them, and keep moving forward. Becoming a better decision maker isn't about eliminating uncertainty; it's about becoming an intentional decision maker. It's about deciding how you're going to decide. It's about knowing when to gather more information and knowing when you have enough.

It's about having the courage to move forward even when every answer isn't available. That's the courage of a leader. So this week I'd like to leave you with one coaching question: What's one decision that you've been carrying that deserves your attention? Maybe it's a conversation you've been putting off. Maybe it's a change you know you need to initiate. Maybe it's simply deciding to trust yourself a little more. Whatever it is, I hope today's conversation gives you a little more confidence to take the next step, leadership doesn't ask us to be perfect. It asks us to keep learning, to keep growing, to keep moving forward, and sharing that with those around us. Thank you for spending this time with me today. If this episode was helpful. I'd love for you to share it with another leader who may be wrestling with an important decision. So many of us are. And until next time, keep showing them that you've got 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 full. Stepping into their leadership potential. Until next time, be bold and be brave because you've got the courage of a leader.