The Leadership Habit

Crestcom International
  • 4.7 (15)
  • Management
  • Biweekly

Welcome to the Leadership Habit podcast from the Crestcom Leadership Institute, the show that brings you inspiration and information to help you transform your leadership style. We use our experience developing leaders in over 60 countries worldwide to help you develop the skills and tools you need to reach your leadership potential, join us in our mission to create a better world by developing stronger, more ethical leaders. How can you make leadership a habit today?

  1. Oct 23

    3 Ways to Overcome Imposter Syndrome with Anya Cheng

    3 Ways to Overcome Imposter Syndrome with Anya Cheng Summary Overcoming imposter syndrome isn’t about eliminating self-doubt. It’s about learning to move forward despite it. In this episode of The Leadership Habit, entrepreneur and former Meta executive Anya Cheng shares three practical strategies for building leadership confidence: challenge negative self-talk, replace “I should” with “I would like to,” and focus on taking action in the present. Drawing from her experiences overcoming rejection, navigating career transitions, and building a successful business, Anya explains how resilience, self-trust, and a willingness to learn can help leaders overcome uncertainty and pursue new opportunities. Even the most accomplished leaders experience moments of self-doubt. Whether you’re stepping into a new role, pursuing an ambitious goal, or navigating an unfamiliar challenge, imposter syndrome can make you question your abilities, even when your experience suggests otherwise. But what if overcoming imposter syndrome isn’t about eliminating self-doubt? What if it’s about learning to move forward despite it? In this episode of The Leadership Habit podcast, host Jenn DeWall welcomes Anya Cheng, Silicon Valley entrepreneur, bestselling author, TEDx speaker, and founder and CEO of Taelor AI. With a career that includes leadership roles at Meta, eBay, Target, and McDonald’s, Anya knows what it means to pursue opportunities without all the answers. She shares her remarkable journey from struggling to find employment during the 2008 financial crisis to leading teams at some of the world’s most recognizable companies. Along the way, she offers three practical strategies to overcome imposter syndrome, build confidence, and develop the resilience to keep moving forward. Meet Anya Cheng Anya Cheng’s career is a testament to the power of persistence, resourcefulness, and believing in your ability to learn. Originally from Taiwan, Anya moved to the United States in 2007 to pursue a master’s degree in marketing at Northwestern University. When she graduated in 2008, the financial crisis made an already competitive job market even harder. With limited professional connections in the United States and a language barrier to overcome, Anya faced repeated rejection. Rather than waiting for opportunities to appear, she started creating her own. She attended networking events, approached recruiters, contacted alumni, and even volunteered at a senior care center to practice her English before job interviews. Eventually, she used the industry knowledge she had gathered through months of networking to develop a business proposal for a publishing company. That initiative helped launch a career that would take her through major organizations, including Sears, Target, McDonald’s, eBay, and Meta. Today, Anya is the founder and CEO of Taelor AI, an AI-powered men’s clothing rental and styling company. Despite her accomplishments, Anya quickly points out that self-doubt doesn’t necessarily disappear with success. Instead, she believes we can learn to manage it. What Is Imposter Syndrome? Imposter syndrome describes doubting your abilities or accomplishments, often accompanied by fear that others will discover you’re not as capable as they believe. For leaders, these feelings can emerge when taking on new responsibilities, making important decisions, managing more experienced employees, or entering unfamiliar situations. Even highly successful professionals can experience imposter syndrome. During the podcast, Anya shares a story about meeting an accomplished startup founder who, despite years of experience and multiple successful businesses, still felt pressure to change how she presented herself to potential investors. The experience reinforced an important lesson: Professional success does not automatically eliminate insecurity. What matters is how we respond when those feelings arise. 3 Ways to Overcome Imposter Syndrome   1. Challenge Negative Self-Talk Before It Takes Over One of Anya’s most practical recommendations is to recognize negative self-talk early. When facing a difficult challenge, it’s easy to let one doubtful thought become an overwhelming internal narrative. A moment of uncertainty can quickly turn into the belief that you’re incapable of succeeding. Anya recommends interrupting that process before it gains momentum. Instead of accepting the thought that you cannot do something, question whether it’s actually true. For leaders, this matters especially when facing situations outside their immediate expertise. A manager promoted into a senior role may worry that they lack the experience to succeed. A leader presenting a new idea may assume others know more than they do. But feeling uncertain is not evidence of being unqualified. Rather than focusing exclusively on what you don’t know, consider the skills, experience, and perspective you already bring to the situation. Leadership takeaway: When self-doubt appears, separate your feelings from the facts. Identify what you already know, recognize what you still need to learn, and take the next reasonable step. 2. Replace “I Should” with “I Would Like To” How often do you catch yourself thinking about everything you should be doing? I should be further along in my career. I should be a better communicator. I should already know how to handle this situation. According to Anya, constantly telling ourselves what we should be doing can reinforce feelings of inadequacy. Her suggestion is surprisingly simple: Replace “I should” with “I would like to.” For example: Instead of “I should be a better leader,” try “I would like to strengthen my leadership skills.” Instead of “I should already know how to do this,” try “I would like to learn how to do this more effectively.” Instead of “I should be ready for a promotion,” try “I would like to prepare myself for the next opportunity.” This small shift changes the focus from perceived shortcomings to opportunities for growth. It also reflects an important principle of effective leadership: Development is an ongoing process, not a destination. Leaders don’t need to have mastered every skill before taking on greater responsibility. They need to remain open to learning, feedback, and improvement. Leadership takeaway: Pay attention to the language you use when evaluating your performance. Frame development goals around what you want to achieve, not what you believe you should have already accomplished. 3. Focus on the Present and Take Action Anya’s third strategy is to spend less time worrying about what might happen and more time focusing on what you can do right now. She explains that much of our anxiety occurs before or after an important event. Before a presentation, we worry about everything that could go wrong. Afterward, we replay what we said and imagine what we could have done differently. But during the experience itself, we’re often too engaged in the task to spend much time worrying. Anya’s career provides a powerful example of this approach. When traditional job applications weren’t working, she tried new ways to meet decision-makers. When she couldn’t afford professional English tutoring, she found another opportunity to practice. When her startup struggled to attract suppliers, she explored creative ways to generate media attention. Not every effort worked. In fact, many didn’t. But each attempt helped her learn something, build a relationship, or discover another possible path forward. For leaders, the lesson is particularly relevant when navigating change or uncertainty. Waiting until you feel completely confident can prevent you from making progress. Taking action, even when the outcome is uncertain, creates opportunities to learn and build confidence through experience. Leadership takeaway: When facing an unfamiliar challenge, identify one action you can take today. Focus on making progress rather than waiting for the perfect conditions. Why Effective Leaders Need to Trust Their Own Judgment Beyond her three strategies, Anya shares another important lesson about leadership confidence. While preparing for a major startup competition, she practiced her business pitch 43 times with former judges. She worked hard to anticipate questions and develop the strongest possible answers. But when the competition arrived, she struggled during the question-and-answer portion. The problem wasn’t that she lacked the knowledge to respond. She had become so focused on remembering the answers others had suggested that she stopped trusting her own understanding of the business. The experience taught her that preparation matters, but so does believing in your ability to think independently. Leaders regularly seek advice from mentors, colleagues, and experts. That input can be valuable, but it shouldn’t replace their own critical thinking. Anya’s experience also reminds us that setbacks can become valuable learning opportunities. After losing the competition, a mentor’s advice helped her reframe the experience as practice for future success. She went on to approach subsequent competitions with greater confidence in her own expertise. Effective leadership requires more than knowing the right answers. It requires the confidence to form a point of view, make decisions, and learn from the results. Where to Find More from Anya Cheng Connect with Anya on LinkedIn Watch her TEDx talk Check out her AI-powered clothing company: Taelor (don’t forget to use Promo Code: podcast to get 25% off, and podcast10 to get 10% off a gift card) Building Leadership Confidence Is an Ongoing Process Imposter syndrome can affect professionals at every stage of their careers. A new manager may question their readiness to lead a team, while an experienced executive may experience the same uncertainty when enter

  2. Oct 9

    Building Organizational Resilience Before a Crisis Hits with Laura McCracken

    What would happen if your organization faced a major disruption tomorrow? Would your leaders know how to respond? Would your team have the information, resources, and confidence to make difficult decisions? Or would the crisis expose weaknesses hiding in plain sight? Organizational resilience is about more than recovering from setbacks. It is about building leadership, culture, and systems. These help a business spot challenges, adapt to uncertainty, and come out stronger. In this episode of The Leadership Habit, host Jenn DeWall welcomes Laura McCracken, founder of Blackheath Advisors, to explore what it really takes to build a resilient organization. Drawing on more than 30 years of global leadership experience, including firsthand insight into one of Europe's largest corporate fraud scandals, Laura shares why resilience must be developed long before a crisis occurs.

  3. Sep 25

    How to Lead in a Polarized Workplace with Louisa Loran

    Political differences. Generational divides. Rapid technological change. Economic uncertainty. People are bringing very different experiences, assumptions, and perspectives to work, and leaders are increasingly responsible for helping them work together. So, how do you lead in a polarized workplace without expecting everyone to think the same way? In this episode of The Leadership Habit podcast, host Jenn DeWall sits down with Louisa Loran, executive advisor, board member, and author of Leadership Anatomy in Motion, to explore how leaders can build trust, encourage curiosity, and help employees stay connected and productive in a divided world. Their conversation offers an important reminder: effective leadership isn’t about eliminating differences. It’s about creating an environment where people can bring different perspectives to the table, challenge their own assumptions, and still move toward a shared goal. Meet Louisa Loran Louisa Loran is an executive advisor, board member, author, and global business leader with more than 20 years of experience across industries, cultures, and geographies. Her career includes leadership roles at global organizations such as Maersk and Google, as well as experience in consumer products and luxury brands. She has built billion-dollar businesses, led major transformations, and advised leaders, boards, and investors across the United States and Europe. Those experiences have shaped a central idea in Louisa’s work: people can look at the same situation and see it from very different vantage points. Her book, Leadership Anatomy in Motion, explores what it takes to lead through changes in both technology and people, drawing on stories and experiences from her international career. Why Leading in a Polarized Workplace Requires Curiosity When people encounter uncertainty, their instinct can be to hold more tightly to what they already know. Louisa argues that leaders need to deliberately interrupt that instinct. Instead of simply looking for more information that confirms an existing belief, she encourages leaders to consider what they may need to unlearn. “What else could be true? What can I be open about?” That doesn’t require leaders to abandon their beliefs or agree with every perspective they encounter. It means being willing to examine their assumptions before making a decision. Louisa describes this openness as an opportunity to either confirm what you already know or expand your understanding. For leaders, that distinction matters. Curiosity makes it possible to hear information that might otherwise never make it into the conversation. The Information Leaders Don’t Know Can Matter Most One of the most interesting ideas in Jenn and Louisa’s conversation is the information gap that develops as decisions move through an organization. People closest to a particular task may understand nearly every detail. As information moves through layers of management, however, some of that context inevitably disappears. By the time an issue reaches senior leadership, executives may only see a small portion of the original picture. For Louisa, the question isn’t simply whether senior leaders have enough information. It’s whether the right information reaches them. That changes the leader’s role. Instead of assuming they already have the answer, leaders can create context, establish direction, and invite employees to contribute what they know. When employees with different experiences and perspectives feel comfortable contributing, leaders get a much richer picture before making decisions. Don’t Eliminate Disagreement. Make It Productive. A polarized workplace doesn’t necessarily become healthier when everyone agrees. In fact, different perspectives can improve thinking when people are willing to engage with them. Louisa describes the value of a “generative conversation,” where two people enter with different perspectives and leave having expanded one another’s thinking. “Talking to someone where they have a perspective, I have a perspective, and we lift each other together.” That is very different from approaching a conversation with the goal of proving another person wrong. For leaders, creating more productive disagreement can start with a few simple questions: What might I need to unlearn? What else could be true? What am I curious about? What information or perspective might I be missing? Those questions create room for employees to contribute instead of simply defending their positions. Build Trust Before You Need It Curiosity and openness may sound simple. Practicing them when emotions are high is much harder. That’s why Louisa encourages leaders to develop these behaviors in smaller, everyday situations. “These are behaviors that you can train in small things or in big things.” A leader who regularly practices listening, admitting when they don’t know something, reconsidering assumptions, and seeking another perspective is better prepared to respond when a significant disagreement or organizational change occurs. Over time, these behaviors can also help create the trust employees need to speak honestly. When people believe their perspective will be heard rather than immediately dismissed, they’re more likely to share the information leaders need to make better decisions. Look Beyond What’s Right in Front of You Louisa also introduces a simple metaphor for navigating uncertainty: look toward the horizon. When people feel threatened or overwhelmed by change, their attention can narrow. They focus on the immediate problem, headline, disagreement, or risk in front of them. Leaders can help teams widen that view. Instead of only asking, “What’s happening right now?” they can consider what might happen next, what possibilities exist, and what role the team can play in shaping that future. That shift moves people from reacting to participating. It can also create space for innovation, partnership, learning, and hope when uncertainty would otherwise cause people to shut down. Four Leadership Behaviors for Navigating Change Toward the end of the conversation, Louisa shares four behaviors at the heart of Leadership Anatomy in Motion: Envision ambitiously. Look toward the horizon and imagine what a different future could look like. Expand with curiosity. Seek out perspectives and possibilities beyond what you already know. Steer decisively. Use new information to determine what matters, what needs to change, and where to focus. Embody change with presence. Don’t simply talk about the future. Show through your own behavior that you are willing to be part of it. Together, these behaviors give leaders a practical way to lead through disagreement, uncertainty, and change. Better Leadership Doesn’t Require Everyone to Think Alike Leading in a polarized workplace isn’t about getting everyone to share the same beliefs, experiences, or perspectives. It’s about creating enough trust and curiosity for people to work together despite those differences. That starts with leaders being willing to examine their own assumptions, invite perspectives they don’t already have, and create conversations where people can contribute rather than defend. As Louisa explains, leaders can practice navigating change and difference. The more they practice it in everyday moments, the more prepared they and their teams become when difficult moments arrive. Where to Find More From Louisa Loran Learn more about Louisa Loran, her work as an executive advisor, and her book, Leadership Anatomy in Motion, through her website. You can also connect with Louisa on LinkedIn and explore her Leadership Anatomy Mirror, an exercise designed to help leaders reflect on the four leadership behaviors discussed in this episode. Listen to the full conversation with Louisa Loran on The Leadership Habit podcast for more insights on curiosity, trust, human agency, and helping employees thrive in a polarized world. Build the Skills to Lead Through Difference and Change Today’s leaders need more than technical expertise. They need the ability to communicate effectively, build trust, make sound decisions, adapt their leadership approach, and bring people together around shared goals. Ready to strengthen the way your leaders communicate, collaborate, and lead through change?  Crestcom’s complimentary Leadership Skills Workshop gives managers and leaders an opportunity to experience Crestcom’s practical approach to leadership development. In just two hours, participants gain actionable tools they can apply to real workplace challenges and leave with a personalized plan for putting those skills into practice.   The post How to Lead in a Polarized Workplace with Louisa Loran appeared first on Crestcom International.

  4. Sep 11

    The Human Edge in AI-Powered Decision-Making with Cheryl Strauss Einhorn

    AI can give leaders answers in seconds. But getting an answer and making a good decision are two very different things. As AI becomes part of how we research, solve problems, and evaluate options, leaders face an important question: Where does human judgment fit? In this episode of The Leadership Habit Podcast, host Jenn DeWall sits down with decision-making expert Cheryl Strauss Einhorn, creator of the AREA Method and author of The Human Edge: Smarter Decisions in the Age of AI. Together, they explore decision-making in the age of AI, including why leaders need to think critically about the problems they are solving, recognize both human and AI biases, and resist the temptation to outsource their judgment to technology. As Cheryl explains: “The problem with AI is we now have this answer machine. So answers are pretty easy to come by. And so what that means is that human judgment actually becomes far more valuable.” Meet Cheryl Strauss Einhorn Cheryl Strauss Einhorn is a decision-making expert, creator of the AREA Method, and founder of the decision sciences company Decisive, where she helps leaders and organizations solve complex problems and make better decisions. She is also an adjunct professor at Cornell University and the award-winning author of several books exploring decision-making, financial research, and the psychology behind how we make choices. Cheryl’s approach to decision-making grew out of more than two decades in investigative journalism, including over a decade at Barron’s. Her reporting required her to evaluate complex information, question assumptions, weigh evidence, and make high-stakes judgments with significant consequences. That experience ultimately led her to develop the AREA Method, a structured approach designed to help people recognize cognitive biases, expand their thinking, and make decisions with greater confidence and conviction. AI Has Answers. Leaders Still Need Judgment. AI has dramatically changed how quickly we can access information. But Cheryl argues that easier access to answers actually increases the value of human judgment. AI does not inherently understand why you are solving a problem. It does not know your organization, your stakeholders, your priorities, your constraints, or what success looks like for you. That is why Cheryl recommends turning to yourself before turning to AI. “What is the problem that I am solving and why am I solving it?” Without that clarity, leaders risk using AI to solve the wrong problem, even if they do it efficiently. Cheryl points out that even experienced leaders sometimes assume they understand the problem in front of them without taking time to define it clearly. The result can be solving an adjacent problem, addressing only part of the issue, or eventually having to start over. For leaders navigating decision-making in the age of AI, defining the problem is still a fundamentally human responsibility. Know When a Decision Requires a Process Leaders make countless decisions every day, and not every choice requires extensive analysis. But some decisions carry consequences that make a structured process especially valuable. Cheryl recommends looking at three factors: Is the outcome unknown? Is the cost of getting it wrong high? Will the decision have a long-term impact? When all three are present, leaders should slow down and use a deliberate decision-making process. Cheryl’s AREA Method stands for Absolute, Relative, Exploration and Exploitation, and Analysis. The process helps decision-makers examine different perspectives, challenge assumptions and judgments, gather evidence, and build greater confidence in their conclusions. A process also creates something leaders often miss: an opportunity to learn from the decision afterward. Instead of simply asking whether the outcome was good or bad, leaders can look back and evaluate the decision quality, whether they gathered the right information, considered the right perspectives, and followed a sound process. Are You Using AI Like a Surgeon or a Lamborghini Driver? One of Cheryl’s most useful distinctions is that leaders can approach AI and decision-making in two very different ways. When you need one specific piece of information, Cheryl suggests thinking like a surgeon. You make a precise incision, extract what you need, and move on. But many leadership challenges are not that simple. When you are exploring a complicated problem and do not yet know exactly where you need to go, Cheryl suggests thinking of yourself as a Lamborghini driver. AI may be an incredibly powerful and fast machine, but you are still behind the wheel. “You need to direct it.” In this mode, AI can help leaders research, analyze, explore, and refine their thinking. But the leader remains responsible for determining what they are trying to understand and where the process should go next. The distinction matters because using the same approach for every interaction with AI can lead leaders to extract information without first understanding whether it is the right information for the problem they are trying to solve. The Eight Human Moments That Matter in AI-Powered Decision-Making In The Human Edge, Cheryl identifies eight pivotal moments where human thinking remains essential: Defining the problem Assessing motivations Gathering context Researching effectively Analyzing options Recognizing biases Involving key stakeholders Building conviction These moments highlight an important limitation of AI: it cannot automatically know the context surrounding your decision. It does not know your budget unless you tell it. It does not know which stakeholders matter most. It does not know that you have until Tuesday to decide or that your organization is operating under a specific resource constraint. As Cheryl explains: “Something that looks plausible that doesn’t work for your context is something that can fail.” Leaders bring the context. AI can help process information within it. Human Bias Meets AI Bias AI does not eliminate bias from decision-making. In fact, Cheryl points out that leaders now have to contend with two sources: their own cognitive biases and the biases in AI systems. Human biases can include confirmation bias, where we look for information that supports what we already believe; liking bias, where we give greater weight to information from people we relate to or trust; and the planning fallacy, where we underestimate how much time or complexity a project will require. AI can also bring its own imperfections into the process. Its answers may be incorrect, outdated, biased, or based on information that does not accurately represent the situation a leader is trying to solve. But Cheryl also sees an opportunity. Rather than asking AI for an answer and accepting the first response, leaders can use the tool to challenge their own thinking. They can ask for disconfirming evidence, explore opposing perspectives, question the credibility of information, and look for weaknesses in the decision they are considering. The goal is not to have AI validate your thinking. Use it as one resource to strengthen your thinking. Speed Is Not the Same as Quality AI has made speed one of its biggest selling points. But faster decision-making does not automatically mean better decision-making. “Speed and efficacy are often different. The speed of a decision says nothing about the quality of it.” That distinction is especially important for leaders. Our brains naturally develop shortcuts based on previous experiences. Those shortcuts help us move quickly, but they can also cause us to apply yesterday’s assumptions to today’s problem. For high-stakes business decisions, Cheryl encourages leaders to create what she calls a “strategic stop,” a moment to evaluate whether the assumptions, information, and approaches that worked before still apply now. AI may accelerate the process, but leaders still need to know when slowing down will ultimately lead to a better outcome. Don’t Outsource Your Thinking Perhaps the biggest takeaway from Cheryl’s conversation with Jenn is that the future of leadership is not about choosing between human expertise and artificial intelligence. It is about knowing what each is good at. AI can research, analyze, generate possibilities, and surface information at extraordinary speed. But leaders still have to define the problem, provide context, evaluate assumptions, consider stakeholders, recognize bias, and ultimately decide what to do. Cheryl’s goal is to help leaders build the confidence and conviction to solve problems effectively, both with and without AI. “I really hope that people gain confidence and conviction that they can solve problems well, both with and without the machine, and that they don’t ever sacrifice their thinking.” As AI becomes more capable, protecting our ability to think critically is not rejecting technology. It is how leaders make better use of it. Where to Find More From Cheryl Strauss Einhorn To learn more about Cheryl Strauss Einhorn, the AREA Method, and her work on decision-making:  Visit areamethod.com Connect with Cheryl on LinkedIn  Explore her latest book, The Human Edge: Smarter Decisions in the Age of AI. Build the Leadership Skills AI Can’t Replace AI can provide information. Leadership requires knowing what to do with it. Crestcom helps leaders develop the practical skills they need to make better decisions, communicate effectively, navigate conflict, build emotional intelligence, and lead their teams with greater confidence. Experience Crestcom’s approach firsthand with a complimentary leadership skills workshop. In just two hours, you’ll explore actionable strategies you can put to work immediately and create a personalized plan for addressing your leadership challenges. Request your complimentary leadership skills workshop today.   The post The

  5. Aug 21

    Why Leadership Impact Matters More Than Intentions with Ciarán Casey

    What is it Like to be Led by You? Summary:  Do you know what it’s like to be led by you? Good intentions do not always translate into positive leadership impact. Ciarán Casey joins The Leadership Habit Podcast to explore why leadership is relational, how leaders can become more aware of the experience they create, and the six elements that help leaders get back “in tune.” Most leaders have good intentions. They want their teams to feel trusted, supported, empowered, and valued.  But good intentions do not always create a good experience. You might give someone more autonomy because you trust them, only for them to walk away feeling abandoned. You might step in to help because you want to make their job easier, while they interpret your help as a sign that you do not trust them. You might send an email late at night simply to clear your inbox, while your team assumes they are expected to be available after hours. That gap between what a leader intends and what others actually experience is at the heart of this episode of The Leadership Habit Podcast. Host Jenn DeWall sits down with leadership practitioner, coach, and author Ciarán Casey to explore why leadership impact matters more than good intentions and how leaders can become more conscious of what it is actually like to be led by them. Meet Ciarán Casey, Leadership Coach and Author Ciarán Casey is a leadership practitioner and coach with more than three decades of senior leadership experience across sectors and international environments. His work focuses on organizational transformation, culture, high-performing teams, and complex human dynamics. More recently, Ciarán has focused on leadership development, working with individuals, leadership teams, senior civil servants, and executive teams to strengthen trust and collaboration. His book, Leadership in Tune, grew out of a question he kept encountering throughout his career: Why do some highly capable, intelligent, confident leaders struggle to connect with the people around them, while others seem to create environments where people naturally flourish? For Ciarán, part of the answer lies in the difference between leadership intent and leadership impact. Your Intentions Are Only Half the Story Leaders rarely set out to frustrate, disengage, or demotivate their teams. The problem is that employees cannot experience a leader’s intentions. They experience their behaviors and interactions. As Ciarán explains: “The intention isn’t the problem. What we need to focus on is the experience.” That distinction can be uncomfortable, especially when we know our intentions were good. But it also gives leaders a more useful way to evaluate their effectiveness. Instead of asking, “What was I trying to do?” effective leaders can ask, “How might that have been experienced?” That shift matters because leadership behaviors carry more weight than we may realize. Ciarán points out that leaders are constantly being observed. A delayed response can be interpreted as a lack of interest. Silence can make people wonder if something is wrong. A rushed conversation can leave someone feeling like their time or contribution does not matter. As he puts it, a leader’s impact is amplified. Becoming more aware of that leadership impact is not about overanalyzing every interaction. It is about recognizing that the meaning we intend to communicate and the meaning someone receives are not always the same. Leadership Does Not Happen in Isolation One of the central ideas in Ciarán’s work is that leadership is relational. We often think of leadership as something an individual possesses. We describe someone as confident, charismatic, decisive, or a strong communicator and conclude that those characteristics make them a good leader. Ciarán challenges that idea. He argues that leadership emerges in the space between people. A leader can offer direction, guidance, or support, but leadership only takes shape when another person is willing to engage with and follow that direction. “Leadership is a relational practice that doesn’t reside within an individual, but emerges between people.” That changes the way we think about leadership development. Instead of focusing exclusively on the leader’s characteristics, we can pay more attention to the quality of their interactions. Are people willing to speak openly? Do they feel trusted? Do they feel heard? Does the leader create the conditions for people to contribute? Those everyday interactions are where leadership impact becomes real. The Six Strings of Leadership In Leadership in Tune, Ciarán introduces his Conscious Relational Impact Model, built around six elements of leadership. As a guitarist, he compares these elements to the guitar’s six strings. A guitar does not need every string to be completely wrong to sound off. One string that is out of tune can change the sound of the entire instrument. Leadership can work the same way. The six strings are organized across three stages: The Connected Self: Authenticity and Emotional Intelligence Effective leadership starts with understanding yourself. That means knowing your values and how they influence your behavior while also having the emotional intelligence to understand and regulate the impact you have on others. Authenticity without emotional intelligence can become an excuse to behave however you feel in the moment. Emotional intelligence without authenticity can feel performative. Leaders need both. The Bridge: Presence and Trust From there, leaders have to create the conditions for connection. Ciarán describes presence and trust as the two spans of a bridge between people. Trust determines whether it feels safe to cross. Presence determines what it feels like to cross. One of the simplest ways leaders can strengthen that bridge is by giving people their undivided attention. Phones, emails, meetings, and competing priorities make genuine presence difficult. But when a leader is distracted during a conversation, that distraction can communicate something they never intended: You are not important enough for my full attention. Shared Impact: Co-Creation and Influence Once leaders have built that connection, they can create shared impact through co-creation and influence. Ciarán describes co-creation as one of the most underused leadership skills. Leaders do not need to have every idea, solve every problem, or provide every answer themselves. Instead, they can involve capable people in designing solutions, processes, products, and outcomes. Influence also changes depending on the situation. Sometimes leaders need to be direct. Other times, they can draw ideas and creativity from the people around them. The key is that shared impact becomes much easier when trust and connection already exist. Which Leadership String Is Out of Tune? The goal of Ciarán’s model is not leadership perfection. It is awareness. A leader may be authentic and emotionally intelligent but struggle to be fully present. Another may care deeply about their team but fail to build trust. Someone else may build strong relationships but rarely give others enough opportunity to co-create solutions. When something is not landing the way you intended, Ciarán’s six strings offer a framework for asking why. “We’re not going for perfection here. We’re just going for improvement.” That can start with small moments of reflection. Think about a recent conversation that did not go as planned. A piece of feedback someone did not respond to well. Or, a meeting where the energy suddenly changed. Maybe a team member who has started pulling back. Rather than immediately focusing on what is wrong with the other person, consider the interaction itself. What might they have experienced? Which leadership string may have been out of tune? What could you adjust the next time? What Is It Like to Be Led by You? Toward the end of the conversation, Ciarán offers a question that captures the central idea of the episode: “What’s it like to be on the receiving end of me?” It is a very different question from “Am I a good leader?” Being a strong leader is an evaluation we can make about ourselves. Understanding how people feel and what it is like to be led by us requires considering someone else’s experience. That is where leadership impacts lives. You will not always get it right. Your intentions and someone else’s experience will not always align. But becoming curious about that gap can help you build stronger relationships, strengthen trust, and create an environment where people are more willing to contribute their best over the long term. Listen to the full episode of The Leadership Habit Podcast to hear Jenn and Ciarán explore the Conscious Relational Impact Model, the six strings of leadership, and how you can become more intentional about the experience you create for the people you lead. Where to Find More From Ciarán Casey Want to learn more from Ciarán Casey? Check out his book, Leadership in Tune Explore his self-evaluation resources Connect on LinkedIn Ready to Strengthen Your Leadership Impact? Understanding how your leadership is experienced is one thing. Building the skills to adapt, communicate, build trust, and lead more effectively takes practice. Crestcom’s award-winning leadership development programs help leaders turn leadership concepts into behaviors they can apply in their everyday interactions with their teams. Experience Crestcom for yourself with a complimentary Leadership Skills Workshop and discover practical tools you can begin using right away.   The post Why Leadership Impact Matters More Than Intentions with Ciarán Casey appeared first on Crestcom International.

  6. Aug 7

    Why Character-Driven Leadership Matters More Than Ever with John Lentini

    Summary: What makes people want to follow a leader? In this episode of The Leadership Habit Podcast, Crestcom Business Owner John Lentini introduces his Six-Dial Framework for character-driven leadership. Learn how discipline, mindset, resilience, integrity, empathy, and influence work together to help leaders build trust, inspire others, and lead with greater confidence. Leadership isn’t defined by a title. It’s defined by character. The most effective leaders don’t earn trust because of their position. They earn it through the decisions they make, the values they demonstrate, and the consistency they show every day. That’s the foundation of character-driven leadership. In the latest episode of The Leadership Habit Podcast, host Jenn DeWall sits down with John Lentini, President of Bold Training Corp. and a licensed Crestcom Business Owner serving organizations throughout New York, New Jersey, Connecticut, Rhode Island, and Delaware. John is also a TEDx speaker with more than 235,000 views on his TEDx talk, where he first shared his practical framework behind his upcoming book, Engineering Character: Six Dials to Build Better Leaders, and explains why becoming a better leader starts with becoming a better version of yourself. Meet John Lentini John Lentini knows that great leadership isn’t about having all the answers. It’s about continually developing the character and habits that earn trust. As President of Bold Training Corp. and a Crestcom Business Owner, John draws on more than two decades of executive leadership experience to help leaders become more resilient, influential, and effective. His perspective is shaped by leading global teams through 9/11, the Fukushima nuclear disaster, and choosing to start a business during the COVID-19 pandemic. What Is Character-Driven Leadership? Character-driven leadership is the intentional practice of developing the habits, values, and behaviors that inspire others to trust and follow you. Rather than focusing solely on technical skills or authority, character-driven leaders cultivate self-awareness, resilience, integrity, empathy, and influence. These qualities allow them to navigate uncertainty, build stronger relationships, and create lasting impact. As John explains: “You must learn to lead yourself effectively before you can really lead others well.” That simple idea forms the foundation of his Six-Dial Framework. Great Leadership Starts with Leading Yourself According to John, every leader must first master three personal leadership habits: Discipline Mindset Resilience These three “dials” represent the internal habits that determine how consistently leaders perform, especially during difficult times. Discipline is often the least glamorous but most essential. “It is the boring, tedious, mundane stuff that we would all love to avoid… But when you start to appreciate the medium-term rewards that can be gained through regular discipline, you’re going to see a difference.” Mindset is the unwavering belief that your vision is achievable, even when progress feels slow. Resilience allows leaders to adapt, recover, and continue moving forward, whether that means persevering through challenges or changing course entirely. Together, these qualities create what John calls a determined leader. Character Is Built Through Integrity, Empathy, and Influence Once leaders learn to lead themselves, they can begin leading others more effectively. John’s second set of leadership dials focuses on: Integrity Empathy Influence Together, these create the trust every high-performing team depends on. One of the episode’s most memorable insights is John’s definition of integrity: “If discipline is consistency in your activity, then integrity is consistency in your values.” Character-driven leadership requires leaders to consistently act according to their values, even when it’s difficult. When actions align with words, trust grows. When they don’t, credibility quickly disappears. Why Empathy Is a Leadership Strength Empathy is often misunderstood as being too soft or avoiding difficult conversations. John challenges that misconception. “Empathy is understanding what someone wants, but not necessarily catering or executing on it.” Character-driven leaders don’t avoid accountability. Instead, they make difficult decisions with compassion, communicate openly, and consider how those decisions affect others. That combination of empathy and accountability builds stronger relationships and healthier workplace cultures. Character Requires Continuous Reflection One of the most practical aspects of John’s framework is that it encourages leaders to assess themselves regularly. Rather than assuming growth happens automatically, character-driven leaders intentionally reflect on where they need to improve and actively seek feedback from others. John recommends using tools such as 360-degree feedback or anonymous surveys to better understand how others experience your leadership. As he reminds listeners: “Always focus on where you are at the moment and why it’s changed… understanding we’re never done. It’s just the journey.” Leadership isn’t about reaching perfection. It’s about continually becoming a better leader. The Future of Leadership Is Character-Driven Today’s leaders face constant change, increasing complexity, and growing expectations from their teams. Technical expertise alone is no longer enough. Character-driven leadership provides a framework for earning trust, navigating uncertainty, and helping others succeed. John’s Six-Dial Framework reminds us that leadership begins within. By intentionally developing discipline, mindset, resilience, integrity, empathy, and influence, leaders create the kind of character that inspires others to follow. Listen to the Full Episode Want to learn more about John’s Six-Dial Framework and discover practical ways to strengthen your own leadership character? Listen to the full episode of The Leadership Habit Podcast featuring Crestcom Business Owner John Lentini for actionable insights you can begin applying today. Ready to Build Character-Driven Leaders? Strong organizations are built by leaders who inspire trust, communicate with integrity, and lead with purpose. Crestcom’s leadership development programs help leaders build these essential skills through practical learning, coaching, and real-world application. Request a complimentary Leadership Skills Workshop to experience Crestcom’s approach firsthand. In this interactive session, your team will explore practical leadership strategies that improve communication, strengthen accountability, and develop the habits that drive long-term success.   The post Why Character-Driven Leadership Matters More Than Ever with John Lentini appeared first on Crestcom International.

  7. Jul 24

    Summer Leadership Rewind: Staying "Forever Human" in the Age of AI with Sylvie di Giusto

    Summer Leadership Rewind: Staying “Forever Human” in the Age of AI with Sylvie di Giusto Artificial intelligence has changed dramatically over the past year. New tools arrive almost weekly. Organizations are experimenting faster than ever. And leaders everywhere are asking the same question: How do you embrace AI without losing what makes great leadership human? This week, we’re taking a summer break, so we’re revisiting one of our most impactful conversations on The Leadership Habit Podcast. Jenn DeWall sits down with leadership expert and Crestcom faculty member Sylvie di Giusto to explore why the leaders who thrive in the age of AI won’t be the ones who know the most about technology. They’ll be the ones who remain unmistakably human. If you missed this episode the first time, or if your relationship with AI has changed since then, now is the perfect time to listen again. Meet Sylvie di Giusto Sylvie di Giusto is an international keynote speaker, author, Certified Speaking Professional (CSP), and Hall of Fame speaker who helps organizations improve leadership, influence, and communication. For years, her expertise has been part of Crestcom’s leadership curriculum, helping leaders around the world strengthen emotional intelligence, executive presence, and decision-making. In this conversation, she offers a refreshing perspective on AI that replaces fear with curiosity and competition with collaboration. The Best Leaders Won’t Compete with AI Many professionals still think of AI as something they have to outwork or outperform. Sylvie challenges that mindset. “The goal was never to beat the machine. It is to build with it.” AI will always process information faster, remember more data, and complete repetitive tasks more efficiently than people. Rather than trying to compete in those areas, leaders should focus on the capabilities that technology cannot replicate. Judgment. Empathy. Trust. Context. Ethics. These are the qualities that separate management from leadership—and they become even more valuable as AI becomes more capable. Why Being “Forever Human” Matters More Than Ever As AI-generated content becomes increasingly difficult to distinguish from human-created work, authenticity becomes a competitive advantage. People don’t simply want information. They want confidence that someone understands their challenges, considers context, and genuinely cares about the outcome. That’s why Sylvie believes leaders should intentionally cultivate the uniquely human skills AI cannot replace. She explains that while AI can generate answers, leaders ask better questions. AI can analyze information, but leaders interpret meaning. AI can suggest actions, but only people can weigh ethics, relationships, and long-term consequences. In other words, AI can assist leadership, but it cannot replace it. Soft Skills Are Becoming Power Skills For years, organizations emphasized technical expertise and productivity. Ironically, AI is now making those skills easier to automate. The result? Communication, emotional intelligence, adaptability, critical thinking, and relationship-building have become even more valuable. As Sylvie notes: “There will be a big comeback for soft skills because those are the skills that AI cannot replicate.” Organizations investing in leadership development today aren’t preparing people for yesterday’s workplace. They’re building the capabilities that will matter most tomorrow. Leadership Still Means Accountability One of the episode’s most powerful reminders is that AI cannot own the consequences of a decision. Leaders still carry that responsibility. AI can recommend hiring decisions, summarize employee performance, or suggest business strategies. But it cannot understand every human circumstance, organizational nuance, or ethical consideration. As Sylvie points out, leaders cannot blame technology for decisions they choose to make. Accountability remains a human responsibility. A Conversation That’s Even More Relevant Today When this episode originally aired, many organizations were just beginning to explore generative AI. Today, AI has become part of everyday work. That makes this conversation even more valuable. Rather than focusing on specific tools or trends that quickly become outdated, Sylvie shares timeless leadership principles that help leaders navigate any technological change. Her message isn’t about resisting AI or blindly embracing it. It’s about learning how to use it wisely while protecting the qualities that make leadership meaningful. Key Takeaways If there’s one message to carry forward from this Summer Leadership Rewind, it’s this: AI will continue to evolve. Great leadership will continue to depend on people. The leaders who succeed won’t be those who simply adopt the newest technology. They’ll be the ones who combine technology with empathy, sound judgment, authentic communication, creativity, and accountability. Or, as Sylvie says best: “Don’t compete with AI. Focus on what you do in the moments that matter most as a human being.” Listen to the Episode Catch this Summer Leadership Rewind episode of The Leadership Habit Podcast with Sylvie di Giusto and discover why staying “Forever Human” may be the most important leadership strategy of the AI era. Where to Find More from Sylvie di Giusto To learn more from Sylvie:  Visit sylviedigiusto.com Connect with her on LinkedIn Buy her books Develop the Human Skills That Matter Most Technology will keep changing, but leadership fundamentals endure. Developing stronger communication, critical thinking, emotional intelligence, and decision-making skills helps leaders succeed regardless of what’s next. To learn how Crestcom helps organizations build these essential leadership capabilities, request a complimentary two-hour leadership workshop at crestcom.com/freeworkshop.   The post Summer Leadership Rewind: Staying “Forever Human” in the Age of AI with Sylvie di Giusto appeared first on Crestcom International.

  8. Jun 26

    Leadership Communication and The Boss with Andy Freed

    Effective leadership communication isn’t just about delivering information. It’s about creating connection, inspiring action, and ensuring people remember what matters long after the conversation ends. On the latest episode of The Leadership Habit Podcast, host Jenn DeWall speaks with communications expert Andy Freed. Andy shares his insights from an unexpected source of leadership inspiration: Bruce Springsteen. Andy draws from more than 95 Springsteen concerts and decades of leadership experience. Through this lens, he shares how great leaders can communicate with greater purpose, prepare more intentionally, and create lasting impact through every interaction. Meet Andy Freed, Author and Chairman of Virtual Inc. Andy Freed is Chairman of Virtual Inc., where he has spent more than three decades helping organizations navigate growth, change, and strategic communication. Throughout his career, he has worked with global organizations like Microsoft, Google, and Meta. He also helps leaders become more intentional communicators.  His newest book, How to Lead Like a Boss, explores leadership communication in an unconventional way. It looks at the habits and behaviors that made Bruce Springsteen a respected performer and leader. While the setting may be a concert stage rather than a boardroom, the leadership lessons translate directly to today’s workplace. Great Leadership Communication Starts with Intention One of Andy’s most important messages is that effective communication begins long before a meeting starts. Rather than simply creating slides or gathering updates, leaders should first ask themselves three questions: What do I want people to think? How do I want them to feel? What do I want them to do? This simple framework shifts communication from information sharing to intentional leadership. Whether you’re announcing organizational change, leading a team meeting, or having a one-on-one conversation, understanding the desired outcome before speaking dramatically improves clarity and impact. Preparation Is a Leadership Skill Bruce Springsteen doesn’t walk onto the stage and hope for the best. Before every concert, he carefully builds a set list that creates an emotional journey for the audience. Every song has a purpose. Every transition is intentional. Leaders should prepare the same way. Instead of opening yesterday’s PowerPoint presentation and making minor edits, Andy encourages leaders to think first about the experience they want their audience to have. Preparation isn’t about creating more slides. It’s about creating a message people will remember. If They Can’t Repeat the Message, It Didn’t Land One of the most memorable ideas from the conversation is that communication isn’t measured by how many times you’ve delivered a message. It’s measured by whether your audience can repeat it back to you. Leaders often become frustrated after explaining something once or twice, assuming everyone understands. In reality, people frequently need to hear important messages multiple times before they truly retain them. Instead of asking, “How many times have I said this?” leaders should ask: “Can my team say it back to me?” That shift in perspective can transform the way leaders communicate organizational priorities, strategic initiatives, and change. Leadership Is Always a Performance Leadership doesn’t end when the presentation is over. Andy explains that leaders are constantly communicating through their behavior, energy, and presence, even when they aren’t speaking. Employees notice whether leaders are engaged during meetings. They notice body language, enthusiasm, and consistency. Your energy sets the tone for everyone around you. The most effective leaders recognize that every interaction communicates something, whether intentional or not. Never Underestimate the Power of Appreciation At the end of every Bruce Springsteen concert, he personally thanks each member of the E Street Band before leaving the stage. For just a few seconds, every musician receives their full attention and appreciation. That simple ritual offers an important reminder for leaders. Recognition doesn’t have to be elaborate to be meaningful. Consistently acknowledging effort, celebrating contributions, and expressing genuine appreciation helps people feel valued. Those small moments often leave a lasting impression. As Andy notes, one of our deepest human needs is simply to feel appreciated. Leadership Communication Creates Lasting Influence Strong leadership communication isn’t about being the loudest voice in the room. It’s about preparing with intention, connecting with people, reinforcing important messages, and creating experiences employees remember. Whether you’re leading organizational change, facilitating a meeting, or simply thanking someone for their contribution, every interaction shapes trust and influence. The best communicators understand that leadership isn’t measured by what they say. It’s measured by what others hear, remember, and ultimately do. Where to Find More From Andy Freed To learn more about Andy Freed, his leadership philosophy, and his book How to Lead Like a Boss, visit andyfreed.com. There you’ll find additional resources on leadership communication, speaking, and practical strategies for becoming a more intentional leader. Develop Leadership Communication Skills with Crestcom Leadership communication is one of the most important skills leaders can develop, yet it’s also one of the most challenging to master. From communicating change to building trust and influencing performance, effective communication shapes every aspect of leadership. At Crestcom, communication isn’t treated as a standalone topic. It’s integrated throughout our leadership development programs, providing leaders with practical tools they can apply immediately in conversations, meetings, coaching sessions, and organizational change initiatives. Listen to the full episode of The Leadership Habit Podcast for even more insights from Andy Freed, and discover how intentional communication can strengthen your leadership influence every day.   The post Leadership Communication and The Boss with Andy Freed appeared first on Crestcom International.

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4.7
out of 5
15 Ratings

About

Welcome to the Leadership Habit podcast from the Crestcom Leadership Institute, the show that brings you inspiration and information to help you transform your leadership style. We use our experience developing leaders in over 60 countries worldwide to help you develop the skills and tools you need to reach your leadership potential, join us in our mission to create a better world by developing stronger, more ethical leaders. How can you make leadership a habit today?

Information

  • Creator
    Crestcom International
  • Years Active
    2019 - 2026
  • Episodes
    286
  • Rating
    Clean
  • Show Website
    The Leadership Habit

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