Do the Right Thing—Even When It’s Hard: The Leadership Playbook | Tara Landes | Episode 353

Clear, honest, and effective communication is the cornerstone of high-performing leadership. Yet, despite communicating constantly, many leaders and teams struggle to connect, align, and truly collaborate. At the heart of the challenge are unconscious habits and patterns—often inherited from families, cultures, and early experiences—that keep conversations stuck in autopilot, limit understanding, and erode trust. Timestamped Overview [00:04:22] Why Communication Goes Wrong: Exploring the challenges of human conversation and why so many leaders struggle with it.[00:06:20] The Blueprint for Better Conversations: Introduction to the need for practical frameworks and new distinctions in how we talk.[00:09:13] The Four Types of Conversations: Overview—storytelling, collaborative, creative, and commitment conversations.[00:09:59] Storytelling Conversations: Understanding how personal narratives shape our interactions and create conflict.[00:12:01] Moving from Closed Fists to Open Hands: How to transition from ego-driven debates to open, collaborative exchanges.[00:13:34] Real-Life Example: Patterns of communication and the impact of ego on conversation flow.[00:20:29] Leveraging Team Members’ Stories: How leaders can recognize and work with the stories their team members hold.[00:22:26] The Four Archetypal Questions: Desires, concerns, power, and standards—tools for unpacking judgments and opening dialogue.[00:30:05] Vulnerability and Humility in Leadership: The courage to share what’s under the surface and model new ways of interacting.[00:30:38] Using Questions to Open Others Up: How to help team members articulate their thinking and move beyond stuck positions.[00:32:21] The Link to Psychological Safety: Creating the conditions where people feel safe to contribute and challenge.[00:37:41] The Commitment Conversation: The importance of clear requests, counteroffers, and following through on promises.[00:42:51] The Creative Conversation: Making space for possibility and collaborative idea generation.[00:46:18] Avoiding Conversational Bypass: The risk of skipping collaboration and creativity in favor of action.[00:51:17] Tracking Your Communication Patterns: How leaders can develop awareness and shift out of unhelpful habits. For the complete show notes be sure to check out our website: https://leaddontboss.com/354

Today’s business landscape is defined by continual disruption—whether from the rapid evolution of artificial intelligence, rising economic and political uncertainty, or shifting demands on how leaders and teams connect in a digital-first world. For leaders, this means grappling with complex questions: How do you train and empower junior talent in the age of AI? How can organizations foster psychological safety and trust amid ongoing change? And how do leaders ground their decisions in authentic core values when faced with tough choices? This episode explores these pivotal themes, offering practical wisdom on building resilient, value-driven organizations. Dive in for actionable insights on leveraging technology thoughtfully, sustaining trust in your team, and using core values as your compass, no matter how turbulent the environment becomes. Timestamped Overview [00:05:58] How AI is Transforming Work and Training: Examining the impact of AI on the professional services and the challenges it poses for developing junior talent.[00:10:14] Navigating Economic and Political Uncertainty: Strategies for leaders to cope with rapid changes in business conditions, from tariffs to global events.[00:11:11] The Shift to Remote and Hybrid Work: How technology has increased productivity by reducing unnecessary travel and broadening client reach.[00:13:04] Building Resilience and Psychological Safety: Practical advice for leaders to foster trust and open communication within their teams.[00:16:11] The Power of Core Values in Decision-Making: Why uncovering and living by genuine organizational values is essential, especially during crises.[00:20:27] From Slogans to Action: Making sure values are truly lived out, not just displayed on company materials.[00:23:34] Real-World Example: Leading Through a Client Crisis: A powerful story illustrating how living core values can guide difficult business decisions.[00:27:54] Organizational Systems for Value-Driven Leadership: How to prepare your business to withstand setbacks while remaining true to your mission.[00:31:14] Navigating Change with Confidence: Using values as a north star during times of uncertainty and disruption.[00:32:29] Just Get Started: Final actionable advice for leaders on overcoming paralysis by analysis and embracing action. For the complete show notes be sure to check out our website: https://leaddontboss.com/353

In an era where artificial intelligence and digital solutions are rapidly reshaping the business landscape, leaders are confronted with both exciting opportunities and significant challenges. Leveraging AI isn't just about adopting flashy new tools or automating mundane tasks; it's about reimagining leadership itself. Today’s leaders must transition from simply managing people to mastering the art of leading with technology—using AI as a collaborative partner to boost efficiency, foster innovation, and build adaptable, future-ready teams. Understanding and embracing AI is no longer optional. It is the new leadership literacy—akin to financial literacy in decades past. Leaders who develop this skill set can cultivate a culture of curiosity, resilience, and proactive problem-solving, all while keeping humanity at the core of their organizations. This episode dives deep into actionable strategies for AI adoption, ways to champion a positive culture amidst technological change, and future trends that every leader needs to track. Timestamped Overview [00:05:03] The Everyday Reality of AI: Why AI isn’t something to fear—everyone is already using it, often without realizing.[00:07:10] AI as Leadership Literacy: Reframing AI as the essential skill set of today’s leaders and how to use it collaboratively.[00:09:38] Adopting a Learning Mindset: Practical first steps for leaders to overcome overwhelm and build AI fluency.[00:11:06] The Power of Small Steps: How to identify and pilot quick-win AI projects as a team.[00:16:19] Prioritization and Incremental Gains: Strategies to pick the right AI initiatives to drive engagement and foster confidence.[00:18:43] Breaking Down Big Projects: The importance of chunking large automation efforts into manageable phases to avoid analysis paralysis.[00:22:46] Fostering a Culture for AI Adoption: Building adaptability, psychological safety, and collaborative mindsets in teams facing technological change.[00:25:40] Training AI Like a New Hire: Why successful integration requires treating AI as a “smart intern” and setting it up for success.[00:31:20] The Future of AI in Leadership: Insights into emerging AI trends, multi-step intelligent agents, robotics integration, and what leaders can expect next.[00:36:04] Learning Across Industries: The importance for leaders to look beyond their own sector for innovative applications of AI.[00:40:48] Final Mindsets for Leaders: Curiosity, adaptability, and treating technological change as an adventure rather than a threat. For the complete show notes be sure to check out our website: https://leaddontboss.com/352

Artificial Intelligence is no longer just a buzzword or looming concept—it's a rapidly evolving force that’s fundamentally transforming the landscape of business, society, and leadership itself. For leaders, AI presents both revolutionary opportunities and profound threats, disrupting traditional models of value creation, workforce engagement, and even redefining what it means to lead. The convergence of AI technology with cultural, economic, and geopolitical factors creates an unprecedented level of complexity and potential impact on humanity. Effective leaders must grapple with questions about short-term efficiency versus long-term human value, the delicate balance between productivity gains and workforce well-being, and the ethical implications of deploying intelligent agents in business and society. This episode explores the depth of these challenges, offering practical frameworks for leaders to navigate this accelerating change while remaining firmly anchored in human-centric values and organizational purpose. Timestamped Overview [00:05:08] The urgency for leaders to engage with AI—and why it's not "just another technology"[00:05:42] Multidisciplinary impacts: AI, culture, economics, geopolitics, and humanity[00:08:22] The limits of our understanding: What do we really know about AI today?[00:09:42] Technology and potential: Opportunities in health care, security, and research[00:12:31] Outsourcing humanity: Risks and the gradual loss of human agency[00:13:54] The dark side: Psychological impacts, AI personas, and vulnerable populations[00:15:30] Economic implications: Automation, agentic AI, and workforce displacement[00:16:06] The need for regulation and transparency—and lessons from Europe[00:18:17] Human impact: The dangers of psychological isolation and erosion of empathy[00:21:26] Detachment and conflict: The shifting nature of work, war, and leadership[00:24:02] The leader's dilemma: Balancing business pressures and ethical responsibilities[00:27:19] The future of value: Purpose, self-actualization, and productivity beyond profit[00:29:43] The leader’s call to action: Building legal and moral frameworks for AI[00:31:47] Rethinking measurement: From efficiency to real human impact[00:33:57] A plea for human-centric, purpose-driven leadership[00:36:05] The hidden cost: Automation, social skills, and the decline of empathy[00:39:25] The rise of hybrid teams: Managing both human and AI agents[00:42:30] Action steps: Asking bigger questions and advocating for collective well-being[00:45:53] Automation and its limits: Contextualizing novelty versus genuine human connection[00:50:40] Where the opportunity lies: Leveraging AI to solve real-world challenges[00:55:21] The ultimate responsibility: Deciding the future of humanity together For the complete show notes be sure to check out our website: https://leaddontboss.com/351

n today’s unpredictable world, leaders are constantly faced with the challenge of managing uncertainty. Whether driven by a lack of key information, insufficient understanding, or wavering trust within teams, uncertainty can erode confidence, stall decision-making, and impact organizational outcomes. For leaders, the ability to effectively navigate uncertainty marks the divide between reactive management and proactive, high-performance leadership. This episode goes beyond simply acknowledging uncertainty, offering a comprehensive framework for diagnosing its sources and actionable strategies for turning ambiguity into opportunity. By understanding how to close gaps in information, knowledge, and trust, leaders can foster greater resilience, empower their teams, and achieve better results in even the most volatile environments. Timestamped Overview [00:00:01] Framing the Problem: Why Uncertainty is Unavoidable—and So Impactful[00:02:08] What Causes Uncertainty? The Three Drivers: Information, Knowledge, and Trust[00:04:54] The Impact of Uncertainty on Leaders: Gaps and Their Consequences[00:09:40] Strategies to Overcome Information Gaps: Asking Better Questions and Seeking Clarity[00:10:27] Tools for Rapid Information Gathering: Frameworks, Dashboards, and Metrics[00:11:24] Turning Information Into Knowledge: Translating Facts to Meaningful Insights[00:11:55] Building Decision-Making Confidence: Addressing Imposter Syndrome and Skill Development[00:12:51] Building Trust Within Teams: Empowerment, Delegation, and Accountability Practices[00:13:16] How to Take Action: Integrating Practical Strategies and Seeking Coaching Support For the complete show notes be sure to check out our website: https://leaddontboss.com/350

Every leader, no matter their level of experience, encounters an inner skeptic—a doubting voice that questions whether they’re hearing genuine input or simply what others think they want to hear. This internal tension can erode trust, create isolation, and hinder clarity in decision-making. Understanding how to distinguish between genuine feedback and filtered information is essential for fostering a culture of psychological safety and truth-telling in any team or organization. Leaders must also contend with evolutionary psychological mechanisms, such as imposter syndrome, past betrayals, and the isolating effects of authority, all of which can amplify these doubts. Today’s episode dives into the practical strategies leaders can use to crush that inner skeptic. By building honest feedback loops, asking smarter questions, and trusting both yourself and your team, leaders can create high-performing cultures where truth is valued over comfort. This episode is packed with actionable insights for leaders seeking to move from suspicion and self-doubt to understanding and empowered leadership. Timestamped Overview [00:00:00] Introduction to leadership challenges and the importance of honest feedback for leaders[00:01:59] Announcing an upcoming leadership book inspired by real-world lessons and guest interviews[00:04:05] Exploring the struggle between what leaders want to hear and what they need to hear[00:05:03] The roots of inner skepticism: evolutionary psychology, imposter syndrome, and isolation[00:06:28] Understanding the power dynamic: why people filter information, and the leader’s role in decoding it[00:07:14] When skepticism is a helpful signal: identifying genuine gaps in communication[00:08:45] When skepticism becomes harmful: overanalyzing, eroding trust, and corroding relationships[00:09:30] Four ways to defeat the inner skeptic: building a culture of truth-telling and psychological safety[00:10:46] The importance of never shooting the messenger and modeling transparent communication[00:11:37] Asking better, open-ended questions to elicit honest and actionable feedback[00:13:08] Leveraging trusted third parties, coaches, or confidants for objective input[00:13:55] The leader’s gut check: questioning your own suspicions to foster genuine trust[00:14:30] Training the inner voice and leading with clarity and trust[00:15:06] Closing thoughts and reminders on the importance of trust in peak performance leadership For the complete show notes be sure to check out our website: https://leaddontboss.com/349

The evolving landscape of artificial intelligence is reshaping how organizations operate, presenting fresh challenges and unprecedented opportunities for leaders. In today’s episode, the discussion centers on how leaders can leverage AI as a powerful tool to enhance performance and operational efficiency—without losing sight of the irreplaceable value of human connection and empathy. The episode delves into the crucial aspects of leadership in this digital age: using AI responsibly, the necessity of self-care, fostering psychological safety, and empowering teams through mentorship and coaching. This conversation is vital for leaders seeking to future-proof their organizations and personal success while navigating increasing complexity and rapid technological change. Timestamped Overview [00:05:37] Exploring the Role of AI in Leadership: Initial thoughts on balancing people-centered leadership with AI advances.[00:07:17] Inspiration Behind "Professional A": Why Tony wrote his book and his mission to support young professionals in an AI-driven world.[00:08:36] Leadership Mistakes and Wisdom: The importance of humane decision-making, relationship-building, and work-life balance.[00:10:17] The Five-Factor Model for Self-Care: Key elements of self-care for leaders, including rest, sleep, compassion, resilience, and breathing techniques.[00:13:42] Overcoming Barriers to Self-Care: Accountability, habit formation, and the critical role of mentorship in leadership development.[00:16:31] Building Psychological Safety and Peer Mentorship: Why organizations must intentionally create safe, supportive mentorship environments.[00:19:18] Investing in Leadership Growth: Emotional intelligence, self-awareness, humility, and how leaders can seek feedback to grow.[00:23:08] Embracing the Digital Age: Practical strategies for leaders to govern and train teams on AI tools and digital transformation.[00:26:44] The Do’s and Don’ts of Digital Leadership: Responsible implementation, transparency about workforce changes, and upskilling team members.[00:29:32] Navigating AI-Driven Workforce Shifts: Historical perspective on technology and jobs, and how leaders can help teams adapt.[00:33:00] The Future of AI in Coaching and Feedback: The emergence of real-time, AI-powered personal assistants for leadership development.[00:33:57] Where to Learn More: Resources for further personal and professional growth. For the complete show notes be sure to check out our website: https://leaddontboss.com/348

In today's rapidly evolving business landscape, leadership demands have shifted dramatically from traditional command-and-control methods to a focus on collaboration, trust, and the development of empowered teams. Modern leaders are expected to foster autonomy, create safe environments for creativity, and respond to the increasing complexity and specialization of today’s workforce. The ability to inspire, listen, and actively nurture the growth of others has become a non-negotiable attribute for those seeking sustainable success. Effective leadership now centers on timeless yet often-overlooked principles—such as integrity, empathy, and focus—that build trust, drive engagement, and yield high-performing teams. This episode explores these concepts in depth, highlighting their practical application, the ongoing journey of leadership development, and the profound impact that thoughtful, conscious leadership can have at every level of an organization. Timestamped Overview [00:05:25] The Changing Landscape of Leadership: Shifts from authoritarian to collaborative styles, increased autonomy, and the value of creativity in modern teams. [00:08:11] Drivers Behind Leadership Evolution: Education, globalization, and the necessity of leveraging specialized knowledge. [00:10:43] The Importance of Listening: Stories highlighting the necessity of active listening as a core leadership skill. [00:13:49] From Mentorship to Authorship: The inspiration and process behind identifying the six pillars and writing the book. [00:18:32] The Six Pillars of Leadership — Overview: IntegrityCompassionEmpathyFocusStabilityHumor [00:23:48] Deep Dive: Integrity as the Cornerstone of Leadership: Defining integrity, its critical role in trust, and how to self-reflect on integrity daily. [00:29:29] Exploring Compassion in Leadership: Practical approaches to supporting team members, recognizing challenges, and fostering retention. [00:35:47] The Never-Ending Journey of Leadership: Leadership as a 24/7, ever-evolving practice and Jim’s commitment to lifelong learning. [00:36:52] Developing the Next Generation: The responsibility and rewards of mentoring upcoming leaders. [00:37:21] Where to Find More: Resources for further learning, Jim’s contact points, and news about upcoming coaching programs. For the complete show notes be sure to check out our website: https://leaddontboss.com/347

Today's episode addresses one of the most pressing challenges for leaders: getting teams to take real ownership of their work and their organizational culture. Encouraging ownership is a proven way to unlock peak performance, improve retention, and foster genuine satisfaction among team members. For many leaders, though, instilling this sense of responsibility goes beyond just handing out incentives—it requires a cultural shift and purposeful leadership tactics. Ownership in the workplace means empowering individuals and teams to see the bigger picture, to make decisions, and to feel personally invested in their organization’s success. When team members truly believe it is “their unit,” engagement and performance skyrocket. This episode breaks down actionable strategies, including drawing inspiration from military tradition, that any leader—no matter their sector or authority level—can use to inspire this powerful sense of ownership. By making it clear that each member has a voice and a stake, leaders can drive transformational results and set their organizations up for lasting success. Timestamped Overview [00:00:00] Why driving team ownership is a top challenge—and a top opportunity—for leaders[00:01:53] Real-world example: How WestJet Airlines used employee ownership to gain a competitive edge[00:04:51] The limits of stock options and traditional incentives for everyday leaders[00:06:23] Military traditions as a tool for building ownership: The coin tradition explained[00:07:59] Changing perspectives: Why “it’s your unit” matters more than “it’s my unit”[00:08:42] The significance of continuity and culture in organizations with high turnover[00:10:51] Practical implementation: Engraving “it’s your unit” onto recognition coins[00:11:37] Overcoming skepticism and building lasting buy-in for team ownership[00:12:57] Adapting the ownership model to various industries and team structures[00:14:00] Empowering teams to localize decision making and drive results[00:14:56] Leadership wrap-up: Using tradition and mentality shifts to build ownership[00:15:50] Free leadership self-assessment resource for continued growth Resources Mentioned Lead Don’t Boss Leadership AssessmentMoving Forward Leadership WebsitePeak Performance Leadership Podcast Subscription For the complete show notes be sure to check out our website: https://leaddontboss.com/346

Culture is often touted as a core driver of organizational success, yet few leaders truly grasp how it is shaped—not by slogans or aspirational values on posters, but by the subtle signals of what is tolerated every single day. Allowing destructive behaviors, even passively, sends a clear message to your team about what is truly acceptable, gradually eroding performance and morale from within. The "silent killers" of team performance don’t announce themselves; rather, they creep in quietly, undermining collaboration, excellence, and engagement. This episode shines a spotlight on three such destructive yet easily overlooked threats: mediocrity, passive resistance, and poor communication. Understanding and proactively confronting these factors is essential for anyone seeking to build a high-performing, resilient culture. Leaders who are willing to audit their own tolerance levels, set clear standards, and address dysfunction early position their teams—and themselves—for sustainable success. Timestamped Overview [00:00:00] Why Culture Is Shaped by What Leaders Tolerate[00:02:08] Understanding Service Offerings: Leader Growth Mastermind and 1:1 Coaching[00:10:33] Support Options for Team and Executive Leadership Development[00:11:21] Silent Killer #1: Tolerating Mediocrity—How Low Standards Become the Norm[00:15:02] Setting Standards and Holding People Accountable (Without Being a Jerk)[00:15:45] Silent Killer #2: Tolerating Passive Resistance—Detecting Hidden Disengagement[00:17:11] Strategies to Address Passive Resistance and Foster Psychological Safety[00:19:55] Silent Killer #3: Tolerating Poor Communication—The Ripple Effect of Ambiguity[00:20:55] Over-Communicating in Uncertain Times & The Mirroring Method[00:23:19] Mirroring in Communication: Ensuring True Understanding[00:23:50] Recap: The Three Silent Killers and Your Role in Culture Auditing[00:24:33] Self-Reflection for Leaders: Are You Reinforcing or Eroding Standards?[00:24:55] How to Support the Podcast and Spread Peak Performance Leadership Mentioned Resources Leader Growth Mastermind1:1 CoachingBook a Clarity CallNever Split the Difference by Chris Voss For the full complete show notes check out our website: https://leaddontboss.com/345