In today’s complex and high-speed environment, leaders are navigating an unprecedented flood of demands, decisions, and disruptions. The constant barrage of emails, meetings, and shifting priorities often leads leaders into a state where urgency outweighs importance and action is mistaken for progress. Amid these pressures, a critical—yet often overlooked—leadership muscle begins to weaken: judgment.

This episode dives deep into how sustained stress affects decision-making and perspective. Recognizing the signs of judgment fatigue and understanding its impact on teams and organizations is essential for anyone in a leadership position. Listeners will uncover strategies to protect, recover, and strengthen their decision-making capabilities, ensuring that both immediate needs and long-term goals are effectively balanced. The insights shared are vital for leaders intent on maintaining clarity, minimizing burnout, and fostering high performance, even during relentless pressure.

Timestamped Overview

• 00:00:00] Leadership Under Pressure: The question of protecting and sharpening judgment under stress
• [00:01:29] The Reality of Modern Leadership: Fast pace, constant demands, and the AI revolution
• [00:02:14] Announcing the Book: “You Don’t Know Sh About Leadership and Neither Do I”
• [00:04:33] The Leadership Muscle That Atrophies First: How sustained pressure impacts leaders
• [00:05:14] Activity vs. Effectiveness: Avoiding the trap of urgency over importance
• [00:06:34] Tunnel Vision and Shrinking Perspective: Recognizing the signs of judgment fatigue
• [00:07:57] Stress and Cognition: How stress narrows thinking and filters out critical data
• [00:08:38] The Short-Term Thinking Trap: How strategy loses to activity during stress
• [00:09:45] Confusing Speed with Quality: The cost of false urgency
• [00:10:24] What Is Judgment?: The skill of weighing trade-offs and anticipating consequences
• [00:10:58] Identity, Cognitive Load & Decision Quality: How always-deliver pressures undermine good judgment
• [00:12:13] Day-to-Day Warning Signs: Rapid decisions, increased rework, and loss of strategic focus
• [00:13:36] Why Experienced Leaders Are at Greater Risk: Endurance vs. reflection and sustainability
• [00:15:25] Team Impact: The cascade effects of poor judgment on clarity, trust, and execution
• [00:17:13] Rebuilding Judgment: How to create space for reflection and protect quality decision-making
• [00:18:24] The Eisenhower Matrix: Separating urgency from importance
• [00:19:09] Truth-Telling Circles: Why leaders need trusted advisors who challenge their thinking
• [00:19:42] Aligning Decisions with Peak Performance: Scheduling critical decisions for optimal cognitive windows
• [00:20:07] Quick Self-Check: Questions for leaders to assess their current decision-making approach
• [00:21:41] Leadership Challenges and Opportunities: Ending with reflection, not reaction

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Check out our complete show notes: https://leaddontboss.com/361

In the world of modern leadership, influence is an essential skill—often making the difference between teams that thrive and those that merely survive. Yet, many leaders misunderstand what it truly means to influence others. Rather than relying on authority or formal power, effective influence is grounded in building meaningful relationships, understanding others' goals, and fostering an environment of collaboration and trust.

This episode explores how intentional relationship-building can create lasting value and resilience within organizations. Listeners will discover the missteps leaders often make, strategies to build credibility before a crisis arises, and how core values such as empathy, transparency, and accountability can transform a team’s culture and performance. Whether facing disengaged teams, skeptical stakeholders, or the need for strategic change, mastering authentic influence is a leadership necessity for sustained success.

Timestamped Overview

[00:04:51] The True Nature of Influence: Why leaders often get it wrong out of the gate and the importance of building relationships proactively.

[00:06:15] Building Emotional Bank Accounts: Why it’s crucial to establish genuine connections before problems emerge.

[00:07:55] Facing Fear and Setting Expectations: The psychological barriers that keep leaders behind their desks and how to encourage team outreach.

[00:09:51] Shifting Culture: Moving from a reactive, “fire drill” mentality to a customer-oriented, proactive organization.

[00:10:52] Family-First Culture and Retention: How focusing on values like work-life balance can outperform higher salaries in employee retention.

[00:12:50] Modeling Healthy Work Habits: Practices like delayed email responses and empowering team members during leadership absences.

[00:14:58] The Power of Trust: How trust frees teams to innovate, take accountability, and focus on organizational priorities.

[00:16:52] Vendor and Partner Relationships: Turning unhappy users into advocates and transforming vendor partnerships for campus-wide success.

[00:19:20] Strategic Vendor Management: Proactive, ongoing communication and how relationships drive better deals and outcomes.

[00:21:28] The Three Principles of Influence: Understanding goals, managing expectations, and genuinely caring about others’ success.

[00:24:08] The Courage to Say “Whoa!”: How to slow down, clarify expectations, and ensure quality under pressure.

[00:28:09] Influencing Teams: Aligning strategy, setting clear goals, and sharing accountability.

[00:31:15] Transparent Communication: Weekly blogs, consistent messaging, and the role of humility in admitting mistakes.

[00:33:25] Crisis Preparedness: Tabletop exercises, emergency planning, and learning from military-inspired response strategies.

[00:35:41] Relationship Mapping: Strategically identifying who to build relationships with and making it a regular practice.

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https://leaddontboss.com/360

In an era of constant change, adaptability is more crucial than ever for leaders determined to thrive. The leadership landscape of 2026 is shifting in ways that extend far beyond AI and machine learning. This episode uncovers five key leadership trends that are quietly reshaping how teams operate, grow, and endure. From micro movements that accelerate culture change to boundary leadership replacing burnout, today’s most successful leaders will need to master new skills and mindsets. Understanding these trends isn’t optional—the future of leadership will be determined by those who are willing to bold adapt and lead intentionally in the face of emerging challenges.

Timestamped Overview

• [00:01:05] Upcoming Book Announcement: "You don't know shit about leadership and neither do I" – scheduled for release February 2026.
• [00:02:06] Five Emerging Leadership Trends of 2026: Why leaders must look beyond AI and focus on real issues.
• [00:02:32] Micro Movements Over Grand Strategies: The importance of visible, weekly wins and short-term momentum to accelerate culture change.
• [00:04:04] Breaking Down Big Goals: How leaders can keep teams engaged with small, continuous victories.
• [00:04:25] Conflict Fluency: Moving past avoidance to handle tension with clarity, emotion decoding, and curiosity.
• [00:05:52] High Trust Teams Need High Conflict Resolution: Setting new standards for courageous conversations.
• [00:06:12] Silent Sabotage—The New Disengagement: Recognizing emotional withdrawal and passive resistance as warning signs.
• [00:07:52] AI Will Expose Poor Leadership: Why automation will highlight broken systems and unclear goals, rather than replace leaders.
• [00:09:10] Boundary Leadership Outperforms Burnout Culture: The value of intentionality, modeling resilience, and prioritizing downtime to sustain performance.
• [00:10:15] Pacing for Long-Term Success: Leaders must pace their teams for sustained energy throughout the year, avoiding burnout.

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https://leaddontboss.com/359

Team engagement remains one of the most vital—and most challenging—aspects of modern leadership. In today’s hyper-digitized and rapidly evolving environment, leaders are inundated with data, obsessed with metrics, and often pressured to drive efficiency at all costs. Yet, despite technological advancements, the roots of high performance still reside in the fundamentals of human connection, trust, and meaningful teamwork. Modern leaders must balance analytics and process with the “soft skills” of conversation, emotional intelligence, and well-being. This episode delves into the why behind poor team engagement, the hidden human needs leaders often overlook, and the practical strategies that foster healthy, creative, and high-performing teams. Listeners will come away with insights into navigating the challenges of AI-driven change, sustaining genuine team connection, and shaping organizational cultures where people feel valued and secure.

Timestamped Overview

• [00:05:31] Why Team Engagement Fails: Exploring causes behind ineffective team engagement and the role of overloaded data in leadership.
• [00:07:23] Metrics vs. Human Connection: The tension between KPIs and cultivating creative, functional teams.
• [00:09:04] Human Fallibility and Leadership: Why leaders know the value of teamwork but struggle to "walk the walk."
• [00:10:37] Crisis, Technology, and Change: Impact of financial crises and technological acceleration on leadership culture.
• [00:12:47] AI, Modernization, and Workforce Anxiety: Addressing fears around job security and adapting messaging as a leader.
• [00:14:59] Cognitive Agility and Overreliance on AI: Studies on ChatGPT’s effects, balancing efficiency with sustained mental engagement.
• [00:17:28] The Importance of Conversation: How dialog, brainstorming, and intellectual challenge enhance team performance and thinking.
• [00:18:40] Observing and Motivating Individuals: Practical ways leaders can notice team members, personalize engagement, and build trust.
• [00:20:12] Continuous Feedback vs. 360 Reviews: Why ongoing conversations outperform retrospective assessments in fast-paced environments.
• [00:21:47] Collective Intelligence in Teams: The essential roles of social sense-making and trust for outperforming technically superior but disconnected teams.
• [00:24:48] Storytelling and Motivation: Using ongoing narrative to inspire teams and move beyond past-focused feedback.
• [00:26:37] Building Organizational Culture: Cascading social well-being, connection, and trust from leadership throughout the organization.
• [00:30:51] Maslow’s Hierarchy Revisited: How modern workplace needs have shifted, with security and connection now key elements for younger generations.
• [00:35:39] Volunteering as the Ultimate Well-being Initiative: Research on what truly improves workplace happiness and engagement.
• [00:37:56] Four-Day Workweeks, Flexibility, and Trust: Assessing trends and best practices for organizational scheduling and respecting individuals’ real lives.
• [00:43:06] The Human Imperative in the Age of AI: Preserving connection, conversation, and true happiness in a rapidly digitizing world.
• [00:44:47] Ways to Follow Nick and Access Resources: Resources for further learning and professional development.

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https://leaddontboss.com/358

Leadership is rapidly evolving as artificial intelligence becomes deeply integrated into how organizations operate and make decisions. In a world where volatility, uncertainty, complexity, and ambiguity are the norm, leaders are being challenged to not only understand the role of AI—but also to harness it in ways that enhance what makes leadership truly human. This episode dives into why leaders can no longer afford to treat AI as a separate technical domain, but rather as a strategic partner that augments decision making, stretches creativity, and humanizes leadership itself.

As generative AI rapidly advances, the question is not whether leaders should use these tools, but how to do so thoughtfully, ethically, and effectively. This conversation explores how leaders can remain at the center, leverage augmentation, and make deliberate choices that will define competitive advantage and organizational health in the next decade. The episode also emphasizes the necessity of skepticism, risk awareness, and the cultivation of skills—like “human calming”—that will set exceptional leaders apart in an AI-rich world.

Timestamped Overview

• [00:05:27] Introduction to AI and Leadership: Exploring why AI is now essential to leadership development and future success.
• [00:07:00] The Human Core of Leadership: Discussing the enduring need for human-centered leadership—augmented, not replaced, by technology.
• [00:08:34] Evolution of Leadership Skills: How classic leadership skills stand the test of time, but require a generative AI lens.
• [00:09:34] Rethinking “Cyborg Leadership”: Moving beyond science fiction to practical digital augmentation for leaders.
• [00:11:46] Developing the 10 AI-Augmented Leadership Skills: Why these skills matter and the unique place of “human calming.”
• [00:15:06] The Role of Human Calming: Centering leaders’ intention and composure in an AI-driven world.
• [00:17:36] The Value of Skepticism: Why questioning, challenging, and stretching assumptions is vital in adopting new technology.
• [00:19:17] Embracing vs. Rejecting AI: Strategies for experimenting, learning, and building organizational trust with emerging tools.
• [00:24:00] Facing Risks and Unknowns: Assessing current and future risks—including cyber threats and over-focusing on efficiency.
• [00:30:03] Effectiveness vs. Efficiency: Shifting the leadership focus toward innovation, not just automation.
• [00:34:03] All Hands on Deck: Why AI is a human and organizational story—not just a technical one.
• [00:35:12] Future-Back Thinking: Blending human and machine, and why leaders must choose to play and prototype.
• [00:39:44] Managing the Noise: How scalable foresight and intentional augmentation can help leaders cut through information overload.
• [00:43:35] Practical Takeaways: Real-life examples of how leaders can use AI tools to augment creativity and effectiveness.
• [00:46:22] Embracing Skeptical Foresight: Encouraging leaders to challenge assumptions and stretch their strategic thinking.
• [00:50:02] Don’t Get Discouraged: The learning curve of AI and the importance of hands-on experimentation.

For the complete show notes be sure to check out our website:

https://leaddontboss.com/357

Every leader eventually grapples with the question: what truly shapes long-term, sustainable success? The answer, more often than not, lies beneath visible strategies and surface-level metrics—it’s the invisible force of organizational culture. Culture isn’t just a backdrop; it’s the water in which every member swims. It quietly shapes mindsets, behaviors, engagement, and ultimately execution on strategy. Unfortunately, culture is often misunderstood, neglected, or reduced to generic values on a wall, leaving organizations unaware of its potential to make or break growth.

Leaders who ignore or underestimate the profound power of culture risk systemic underperformance and widespread disengagement. In contrast, those who understand, measure, and actively shape their culture can align their teams, realize their business strategy, and nurture workplaces where people thrive. This episode explores the science of culture—why it’s hard to define and shift, how leaders see it differently than frontline members, and tactical steps for identifying and closing the critical gap between aspirational values and day-to-day reality.

Timestamped Overview

• [00:05:42] Why Culture? Exploring why culture, not just engagement or well-being, became Laura’s core focus—and why it matters for leaders.
• [00:07:49] The Challenge of Studying Culture: Why culture is difficult to define, measure, and manage across different organizations.
• [00:09:11] Invisible Forces: The “goldfish in water” metaphor—why leaders and employees experience culture differently and may not recognize its influence.
• [00:11:50] Leadership Perception Gap: How and why leaders usually have a rosier view of culture than employees, with insights from acquisition research and psychological ego dynamics.
• [00:17:17] Systems vs. People: Why system-level thinking is critical, and how culture and strategy must be aligned for organizational effectiveness.
• [00:20:29] Measuring and Understanding Culture: Practical advice for leaders on getting honest feedback, identifying recurring problems, and surfacing gaps between values and reality.
• [00:22:24] The Values Disconnect: A simple exercise for revealing the difference between posted values and real behaviors—and how to use that gap as a starting point.
• [00:28:47] Activating, Embodying, and Embedding Culture: The three core phases of building a meaningful, sustainable culture beyond slogans and parties.
• [00:31:09] Leadership Ownership vs. HR Delegation: Why culture cannot be outsourced to HR, and must be championed by CEOs and top leadership for true impact.
• [00:33:29] Where to Begin: Guidance for leaders confronted with an unhealthy culture; how to diagnose what’s holding the team back and prioritize the first steps for change.

For the complete show notes be sure to check out our website:

https://leaddontboss.com/356

Accountability is often misunderstood and even dreaded in many workplaces, largely because it has been associated with blame and punishment instead of empowerment and ownership. For leaders striving to create high-performing teams, understanding and promoting true accountability is critical. This episode explores how accountability, when properly defined and modeled, shifts team dynamics from finger-pointing to taking ownership of results and supporting each other to achieve continuous improvement. Listeners will discover why traditional approaches to accountability are holding leaders and organizations back—and how adopting practices rooted in responsibility for results, not just tasks, forms the bedrock of a resilient and successful culture. By reframing accountability as a leadership asset rather than a threat, this conversation provides essential insights for anyone seeking to build trust, drive performance, and unleash the full potential of their teams.

Timestamped Overview

• [00:04:52] Why Accountability Has a Bad Rap: The pitfalls of associating accountability with blame and punishment.
• [00:07:04] Redefining Accountability: Distinguishing true accountability from mere responsibility for tasks, and emphasizing ownership of results and future improvement.
• [00:10:23] Practical Leadership Application: An inside look at how leaders can embody and communicate this mindset, with tangible examples from military and organizational contexts.
• [00:12:17] The Blame Game—And Why We Play It: Psychological and biological roots of finger-pointing, including the "fundamental attribution error."
• [00:18:48] Why We Struggle with Self-Examination: How the self-enhancement bias shapes our reluctance to look in the mirror and claim our own mistakes.
• [00:23:42] Building Teams that "Have Each Other's Back": Steps to replace blame with ownership, psychological safety, and team cohesion.
• [00:25:07] Modeling Accountability as a Leader: The importance of openly acknowledging your contribution to problems and making it safe for others to do the same.
• [00:28:04] The Moral Authority to Hold Others Accountable: Earning trust and credibility by going first and taking responsibility.
• [00:29:34] Final Insights for Leaders: The superpower of requesting specific feedback and advice from your team to build self-awareness, growth, and a culture of accountability.
• [00:32:02] Additional Resources and Where to Learn More: Recommendations for going deeper with Michael Timms’s materials.

For the complete show notes be sure to check out our website:

https://leaddontboss.com/355

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.

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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:

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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