James Clear
#1 New York Times Bestselling Author of Atomic Habits | Top Booked Keynote Speaker | Founder of Habits Academy
Jesse Lipscombe
Dynamic Leadership and Achievement Expert | Bestselling Author | Actor
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Book Jesse Lipscombe, Change Management Speaker
About This Speaker
Jesse Lipscombe is a powerful keynote speaker and expert on leadership, productivity and belonging. Jesse has inspired organizations to make significant changes in workplace culture, fostering collaborative and empowered teams. Educators turn to him to instill confidence in youth and challenge them to be more inclusive and accepting. Major institutions and leading speaker series’ trust Jesse to educate and energize their audiences. His clients have included Shopify, Kraft, TD Bank, Canadian Tire, Loblaws, and Giants of Africa and many more.
Jesse first stepped into the spotlight at age 14, starring in Children of the Dust alongside Hollywood icon Sidney Poitier. He later attended the prestigious Morehouse College in Atlanta, Georgia, on a full athletic scholarship, emerging as a breakout track star.
After college, Jesse returned to the screen, producing and starring in critically acclaimed films and TV series, including It’s Not My Fault and I Don’t Care Anyway, Tiny Plastic Men, Black Summer, and most recently, Netflix’s hit series My Life With the Walter Boys, where he plays Coach Walter.
In 2023, Jesse debuted as an author with Jars, a coming-of-age novel about identity, acceptance, and self-discovery. He followed this with The Art of Doing (HarperCollins, 2025), a motivational guidebook that shares his signature strategies for passion, pursuit, and productivity – including how to win through losing, shift from macro to micro planning, and only do what you love or learn to love what you do.
A passionate advocate and entrepreneur, Jesse co-founded the #MakeItAwkward campaign to challenge racism, misogyny, and homophobia, and co-created Not That Funny, the first tabletop game designed to gamify activism and spark difficult conversations. He is a recipient of the Obsidian Award for Top Business Leader in Western Canada and was named Community Man of the Year by Diversity Magazine.
What people are saying about Jesse
Jesse’s relatable analogies and approach really helped folks understand important concepts like white privilege, intersectionality, performative allyship, de-centering one’s self, and more.
– Canadian Tire
Speaking Topics: Jesse Lipscombe
Make It Awesome: Building Belonging in Schools 
As a belonging advocate and creator of the #MakeItAwkward movement, Jesse Lipscombe challenges educators and students to move beyond passive awareness and toward meaningful action when bias, exclusion, or inequity shows up in school communities. Too often, harmful moments are ignored in the name of comfort; this keynote demonstrates why courageous engagement is essential to building cultures of belonging where every student can thrive. Jesse blends personal storytelling, social research, and real-world classroom scenarios to show how addressing uncomfortable moments with empathy and intention strengthens trust and connection. He illustrates how educators and students alike can transform awkward situations into opportunities for learning, accountability, and growth—laying the foundation for safer, more inclusive learning environments.
What audiences walk away with:
1. A clearer insight into how bias shows up in everyday interactions, with a practical understanding of intent vs. impact that they can apply in classrooms and staff spaces.
2. An understanding of why “awkward” moments matter and feel better equipped to interrupt harm and influence school culture in real time.
3. Concrete tools for peer-to-peer intervention, modelling allyship, and supporting inclusive behaviour among students and colleagues.
4. Practise responding to realistic situations and leave with strategies they can adapt to their own school contexts.
What audiences walk away with:
1. A clearer insight into how bias shows up in everyday interactions, with a practical understanding of intent vs. impact that they can apply in classrooms and staff spaces.
2. An understanding of why “awkward” moments matter and feel better equipped to interrupt harm and influence school culture in real time.
3. Concrete tools for peer-to-peer intervention, modelling allyship, and supporting inclusive behaviour among students and colleagues.
4. Practise responding to realistic situations and leave with strategies they can adapt to their own school contexts.
The Art of Doing
The most important aspect of achieving results starts with action. A simple concept but a difficult one to master when habits and self-doubt often infringe on the desired outcome. Lipscombe uses lessons from his life as an actor, speaker, writer, entrepreneur, pro-athlete, singer, etc. to craft a simple template that anyone can utilize to ensure they get out of the blocks and continue the momentum towards their dreams and goals.
Lipscombe will discuss:
1. How thoughts become things.
2. The macro to micro-planning strategy
3. Only do what you love or find a way to love what you do
4. Keeping it new
5. Shooting for the stars.
These five steps will put anyone in the best position to do any and everything they hope for, on a personal and/or corporate scale.
Lipscombe will discuss:
1. How thoughts become things.
2. The macro to micro-planning strategy
3. Only do what you love or find a way to love what you do
4. Keeping it new
5. Shooting for the stars.
These five steps will put anyone in the best position to do any and everything they hope for, on a personal and/or corporate scale.
The Equitable Leader: Driving Innovation, Growth, and Sales Through Human-Centered Leadership
As a leadership coach, Jesse Lipscombe takes the essential principles of equity and diversity and transforms them into a powerful blueprint for transformational leadership and organizational growth. Too often, conversations about equity live in a silo; this presentation proves that human-centered leadership is the only sustainable path to future innovation and increased sales.
Lipscombe weaves together statistical evidence, psychological patterns, and an array of cross-cultural perspectives to reveal how genuinely responsive leadership unlocks the full potential of diverse teams. He demonstrates that when leadership "looks different" and is tailored to how individuals uniquely arrive at their roles, it creates an environment of psychological safety and high performance—critical for navigating the complexities of modern markets and technological change.
Key Section: You Can’t Lead the Future Until You Understand the Present.
This segment offers leaders a new perspective on how cross-cultural differences and varied arrival points influence team responsiveness. By widening this understanding, leaders can significantly increase productivity, spark organic innovation, and directly impact the bottom line.
Three Takeaways:
- Quantifiable Growth: Understand how fostering an equitable and inclusive culture directly correlates to increased innovation and market growth, demonstrating the ROI of human-centered leadership.
- Adaptive Leadership Blueprint: Gain a framework for responsive leadership that adapts to a diverse workforce, ensuring all team members are led in a way that maximizes their output and engagement.
- Future-Proofing Talent: Learn to identify and mitigate biases that hinder talent development, thereby future-proofing your organization by building a stronger, more resilient, and more adaptable leadership pipeline.
Lipscombe weaves together statistical evidence, psychological patterns, and an array of cross-cultural perspectives to reveal how genuinely responsive leadership unlocks the full potential of diverse teams. He demonstrates that when leadership "looks different" and is tailored to how individuals uniquely arrive at their roles, it creates an environment of psychological safety and high performance—critical for navigating the complexities of modern markets and technological change.
Key Section: You Can’t Lead the Future Until You Understand the Present.
This segment offers leaders a new perspective on how cross-cultural differences and varied arrival points influence team responsiveness. By widening this understanding, leaders can significantly increase productivity, spark organic innovation, and directly impact the bottom line.
Three Takeaways:
- Quantifiable Growth: Understand how fostering an equitable and inclusive culture directly correlates to increased innovation and market growth, demonstrating the ROI of human-centered leadership.
- Adaptive Leadership Blueprint: Gain a framework for responsive leadership that adapts to a diverse workforce, ensuring all team members are led in a way that maximizes their output and engagement.
- Future-Proofing Talent: Learn to identify and mitigate biases that hinder talent development, thereby future-proofing your organization by building a stronger, more resilient, and more adaptable leadership pipeline.
Leading the AI Age: Becoming an Effective and Human Ally in a World of Change
The rapid advancement of AI and automation is not just a technological challenge; it's a human-centered leadership challenge. This talk reframes the concept of "allyship" from a social justice term to a future-forward leadership competency, essential for managing organizational transformation and change.
Jesse Lipscombe uses his powerful storytelling and understanding of systemic change to help leaders and educators navigate the immediate future. He helps organizations recognize and respond to the human challenges—the fears, biases, and need for reskilling—that arise when technology like AI shifts the landscape. He provides practical, actionable steps for leaders to become true 'Allies to the Future'—actively championing both technological adoption and the human development needed to succeed alongside it.
This presentation offers an essential lens for industries like education, showing how transformational leadership must be empathetic and proactive in integrating AI influences while ensuring equitable access and upskilling for all.
Three Takeaways:
- Actionable AI Strategy: Develop an ethical, human-first strategy for integrating AI influences into organizational or educational models, focusing on increasing efficiency and fostering future-ready skills.
- Change Management Competency: Acquire practical steps for leaders to address and diffuse the natural resistance to change, cultivating a culture where employees and students see technology as an opportunity for growth, not a threat.
- Future-Ready Communication: Learn to communicate organizational transformation and the necessity of new technologies with the empathy and clarity required to maintain team motivation, trust, and alignment during periods of rapid change.
Jesse Lipscombe uses his powerful storytelling and understanding of systemic change to help leaders and educators navigate the immediate future. He helps organizations recognize and respond to the human challenges—the fears, biases, and need for reskilling—that arise when technology like AI shifts the landscape. He provides practical, actionable steps for leaders to become true 'Allies to the Future'—actively championing both technological adoption and the human development needed to succeed alongside it.
This presentation offers an essential lens for industries like education, showing how transformational leadership must be empathetic and proactive in integrating AI influences while ensuring equitable access and upskilling for all.
Three Takeaways:
- Actionable AI Strategy: Develop an ethical, human-first strategy for integrating AI influences into organizational or educational models, focusing on increasing efficiency and fostering future-ready skills.
- Change Management Competency: Acquire practical steps for leaders to address and diffuse the natural resistance to change, cultivating a culture where employees and students see technology as an opportunity for growth, not a threat.
- Future-Ready Communication: Learn to communicate organizational transformation and the necessity of new technologies with the empathy and clarity required to maintain team motivation, trust, and alignment during periods of rapid change.
The 1000% Leader: Leveraging Success Through Strategic Failure
In an environment demanding constant innovation and aggressive sales targets, failure is inevitable—it is also the most potent accelerator for growth. Lipscombe draws on his high-performance experience as a professional athlete and actor to redefine the relationship between risk, failure, and ultimate business success and sales growth.
This high-energy, motivational keynote introduces the theory of "Batting 1000"—the concept that successful failures occur only when you push limits to the absolute maximum. A future-forward leader views failure not as a loss, but as the most honest data point for where the organization is and what must change. This session provides a tangible framework for building an organizational culture that rewards smart risk-taking, rapidly iterates on lessons learned, and converts market misses into a blueprint for increased sales and innovation.
Three Takeaways:
- Innovation Culture: Gain a blueprint for structuring teams and projects to encourage strategic, high-value risk-taking, turning failure into the engine that drives product and service innovation.
- Growth Mindset to Sales: Learn to apply the "Batting 1000" philosophy to sales and market development, encouraging your teams to pursue ambitious targets, use setbacks as rapid market intelligence, and sustain higher levels of activity and motivation.
- Resilient Leadership: Walk away with concrete tools to help leaders and employees shift their relationship with failure, transforming fear and self-doubt into a source of personal drive and organizational resilience, essential for navigating volatile market conditions.
This high-energy, motivational keynote introduces the theory of "Batting 1000"—the concept that successful failures occur only when you push limits to the absolute maximum. A future-forward leader views failure not as a loss, but as the most honest data point for where the organization is and what must change. This session provides a tangible framework for building an organizational culture that rewards smart risk-taking, rapidly iterates on lessons learned, and converts market misses into a blueprint for increased sales and innovation.
Three Takeaways:
- Innovation Culture: Gain a blueprint for structuring teams and projects to encourage strategic, high-value risk-taking, turning failure into the engine that drives product and service innovation.
- Growth Mindset to Sales: Learn to apply the "Batting 1000" philosophy to sales and market development, encouraging your teams to pursue ambitious targets, use setbacks as rapid market intelligence, and sustain higher levels of activity and motivation.
- Resilient Leadership: Walk away with concrete tools to help leaders and employees shift their relationship with failure, transforming fear and self-doubt into a source of personal drive and organizational resilience, essential for navigating volatile market conditions.
The Equity Toolkit for Growth: Building Transformational Leadership
This workshop is a hands-on masterclass designed for leaders committed to transformational leadership that delivers tangible organizational results. Drawing on over a decade of advocacy and coaching, Jesse moves beyond foundational awareness to equip leaders with concrete, data-driven tools that build equitable structures designed for sustained growth and high-performance.
This session emphasizes that true equity is not about compliance; it's about optimizing the environment to maximize the contributions of all employees. Leaders will learn practical strategies to dismantle systemic inefficiencies, address unconscious biases in hiring and promotion (critical for scaling), and foster a culture of psychological safety where diverse teams feel empowered to contribute their best, most innovative work. This is the toolkit for leaders who understand that the future of their organization depends on fully mobilizing every part of their talent pool.
Three Takeaways:
- Diagnostic Tools: Receive a practical, Equity Audit Toolkit to identify and dismantle hidden barriers to growth in organizational processes (e.g., hiring, performance reviews).
- Transformational Dialogue Skills: Acquire specific language and coaching techniques to lead difficult, meaningful conversations that build understanding and push colleagues forward, enhancing team cohesion and productivity.
- Measurable Impact: Learn how to set and track metrics for equitable talent development, directly linking leadership practices to the organization's goals for innovation, employee retention, and increased market share.
This session emphasizes that true equity is not about compliance; it's about optimizing the environment to maximize the contributions of all employees. Leaders will learn practical strategies to dismantle systemic inefficiencies, address unconscious biases in hiring and promotion (critical for scaling), and foster a culture of psychological safety where diverse teams feel empowered to contribute their best, most innovative work. This is the toolkit for leaders who understand that the future of their organization depends on fully mobilizing every part of their talent pool.
Three Takeaways:
- Diagnostic Tools: Receive a practical, Equity Audit Toolkit to identify and dismantle hidden barriers to growth in organizational processes (e.g., hiring, performance reviews).
- Transformational Dialogue Skills: Acquire specific language and coaching techniques to lead difficult, meaningful conversations that build understanding and push colleagues forward, enhancing team cohesion and productivity.
- Measurable Impact: Learn how to set and track metrics for equitable talent development, directly linking leadership practices to the organization's goals for innovation, employee retention, and increased market share.
Workshop: The AI Implementation Lab
A deep-dive interactive session where participants move from theory to execution. We will audit your current workflow through the lens of The Art of Doing, identify bottlenecks, and build custom AI-driven systems to dissolve them. Participants will leave with a personalized "Productivity Stack" that allows them to produce more while feeling less drained.
Outline
Module 1: The Productivity Audit – Mapping out your current "to-do" list and identifying the difference between "busy work" and "the work."
Module 2: Prompting with Purpose – A hands-on tutorial on "Artful Prompting"—using the book's principles to communicate effectively with AI tools.
Module 3: Building Your AI Workflow – Live build of three core automations (e.g., content creation, email management, or project planning).
Module 4: The Resistance Guardrail – Discussion on the psychological barriers to new tech and how to maintain the discipline of "Doing" when things get "easier."
Module 5: The Execution Roadmap – Finalizing a 30-day plan to integrate these tools into daily habits.
Outline
Module 1: The Productivity Audit – Mapping out your current "to-do" list and identifying the difference between "busy work" and "the work."
Module 2: Prompting with Purpose – A hands-on tutorial on "Artful Prompting"—using the book's principles to communicate effectively with AI tools.
Module 3: Building Your AI Workflow – Live build of three core automations (e.g., content creation, email management, or project planning).
Module 4: The Resistance Guardrail – Discussion on the psychological barriers to new tech and how to maintain the discipline of "Doing" when things get "easier."
Module 5: The Execution Roadmap – Finalizing a 30-day plan to integrate these tools into daily habits.
The Productivity Paradox
Curiosity is the key to finding your footing in this ever-changing, fast-paced tech world. Being productive isn’t about doing more things; it’s about doing the right things with higher presence. We are currently "molting" (to use the Lobster Life metaphor). AI is the new exoskeleton that allows us to expand our capacity. However, without Intentionality, AI just helps us do the wrong things faster. This speech shifts the narrative from AI as a "replacement" to AI as a "force multiplier" for the human spirit.
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