The Jonathan Raymond Show

Join Jonathan Raymond, author and thinker as he delves into the multifaceted aspects of leadership. Each episode features Jonathan and a variety of thought leaders, CEOs, and authors discussing the complexities of authority and leadership. They share personal insights, fostering authentic connections and profound reflections. In addition to these candid conversations, Jonathan presents monologues and short videos, covering diverse topics like parenting, relationships, spirituality, and wellness. Jonathan offers a unique lens on leadership, inviting you to explore its depths and implications in your life.

You Don't Usually Get To Witness This | Real Executive Coaching 03/31/2025

Your Most Underdeveloped Skill: Boundaries 01/01/2025

#033 - Find Healthy Conflict In Your New Year 12/31/2024

#033 - Find Healthy Conflict In Your New Year In today’s episode, Jonathan introduces a transformative way to approach the new year by rethinking the traditional idea of setting external goals. Instead of focusing on resolutions like losing weight, saving money, or changing jobs, he explores how creating productive internal conflicts can drive lasting change and deeper fulfillment. Sign Up For The Newsletter: https://jonathanraymond.com/#newsletter Jonathan explains that true growth comes not from aiming for binary success or failure with external achievements but from fostering tension between the version of yourself who made past choices and the future version of you who lives differently. This inner dialogue becomes the foundation for meaningful progress, offering clarity and motivation to bridge that gap over time. In the conversation, Jonathan provides practical examples of how to apply this principle across various aspects of life—work, relationships, health, and finances. Whether it’s improving your job satisfaction, standing up for yourself in a relationship, or making healthier choices, the key is to embrace the discomfort of this internal conflict rather than avoiding it. He emphasizes that sustainable change isn’t about quick fixes or drastic actions but about building awareness and resilience day by day. Jonathan also underscores the importance of seeking support from trusted friends, family, or colleagues who can help you stay grounded and accountable. Sharing your intentions and progress with others who align with your values can make all the difference in your journey. This episode is a fresh take on personal growth—one that encourages you to ditch the quick resolutions and instead embrace the tension between who you are today and who you want to become. By doing so, you set the stage for a year that feels truly different and aligned with your authentic self. Thanks for listening. /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/34667395

#032 - How To Be Yourself 12/22/2024

#031 - Fitter, happier, and more productive? 12/09/2024

#030 - Wendy Smith, PhD | Finding Harmony in Conflict with Both/And Thinking 11/03/2024

#030 - Wendy Smith, PhD | Finding Harmony in Conflict with Both/And Thinking Sign Up For The Newsletter: On today's episode of Good Authority, Jonathan sits down with Wendy Smith, the renowned author of Both/And Thinking, to delve into the traps of either-or thinking that affect our decision-making, relationships, and even political discourse. Wendy shares insights from her journey as a self-proclaimed "uncertain academic," exploring how embracing ambiguity and conflicting forces can become powerful tools in both personal and professional contexts. Together, they discuss why a “both/and” mindset is crucial for fostering understanding and avoiding the polarization that often stems from black-and-white thinking. Wendy explains how our natural comfort with certainty and simplicity can often limit our creativity, while a more expansive approach can help us see opposing ideas as interconnected rather than mutually exclusive. Throughout the episode, Jonathan and Wendy also examine how this mindset can aid leaders in guiding teams through complex challenges by balancing diverse perspectives, allowing them to navigate seemingly contradictory goals more effectively. Key takeaways from this episode are the value of embracing ambiguity to foster growth and creativity, practical methods for moving beyond polarizing perspectives, and strategies for leaders to guide teams through complex, contradictory challenges. Wendy Smith earned her Ph.D. in organizational behavior at Harvard Business School, and is currently a professor of management at the Alfred Lerner College of Business & Economics and Co-director of the Women’s Leadership Initiative at the University of Delaware. Wendy’s research focuses on strategic paradoxes – how leaders and senior teams effectively respond to contradictory agendas. She studies how organizations and their leaders simultaneously explore new possibilities while exploiting existing competencies, and how social enterprises simultaneously attend to social missions and financial goals. Her research has been published in journals such as Academy of Management Journal, Academy of Management Review, Administrative Science Quarterly, Harvard Business Review, Organization Science and Management Science. In 2018, she won the University of Delaware’s first Mid-Career Excellence in Scholarship Award. In 2015, she won the Lerner College Outstanding Scholar Award. Wendy teaches leadership, organizational behavior and business ethics. She has taught MBAs and undergraduates at University of Delaware, Harvard and University of Pennsylvania – Wharton. Wendy was awarded the University of Delaware MBA Teaching Award in 2016. Wendy has also taught executive and senior leadership teams how to manage interpersonal dynamics, emotional intelligence, high performing teams, organizational change and innovation, managing in times of crisis, and managing strategic paradoxes. Connect with Wendy: ⁠⁠⁠⁠Try Ren, our AI Accountability Platform: Get the FREE Good Authority Audiobook: Instagram: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/33763732

#029 - Rand Fishkin | Founding, Failing, and Finding Balance 09/23/2024

#028 - Matt Dixon | Using AI To Analyze 2.5 Million Sales Calls 08/30/2024

#028 - Matt Dixon | Using AI To Analyze 2.5 Million Sales Calls Sign Up For The Newsletter: In today's episode of Good Authority, Jonathan sits down with Matt Dixon, a renowned sales researcher and author, for a deep dive into modern sales strategies. They explore how sales is not just a profession but a way of showing up authentically in life, whether you're a business leader, coach, or parent. Matt shares insights from his extensive research, debunking outdated sales tactics and emphasizing the importance of authenticity, trust, and empathy in today's sales environment. This episode is a masterclass in how to approach sales conversations with integrity and make meaningful connections. Whether you're in sales or simply interested in improving your communication skills, this conversation is packed with valuable lessons. About Matt Dixon: Known for his ground-breaking research, he is a frequent contributor to and is the author of some of the most important business books of the past decade. He is a founding partner of DCM Insights, a boutique consultancy focused on using data and research-backed frameworks to help companies attract, retain and grow their customers. His first book, (Portfolio/Penguin 2011), was a #1 Amazon and Wall Street Journal bestseller and has sold nearly a million copies worldwide and has been translated into a dozen languages. The Challenger Sale has won acclaim as “the most important advance in selling for many years” (SPIN Selling author Neil Rackham) and “the beginning of a wave that will take over a lot of selling organizations in the next decade.” (Business Insider). He is also the author of (Portfolio/Penguin 2013), which introduced the concept of customer effort reduction and the Customer Effort Score to companies around the world, as well as (Portfolio/Penguin 2015), the celebrated sequel to The Challenger Sale. His newest book, , was released by Penguin in September 2022. Matt’s work has been published in the print and online editions of on more than twenty occasions. Among his noteworthy HBR articles are “” (November 2013) and “” (July-August 2012), both of which appear in . He is also the author of some of the most widely cited HBR articles on customer experience and customer service, including (November-December 2018), “” (January-February 2017), and “” (July-August 2010). In addition to his research and writing, Matt is a seasoned practitioner having held executive leadership roles in strategy, new product development, product management, research and innovation for companies like Tethr, Korn Ferry Hay Group and CEB (now Gartner). He is a sought-after speaker and advisor to management teams around world, having presented his findings at a wide range of industry conferences as well as to hundreds of senior executive teams around the world, including those of many Fortune 500 companies. Matt holds a Ph.D. from the Graduate School of Public and International Affairs at the University of Pittsburgh as well as a B.A. in International Studies from Mount Saint Mary’s University in Emmitsburg, Maryland. He currently resides in the Washington, D.C. area with his wife and four children. Connect with Matt: Try Ren, the AI Leadership Coach: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/32805417

#027 - Ruben Harris | Balancing Technology, Emotions, & Human Connection 07/18/2024

#027 - Ruben Harris | Balancing Technology, Emotions, & Human Connection Sign Up For The Newsletter: In today's episode of Good Authority, Jonathan and Ruben Harris sat down to talk about their shared experiences as business owners, founders, and CEOs navigating the tech space amidst the massive disruption brought on by AI. They explored topics like childhood, music, and the ways we relate to our minds and hearts. Ruben detailed his journey from musician to co-founder and CEO of Career Karma, highlighting his transition from music to investment banking and the founding and growth of Career Karma. Jonathan and Ruben discussed the evolving landscape of careers, the future of AI, and its impact on job markets. They touched on the potential of AI to enhance human capabilities and the importance of maintaining balance between the mind and heart. They shared personal stories, including Ruben's long-standing passion for the cello and Jonathan's reflections on his daughter's piano lessons and their family music sessions. As you listen, reflect on the significance of embracing emotions, the potential of AI to enhance human capabilities if we manage it correctly, and the enduring value of relationships and community in achieving true happiness. About Ruben Harris: Ruben Harris is a Bay Area transplant from Atlanta, Georgia where he served as an Advisor for Forge and organized Atlanta's first Healthcare Hackathon. Over the past couple of years, Ruben has worked with academics, organizers, politicians, and union leaders at Hustle, Honor and AltSchool focused on improving their personalized outreach, healthcare and education. Ruben began his technology career working in Partnerships and Sales after writing a viral blog post called Breaking Into Startups about how he moved to San Francisco without a job and landed a position 3 weeks later. After receiving thousands of e-mails asking how to break into tech, Ruben Co-Founded the Breaking Into Startups Podcast to demystify the process, resulting in a social media reach of ~3 million people, 200,000+ downloads, 10,000+ website visits per month, over 100+ reviews on iTunes, a Facebook Community of 10,000+ people, and invitations to be a Contributor for TechCrunch and Black Enterprise. Prior to working in tech, Ruben worked as an Investment Banker focused on Food, Consumer, and Retail companies in Chicago and Atlanta. As a member of the Chicago Council on Global Affairs, he recruited others to focus on issues related to food security, climate change, and agriculture. In 2010, Ruben worked on operational improvements for Senior Living Communities after completing a double major in Business Administration and Music. During college, Ruben organized 50+ events for non-profits, athletes, and celebrities including Tyrese, Kim Kardashian, and Jay-Z. Ruben has been playing the cello for ~25 years, taught music, performed in venues all over the world - including Carnegie Hall, and landed placements from Def Jam. He is also an active member of the NAACP. Connect with Ruben: Continue the conversation with Jonathan: Try Ren, the AI Leadership Coach: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/32191127

#026 - Getting Involved In AI Isn't An Option Anymore 07/11/2024

#025 - Christian Idiodi | Innovation, Empathy, & Human-Focused Product Design 07/04/2024

#025 - Christian Idiodi | Innovation, Empathy, & Human-Focused Product Design Sign Up For The Newsletter: In today's episode of Good Authority, Jonathan and Christian Idiodi discuss the future of work, human-centric product design, and the importance of empowering people and leadership in the face of emerging technologies like AI. Throughout this episode, you'll gain a deeper understanding of the need for companies to prioritize human skills such as empathy and curiosity to create an empowering work environment where talented people are given problems to solve and are trusted to discover the best solutions. Christian and Jonathan also explore the importance of maintaining a beginner's mindset, experimenting with new approaches, and taking action without fear of failure in leadership roles. As a bonus, you'll learn a bit about what Christian is up to in Africa with his non-profit organization, the Innovate Africa Foundation. They discuss the growing gap between technologists and government officials in Africa and the need for education, collaboration, and critical thinking to address ethical practices and societal impacts. About Christian: Christian has been a product leader for over 15 years, building teams and developing enterprise and consumer products that have shaped companies such as CareerBuilder and Merrill Corporation as well as clients such as Microsoft, Starbucks, and Squarespace. Christian is passionate about helping companies implement the discipline of product management to build world-class products and new technologies. At CareerBuilder, Christian founded and managed CareerBuilder Institute, the industry’s first combined human capital and consumer training platform, creating a new stream of revenue for the company. As VP of Enterprise Product at Snagajob, Christian conceptualized a new-to-market solution and led the discovery, development, and successful launch of the ReadyHire business line. He designed and led the B2B product strategy for IdentityForce, a leading provider of identity, privacy, and credit protection for individuals, businesses, and government agencies. He then founded Firtsi, a product consulting company that has overseen the product development lifecycle from ideation to launch for over 120+ new products. Before joining Silicon Valley Product Group, Christian was the Global Head of Product for Merrill Corporation. Christian built the company’s product organization and led them through a transformational, large-scale industry launch of the first SaaS app for due diligence in the finance industry. Christian teaches product management and innovation at Virginia Commonwealth University in Richmond, VA. He also gives back to his local product community each year by supporting and advising two student-led startups from conceptualization to product delivery. Christian graduated from Emory University with a B.A. in Psychology and Community Building and earned a dual MBA and MPM from Keller Graduate School of Management. Connect with Christian: Continue the conversation with Jonathan: Try Ren, the AI Leadership Coach: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/32010622

#024 - The Masculinity Crisis 06/27/2024

#023 - Gary Barker | Masculinity, Equality, & Gender Roles 06/20/2024

#023 - Gary Barker | Masculinity, Equality, & Gender Roles In today's episode of Good Authority, Jonathan and Gary Barker engage in a thought-provoking conversation about challenging traditional gender norms and binary labels, particularly those associated with masculinity. They share personal experiences and observations on the harmful effects of toxic masculinity and the importance of creating safe spaces for men to express emotions and open up about their struggles. They also discuss the challenges of expressing emotions and prioritizing mental health in a society that expects men to be stoic and unemotional, and the effects of social media on young people. The conversation highlights the need for ongoing support and dialogue to empower girls and boys and break down barriers that restrict their full equality, while also emphasizing the importance of self-care, empathy, and open communication in fostering a more emotionally authentic and supportive environment for men. Gary Barker, PhD, has been a global voice in engaging men and boys in advancing gender equality, gender justice and positive masculinities for three decades. He is the CEO and co-founder of Equimundo Center for Masculinities and Social Justice, a major contributor to international activism on male allyship in gender equality. He was the first Executive Director of Instituto Promundo in Brazil and led its pioneering work on healthy masculinities. He is co-founder of MenCare, a global campaign in more than 50 countries to promote men’s involvement as caregivers, and co-founder of MenEngage, a global alliance of more than 700 NGOs. He co-created the International Men and Gender Equality Survey (IMAGES), the largest survey of men’s attitudes and behaviors related to violence, fatherhood, and gender equality. He leads Equimundo’s State of the World’s Fathers reports, which has become a major advocacy platform for the global care economy. He has coordinated Equimundo’s partnerships in conflict-affected settings including work on community-based trauma support and restorative justice in the Democratic Republic of Congo, the Balkans, the US and Brazil. He advises the UN, the World Bank, national governments, international foundations and corporations on strategies to engage men and boys in promoting gender equality. In 2017 he was named by Apolitical as one of the 20 most influential people in gender policy worldwide. He is an Ashoka Fellow and received the Voices of Solidarity Award from Vital Voices for his work to engage men for gender equality. He holds a PhD in Developmental Psychology and a Research Affiliate position at the Center for Social Sciences, University of Coimbra, Portugal. He lived nearly 20 years in Latin America and is fluent in Spanish and Portuguese. Connect with Gary: Continue the conversation with Jonathan: Sign Up For The Newsletter: Instagram: Try Ren, the AI Leadership Coach: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/31818942

#022 - Digital Transformation Is More Than Just New Technology | David Rogers | Bestselling Author & Academic Director At Columbia Business School 06/06/2024

#022 - Digital Transformation Is More Than Just New Technology | David Rogers | Bestselling Author & Academic Director At Columbia Business School In today's episode of Good Authority, Jonathan sits down with David Rogers. They discuss digital transformation, emphasizing its holistic nature and the need to align all functions and teams towards a shared vision. They highlight the challenges of navigating organizational change and the importance of defining a clear and shared vision for digital transformation. They also discuss the importance of aligning incentives and purpose for successful organizational transformation, and provide insights on how to communicate a shared vision and elicit motivation from employees. David Rogers is the world’s leading expert on digital transformation, a member of the faculty at Columbia Business School, and the author of five books. In his newest book, The Digital Transformation Roadmap (2023), Rogers tackles the barriers behind the 70% of businesses that fail in their own digital efforts. He shows why every business must transform not just its products―it must transform the organization itself. Rogers offers a five-step roadmap to rebuild any organization for continuous digital change. His previous landmark bestseller, The Digital Transformation Playbook (2016), was the first book on digital transformation and put the topic on the map. Now published in thirteen languages, it defined the discipline by arguing that digital transformation (DX) is not about technology; it is about strategy, leadership, and new ways of thinking. Rogers has helped companies around the world transform their business for the digital age, working with senior leaders at corporations including Google, Microsoft, Citigroup, Visa, HSBC, Unilever, Procter & Gamble, Merck, GE, Toyota, Cartier, Pernod Ricard, China Eastern Airlines, NC Bank Saudi, and Acuity Insurance, among others. Rogers regularly delivers keynotes at conferences on all six continents and has appeared on CNN, ABC News, CNBC, Channel News Asia, and in The New York Times, The Financial Times, The Wall Street Journal, and The Economist. At Columbia Business School, Rogers is faculty director of executive education programs on digital business strategy and on leading digital transformation. He has taught over twenty-five thousand executives through his programs in New York City, in Silicon Valley, and online. His recent research has focused on new business models, innovating through experimentation, governance for growth, and barriers to change in digital transformation. Connect with David: Continue the conversation with Jonathan: Sign Up For The Newsletter: Instagram: Try Ren, the AI Leadership Coach: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/31625577

#021 - How To Break Up With Your Parents (And Why You Might Need To) 05/30/2024

#020 - What's Your Problem? | Thomas Wedell-Wedellsborg 05/23/2024

#020 - What's Your Problem? | Thomas Wedell-Wedellsborg In today's episode of Good Authority, Jonathan sits down with Thomas Wedell-Wedellsborg. They discuss the importance of approaching problems differently to achieve innovation and success. They emphasized the need for emotional and intellectual distance to solve the right problems, and for a simple method that can be applied by anyone. Jonathan also highlights the importance of understanding personal journeys and pain points to address complex problems, while Thomas emphasizes the need to recognize and reframe one's own biases and assumptions. As the episode winds down, you'll hear Jonathan and Thomas discuss a few personal topics, including the challenges of maintaining the purity of advisory work while balancing personal interests and client needs. Thomas Wedell-Wedellsborg is a globally recognized expert in innovation and problem-solving. He authored "Innovation as Usual" (2013) and "What's Your Problem?" (2020), both published by Harvard Business Press. His work focuses on practical approaches to drive innovation and solve complex problems within organizations. Wedell-Wedellsborg's expertise has been sought by numerous high-profile clients, including Microsoft, Cisco, Citigroup, and the United Nations. He is particularly known for his "reframing" method, which helps individuals and organizations approach problems more effectively by changing how they define and understand them. He has been featured in various publications and recognized as a top thinker in his field by institutions like Thinkers50 and HR Magazine. "Thomas makes a compelling case that we often start solving a problem before thinking deeply about whether we are solving the right problem. If you want the superpower of solving better problems, read this book." -- Eric Schmidt, former CEO, Google Connect with Thomas: Continue the conversation with Jonathan: Sign Up For The Newsletter: Instagram: Try Ren, the AI Leadership Coach: /episode/index/show/667c7f98-3707-460c-9141-817b3f83c0d0/id/31429247