How to Diplomat - stories from ordinary people doing extraordinary things

JenUpton
  • 0.0 (0)
  • POLITICS
  • UPDATED WEEKLY

How to Diplomat reveals the hidden world of diplomacy - part intrigue, part human story. Forget protocol and cocktail parties: these are candid conversations with people who’ve navigated revolutions, crises, and impossible negotiations. Host Jen Upton brings wit, honesty, and insider experience to show how the skills of diplomacy - listening, influence, connection - aren’t just for diplomats. They’re tools we all need to lead and thrive in a world that’s constantly shifting.

Episodes

  1. JAN 16

    The UN Diplomat: the secrets to effective negotation (and they're not what you think)

    Simon and I properly geek out on UN-ery: what silenceprocedure actually means and how annoying it is when someone breaks it, how resolutions go into blue, how resolutions are actually written, what really happens in those back-corridor negotiations AND a hugely awkward storyinvolving a missing coat and a foreign minister. I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. Simon Cleobury is now Head of Arms Control and Disarmament at the Geneva Centre for Security Policy and runs the course Diplomatic Tradecraft for Non-Diplomats.  Sign up for the next course here: https://www.gcsp.ch/courses/diplomatic-tradecraft-non-diplomats-2026  You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of theUK Foreign Office or any government.

    54 min
  2. The Crisis Diplomat: how to ignore the panic, and lead through the chaos

    JAN 8

    The Crisis Diplomat: how to ignore the panic, and lead through the chaos

    In this conversation, John Devine shares his journey from aworking-class upbringing in Glasgow to becoming the head of the Scottish Government's office in Canada. He discusses his experiences in the Foreign Office, the challenges of consular work, and the emotional toll it can take. John reflects on his leadership style, the importance of crisis management, and his experiences with high-level diplomatic events. He also shares insights from his personal journey on the Camino, emphasizing the significance of self-discovery and the impact of his career on his life choices. Throughout the conversation, John offers valuable advice for aspiring diplomats, encouraging them to embrace their backgrounds and pursue opportunities in internationalrelations. I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. You can also find me here: LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government. This podcast shares human stories and transferable lessons from diplomacy - not day-to-day operational details

    55 min

  3. 12/11/2025

    Is Diplomacy Still Worth It? Lessons From the Coalition That Defeated ISIS

    Ben Moore, once a US diplomat and now San Diego’s Global Affairs brain, joins me for a conversation about cat herding, goat rodeos, and why diplomacy still matters even when everyone pretends it doesn’t.This episode is for the diplomats doing the hard, invisible graft. Chapters 00:00 Introduction to Ben Moore's Journey 04:52 Cultural Influences and Worldview 07:32 Early Career in Diplomacy 10:11 Engaging with Adversaries in Diplomacy 13:00 Experiences in New York and Syria 15:35 The Coalition Against ISIS 18:15 Bridging Civilian and Military Perspectives 21:08 Challenges and Successes in the Coalition 23:52 The Importance of Dialogue in Diplomacy 26:45 Field Experiences and Forward Deployment 28:15 Building Trust on the Ground 30:55 Understanding Local Needs 34:44 The Role of Diplomacy in Crisis 34:56 The Importance of Diplomacy for National Security 39:22 Long-Term Solutions to Migration Issues 40:32 Transitioning from National to Local Diplomacy 45:24 Engaging the Community in Global Issues 47:32 Skills from Diplomacy Applied Locally 52:54 Advice for Future Generations I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government. This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

    57 min

  4. 10/31/2025

    The only woman in the room: how one junior diplomat built real power

    Jenny Wilcox reveals the hidden reality of diplomatic life—where managing powerful personalities, navigating male-dominated spaces, and leading through crises requires mastering the small details that make big outcomes possible. From her early days in the Foreign Secretary's private office to serving as Deputy High Commissioner during international crises, she shares the unexpected skills that translate from diplomatic corridors to corporate boardrooms. I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-upton Instagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government. This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

    42 min
  5. Nothing Ventured Podcast: Jen

    10/17/2025

    Nothing Ventured Podcast: Jen

    Our guest for this episode is Jennifer Upton - former British diplomat, now executive coach and founder of How to DiplomatIn this warm and deeply human conversation, Rebecca Rees and Caroline Bridge talk with Jen Upton - a former British diplomat who has been posted to some of the world’s toughest countries and now helps leaders and teams communicate, influence, and stay grounded when the pressure’s on. As Jen says, she was “posted to places I wouldn’t get to see on holiday” - and some of those postings came with extraordinary challenges. She shares what it was like to evacuate twice with two small children and her husband, and to survive the Marriott Hotel bombing in Pakistan. These experiences gave her a powerful perspective on leadership, resilience, and how to stay composed when everything around you feels uncertain. Now an executive coach and founder of How to Diplomat, Jen helps others learn the art of diplomacy in everyday life - connecting with empathy, handling pressure with grace, and leading through influence rather than authority. Together, the trio explore: How to manage fear and uncertainty in high-stakes situationsWhy influence starts with curiosityHow courage often looks quiet, calm, and deeply humanThe lessons diplomacy can teach us about work and life If you want to work with Jen contact her by email:  jennifer@howtodiplomat.com If you want to follow her for more insights: LinkedIn: www.linkedin.com/in/jennifer-s-upton Diplomatic Dispatches newsletter:newsletter Instagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat  The views expressed in this episode are the personal reflections of our guest. They do not represent the official positions of the UK Foreign Office or any government. Last week, Tom Bridge launched something new for us - the NVNG Top 3: three guiding principles or suggestions that help our guests when they’re facing new challenges or difficult situations. Nothing Ventured, Nothing Gained is hosted by Rebecca Rees and Caroline Bridge. Rebecca is an Executive Coach and Co-Founder of Peak 15 Coaching, passionate about how our brains work and helping people unlock possibility. Caroline won BBC’s Race Across the World 2025 with her son Thomas - a series watched by over six million and shortlisted at the National Television Awards. 🎯 Our Mission: To help people pause, see beyond what holds them back, and discover new possibilities for greater happiness and wellbeing. We’re rookie podcasters determined to keep going, keep improving, and share the adventure with you. Trying something new is rarely perfect - but it’s always real. 🎧 Creative Team : Angela Young – Podcast Production, Cambridge Podcasts, Zainab Uzair – Graphics, Logo & Cover Art, Gabriella Füzi – Portrait Photography 📩 Contact Us : We’d love to hear your questions, ideas, or stories of stepping outside your comfort zone: WhatsApp: https://wa.me/447375220027 Instagram @nothingventuredpodcast 👉 Please follow, share, and be part of the NVNG adventure — it all starts with daring to try. FollowApple PodcastsSpotifyPodcast IndexRSS Feed

    48 min

  6. 10/16/2025

    The Briefing: The Real Power Networks 99% of Leaders Never See

    I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government. This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

    12 min

  7. 10/09/2025

    The Trailing Spouse: The Reinvention Strategy No-One Teaches & How to Build Your Identity Anywhere

    In this conversation, Carlos and Jennifer explore the complexities of life as a spouse in the foreign service, discussing the accountability paradox, the importance of adaptability, and the challenges of maintaining a professional identity while supporting a partner's career. They delve into personal growth, the dynamics of relationships in a foreign context, and the need for policy changes to support spouses. Carlos shares insights on navigating job markets, the emotional aspects of career transitions, and the significance of self-discovery in shaping one's professional journey. Chapters 00:00 The Role of a Trailing Spouse 04:45 Marsupial Identity and Independence 06:53 Navigating Relationships and Autonomy 07:46 The Science of Relationships 09:32 Proximity vs. Emotional Connection 11:02 Adaptability in Foreign Service Life 13:18 Skills for Success in Foreign Service 14:49 Crafting Your Professional Identity 16:33 Reinventing Yourself in New Environments 17:57 Finding Your Core Interests 19:50 The Journey of Self-Discovery 22:03 Breaking Free from Attachments 22:51 Navigating Personal Growth and Change 24:55 Supporting Diplomatic Families: A Policy Perspective 27:58 Advice and Experiences as a Diplomatic Spouse 32:08 Reflections on Career and Identity 37:08 The Vocation of Diplomacy: A Call to Service I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-upton Instagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government. This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

    41 min
  8. The Diplomat's Dilemma: Why Being 100% Mom AND 100% Ambassador Is the Only Way That Works

    10/02/2025

    The Diplomat's Dilemma: Why Being 100% Mom AND 100% Ambassador Is the Only Way That Works

    I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches. You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat Maria's contact details: LinkedIn: https://www.linkedin.com/in/maria-brewer-b426b0180/ Website: https://paperbell.me/maria-brewer The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government. This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details. Chapters 00:00 The Calling of Diplomacy 04:58 Creating Community Abroad 07:13 The Journey to Diplomacy 09:44 Moments of Impact in Consular Work 11:46 Lessons in Listening and Understanding 14:32 Balancing Diplomacy and Motherhood 16:47 Navigating Crisis as a Parent 19:20 The Dynamics of Tandem Careers 21:46 Resilience in Diplomatic Families 24:16 Leadership Lessons from Experience 28:13 The Challenges and Rewards of Diplomacy 29:58 The Ambassador's Writing Style 31:36 Negotiation Techniques in Diplomacy 33:18 The Role of Ambassadors in Democracy 36:09 The Importance of Convening in Diplomacy 37:34 The Human Touch in Diplomacy 38:26 The Autonomy of Smaller Posts 40:08 Transitioning from Ambassador to Civilian Life 42:35 Embracing Change and New Beginnings 46:08 Coaching and Leadership Development 48:38 Authenticity in Leadership 52:41 Authentic Leadership and Strategic Intelligence 54:33 The Transition Paradox in Leadership 54:59 Overcoming Imposter Syndrome

    55 min
  9. The Australian Diplomat: Why I left my dream job after Egypt's revolutions & the hidden skill that makes diplomats unstoppable in business

    09/25/2025

    The Australian Diplomat: Why I left my dream job after Egypt's revolutions & the hidden skill that makes diplomats unstoppable in business

    I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly ⁠newsletter⁠, Diplomatic Dispatches. You can also find me here:LinkedIn: ⁠www.linkedin.com/in/jennifer-s-upton⁠ Instagram: ⁠https://www.instagram.com/howtodiplomat/⁠Youtube: ⁠https://www.youtube.com/@howtodiplomat ------------------------------------------------------ In this episode of the How to Diplomat podcast, I speak to Josue Castro, an experienced diplomat who shares his journey through the complexities of diplomacy, particularly during the Arab Spring in Egypt. We talk about the challenges of navigating moral and ethical dilemmas, the importance of personal growth through adversity, and the skills gained from diplomatic experiences. Josue reflects on his transition from diplomacy to sustainability consulting, emphasizing the significance of leadership and personal development. The conversation concludes with insights on career choices and the unique superpowers diplomats bring to the private sector. -------------------------------------------------------- Chapters 00:00 Introduction 02:25 The Journey into Diplomacy 03:05 Finding Purpose in Foreign Affairs 04:34 Balancing Idealism and Pragmatism 06:50 Navigating Human Rights and Trade Interests 07:57 Experiences in Cairo: The Dream Team 09:10 The Emotional Toll of Diplomacy 10:41 Personal Growth and Leadership Development 12:47 Staying Grounded in Intense Situations 14:50 Transitioning from Government to Private Sector 19:21 Navigating Leadership Journeys 19:55 The Importance of Reflection in Career Growth 21:55 Lessons from Diplomacy: Skills and Insights 25:12 The Value of Boundary Spanning in Professional Life 29:10 Systems Thinking: A Diplomat's Perspective 31:17 Advice for Future Diplomats and Leaders 34:16 Final Takeaways The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of theUK Foreign Office or any government. This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

    35 min

  10. 09/11/2025

    The Secret Service Agent: How 9/11 shaped a generation & why the best agents think like diplomats

    In this episode, I chat with John Constantine - former US Secret Service Agent, leadership pro, and someone I’ve (apparently) known for over a decade without realising it. We cover leadership, ego, cultural diplomacy… and the time one of his colleagues elbowed me in the face in New York. ------------------------------------- I write more deeply about what I learn from my interviewees along with insights from 20+ years as a diplomat and army officer — in my weekly newsletter, Diplomatic Dispatches. You can also find me here: LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/ Youtube: https://www.youtube.com/@howtodiplomat ----------------------------------------------------Chapters 00:00 Introduction to John's Background 02:56 Joining the Secret Service: A Personal Journey 05:57 The Importance of Diplomacy in Security 09:36 Cultural Sensitivity in Operations 12:13 Navigating Cultural Differences 13:12 Decision-Making Under Pressure 15:52 Crisis Response and Decision Making 20:10 Surreal Experiences in the Field 24:33 Lessons from Political Leaders 29:04 The Journey to Personal Philosophy 32:18 Identity Beyond Profession 36:44 The Essence of Leadership 38:54 Navigating Identity Beyond Titles

    45 min

  11. 08/21/2025

    Trailer

    Welcome to How to Diplomat! I’m Jen Upton - former army officer and diplomat with 20 years in the field. This podcast isn’t about the handshakes on red carpets or the headlines you already know. It’s about the unsung heroes of diplomacy - the people who worked behind the scenes in revolutions, disaster zones, and tense negotiations. Ordinary people who found themselves in extraordinary moments. In each episode, you’ll hear their stories. What they saw, what they learned, and the skills they used to connect, calm, and lead under pressure. Because diplomacy isn’t just for diplomats. It’s about how we all navigate conflict, influence people, and build trust in a complex world. Subscribe to How to Diplomat and and discover the tools that can help you connect and lead, wherever you are.

    1 min
  • 11 Episodes

About

How to Diplomat reveals the hidden world of diplomacy - part intrigue, part human story. Forget protocol and cocktail parties: these are candid conversations with people who’ve navigated revolutions, crises, and impossible negotiations. Host Jen Upton brings wit, honesty, and insider experience to show how the skills of diplomacy - listening, influence, connection - aren’t just for diplomats. They’re tools we all need to lead and thrive in a world that’s constantly shifting.

Information