Risky Conversations with Jamie Lee

Jamie Lee
  • 4.9 (28)
  • Careers
  • Updated Semiweekly

Everything that's rewarding is on the other side of a Risky Conversation. In this podcast for professional women, we have honest talks about topics often considered taboo or "too risky" at work -- salary negotiation, mental and reproductive health, office politics, social injustices, and unconventional ways smart women navigate their path forward despite a flawed and sexist society.  Join me as we dive deeper into these risky yet rewarding conversations, embracing the growth they bring. 

  1. 3d ago

    Anti-Networking: The Surprising Power of Not Asking for Anything At All

    The truth is, some of the most powerful career moves happen when you don't ask for anything at all.  This Friday, July 24th, my client Sarah-Neel Smith and I are going to teach you exactly how to have those career conversations where you don't ask for anything at all and generate power for your negotiation outcomes. All the details here: https://antinetworking.jamieleecoach.com/ If you're going, "Wait, what? How does that happen?"  I explain it in detail in this episode.  What you'll learn:  How not asking for anything in preliminary conversations can grow your negotiation leverage for job offer or promotion negotiation Key questions I ask about my client's organization’s promotion cycle, decision-makers, and influencers and why answering those questions matter How curious, no-ask conversations across functions and levels help you better understand the system and negotiate better outcomesHow can you use informational interviews to cut through information asymmetry when you’re negotiating a job offer or raise?Case Study 1: How a client used informational interview to secure a $250K base salary as director of finance at an AI startup Case Study 2: How another client used informational interviews to compel her boss to secure the highest pay increase possible as director of marketing What you'll learn and gain from joining Anti-Networking workshop with Sarah-Neel and me on Friday, July 24th Mentioned:  Interview with client Grace Anniskett: https://podcast.jamieleecoach.com/2033808/episodes/12125488-from-minimum-wage-to-ceo-with-grace-anniskett-of-anniskett-consulting-groupInterview with client Sarah-Neel Smith: https://podcast.jamieleecoach.com/2033808/episodes/19111448-50-raise-self-advocacy-informational-interviews-sarah-neel-smith-phd-with-coach-jamie-lee Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

  2. 3d ago

    Diverse Books and Risky Career Pivots with Literary Agent Kat Kerr and Executive Coach Jamie Lee

    In this episode of Risky Conversations, I interviewed my good friend and literary agent Kat Kerr about her unconventional path from Florida state government to championing marginalized voices in publishing. Kat shares how her childhood love of books, early encounters with racism, and a mid-career pivot led her into advocacy-driven literary agenting and involvement with programs like We Need Diverse Books. Together, we talk about some of our favorite Asian American authors, why representation in literature matters, the realities of the publishing industry (including agents, querying, and self-publishing), and what it really takes to take bold risks for your career, your values, and your family. You'll learn:  Why diverse representation of marginalized voices is not a luxury, but foundational to empathy, identity, and genuine human connectionHow advocacy and self-advocacy are learned, practiced skills—and what mindsets make it possible to speak up when it feels riskyHow Kat’s decision to speak up boldly against bigoted remarks in high school created a ripple effect that emboldened other students of color to advocate for themselvesHow traditional publishing, self-publishing, and hybrid models are different and how authors can make informed business choices that fit their goals and resourcesHow taking big, values-aligned risks (for your family, identity, and justice) reshape your career and your life, even when success isn’t guaranteedWhy building or joining supportive communities—like We Need Diverse Books or identity-centered indie bookstores—matter so much for writers and readers from marginalized backgroundsFeatured:  Kat's agency, Donald Maass Literary Agency: https://maassagency.com/Yu & Me Bookstore in NYC: https://yuandmebooks.com/Jamie's coaching practice https://www.JamieLeeCoach.com/ Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

    Diverse Books and Risky Career Pivots with Literary Agent Kat Kerr and Executive Coach Jamie Lee

  3. Jul 14

    Building Bridges Across Cultures: Redefining Leadership with Ai Asakura of TOMODACHI Initiative and Executive Coach Jamie Lee

    What do you do when you're offered an opportunity that will definitely stretch you but also scares you, and your first instinct is to hand it to someone else, because you feel you're not quite qualified?  That's the moment we unpack in this interview with Ai Asakura, Alumni Program Manager for the TOMODACHI Initiative at the U.S.-Japan Council, who I met at an expat meetup in Fukuoka this spring — one with that same eclectic, cross-cultural energy as New York City, where you connect peer to peer with people from all walks of life.  Ai is bicultural like me, and she's spent her career building bridges — between Japan and the U.S., and between mentees and the mentors who help shape their paths.  But it took her some time to recognize being bicultural as her own superpower, and when she did, it empowered her to say yes to an opportunity most people would've handed to someone with a bigger title. Key Takeaways Leadership is not a job title: You can be a leader as a mentor, a community organizer, a parent, or a volunteer—impact and initiative matter more than status.Networking is people-to-people connection, not transaction: Powerful “networking” often looks like simply being curious about others and building genuine human relationships.Bicultural identity is a superpower: Living between cultures, as Ai does between Japan and the U.S., creates unique insight, empathy, and the ability to act as a bridge.Opportunities often arrive through community: Ai’s major career transitions—from hospitality to translation to TOMODACHI—came through relationships and community involvement.Saying yes can be the real “risky conversation”: Accepting the invitation to represent her region as a mentor felt risky to Ai, but turning it down would have meant betraying the message she gives her mentees about stepping up.Operation TOMODACHI to TOMODACHI Initiative: The humanitarian response to the 2011 Great East Japan earthquake evolved into a long-term leadership and exchange program impacting over 10,000 alumni.Exposure to hope changes trajectories: Young people from disaster-affected regions returned from U.S. programs with renewed hope, agency, and a desire to rebuild their communities.Community work can clarify your own identity: Serving Japanese communities in the U.S. helped Ai reconnect to her Japanese roots and recognize her role as a cultural bridge.Curiosity is a core leadership habit: Being genuinely interested in people—their stories, cultures, and experiences—naturally expands your world and your opportunities.There is still hope in the world: Despite global uncertainty, Ai emphasizes that human-to-human connection, especially across cultures, is a powerful source of hope.Featured Connect with Ai Asakura on LinkedIn: https://www.linkedin.com/in/ai-asakura0977/Learn about the US-Japan Council: https://www.usjapancouncil.org/Connect with Jamie Lee on LinkedIn: https://www.linkedin.com/in/leejieunjamie/Learn about 1:1 executive coaching with Jamie Lee here: https://www.jamieleecoach.com/applyText me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

    Building Bridges Across Cultures: Redefining Leadership with Ai Asakura of TOMODACHI Initiative and Executive Coach Jamie Lee

  4. Jul 7

    How to Exit Toxic Jobs and Make More Money Without Burning Bridges: Two Client Case Studies

    Just in 2025, nearly half a million women left the workforce. 23% of all new businesses were started by women, and 50% of all solopreneurs are women. Perhaps a part of you knows you need to leave. Maybe the job is toxic. Maybe you're underpaid. Maybe you're just done. But here's what's keeping you stuck: you don't know how to exit without burning bridges, tanking your finances, or sabotaging your next move. So how do you leave a bad situation and actually land on your feet? What strategies, support, and resources do you need to negotiate before you promote yourself to CEO of your life, your career, and your own company? In this episode, I'm showing you exactly that—through two real women, my coaching clients, who exited toxic jobs and made it work. One doubled her income by negotiating her exit strategically. One quadrupled hers. Both knew exactly what to ask for and who to ask it from. Their stories are your roadmap. Let's dig in. Featured: https://podcast.jamieleecoach.com/2033808/episodes/12125488-from-minimum-wage-to-ceo-with-grace-anniskett-of-anniskett-consulting-group Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

  5. Jun 30

    How to Pivot in Your Career, Claim Your Value, and Negotiate Higher Pay: A Case Study

    Women are asking to be paid better and promoted but we’re also getting "no" more often than men. What gives? The problem isn't that women can't negotiate. The problem is that we're negotiating the wrong way—playing by rules that were never built for us. So what's the right way? Surprisingly, it starts with an internal orientation rather than an external one. Today, I'm walking you through the three core negotiation skills, which happen to be the ones you're already using every day. And then I'm diving deep into the first step of the sovereign framework: Vote For Yourself. You'll see exactly how this played out for one of my clients, Sarah Neel, who went from burnt out professor to increasing her pay 7% and then again by 50% while successfully pivoting into a new career. I'm also introducing you to something called the "locus of control" – a fancy phrase for addressing this key question: Who's actually in charge here? And once you answer that question honestly, everything changes. [Quick note: This is a recording of a live training we ran earlier this year called “Exit Negotiations: How to Get Better Paid So You Can Become Your Own Boss.” To stay in the loop for the next live training, take the 2-minute Leadership Archetype quiz at http://www.jamieleecoach.com and subscribe to the weekly newsletter.] Featured: https://podcast.jamieleecoach.com/2033808/episodes/19111448-50-raise-self-advocacy-informational-interviews-sarah-neel-smith-phd-with-coach-jamie-lee Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

  6. Jun 23

    De-Risking Pay Negotiation for Women Professionals: Three Core Skills to Implement Right Away

    Ever felt anxious about negotiating your pay? Wondered why it feels so risky when you already know you’re beyond pulling your weight at work? Here’s the truth I see as a coach for marginalized leaders who don’t like office politics: We've been taught that asking for what we want is risky. Greedy. Aggressive. Ungracious. But here's the thing. Women and minorities aren't bad negotiators. We've just been sold a lie about what negotiation actually is. In this episode, I'm sharing why I walked away from a six-figure tech career to become my own boss and an independent coach. And I'm showing you the one mindset shift that changed everything for me and my clients. We're talking sovereignty, locus of control, and why that metaphorical tiara (as in: recognition and respect) you're waiting for? You have to put it on your own head. Stick around. This one's foundational. [Quick note: This is a recording of a live training we ran earlier this year called “Exit Negotiations: How to Get Better Paid So You Can Become Your Own Boss.” To stay in the loop for the next live training, take the 2-minute Leadership Archetype quiz at www.jamieleecoach.com and subscribe to the weekly newsletter.] Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

  7. Jun 18

    The Ingenious Ways Senior-Level Mothers Cope with the Intense Pressures of Corporate America with Journalist Shalene Gupta and Executive Coach Jamie Lee

    What happens when the pressures of work intensify AND parenting intensifies at the same time? Senior-level mothers are caught in a two-way trap—and many are quietly burning out, believing it's a personal failure rather than a systemic one. In this episode, I talk with Shalene Gupta, staff editor at Fast Company, about her groundbreaking investigation into how senior-level women are coping with the impossible. After putting out a call on LinkedIn, Shalene received over 100 responses—48,000 words' worth—revealing both the ingenuity and the despair of working mothers trying to have it all. Discover the creative solutions that are actually working: job-sharing arrangements that have lasted 13 years, radical transparency about boundaries that builds trust, and companies (like Cakes) that are redesigning the workplace from the ground up. But also understand why these individual hacks aren't enough—and why the real answer requires systemic change. If you're a working parent, an ambitious woman in corporate America, or someone who wants to understand what's really happening behind closed doors, this is a conversation you need to hear. Because as Shalene says: "It's not you. The system is broken. And it can be redesigned." Featuring: Fast Company article: Corporate America is Crushing Senior-Level Mothers. Here's How They're Coping by Shalene Gupta The 13-year job-share that changed everythingHow transparency becomes a negotiation superpowerWhy women entrepreneurs are building their own solutions and winningWhat real support for working mothers actually looks likeSHALENE GUPTA BIO: Shalene Gupta is a staff editor at Fast Company covering work life and leadership. Her investigative journalism on women, work, and wellness has appeared in The Atlantic, Fortune, Harvard Business Review, ESPN The Magazine, and TIME. She is co-author of The Power of Trust and author of The Cycle: Confronting the Pain of Periods and PMDD. Shalene holds an MS from Columbia Journalism School, a BA in creative writing and psychology from Johns Hopkins University, and is a Fulbright grant recipient. Her work focuses on the systemic barriers women face in corporate America—from motherhood to menopause—and the creative solutions women are building to survive (and thrive) in broken systems. Connect with Shalene on LinkedIn: https://www.linkedin.com/in/shalenegupta/ Connect with Jamie on LinkedIn: https://www.linkedin.com/in/leejieunjamie/ Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

    The Ingenious Ways Senior-Level Mothers Cope with the Intense Pressures of Corporate America with Journalist Shalene Gupta and Executive Coach Jamie Lee

  8. Jun 5

    Calm, Confident, and In Control: on Hypnobirthing and Self-Advocacy with Hypnotist Maria Lernerman and Executive Coach Jamie Lee

    Everything worthwhile is on the other side of a risky conversation—especially when it comes to women’s health, birth, and career. In this episode, I sit down with professional investor–turned–hypnobirthing educator Maria Lernerman to talk about how hypnosis, birth preparation, and self-advocacy can transform one of life’s most intense experiences into a joyful, empowering memory. Maria shares how she navigates being a daytime asset manager and nighttime hypnobirthing educator, hypnotist, lactation counselor, and mom of three, and why talking openly about hypnosis in a buttoned-up industry was a risky (and worthwhile) career conversation.  You’ll learn what hypnobirthing actually is (beyond the woo), how it helps many parents have calmer births—often with less or no medication—and why these tools become “meta skills” you can use in high-stakes work situations, from boardrooms to hospital rooms.  Maria also offers grounded advice for women and couples planning to grow their families, including those going through IVF or navigating “high-risk” labels in the medical system. If you care about self-advocacy, emotional regulation, and having real choices in your healthcare, this conversation will expand what you think is possible—for birthing, working, and beyond. Timestamps  00:00 – Who is Jamie Lee? Introducing executive coaching, “risky conversations,” and guest Maria Lernerman03:17 – Maria’s “risky conversation”: bringing hypnobirthing and hypnosis into a traditional investment career09:24 – What is hypnobirthing? The Mongan Method, full-spectrum birth prep, and why partners matter14:12 – How can birth be more comfortable with little or no medication? Fear, tension, relaxation, and the body’s design18:08 – Maria’s own birth stories: from terrified first-time mom to hypnobirthing educator (and the Uber-driver tipping point)23:12 – Self-hypnosis as a meta skill: staying grounded in chaotic hospitals, high-stakes meetings, and everyday conflict26:22 – Client success stories: natural births, empowered C-sections, partners stepping up, and redefining what a “good birth” looks like31:55 – Advice for women and couples (including IVF and “high risk”): choice, providers, and protecting your sense of agencyYou can learn more about Maria’s work at DiscoverYourPowerBirth.com and about the Mongan Method at hypnobirthing.com. Learn more about bespoke executive coaching with Jamie Lee at JamieLeeCoach.com and book a free hour-long consultation with Jamie here.  Text me your thoughts on this episode! Enjoy the show?  Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify.  Leave me a review in Apple Podcasts. Connect with me Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

    Calm, Confident, and In Control: on Hypnobirthing and Self-Advocacy with Hypnotist Maria Lernerman and Executive Coach Jamie Lee
See All (137)

Trailer

4.9
out of 5
28 Ratings

About

Everything that's rewarding is on the other side of a Risky Conversation. In this podcast for professional women, we have honest talks about topics often considered taboo or "too risky" at work -- salary negotiation, mental and reproductive health, office politics, social injustices, and unconventional ways smart women navigate their path forward despite a flawed and sexist society.  Join me as we dive deeper into these risky yet rewarding conversations, embracing the growth they bring. 

Information

You Might Also Like