Risky Conversations with Jamie Lee

Executive presence doesn’t exist, at least not the way most people conventionally define it. In this solo episode, I share why “she lacks executive presence” has become the feedback that quietly holds women and underrepresented leaders back, and what Maya Rupert’s book The Real Ones   taught me about the authenticity trap. I also talk about my immigrant mom, who never fit the traditional mold of l...

In spring 2013, I realized I was being pushed out of a sales job at a startup founded by a friend and mentor I had admired for years. I quit, went home, and cried my eyes out. Thirteen years later, I'm sharing what that day gave me: relief from a job that was never going to fit, and the first glimmer of the coaching work I do now. I also tell the stories of three clients who each felt grief,...

When I was a teenager and a member of a church youth group, someone crossed a physical line with me, and when they saw how angry I was, they asked me to lead the group prayer, as if that would pacify me.  I said no, because that was not the moment for grace, and that story is exactly why Sade Curry and I spent Part 2 of our open discussion stress-testing the framework.  If gracefully assertive onl...

Once upon a time, when I was the only woman working at a nearly all-male equities trading desk, I was told I was too quiet, like it was a problem to be fixed. Some time later, I was told I was too loud, with a "will you please pipe down" tone. Here's what I noticed: "too much" in other people's estimation can just mean "different from the version they were used t...

What if leadership is really about following?  I sat down with my friend Kimberly Lai, coach, leadership facilitator, and Brazilian Zouk dancer whose infectious joy for the dance got me into dance classes for a whole year.  In this episode, she shares how Zouk taught her to embody leadership in a new way, and how she landed the exact job and salary she wanted after everyone told her that it would...

If you just stepped into a leadership role and your team keeps avoiding the one task that actually moves the needle, there's something simple and concrete you can do to start motivating people the right way.  In this episode, I walk through the exact reframe I taught a sales manager client to get her team motivated without micromanaging, making ultimatums, or losing her own voice in the proce...

In this episode, I sit down with my longtime friend and Iron Feather co-founder Jeff Vicente to explore how he built a hybrid salon, art gallery, and community “third space” in the heart of SoHo.  From risky career pivots and “successful failures” to surviving cancer and addiction, Jeff shares how his resilience, queerness, and devotion to Madonna have shaped his leadership and vision.  Together,...

In this episode of Risky Conversations , I sit down with Poornima Vijayashanker , founding engineer of Mint.com, former Apple engineering leader, and founder of Femgineer , to talk about why communication is the edge technical professionals can’t afford to ignore. We explore how her “planned exits” from both Mint and Apple shaped her philosophy on career agency, and how a painful startup shutdown...

In this episode of Risky Conversations , I reveal a subtle but costly pattern I see over and over again with my highest-achieving clients—something I call “the Coverage Trap.” You know that feeling: you work nights and weekends, you hold everything together when your teammates are out, you quietly make miracles happen…and your reward is, “Great, keep it up.”  No promotion, no extra resources, no r...

In this episode, I sit down with my friend Alexis Morin , founder and principal of Soul Work Coaching , for a deep, tender, and surprisingly practical conversation about money, justice, spirituality, and leadership. Alexis co-founded and led a national nonprofit, Students for Education Reform , through her 20s, earned a Master of Divinity from Union Theological Seminary, won the Interreligious Eng...

Ever feel stuck or trapped in your work or life? My guest Irina F. Cozma, PhD is an organizational psychologist and executive coach who has repeatedly generated bold options for herself in moments when most people would have resigned with a defeated “it is what it is.” In this conversation, we talk about surviving a micromanaging boss, why that experience became one of the biggest gifts of Irina’s...

In this episode, I talk with business coach and servant leadership educator Debbie Heiser about why risky conversations are often the doorway to our greatest freedom, fulfillment, and financial growth. We explore how subconscious “loyalty pacts,” double binds, and competence-as-survival strategies keep high-achieving women over-functioning, under-receiving, and burning out. Debbie also shares how...

Gracefully Assertive -- I first heard this from my peer coach Sade Curry , an expert relationship coach, and I immediately thought, This is so good! I need to share it with every one of my clients. On Thursday, August 20th, Sade and I went live on a podcast-style conversation where we unpack Gracefully Assertive for women who've been told they're too much (both of us have!) and share rea...

Know what it’s like to feel like you don’t fit into any box? And silently suffer while second-guessing yourself in a workplace where you're one of the extreme few?  Yep, me too. In this episode, I’m talking with psychotherapist Steve Alexander, Jr. , a first-gen, Black, sensitive human who left a “safe” corporate job in risk management to become a healer for folks who, like me, feel too compl...

Beneficiary forms...sexy? In this episode, I’m joined by my friend Allie Irwin —hypnotist, coach, and creator of the Treasure Map, an end‑of‑life planning process—who makes a compelling case that it can be. You’ll hear why preparedness is an act of care and freedom , how Allie’s clients literally find money (forgotten accounts, double charges, missed benefits), and what really happens in the first...

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&a...

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 Diver...

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 Fukuok...

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 fina...

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&...

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 negotiato...

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 wit...

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...

In this episode, I sat down with leadership coach and former HR leader Ashley Paré to pull back the curtain on the "risky conversation" that cost her a corporate role but won her ultimate freedom and self-respect. We dive into how that experience became the catalyst for her mission: helping women navigate the complex systems of corporate power to advocate for their worth—without the burn...

In this episode of Risky Conversations, I sit down with global storytelling expert Gabrielle Dolan , author of Story Intelligence: The craft of authentic storytelling made smarter with AI . Gabrielle shares how one risky career conversation led her to leave a secure executive role at a major bank to build a global storytelling practice, eventually training leaders at the Obama Foundation. Together...