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Risky Conversations with Jamie Lee

Jamie Lee
Leadership
Neuroscience
Mu (empty/non-Being)
Risky Conversations
Glue Work
Office Politics
Neurodiversity
Circle Of Self-Trust
Executive Coaching
Career Development
Artificial Intelligence
Informational Interviews
Ageism
Autism
Feminist Coaching
Career Pivot
Wealth
Trust Framework
Inclusion
Violence

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... more

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Artwork for Risky Conversations

Latest Episodes

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... more

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 bec... more

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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 t... more

YouTube

Informational interviews, job interviews, and offer negotiations: these are the "risky" conversations that stand between you and a career you actually love. But what if you could de-risk these moments and catapult yourself into a new dimension of suc... more

YouTube

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Recent Guests

Gabrielle Dolan
Global expert in strategic storytelling and real communication
Author of Story Intelligence; Co-host of Keeping It Real with Jac and Raoul
Episode: Story Intelligence: Authentic Leadership Storytelling in the Age of AI with Gabrielle Dolan and Jamie Lee
Sarah-Neel Smith
PhD, former professor, now private investigator and think tank professional
Milken Institute
Episode: 50% Raise, Self-Advocacy & Informational Interviews: Sarah-Neel Smith, PhD with Coach Jamie Lee
Cristina Alcalde
Guest, gender and women's studies scholar, anthropologist, professor, and coach
Miami University (Ohio)
Episode: When the Goalposts Keep Moving: A Conversation on Systemic Exclusion with Dr. Cristina Alcalde and Jamie Lee
Neelam Patel
Poet, dancer, actress, former tech executive, author of Burning It Down, Dancing in the Rubble
Tailored Poetry / Tailored Poetry (speaker and author)
Episode: How to Turn Anger and Joy into Power with Poet and Speaker Neelam Patel and Executive Coach Jamie Lee
SD Shanti
Founder of World Love Forum; psychologist focused on violence prevention and women's mental health
World Love Forum
Episode: Self-Compassion & Social Change with Dr. SD Shanti and Jamie Lee
Tara May
CEO of Aspiritech
Aspiritech
Episode: How Neurodiversity Drives Innovation: Tara May, CEO of Aspiritech
Andrea Liebross
Results-driven strategic business coach for unapologetically ambitious women
Episode: Unlocking Wealth & Big Thinking: TRUST Framework for Women Entrepreneurs with Andrea Liebross

Host

Jamie Lee
Host of Risky Conversations; executive coach focused on professional women navigating risk and tough workplace conversations.

Reviews

4.9 out of 5 stars from 36 ratings
  • Jamie is an incredible host & thought leader ✨

    I’ve followed Jamie for a while & I find her to be such a kind, empowering leader & advocate. Love the pod, how thoughtful she is with her guests & ultimately, how she is a resource in so many meaningful ways to professional women!

    Apple Podcasts
    5
    yogagirlnyc1213
    United States9 months ago
  • So helpful!

    Thank you for helping me step into risky conversations with more ease and more confidence, Jamie! Your teachings and generous conversations with guests have helped me see how to embrace the opportunities that come with difficult conversations, as well as armed me with new tools to create productive, healthy, and mutually beneficial outcomes.

    Apple Podcasts
    5
    SelfishMomSara
    United States9 months ago
  • Jamie knows her stuff!!

    I've been diving into Jamie's "Risky Conversations" podcast and I'm genuinely impressed. As someone who's spent years in HR and coaching, I can recognize exceptional talent when I see it - and Jamie has it in spades.

    What sets this podcast apart is Jamie's ability to ask the questions that actually matter. She doesn't stay on the surface where it's comfortable; she goes deeper into the real issues people are facing. Her coaching instincts shine through in every conversation, and you can tell s... more

    Apple Podcasts
    5
    Rosey Singh
    United States10 months ago
  • Thought Provoking and Insightful

    I really enjoy listening to Risky Conversations with Jamie Lee. She has a compassionate way of connecting with her guests and draws out insights. Her interviews feature a range of guests and work topics relevant to women. Recommend highly!

    Apple Podcasts
    4
    Sonora21
    United States10 months ago
  • Practical & Impactful Support

    Jamie offers practical and impactful support, tools, and wisdom to support you to navigate, negotiate, and leverage your career.

    Apple Podcasts
    5
    Amy Babish
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Thoughtful host who asks meaningful questions and digs deep with guests.
Audience notes the conversations feel empowering and approachable, with real-world impact.
Listeners praise practical tools and strategies you can apply immediately.
Shows consistently high-quality guests and coaching insights for women in work.

Top Careers Podcasts

Think Fast Talk Smart: Communication Techniques
Think Fast Talk Smart: Communication TechniquesMatt Abrahams, Think Fast Talk Smart
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Workday PlaydateErin Diehl - Workday Playdate
SHeCOMMERCE
SHeCOMMERCECristina Marinucci & Jacqueline Dynowski
Becoming You with Suzy Welch
Becoming You with Suzy WelchNYU Stern Professor Suzy Welch
Let Me Speak To A Manager
Let Me Speak To A ManagerIan Mathews and Frank Cava
Per My Last Email
Per My Last EmailMorning Brew

Talking Points

Recent interactions between the hosts and their guests.

Unlocking Wealth & Big Thinking: TRUST Framework for Women Entrepreneurs with Andrea Liebross
Q: What is one of the riskiest conversations you have had and why was it worth it?
quitting a corporate job after ten years, which initially felt risky but ultimately opened doors to coaching, entrepreneurship, and personal freedom, proving that honest conversations can unlock significant growth.
Story Intelligence: Authentic Leadership Storytelling in the Age of AI with Gabrielle Dolan and Jamie Lee
Q: What was one of the riskiest conversations you've engaged in and why was it worth it?
Leaving a secure banking job after not getting the promotion, and being encouraged to pursue storytelling, was risky but ultimately transformative, leading to 21 years of work teaching storytelling as a business skill.
How Neurodiversity Drives Innovation: Tara May, CEO of Aspiritech
Q: Where can people learn more about Aspiritech and engage with your work?
Tara points to Aspiritech's website and LinkedIn presence as primary channels for information and discussion, inviting both potential clients and people interested in neurodiversity and inclusive workplaces to connect.
How Neurodiversity Drives Innovation: Tara May, CEO of Aspiritech
Q: Can you share an example of how you've built confidence in your autistic employees and what that demonstrates about leadership?
She highlights Maxwell's career progression from retail to VP of Operations, showing how training, support, and rightful recognition can unlock leadership potential in autistic employees and rebuild organizational confidence.
How Neurodiversity Drives Innovation: Tara May, CEO of Aspiritech
Q: What was one of the riskiest conversations you've ever engaged in, and why was it worth it?
Tara describes telling her husband about donating a kidney to her father; despite his initial refusal, the decision allowed her dad to have more time with the family, illustrating how brave, values-aligned conversations can yield profound personal and professional rewards.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Risky Conversations

What is Risky Conversations about and what kind of topics does it cover?

This show centers professional women navigating high-stakes conversations, workplace politics, and systemic barriers with practical coaching and real-world stories. Across episodes, listeners hear frameworks for salary negotiations, informational interviews, power-building through authentic storytelling, and strategies to balance ambition with integrity in male-dominated or biased environments. Notable throughlines include leveraging personal narratives for leadership credibility, using coaching tools to establish boundaries and influence, and examining how AI, neurodiversity, and feminist perspectives reshape career growth. The host frequently invites guests who bring clinical, academic, or practitioner expertise on leadership, inclusion, ... more

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Which podcasts are similar to Risky Conversations?

These podcasts share a similar audience with Risky Conversations:

1. Tips for Work and Life with Andrew LaCivita

How many episodes of Risky Conversations are there?

Risky Conversations launched 4 years ago and published 130 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Risky Conversations?

Recent guests on Risky Conversations include:

1. Gabrielle Dolan
2. Sarah-Neel Smith
3. Cristina Alcalde
4. Neelam Patel
5. SD Shanti
6. Tara May
7. Andrea Liebross

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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