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Befriending Dragons: The Leadership Compass — Practical Influence & Impact

Befriending Dragons: The Leadership Compass — Practical Influence & Impact

Written by: Cindy Gross
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About this listen

Welcome to Befriending Dragons: The Leadership Compass — Practical Influence & Impact.


Together, we’ll unpack what it takes to navigate complex systems, embody adaptive leadership, and lead with clarity and courage — without burning out or selling out.


Whether you’re a woman or non-binary leader in tech, or someone with influence in your organization who cares enough to support underestimated leaders within your scope of control, you’ll find practical insights and stories here that light the way toward influence and impact in action.


I’m Cindy Gross, a collective leader rooted in Gadugi and my Cherokee and Delaware heritage, with 25 years in corporate tech and 5 years coaching underestimated leaders. I know what it takes to thrive in spaces where you’re always spending extra energy to prove you belong — because I’ve lived it.

This podcast blends both theory and practice: candid conversations, leadership frameworks, practical skills, tips, and reflective questions. It’s practical influence — tools and practices that help underestimated leaders step into their power, shape culture, and create lasting impact.


Lead from who you are. Grow into who you’re becoming.

© 2025 Befriending Dragons: The Leadership Compass — Practical Influence & Impact
Careers Economics Personal Success
Episodes
  • Too Much, Not Enough, and Still Showing Up
    Sep 12 2025

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    What if the part of you that’s exhausted, code-switching, and quietly unraveling… isn’t broken? What if it’s the part of you that’s telling the truth?


    In this episode, I share something deeply personal — not just mine, but something I hear in the unspoken fears and late-night confessions of women and non-binary leaders in tech. This is the story so many of us carry but rarely say out loud.

    You’ll hear an AI voice narrate a monologue generated by Claude AI, written from the perspective of someone who’s spent decades succeeding in male-dominated STEM environments — someone who’s mastered emotional labor, navigated unspoken bias, and is quietly wondering how much longer she can keep going like this.

    It’s startling in its accuracy. Brutal in its honesty. And if you hear yourself in it, know this: you’re not alone.

    This story is:

    • For the woman who gets praised for grace under pressure while screaming inside.
    • For the leader who’s afraid that healing means losing her edge.
    • For the high-achiever wondering if her brokenness is part of her brilliance — and if letting go of that pain might make her ordinary.

    After the story, I come back to offer my perspective — not as a voice of authority, but as someone who’s lived this too. I talk about what it means to build sustainable, values-aligned leadership without losing the depth, fire, and edge that make you powerful.

    This is more than a podcast episode. It’s a mirror. And maybe, just maybe, it’s your permission slip to stop surviving and start becoming who you were always meant to be.

    If this resonates, book your clarity call at BefriendingDragons.com.
    You don’t need to be “ready.” You just need to be honest.

    Content warning: Topics include burnout, identity-based stress, internalized self-doubt, trauma-informed leadership, and systems of oppression. Listener discretion advised if you’re in a vulnerable emotional state.

    Written and produced by Cindy Gross
    Host: Cindy Gross
    Voiced by AI (Claude + Descript)
    All words generated or curated by a human with care.

    Support the show

    Let’s talk! Book a call at BefriendingDragons.com and start your journey.


    Roar with dragonfire warmth and enduring wisdom!

    Cindy Gross, Leadership Culture Coach and CEO at Befriending Dragons


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    26 mins
  • Who Are You When the Badge Comes Off?
    May 14 2025

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    Layoffs don’t just take your job—they shake your identity.

    If you’ve recently been laid off from a tech company or are bracing for what's next, this episode is for you. Cindy shares her personal story of being laid off from Microsoft in 2014. What it broke open, what it revealed, and what it took to begin again.

    You’ll hear:

    • Why tech layoffs feel so personal (because they are)
    • What identity rupture looks like - and how to begin healing it
    • Grounding prompts to help you reclaim who you are
    • A gentle reminder that you are more than your job title
    • An invitation to a free live session designed for people just like you

    This isn’t about hustle or toxic positivity.
    It’s about finding your footing when the ground gives way and choosing who you’ll become on the other side.

    Renew your fire in Layoff Renewal Circles: https://community.BefriendingDragons.com/pages/layoffrenewalcircles

    * If cost is a barrier I can offer a coupon code.

    Support the show

    Let’s talk! Book a call at BefriendingDragons.com and start your journey.


    Roar with dragonfire warmth and enduring wisdom!

    Cindy Gross, Leadership Culture Coach and CEO at Befriending Dragons


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    5 mins
  • Befriend the Boundaries Dragon
    Apr 12 2025

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    In this episode of Befriending Dragons, I explore the power of boundaries—how they protect my values, strengthen relationships, and help me lead with integrity. Boundaries aren’t about controlling others; they’re about deciding how I show up, no matter what anyone else does.

    I share personal stories, like how a miscommunication with a personal trainer felt like a violation of my integrity. That experience taught me that setting boundaries isn’t rude—it’s an act of self-respect and trust. If a relationship falls apart because I express a boundary, maybe it’s one I need to let go.

    I also talk about workplace dynamics, like when senior team members take all the high-impact projects, leaving newcomers without real opportunities to shine. I encourage listeners to recognize when their values are being challenged and to set boundaries that protect their energy and leadership strength.

    My takeaway? Befriending your boundaries dragon allows you to reclaim your time, your voice, and your authenticity. Ready to explore your own boundaries?

    If you’re listening and realizing you need language for the boundaries you don’t know how to put into words, check out my Dragonfire Boundaries GPT. It helps you create scripts you can use right away: https://befriendingdragons.com/boundariesgpt

    Support the show

    Let’s talk! Book a call at BefriendingDragons.com and start your journey.


    Roar with dragonfire warmth and enduring wisdom!

    Cindy Gross, Leadership Culture Coach and CEO at Befriending Dragons


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    12 mins
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