Author: Cindy Gross | Befriending Dragons

  • The Question No One Budgeted For

    Text graphic reading 'The Question No One Budgeted For' on a green background with a hexagonal pattern.

    A state agency manager was handed an AI rollout she didn’t design, and her team stopped engaging. The turning point was one question she hadn’t thought to ask them. Originally published by The Athena Group: The Question No One Budgeted For.

    Cindy is a contributing writer and subcontractor with The Athena Group.

  • Who’s In Your Trust Chain?

    Text on a green background reading 'Who's In Your Trust Chain?'

    Every decision passes through a chain of people and tools, and each link can quietly add an assumption. With AI showing up in daily work, often before any policy does, leaders need to know where their confidence actually comes from. Originally published by The Athena Group: Who’s In Your Trust Chain?

    Cindy is a contributing writer and subcontractor with The Athena Group.

  • Future of Work: How Coaching Can Support Lifelong Adaptation for Tech Leaders

    Title graphic for 'Future of Work: How Coaching Can Support Lifelong Adaptation for Tech Leaders', featuring white text on a green background.

    Tech modernization projects rarely stall on the technology. They stall on the questions no one asked early, when changing course was still cheap. This piece looks at how coaching helps leaders surface leadership debt and friction before it turns into rework. Originally published by The Athena Group: Future of Work: How Coaching Can Support Lifelong Adaptation for Tech Leaders

    Cindy is a contributing writer and subcontractor with The Athena Group.

  • Befriending Dragons: From Burnout to Confidence

    Cover of the book titled 'Empowering Women in STEM: Building a Culture of Resilience', edited by Sanya Mathura, featuring three women and one man in hard hats discussing around a tablet.

    Burnout rarely starts with a personal failing. It starts with signals we’ve learned to fight instead of read, inside systems that were never built for everyone. This chapter from Empowering Women in STEM: Building a Culture of Resilience is shared here in full.

    Chapter 23 by Cindy Gross

    I’M BROKEN

    I shrank. My head started pounding, my stomach twisted into knots, and I stared back dispassionately as if nothing had happened. I was at a team event with about 50 people – and once again I was the only woman. The speaker, a coworker, started off with “Gentlemen.” Then a long pause as he pivoted his entire body toward me. “And Cindy.” He made it clear to the whole room that I was the “other” – different, wrong, broken. I felt both invisible and hyper-visible. I could feel every person in the room spend a second contemplating me and how I didn’t fit, then dismiss me as irrelevant. I knew a few of my friends would pity me – we had talked about how this person propped up his own confidence by belittling others – and that wasn’t any better. No one protected me, no one made it clear he couldn’t treat me that way. I felt unsafe, off-balance, and broken. It was the latest in a string of blows that made me feel like I had no path forward. I felt like I was growing smaller and the distance between me and the others in the room grew exponentially. I mentally slumped in exhaustion.

    The thought just wouldn’t leave – I was broken. There was no other way to explain it. I was disappearing in plain sight. Every day I was frustrated, exhausted, making mistakes. With every failure I would add a piece of armor, another way to distance myself from the people telling me I wasn’t doing it right. The distance also created procrastination – why start things that were destinated to fail painfully? I tried to get everything perfect – with no clear idea of what that looked like. I felt incredibly lonely – if I let people in, they would see how broken I was and that would make me feel worse. I wanted to fight the dragons in front of me – the people, the system, the bias.

    My reaction was to overprepare. My emails and documents became impenetrable walls of text that showed I was competent and had thought things through. I avoided confrontation so others would like and support me. You’re all familiar with this, right? It’s the well-documented competence-likability paradox that women face – the double bind that it’s hard to see women as both competent and likable. I knew I was competent, so I felt I needed to become more likeable. My manager even told me that one of my top criteria for a great review the following year was to get a manager on a partner team to like me.

    Another year, a different manager put on my review that I was abrasive. I reached out to a coworker who thought I was joking and told me I was by far the least abrasive and most diplomatic person on the team. Again – the double bind. And it was all exhausting. I was burning out.

    I blamed myself for the truth behind their messages – I wasn’t performing up to the level I knew I could. Again – I felt broken.

    WE’RE NOT BROKEN

    What I would tell my younger self, with the wisdom of my experience, is that I had internalized the leadership friction in the system as personal failings. I wasn’t broken – I was hitting more of the friction than others were because I didn’t fit into the system the same way they did. And it accumulated over time. No system can be built for everyone, and I was feeling the weight of where I didn’t fit the norms and expectations. I was incredibly good at the technical aspects of my job, but I was so exhausted from fighting the system – the friction – that I couldn’t see a way forward. I couldn’t see the system objectively. I couldn’t even see myself anymore. I didn’t know who I was. The friction burned, and it was consuming me.

    Of course, my performance suffered because I was spending so much energy managing other people’s emotions. Living like that, for months on end, meant my body started treating every interaction as a threat. Every project, every meeting, I came up with a playlist of things that might go wrong, of confrontations that might occur, and how I could head them off. I was burning out.

    ANOTHER FRICTION POINT

    One day I walked into a team meeting and announced with excitement that I had two highly qualified women candidates for the open position on the team. My manager’s instant reaction was “we’re not going to lower the bar for them.” Did you hear what I heard? He felt someone had lowered the bar to let me in. I didn’t belong. I wasn’t good enough. No woman could be. And there was no way out.

    I want to give that younger version of me a big hug and a pep talk, to tell her to speak up for herself in the moment, but that version of me didn’t have the energy to do that. No one else spoke up for her – for me.

    Today I can see that my manager thought “the bar” was a clear, highly aligned set of objective criteria. What I see in most hiring and promotion bars is a confusing mess of ambiguous and often hidden criteria that are unevenly applied. I no longer think of it as a bar on a chart and more like a winding, twisty mass with some spots shaped more like a white man than anything else. It’s easier for some people to get through that bar not because they’re more competent but because they look and act like whatever part of the bar the hiring manager is attuned to. No wonder so many women burn out and leave the tech industry after 15–20 years.

    BEFRIENDING DRAGONS

    I gave myself permission to pause, grieve, and build a new map for myself. I took the space to discover and internalize new ways of leading and being. I built relationships with coaches and others who helped me get curious about myself without judgment. I quit my job and went on a discovery journey.

    Instead of thinking of all these dragons I needed to fight – my inner critic, my depression, the burnout, the bullies, the tech industry, individual people, and teams that I’d worked with in the past – I worked to separate the signal from the meaning and the meaning from my actions. Those dragons give us signals we can use. That’s what I call Befriending Dragons™. When we spend our energy getting curious, intentional, and insightful, we can navigate the systems around us with authenticity and clarity – without burning out. The friction becomes a signal instead of fuel on the fire. We redirect our flame, our roar, our energy from an all-consuming inferno to a life-sustaining warmth.

    Our dragons are not monsters to be slain. They give us messages and stand with us when we need them. They are our power. Dragons are our hopes, dreams, and fire – sometimes disguised as fear, criticism, or hopelessness. When we befriend our dragons and deeply listen to their signals, we can lead ourselves and others with self-trust and courage.

    As I figured out the next phase of my work life, I got truly curious about everything in and around me. I let go of the need to know the outcome in advance or to jump straight to action. I learned to stop thinking that I, other people, or systems need to be fixed. Because none of us are broken. Let me say that again. I’m not broken. You’re not broken. The system is not broken.

    MAPS AND TOOLS

    The system works as designed. It works differently for different people, and it funnels resources and energy where it’s designed to do so. When we make space to map out the system and the friction points within it, we can navigate it differently. We can apply our energy where it makes sense for us. We can use that to build our influence and impact, to be rewarded for the work that matters to the organization. Clarity through this mapping is how we step out of overwhelm and into sustainable work. Friction isn’t failure, it’s feedback about the system.

    We need maps of ourselves – our own internal compass – and maps of the systems around us. Then we can see the friction points and have more choices in how to show up and what work to do. I collect those in a Leadership Navigation Playbook™. I’ll share some of the tools that are in my playbook.

    Start with a Navigation Logbook™. Once a day, write down at least one thing you observed – without judgment – about yourself, others, the system, and the friction points. Once a week, read it out loud to an AI tool and ask it to identify patterns including friction points, energy drains, boundary openings, and impact opportunities. Reflect with friends or in a journal about what you’re learning. This is input into your maps.

    There are a variety of ways to learn about ourselves and how others see us. Our Navigation Compass™ indicates how we show up even when the system fails us. What moves you to action? What relationships feel authentic? When do you act from your most authentic self? What helps you see and calibrate to the system? What enables you to see that you’re a person too – imperfect, human, and worthy? Write down anything that makes you feel more or less like yourself.

    Popular compass options include values exercises, leadership or personality profiles, and skills assessments. I’m a fan of the Meaningful Work Kit and the Leadership Circle Profile®. They both go beyond a simple list and help you see and communicate the conditions you need to thrive. Compile this information about yourself in a central location and periodically re-summarize it for the person you have evolved into. This helps you “get on the balcony” and see the big picture.

    I also recommend building a Personal Language Library™. You know those moments when you come up with the perfect thing to say hours after you needed it? Write it down once you figure it out – situations often repeat themselves. We also have those times where we never figure out what to say, such as stating a boundary with the boss. Be proactive and talk a few key scenarios through with a coach, friend, or mentor. Collect that language to use as needed.

    Pay attention to how people and systems work around you. That’s your System Map. What relationships matter? Who has the institutional knowledge that may not be written down anywhere? How are the big decisions truly made? Where are the levers of power and who holds them? What metrics drive the people and decisions around you? What’s hidden – and often wants to remain hidden? When you see “technical debt” – go deeper and name the “leadership debt” that lets it linger. This is how you deepen your understanding of what’s in motion around you and see where you have choices to navigate differently.

    As you navigate with intent, track the positive impact you have. Use metrics that matter to your organization and leaders. Know what metrics your boss and their boss need to hit this quarter – track how you can and did impact that. Gather all the data you can find to quantify your impact and collect anecdotal feedback as you go. Give feedback and data to others – many people will pick up on that and mirror the habit, creating more data about the system and nurturing relationships that matter. This impact goes in your Navigation Impact Log™. This feeds your 1:1 conversations with your manager and your performance reviews. Create a cadence to provide a written summary to people with control over your career – start with the impact you had, then what you did and what evidence you have. Keep it concise and focused.

    As you see yourself and the system more clearly, start experimenting with navigating differently. How do people react? What changes for you? What impact are you having? How do you feel in various situations? This feeds back into your Navigation Logbook and that continues to feed into your maps.

    WE’RE WHOLE, CAPABLE, RESOURCEFUL, AND CREATIVE

    I’ve spent the last few years working to become the person I wish I’d had back when I was struggling in the tech industry. I feel connected, expansive, sovereign. I don’t feel the need to shrink myself or make people like me. I often feel energized. I rarely give in to doing other people’s emotional labor for them. I replaced impenetrable armor with useful boundaries. I moved from surviving to thriving. I walk with confidence, speak my truths, and create ripples of change in the world. My fire now fuels me instead of burning me out. I am not broken. You are not broken. We are whole, capable, resourceful, and creative.

    Because I see the systems around me more clearly, and I know myself much better, I can identify friction points more easily. I can see, with neutrality, when bias like a double bind shows up. I can see when what’s hidden, like a vague success bar, pretends to be a clear metric. If someone calls me abrasive, I can read it as a signal that there’s friction in the system, not a truth about my character. That means I spend less energy fighting and can focus on what’s useful and impactful. I make choices, I navigate with intent, and I iterate as long as it’s useful. I befriend my dragons with curiosity, intent, and ease so they walk beside me and I don’t feel the need to fight them.

    I’ve put together the mindset, tools, and structure that I believe would have let me thrive in my high-paying tech job. It was a rough road for a while, and I’m here on the other side. I’ve built my maps, made choices that feel aligned, and led myself and others in ways that feel sustainable, joyful, and impactful. I wish you the same on your journeys!

    ABOUT CINDY

    Cindy Gross coaches high-capacity women in tech to stop absorbing the friction and start navigating it. After 25 years in enterprise technology, including 18 at Microsoft, she brings technical fluency and human insight to burnout recovery and sustainable leadership. She is an ICF-credentialed coach (PCC), a certified Leadership Circle Profile® practitioner, and the creator of Befriending Dragons™.

    This chapter first appeared as Chapter 23, “Befriending Dragons: From Burnout to Confidence,” in Empowering Women in STEM: Building a Culture of Resilience (CRC Press, 2026). DOI: 10.1201/9781003712589-33.

    Ready to map your own signals?

  • My cat was on fire. He still doesn’t know.

    My cat was on fire. He still doesn’t know.

    Cindy Gross

    Befriending Dragons

    Hi Reader,

    My cat was on fire.

    Yes, literally.

    I was reading in my chair, and Goose – the orange menace – was walking through the tray full of candles toward me, tail twitching left, right, left, right, left… right into the one lit candle.

    Readers, he still doesn’t know he was ever on fire.

    My heart was racing, anxiety rising (Hollander, you are having panic attack! IYKYK). The last inch of his tail was flaming as Goose circled my lap looking for the perfect place to settle. I grabbed his tail, got the flames out, and was immediately rewarded with deep feline indignation — because I’d had the audacity to jump up and dislodge him. Then came the insult of a wet cloth running along his tail to remove the soot.

    His brother Zeke sprinted in from the other room to see what the fuss was about.

    Neither of them ever figured it out.

    The soft top coat was gone. The undercoat never caught. Goose wandered off, mildly offended, and resumed his afternoon as if nothing had happened. Because for him, nothing had.

    I’ve told this story a few times now, with a mix of horror and relief and genuine amusement at the audacity of that cat. And every time, I notice the same thing pulling at me.

    Because you know what you almost never are? Goose.

    You’re not wandering through the room unaware. You already know something is wrong. You’ve known for a while. You feel the friction, you see the dysfunction, you read the room faster than anyone else in it.

    What you’re less sure about is whether the friction is a you problem, or whether it’s just the cost of doing business at this level. So you absorb it. You build it into your workload. You take on the translation, the smoothing, the managing of what nobody else wants to manage, and the project moves forward and nobody lights on fire and nobody ever quite connects that outcome to what you quietly did to make it happen.

    There’s no retrospective on the near-miss. No recognition that the room almost looked very different.

    The project lands. Goose is fine. You go back to your chair.

    And you do it again next week.

    It was just the tip. One inch. The soft top coat on the last inch of his tail took the damage, and the undercoat held. This time. One exposure, contained.

    The problem is that complex workplaces don’t offer one exposure. The dysfunction cycles back. The friction is structural. The thing nobody else wants to manage becomes yours again next quarter, with a different name on it. And the soft coat doesn’t grow back overnight. Enough rounds of this and you’re not dealing with a singed tip anymore. You’re into the undercoat. You’re into the layers that were never meant to take that kind of heat.

    That’s what sustained, unacknowledged friction actually does. It doesn’t announce itself. It doesn’t look like a crisis. It looks like Tuesday. It looks like you handling one more thing that shouldn’t be yours, absorbing one more round of dysfunction, smoothing one more thing over so the project lands and the room stays calm. Each one: just a tip. Just an inch. Perfectly manageable.

    Until the undercoat is involved and you’re wondering why you’re so tired when nothing catastrophic has happened.

    Nothing catastrophic happened because of you. Repeatedly. And that cost has to go somewhere.

    The question isn’t whether you can keep absorbing it. You clearly can. The question is what it’s costing you in the places nobody sees.

    What does this bring up for you? Hit reply. I read everything.

    Navigating with you,
    ​Cindy Gross | Leadership Navigation System for High-Capacity Women in Tech​
    🐉 https://befriendingdragons.com

    ​

  • Are you still yourself?

    Are you still yourself?

    Cindy Gross

    Befriending Dragons

    Hi Reader,

    Something I hear a lot right now, underneath the composed exterior:

    “I don’t know if I trust my own instincts anymore.”

    ​

    Not because she’s lost her edge. But because the signals have been contradictory long enough that the self-doubt has started to feel like clarity.

    ​

    If that’s where you are — or somewhere close — I’d like to talk.

    Grab some time with me here: https://befriendingdragons.com/meet

    ​

    I’m also asking a simple question: what’s the thing you’re navigating right now that doesn’t have a clean answer? The one where you’re not sure if the friction is yours to fix, or the system’s.

    ​

    Reply and tell me. I read every one.

    ​

    The leaders I work with are not struggling because they’re not capable. They’re navigating the specific exhaustion of being highly competent inside a system that keeps asking them to be someone slightly different than who they actually are.

    ​

    That is a solvable problem. Not with inspiration. With infrastructure.

    Navigating with you,
    ​Cindy Gross | Leadership Navigation System for High-Capacity Women in Tech​
    🐉 https://befriendingdragons.com

    ​

  • The thing no one tells you about being this good at your job

    The thing no one tells you about being this good at your job

    Cindy Gross

    Befriending Dragons

    Hi Reader,

    The most capable woman in the room is often navigating the most alone.

    Not because she lacks support — but because the systems around her weren’t built to see what she’s actually carrying. The scope that expanded without authority. The feedback that doesn’t add up. The political weather that shifted and nobody named it.

    She’s not confused. She’s operating without a map in terrain that keeps changing.

    That’s what I build.

    I’m offering a Strategic Clarity Call — a working diagnostic where you bring one real situation and leave with a clear read and your first concrete moves. It’s not a consultation. It’s infrastructure.

    If something is shifting for you right now — your role, your positioning, your next move — this is where we start:

    → Book your Strategic Clarity Call​

    P.S. Know someone who’s navigating a reorg, a comp conversation, or a role that’s shifted under them? Forward this. The right conversation at the right moment changes everything.

    Navigating with you,
    ​Cindy Gross | Leadership Navigation System ​
    🐉 https://befriendingdragons.com

    ​

  • The exhaustion of caring more than the system does

    The exhaustion of caring more than the system does

    Cindy Gross

    Befriending Dragons

    Hi Reader,

    I just wrapped up a session using my new Untangle One Thing sprint format, and I want to share the shift that happened—because it’s a pattern I see in almost every high-performing leader I coach.

    The client came in carrying a heavy mental load regarding a broken situation at work. It felt exactly like the knot above: a tight, chaotic loop that seemed to get worse the harder she tried to fix it.

    A single conversation had gone wrong, and she was stuck in a cycle of offering data, explaining her intent, and assuming all the responsibility for the interaction.

    She wasn’t being difficult. She was just caring more than the system did.

    The invisible dynamic at play was simple: She was taking responsibility for a system that refused to be fixed.

    In 90 minutes, we shifted her strategy from “repairing the unfixable” to “protecting her energy.”

    She walked away with a Leadership Navigation Reset Plan that included:

    • A “Stop” List: The specific efforts she is releasing immediately (without guilt).
    • Decision Rules: A logic gate to help her know when to say “not my circus.”
    • Exact Scripts: Language to protect her reputation without over-explaining.

    The relief was visible. She realized she didn’t need to solve the problem to be safe; she just needed to stop carrying it.

    This is for you if:

    • You are replaying a specific conversation or conflict in your head at night.
    • You feel like you are the only one trying to solve a problem that everyone else is ignoring.
    • You are exhausted from explaining your intent.

    If you are currently carrying a tangled loop that feels stuck, unfair, or endlessly draining—you do not have to carry it for another month.

    I have 5 spots left for this January sprint at the pilot rate ($750).

    ​Book Your Reset Sprint​

    ​Read the full details

    You don’t need to fix the whole system to find peace. You just need to untangle yourself from it.

    With dragonfire warmth and enduring wisdom,
    ​Cindy Gross | Founder, Befriending Dragons | Your Leadership Navigation Coach
    🐉 https://befriendingdragons.com

    ​📅 Book a call to explore coaching together

    ​

    🎁 Grab your Starter Kit​

    Start with:

    1. Culture Compass – Define what you need to thrive in a work culture.
    2. Boundaries for Thriving – Name, refine, and express values-based boundaries that protect your energy (perfect to use with my AI tools!).

    ​

  • A gentle reset for the in-between week (free + live Monday)

    A gentle reset for the in-between week (free + live Monday)

    Cindy Gross

    Befriending Dragons

    Hi Reader,

    A small reframe I keep coming back to:

    Overwhelm isn’t always “too much work.”
    It’s often the cognitive cost of carrying too many unfinished things at once — half-decisions, outdated obligations, invisible responsibility, and the old scripts that keep running even when they’re no longer true.

    This in-between week is a rare moment to release some of that before 2026 begins.

    So I’m hosting a free, live reset:

    The Let It Go RESET: A Strategic Capacity Workshop​
    ​Monday, Dec 29 | 11:00 AM – 1:00 PM PST​
    Free (my gift to your nervous system)

    We’ll do four things together:

    • Reflect on what mattered this year
    • Release 3 things you’re leaving in 2025 (one physical item, one mindset, one obligation)
    • Clear one small area in real time (cords / papers / expired meds — your choice)
    • Protect your new capacity with a simple Q1 “Navigation Anchor”

    If you want to start 2026 lighter, I’d love to have you.

    Register: https://luma.com/uwngib2x

    P.S.: I’m considering a short series that decodes workplace dynamics through scenes from Heated Rivalry — using my “befriending dragons” lens (the conversations we avoid until they cost us). If you’ve watched, reply with your favorite scene and the workplace moment it reminds you of.

    With dragonfire warmth and enduring wisdom,
    ​Cindy Gross | Founder, Befriending Dragons | Your Leadership Navigation Coach
    🐉 https://befriendingdragons.com

    ​📅 Book a call to explore coaching together

    ​

    🎁 Grab your Starter Kit​

    Start with:

    1. Culture Compass – Define what you need to thrive in a work culture.
    2. Boundaries for Thriving – Name, refine, and express values-based boundaries that protect your energy (perfect to use with my AI tools!).

    ​

  • Finding direction (for us and the people we care about)

    Finding direction (for us and the people we care about)

    Cindy Gross

    Befriending Dragons

    Hi Reader,

    I’ve been thinking a lot lately about the invisible loads we carry.

    We all know someone—maybe it’s a colleague, a dear friend, or maybe it’s you—who is holding everything together at work. They are brilliant and indispensable, but they are also navigating a system that wasn’t built for them. They are tired, not from the work itself, but from the friction of just trying to lead authentically.

    For a long time, the conversation has been “should I stay or should I go?”

    But I believe what we really need is direction. We need a compass, not just an exit sign.

    That deep desire to help—to be the guide I wish I had—is why I am focusing my work on The Befriending Dragons Leadership Navigation System.

    This isn’t just about business strategy; it’s about human sustainability. It’s about ensuring that the people we care about don’t just survive their roles, but navigate them with clarity, intention, and their health intact.

    I am ready to help, and I’d love your support in reaching the people who need this most.

    I am opening up space to support leaders in two specific ways:

    1. Deep 1:1 Navigation: For the individual leader who needs a confidential strategic partner to map their path.
    2. Organizational Cohorts: Partnering with companies to support groups of “Keystone Leaders” so they can navigate together.

    Come say hi (and see the system) – I’m hosting a few 45-minute Strategic Briefings this week to walk through this approach. I’d love to see your face, catch up, and share how we can “befriend the dragons” in our professional lives. You can RSVP here: [Eventbrite]​

    How we can help each other You are often in rooms I am not in, and you see the struggles of friends that I don’t see. I would be so grateful for introductions to the people who are currently looking for a guide:

    • Leaders navigating new or expanding roles who need a strategic partner to find their footing.
    • HR and L&D teams who are trying to grow leadership capacity but aren’t sure how to support their senior talent.
    • ERG and affinity group leaders who are working hard to build inclusive cultures.
    • Conferences or podcasts exploring strategic leadership and the future of work.

    If someone comes to mind—or if you are feeling the need for better navigation right now—please just hit reply.

    I’d love to hear how you are doing and how I can support you.

    With dragonfire warmth and enduring wisdom,
    ​Cindy Gross | Founder, Befriending Dragons | Your Leadership Navigation Coach
    🐉 https://befriendingdragons.com

    ​📅 Book a call to explore coaching together

    ​