Member since August 2022
Cindy Gross is an Executive Coach and Systems Expert who equips organizations to retain their most critical talent: the indispensable Keystone Leaders, focusing on senior women and non-binary tech professionals facing burnout and systemic friction. Drawing on decades of systems mastery at Microsoft and the ethical rigor of ICF coaching, Cindy shows organizations how to manage the Leadership Friction that causes employees to leave. Unaddressed, the turnover of a senior leader can cost the company 1X-2X their annual salary to replace. Her Leadership Navigation System methodology delivers measurable impact by stabilizing teams, accelerating strategic initiatives, and ensuring leaders operate with sustained influence, not exhaustion.
I support indispensable leaders to own their strategic influence—they lead from who they are, not who others force them to be.
Decades of navigating complex tech workplaces taught me how systemic friction—a core problem in complex systems—causes burnout and self-doubt. I created the Leadership Navigation System to help leaders map and navigate that friction, delivering measurable strategic impact and affirming authentic influence as the greatest organizational asset.
I love watching the light come back when someone realizes: "I’m not behind. I’m becoming."
Many of my clients come in with some version of, 'I think I need to blow up my career.' They’re burned out, doubting themselves, and stuck in a loop of imposter syndrome and second-guessing. Instead of rushing into drastic change, we start by befriending their dragons—their instincts, their anger, their fear, and their exhaustion. One client realized she didn’t need a new career. She needed new clarity. Within weeks, she redefined her values, set boundaries, and reshaped her role into something sustainable and aligned. She didn’t need to escape. She needed to come home to herself. That’s the power of leading and acting from our authentic selves.
Forged in Friction: Cindy's journey began with decades of systems mastery in the tech industry, where she spent 25 years witnessing the cost of Leadership Friction and systemic failure. That experience ignited her commitment to helping Keystone Leaders—the indispensable talent facing burnout and high attrition risk—navigate complex environments. This passion led her to establish Befriending Dragons, where she combines her rich ICF coaching background with a methodology for strategic culture transformation. She equips leaders to lead from who they are and secure their influence, proving that authenticity drives measurable impact.
Audience: Tech leaders, women in business, mid-career professionals, entrepreneurs
Level: 200–400
Your emotions, instincts, and fears aren’t obstacles, they’re intel. Befriending Dragons means listening differently to the parts of you that carry instincts, emotions, fears, hopes, and dreams. When you separate signal from story, you gain the clarity to lead from who you are and grow into who you’re becoming. This keynote pulls from the Dragon Playbook: A Leadership Clarity System to help high-achieving professionals and quietly powerful women stop fighting themselves and start showing up with courageous alignment.
Takeaways:
- Stop fighting your inner dragons—start listening to them
- Separate signal from story and action
- Embrace your next version instead of clinging to old patterns
- Apply mindset tools from the Dragon Playbook: A Leadership Clarity System
- Lead from who you are and grow into who you're becoming
Audience: Women in tech, people managers, leadership cohorts
Level: 200–300
This session is for leaders who are done trying to fit a mold. Befriending Dragons means listening differently to your inner instincts, emotions, fears, hopes, and dreams. You’ll use tools from the Dragon Playbook: A Leadership Clarity System to reframe how you see yourself and how others see you. Shift your mindset, language, and internal narrative—so the stories you tell yourself and others support your growth and help you thrive.
Takeaways:
- Unlearn leadership myths that silence your voice
- Communicate about yourself from an identity-first lens
- Reclaim clarity with tiny, incremental mindset shifts
- Understand how identity is your strategic advantage
- Use tools from the Dragon Playbook: A Leadership Clarity System
Audience: Mid-career professionals, women in tech, career shifters
Level: 200–300
When work feels like chaos - after a layoff, burnout, or misalignment - it’s not the end, it’s a beginning. Befriending Dragons means listening to what your instincts and emotions are trying to tell you about your next move. Using tools from the Dragon Playbook: A Leadership Clarity System, you’ll identify what's calling you forward and take action that aligns with who you are becoming.
Takeaways:
- Listen to your inner dragons instead of fighting them
- Embrace your next version instead of clinging to outdated roles
- Apply identity-aligned decision-making tools from the Dragon Playbook
- Use chaos as a leadership catalyst, not a detour
- Practice clarity through micro-experiments
Audience: Culture carriers, people managers, women in tech, senior ICs
Level: 300–400
Invisible labor is the glue of many workplaces - and it’s wearing people out. Befriending your dragons means recognizing internal signals of over-capacity and resetting expectations. You’ll use the Dragon Playbook: A Leadership Clarity System to communicate value, set clear boundaries, and protect your capacity.
Takeaways:
- Name and map your invisible workload
- Set identity-aligned boundaries without guilt
- Shift how you communicate your value at work
- Use insights from the Dragon Playbook to reset expectations
- Reclaim your time and capacity without apology
Audience: High-achieving professionals, people nearing burnout, solo entrepreneurs
Level: 300
Burnout is a signal, not a personal failure. Befriending Dragons means listening to fear, fatigue, and frustration as data, not judgment. Learn how to separate signal from story, using the Dragon Playbook: A Leadership Clarity System to reclaim your energy and rewrite the narrative that’s been draining you.
Takeaways:
- Identify and reframe the internal narratives behind burnout
- Separate emotional signals from meaning and action
- Reconnect with clarity using tools from the Dragon Playbook
- Shift from self-blame to self-leadership
- Begin writing a new story that honors your needs and power
Audience: Women entrepreneurs, solo practitioners, coaches, creators
Level: 200–300
Your business should feel like home - not like another job you dread. Befriending Dragons in entrepreneurship means listening to what your instincts and values are telling you about your offers, audience, and message. This talk introduces tools from the Dragon Playbook: A Leadership Clarity System to help you lead a business that aligns with who you are.
Takeaways:
- Communicate your value from a place of identity, not performance
- Use tools from the Dragon Playbook to clarify your core message
- Design offers that align with your real values
- Build a business that feels sustainable, not performative
- Lead from your inner truth, not market trends
Full-Day Workshop
Professionals often navigate the challenges of being "the only one," managing shifting team dynamics, demanding projects, and the complexities of cross-functional communication. But true leadership isn’t about doing more—it’s about leading with clarity, setting boundaries, and using your voice with impact.
In this fire-filled session, you’ll unlock real, actionable strategies to transform how you communicate across silos, advocate for career growth, and manage time effectively—all while keeping burnout at bay.
Through bold conversations, boundary-setting frameworks, and strategic exercises, you’ll forge the tools to lead without apology and breathe fire into your work with confidence and clarity. Whether you’re looking to step into leadership, create momentum, or reclaim your time, this session will light the path forward—and it’s never boring. Expect the most fun you'll have in a session all week!
This work is personal, real, and powerful—it’s not about fixing you. It’s about reframing your narrative, shedding limiting expectations, and forging the leader you were always meant to be.
Let’s get curious, take bold steps, and embrace the fire within.
Your Takeaways:
- Communication strategies to engage across teams, influence decisions, & advocate for yourself.
- Leadership frameworks that help you navigate career growth & professional development with confidence.
- Clear, actionable boundaries that protect your time & energy while fostering collaboration.
You fought for it. You worked long and hard, grew in ways you didn’t know you could, and sacrificed other parts of your life to land that dream leadership role. And now… what? Like the dog who finally caught the big red car, you’re staring at this new reality, feeling off-balance and unsure of what comes next.
Welcome to the Dragon Toolkit—not just checklists and how-to guides, but real conversations about what happens inside you when everything shifts. The relationships that evolve or disappear. The discomfort of no longer being the expert at everything. The changed power dynamics that leave you questioning where you stand.
I get it. I went from a hyper-logical, high-stakes role at Microsoft to deeply empathetic, one-on-one coaching, asking people to talk about what makes them uncomfortable. That was a culture shock. I had to redefine everything—how I saw myself, how I communicated, and how I led in an unfamiliar space.
In this session, we’ll talk about navigating uncertainty, embracing growth, and becoming the leader you already know you can be. You’ll leave with a Dragon Toolkit packed with curious questions, awareness exercises, and evidence-based strategies to help you step into leadership with clarity and confidence.
Takeaways:
- A toolkit for understanding and adapting to your new leadership identity
- Strategies for balancing power dynamics, evolving relationships, and handling discomfort
- A grounded, confident approach to leading without losing yourself
Note: Works well with a local co-presenter.
Join esteemed tech professional and leadership coach Cindy Gross as she explores the pervasive impact of workplace biases on individual careers & the tech industry’s ability to innovate & compete. Drawing from her personal journey, she connects pivotal moments to data, case studies, & cultural competencies, vividly illustrating how bias shapes tech workplaces & the products we create.
Cindy's perspectives are both unique & highly relatable to anyone who has struggled with inauthenticity, imposter syndrome, bullying, or career advancement. She discusses unconscious assumptions, unexamined norms, & cognitive biases such as stereotype threat, affinity bias, & the halo effect. Cindy candidly shares her firsthand experiences – both subtle & overt challenges - and the resilience & strategies she has developed.
You’ll walk away with a “Monday Toolkit” of actionable evidence-based strategies that open career pathways, improve workplace culture, & retain more women and underrepresented folks in tech. These actions help slow the outflow of highly skilled, highly connected women and others who leave the industry in huge numbers at around 10-20 years into their careers – leaving a gap in tech organizations’ innovation & competitiveness.
Prepare to engage in dynamic discussions about real problems. With this knowledge & practical tools, you’ll be empowered to drive cultural change where everyone thrives & is celebrated.
Pre-Req
Curiosity, openness, & a readiness to create culture change.
Goals
Empathy towards experiences different from our own.
A "Monday Toolkit" of practical actions to retain a wider variety of people in tech.
This can be an interactive workshop, series of workshops, main-stage session, or keynote.
DEIB is tough to implement. We've been to training. We want our orgs to do better. We listen sympathetically to our coworkers' tales of bullies and harassers. But it's hard to know what to actually DO on a daily basis in the middle of our regular work. What do you feel and do when someone talks about the racism they just experienced? When you hear "we won't lower the bar" how quickly can you translate that to seeing how the bar is shaped like a white man, with the rough edges cutting the rest of us as we try to squeeze through? Is the bully a bad actor or is the system just flawed? What is YOUR responsibility? What's within your scope of control? How do you know which DEIB changes to prioritize on your team, or even what to call it?
Race + Gender Equity is a difficult, complex, and messy challenge that requires systems thinking leadership and a commitment from the heart. It begins with curiosity, relationships, empathy, and disruption of the status quo - starting inside ourselves. In this session, I’ll provide practical tools, probing questions, and frameworks to help you step forward from learning to equitable actions.
As coaches, we can be more intentional and impactful in disrupting racial and gender inequities in our practice and our coaching communities.
We can help clients balance thriving in existing inequitable systems, even when personal/org values aren’t quite aligned, with disrupting and changing inequitable systems.
We can help clients create lasting systemic change, especially changes which disrupt white supremacy (racism) and patriarchy (sexism).
As coaches, we can become more aware of how macro and micro aggressions that reinforce inequitable systems impact our clients, and how to help clients mitigate that.
We can reduce our own unintentional harm to “othered” (marginalized, oppressed, minority) clients by understanding and replacing common harmful words and acts that uphold white supremacy and patriarchy (word examples: tribe, crazy, bossy, hysterical, emotional, spirit animal, totem).
Many of my clients come in with some version of, 'I think I need to blow up my career.' They’re burned out, doubting themselves, and stuck in a loop of imposter syndrome and second-guessing. Instead of rushing into drastic change, we start by befriending their dragons—their instincts, their anger, their fear, and their exhaustion. One client realized she didn’t need a new career. She needed new clarity. Within weeks, she redefined her values, set boundaries, and reshaped her role into something sustainable and aligned. She didn’t need to escape. She needed to come home to herself. That’s the power of leading and acting from our authentic selves.
Forged in Friction: Cindy's journey began with decades of systems mastery in the tech industry, where she spent 25 years witnessing the cost of Leadership Friction and systemic failure. That experience ignited her commitment to helping Keystone Leaders—the indispensable talent facing burnout and high attrition risk—navigate complex environments. This passion led her to establish Befriending Dragons, where she combines her rich ICF coaching background with a methodology for strategic culture transformation. She equips leaders to lead from who they are and secure their influence, proving that authenticity drives measurable impact.
Audience: Tech leaders, women in business, mid-career professionals, entrepreneurs
Level: 200–400
Your emotions, instincts, and fears aren’t obstacles, they’re intel. Befriending Dragons means listening differently to the parts of you that carry instincts, emotions, fears, hopes, and dreams. When you separate signal from story, you gain the clarity to lead from who you are and grow into who you’re becoming. This keynote pulls from the Dragon Playbook: A Leadership Clarity System to help high-achieving professionals and quietly powerful women stop fighting themselves and start showing up with courageous alignment.
Takeaways:
- Stop fighting your inner dragons—start listening to them
- Separate signal from story and action
- Embrace your next version instead of clinging to old patterns
- Apply mindset tools from the Dragon Playbook: A Leadership Clarity System
- Lead from who you are and grow into who you're becoming
Audience: Women in tech, people managers, leadership cohorts
Level: 200–300
This session is for leaders who are done trying to fit a mold. Befriending Dragons means listening differently to your inner instincts, emotions, fears, hopes, and dreams. You’ll use tools from the Dragon Playbook: A Leadership Clarity System to reframe how you see yourself and how others see you. Shift your mindset, language, and internal narrative—so the stories you tell yourself and others support your growth and help you thrive.
Takeaways:
- Unlearn leadership myths that silence your voice
- Communicate about yourself from an identity-first lens
- Reclaim clarity with tiny, incremental mindset shifts
- Understand how identity is your strategic advantage
- Use tools from the Dragon Playbook: A Leadership Clarity System
Audience: Mid-career professionals, women in tech, career shifters
Level: 200–300
When work feels like chaos - after a layoff, burnout, or misalignment - it’s not the end, it’s a beginning. Befriending Dragons means listening to what your instincts and emotions are trying to tell you about your next move. Using tools from the Dragon Playbook: A Leadership Clarity System, you’ll identify what's calling you forward and take action that aligns with who you are becoming.
Takeaways:
- Listen to your inner dragons instead of fighting them
- Embrace your next version instead of clinging to outdated roles
- Apply identity-aligned decision-making tools from the Dragon Playbook
- Use chaos as a leadership catalyst, not a detour
- Practice clarity through micro-experiments
Audience: Culture carriers, people managers, women in tech, senior ICs
Level: 300–400
Invisible labor is the glue of many workplaces - and it’s wearing people out. Befriending your dragons means recognizing internal signals of over-capacity and resetting expectations. You’ll use the Dragon Playbook: A Leadership Clarity System to communicate value, set clear boundaries, and protect your capacity.
Takeaways:
- Name and map your invisible workload
- Set identity-aligned boundaries without guilt
- Shift how you communicate your value at work
- Use insights from the Dragon Playbook to reset expectations
- Reclaim your time and capacity without apology
Audience: High-achieving professionals, people nearing burnout, solo entrepreneurs
Level: 300
Burnout is a signal, not a personal failure. Befriending Dragons means listening to fear, fatigue, and frustration as data, not judgment. Learn how to separate signal from story, using the Dragon Playbook: A Leadership Clarity System to reclaim your energy and rewrite the narrative that’s been draining you.
Takeaways:
- Identify and reframe the internal narratives behind burnout
- Separate emotional signals from meaning and action
- Reconnect with clarity using tools from the Dragon Playbook
- Shift from self-blame to self-leadership
- Begin writing a new story that honors your needs and power
Audience: Women entrepreneurs, solo practitioners, coaches, creators
Level: 200–300
Your business should feel like home - not like another job you dread. Befriending Dragons in entrepreneurship means listening to what your instincts and values are telling you about your offers, audience, and message. This talk introduces tools from the Dragon Playbook: A Leadership Clarity System to help you lead a business that aligns with who you are.
Takeaways:
- Communicate your value from a place of identity, not performance
- Use tools from the Dragon Playbook to clarify your core message
- Design offers that align with your real values
- Build a business that feels sustainable, not performative
- Lead from your inner truth, not market trends
Full-Day Workshop
Professionals often navigate the challenges of being "the only one," managing shifting team dynamics, demanding projects, and the complexities of cross-functional communication. But true leadership isn’t about doing more—it’s about leading with clarity, setting boundaries, and using your voice with impact.
In this fire-filled session, you’ll unlock real, actionable strategies to transform how you communicate across silos, advocate for career growth, and manage time effectively—all while keeping burnout at bay.
Through bold conversations, boundary-setting frameworks, and strategic exercises, you’ll forge the tools to lead without apology and breathe fire into your work with confidence and clarity. Whether you’re looking to step into leadership, create momentum, or reclaim your time, this session will light the path forward—and it’s never boring. Expect the most fun you'll have in a session all week!
This work is personal, real, and powerful—it’s not about fixing you. It’s about reframing your narrative, shedding limiting expectations, and forging the leader you were always meant to be.
Let’s get curious, take bold steps, and embrace the fire within.
Your Takeaways:
- Communication strategies to engage across teams, influence decisions, & advocate for yourself.
- Leadership frameworks that help you navigate career growth & professional development with confidence.
- Clear, actionable boundaries that protect your time & energy while fostering collaboration.
You fought for it. You worked long and hard, grew in ways you didn’t know you could, and sacrificed other parts of your life to land that dream leadership role. And now… what? Like the dog who finally caught the big red car, you’re staring at this new reality, feeling off-balance and unsure of what comes next.
Welcome to the Dragon Toolkit—not just checklists and how-to guides, but real conversations about what happens inside you when everything shifts. The relationships that evolve or disappear. The discomfort of no longer being the expert at everything. The changed power dynamics that leave you questioning where you stand.
I get it. I went from a hyper-logical, high-stakes role at Microsoft to deeply empathetic, one-on-one coaching, asking people to talk about what makes them uncomfortable. That was a culture shock. I had to redefine everything—how I saw myself, how I communicated, and how I led in an unfamiliar space.
In this session, we’ll talk about navigating uncertainty, embracing growth, and becoming the leader you already know you can be. You’ll leave with a Dragon Toolkit packed with curious questions, awareness exercises, and evidence-based strategies to help you step into leadership with clarity and confidence.
Takeaways:
- A toolkit for understanding and adapting to your new leadership identity
- Strategies for balancing power dynamics, evolving relationships, and handling discomfort
- A grounded, confident approach to leading without losing yourself
Note: Works well with a local co-presenter.
Join esteemed tech professional and leadership coach Cindy Gross as she explores the pervasive impact of workplace biases on individual careers & the tech industry’s ability to innovate & compete. Drawing from her personal journey, she connects pivotal moments to data, case studies, & cultural competencies, vividly illustrating how bias shapes tech workplaces & the products we create.
Cindy's perspectives are both unique & highly relatable to anyone who has struggled with inauthenticity, imposter syndrome, bullying, or career advancement. She discusses unconscious assumptions, unexamined norms, & cognitive biases such as stereotype threat, affinity bias, & the halo effect. Cindy candidly shares her firsthand experiences – both subtle & overt challenges - and the resilience & strategies she has developed.
You’ll walk away with a “Monday Toolkit” of actionable evidence-based strategies that open career pathways, improve workplace culture, & retain more women and underrepresented folks in tech. These actions help slow the outflow of highly skilled, highly connected women and others who leave the industry in huge numbers at around 10-20 years into their careers – leaving a gap in tech organizations’ innovation & competitiveness.
Prepare to engage in dynamic discussions about real problems. With this knowledge & practical tools, you’ll be empowered to drive cultural change where everyone thrives & is celebrated.
Pre-Req
Curiosity, openness, & a readiness to create culture change.
Goals
Empathy towards experiences different from our own.
A "Monday Toolkit" of practical actions to retain a wider variety of people in tech.
This can be an interactive workshop, series of workshops, main-stage session, or keynote.
DEIB is tough to implement. We've been to training. We want our orgs to do better. We listen sympathetically to our coworkers' tales of bullies and harassers. But it's hard to know what to actually DO on a daily basis in the middle of our regular work. What do you feel and do when someone talks about the racism they just experienced? When you hear "we won't lower the bar" how quickly can you translate that to seeing how the bar is shaped like a white man, with the rough edges cutting the rest of us as we try to squeeze through? Is the bully a bad actor or is the system just flawed? What is YOUR responsibility? What's within your scope of control? How do you know which DEIB changes to prioritize on your team, or even what to call it?
Race + Gender Equity is a difficult, complex, and messy challenge that requires systems thinking leadership and a commitment from the heart. It begins with curiosity, relationships, empathy, and disruption of the status quo - starting inside ourselves. In this session, I’ll provide practical tools, probing questions, and frameworks to help you step forward from learning to equitable actions.
As coaches, we can be more intentional and impactful in disrupting racial and gender inequities in our practice and our coaching communities.
We can help clients balance thriving in existing inequitable systems, even when personal/org values aren’t quite aligned, with disrupting and changing inequitable systems.
We can help clients create lasting systemic change, especially changes which disrupt white supremacy (racism) and patriarchy (sexism).
As coaches, we can become more aware of how macro and micro aggressions that reinforce inequitable systems impact our clients, and how to help clients mitigate that.
We can reduce our own unintentional harm to “othered” (marginalized, oppressed, minority) clients by understanding and replacing common harmful words and acts that uphold white supremacy and patriarchy (word examples: tribe, crazy, bossy, hysterical, emotional, spirit animal, totem).
