Member since August 2022
Cindy Gross is a Leadership & Executive Coach who helps the women in tech everyone depends on turn friction into fuel instead of burnout. After 25 years in enterprise technology, including 18 at Microsoft in program management, software engineering, architect, and consulting roles, she knows how complex tech environments work and where they wear people down. She is an ICF PCC coach, a certified Leadership Circle Profile® practitioner, a certified Gracious Space trainer, and a contributing author of Empowering Women in STEM: Building a Culture of Resilience (CRC Press, 2026). Her talks help audiences sort out what’s theirs and what’s the system’s, set boundaries that hold, and lead through transitions without burning out.
Selected engagements: City of Kirkland Women’s Leadership Summit, Microsoft Executive Briefings, Native Women’s Leadership Forum, PDXWIT, Leadership Eastside, Wonder Women Tech, Women in Cloud, SQL PASS Summit, Ellevate Network, and Idaho Public TV’s Dialogue series.
She is a citizen of the Cherokee Nation and the Delaware Tribe of Indians.
I help the women in tech everyone depends on turn friction into fuel instead of burnout, so they can lead from who they are, not who others expect them to be.
Decades in complex tech workplaces taught me how systemic friction becomes burnout and self-doubt when people absorb it as a personal failing. I created the Leadership Navigation System to help leaders map that friction, sort out what’s theirs and what’s the system’s, and spend their energy where it creates real impact.
I love watching the light come back when someone realizes: “I’m not behind. I’m becoming.”
At the City of Kirkland Women’s Leadership Summit, I led a two-hour boundaries workshop for city leaders. When we started, boundary-setting was the top growth area the room named, and many people wanted to set limits without guilt, or before resentment built up. By the end, the shift was visible. People realized they didn’t have to solve every problem themselves, that boundaries can build trust rather than damage it, and that accepting help is a strength. Several committed to practicing a specific boundary and checking in with themselves again in three months.
I spent 25 years in tech, including 18 at Microsoft. One manager told me my top goal for the year was to get a manager on a partner team to like me. A different manager wrote in my review that I was abrasive. A coworker thought I was joking when I told him; he said I was by far the least abrasive and most diplomatic person on the team. When I brought my manager two highly qualified women candidates, his first response was “we’re not going to lower the bar.” Each time, I turned it inward. I overprepared, recalibrated, and adapted until I was sure I was broken. I wasn’t. I was absorbing friction from a system that wasn’t built for me. Untangling what’s mine and what’s the system’s is the work I do now, and it’s the heart of Befriending Dragons.
Is It Me or the System?
Audience: Women in tech, people managers, high-capacity ICs, leadership cohorts
You’re a high-capacity leader. You hold vision, values, and tension, often all at once. And lately, something keeps feeling off. The feedback is inconsistent. The goalposts move. The room reads differently than it used to. So you do what high-capacity people do: you turn inward. You wonder if you’re missing something. You recalibrate. You adapt.
But what if the problem isn’t you?
This talk gives you a practical framework for doing something most leadership development skips entirely: accurately diagnosing whether the friction you’re experiencing is internal or structural. Because that distinction changes everything. It changes what you do next, what you stop doing, and how much energy you stop spending on fixing yourself when the system is the actual variable.
You’ll leave with:
This is not a talk about resilience. It’s not about mindset. Friction isn’t failure; it’s feedback about the system. This talk is about reading organizational systems accurately and navigating them with clarity and care, so you can keep leading the way you’re actually built to lead.
For women in tech at any stage: whether you’re leading a team, navigating a transition, or still making sense of what just happened at your last company. If you’ve ever turned the uncertainty inward and wondered whether it’s you, this talk is for you.
Available as a keynote, breakout, or full-day workshop. Workshop participants leave with a tangible artifact: their own Leadership Navigation Playbook, started and ready to continue.
Negotiate Boundaries for Success
Audience: Women in tech, people managers, high-capacity ICs, leadership cohorts
You’re the one everyone depends on. You pick up the work no one else sees, absorb the friction so others don’t have to, and say yes because someone has to. Then the resentment arrives before the boundary does.
Boundaries aren’t walls, and they aren’t selfish. They’re how you protect your capacity and build trust at the same time. In this interactive session, you’ll name the invisible load you’re carrying, find what’s really getting in the way of your boundaries, and practice stating them with clarity instead of guilt or blame.
You’ll leave with:
Delivered at the City of Kirkland Women’s Leadership Summit and the Native Action Network's Women’s Leadership Forum.
Available as a keynote, breakout, or full-day workshop. Workshop participants leave with a tangible artifact: their own Leadership Navigation Playbook, started and ready to continue, plus an optional creative piece.
I Got the Role… Now What? Leading Through Transitions Without Losing Yourself
Audience: New and newly promoted leaders, women in tech, anyone navigating a role change
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. Or maybe the role changed around you: a reorg, a new scope, a layoff and rehire, or a role you took because the market left few options.
This isn’t about checklists and how-to guides. It’s 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 curious questions, awareness exercises, and evidence-based strategies to help you step into your new role with clarity and confidence.
You’ll leave with:
Available as a keynote, breakout, or full-day workshop. Workshop participants leave with a tangible artifact: their own Leadership Navigation Playbook, started and ready to continue, plus an optional creative piece.
At the City of Kirkland Women’s Leadership Summit, I led a two-hour boundaries workshop for city leaders. When we started, boundary-setting was the top growth area the room named, and many people wanted to set limits without guilt, or before resentment built up. By the end, the shift was visible. People realized they didn’t have to solve every problem themselves, that boundaries can build trust rather than damage it, and that accepting help is a strength. Several committed to practicing a specific boundary and checking in with themselves again in three months.
I spent 25 years in tech, including 18 at Microsoft. One manager told me my top goal for the year was to get a manager on a partner team to like me. A different manager wrote in my review that I was abrasive. A coworker thought I was joking when I told him; he said I was by far the least abrasive and most diplomatic person on the team. When I brought my manager two highly qualified women candidates, his first response was “we’re not going to lower the bar.” Each time, I turned it inward. I overprepared, recalibrated, and adapted until I was sure I was broken. I wasn’t. I was absorbing friction from a system that wasn’t built for me. Untangling what’s mine and what’s the system’s is the work I do now, and it’s the heart of Befriending Dragons.
Is It Me or the System?
Audience: Women in tech, people managers, high-capacity ICs, leadership cohorts
You’re a high-capacity leader. You hold vision, values, and tension, often all at once. And lately, something keeps feeling off. The feedback is inconsistent. The goalposts move. The room reads differently than it used to. So you do what high-capacity people do: you turn inward. You wonder if you’re missing something. You recalibrate. You adapt.
But what if the problem isn’t you?
This talk gives you a practical framework for doing something most leadership development skips entirely: accurately diagnosing whether the friction you’re experiencing is internal or structural. Because that distinction changes everything. It changes what you do next, what you stop doing, and how much energy you stop spending on fixing yourself when the system is the actual variable.
You’ll leave with:
This is not a talk about resilience. It’s not about mindset. Friction isn’t failure; it’s feedback about the system. This talk is about reading organizational systems accurately and navigating them with clarity and care, so you can keep leading the way you’re actually built to lead.
For women in tech at any stage: whether you’re leading a team, navigating a transition, or still making sense of what just happened at your last company. If you’ve ever turned the uncertainty inward and wondered whether it’s you, this talk is for you.
Available as a keynote, breakout, or full-day workshop. Workshop participants leave with a tangible artifact: their own Leadership Navigation Playbook, started and ready to continue.
Negotiate Boundaries for Success
Audience: Women in tech, people managers, high-capacity ICs, leadership cohorts
You’re the one everyone depends on. You pick up the work no one else sees, absorb the friction so others don’t have to, and say yes because someone has to. Then the resentment arrives before the boundary does.
Boundaries aren’t walls, and they aren’t selfish. They’re how you protect your capacity and build trust at the same time. In this interactive session, you’ll name the invisible load you’re carrying, find what’s really getting in the way of your boundaries, and practice stating them with clarity instead of guilt or blame.
You’ll leave with:
Delivered at the City of Kirkland Women’s Leadership Summit and the Native Action Network's Women’s Leadership Forum.
Available as a keynote, breakout, or full-day workshop. Workshop participants leave with a tangible artifact: their own Leadership Navigation Playbook, started and ready to continue, plus an optional creative piece.
I Got the Role… Now What? Leading Through Transitions Without Losing Yourself
Audience: New and newly promoted leaders, women in tech, anyone navigating a role change
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. Or maybe the role changed around you: a reorg, a new scope, a layoff and rehire, or a role you took because the market left few options.
This isn’t about checklists and how-to guides. It’s 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 curious questions, awareness exercises, and evidence-based strategies to help you step into your new role with clarity and confidence.
You’ll leave with:
Available as a keynote, breakout, or full-day workshop. Workshop participants leave with a tangible artifact: their own Leadership Navigation Playbook, started and ready to continue, plus an optional creative piece.