Cindy Gross she-her

Uplevel Your Career at Befriending Dragons

Professional Training and Coaching

Education: University of Oklahoma Business / Computers - Certificates: University of Pennsylvania: Leadership, InviteChange: Coaching, Saybrook+Leadership Eastside:Leadership, Kapor Center: DEIB in Tech
Issaquah, WA, USA


I left a 25-year tech career to start Befriending Dragons when reporting harassment led me down a path of discovery, systems thinking, adaptive leadership, and community focus. I help you discover your own path forward to a successful, fulfilling career.


Justice, Equity, Dragons, and Waterfalls.

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I am willing to travel

More than 100 miles

When it comes to payments

I generally get paid for speaking but make exceptions


antiracism diversity in the workplace diversity equity and inclusion technology women gender equity transformation perspectives adaptive leadership workplace thrival leadership racial equity thrive career culture change quiet quitting burnout

Best Story

How I pivoted from the hyper-logical world of one of the largest tech companies in the world to working for myself as an empathetic Leadership Coach.

Origin Story

After 25 years in corporate tech I was burned out. I couldn't think. I couldn't make decisions. I couldn't cope with anything. So I took a lot of time off and slowly, so slowly, worked through the trauma of reporting harassment at work, of being involved in a pay inequity fight, of so much bias and so many white male shaped bars. I realized what was missing was connection, community, values-based leadership. So I became that. The connector. The community nurturer. The coach who really gets systemic inequities and wants to lead with relationships. I befriended all those dragons, and now I help my clients befriend dragons.

Example talks

Acting on Our Truths (Keynote)

Tech lost me. It doesn't have to be this way. These days we talk about being authentic, creating safe spaces, and cultures of belonging. Yet it's hard to actually be and do these things at scale. I took the time to heal and went down a path of discovery, systems thinking, adaptive leadership, and community focus. I'll take you through my journey and share my key learnings.

- You're not alone, you're not imagining it, and it's not a little thing.
- There are alternate paths forward, with more options for small changes that can have a big impact.
- Leadership of Self opens options to thrive.

This is a story, a life journey with learnings along the way. I'll acknowledge the low points, modeling vulnerability to create safety. Then we'll talk about alternatives, other choices that the industry, orgs, and individuals can make to reduce the low points and create space for people to thrive.

Who do I want to be when I grow up?

Interactive workshop. The older I get, the more I wonder who I will be when, someday, I get to be whatever and whoever I want. Today is a great day to start redefining and remaking ourselves. We'll start with who we ARE, and who we want to BE, before we focus on what we want to DO. Our identity is so much more than our work, so much more than a list of accomplishments for our resumes.

- Curiosity, questions, and goodwill.
- Willing to let go of judgment.

- New ways to think about identity.
- A tangible identity artifact of your choice - a story, a drawing, a collage, etc.
- Tools to integrate clarity about your identity into your life goals.

I'll have colorful paper and art materials for attendees. This is more impactful as a 3-4 hour workshop or it can be done in one hour.

Adaptive Leadership in Tech Workplaces

Adaptive Leadership is a model that equips leaders with the skills to lead people through difficult, messy, and complex challenges with a systems thinking approach. Addressing an adaptive challenge, by definition, often involves an honest examination of the current roles, norms, values, and priorities, how they maintain the status quo, and how they will need to evolve if equitable change is to happen. Learn how and when to apply adaptive leadership in the tech industry for maximum impact on workplace systems. This session blends Adaptive Leadership, Gracious Space, Cindy's 25+ years in the tech industry, and Generative Coaching principles.

You lead or want to lead in any area of your life, with or without a formal title.

See how Adaptive Community Leadership creates systemic change through relationship-first leadership.

Note: I co-facilitate and coach teams in the 2-year Adaptive Community Leadership program at Leadership Eastside.

Set Boundaries for Healthy Work Relationships

Claim what you want and set boundaries against what you don't want.
Learn ways to recognize when & how your boundaries, values, or purpose are not working for you. Know how to identify & act on your non-negotiables. Practice meaningful responses when someone makes you uncomfortable.

Experience in work environments that don't work for you.

- Understand how boundaries improve your work relationships.
- Tips for how to nurture useful boundaries.

Navigate Work Culture with Confidence

Tips and tricks to navigate work culture with confidence, claim what you want, set boundaries against what you don’t want, and own your value.

You or the people you lead feel left behind. You can see and feel the bias and inequities in the system, and your options for a successful, thriving career have narrowed or vanished. Your workplace isn't working for you, and you want a new path forward.

We'll cover how to
- See, name, & talk about common DEI issues that get in our way
- Identify & remove leadership and career roadblocks
- Align your career with your values, strengths, goals, & deep needs
- Name and nurture boundaries that truly work for you
- Listen differently to your inner critic and instincts

- Willingness to see and do something about systemic inequities
- Genuine curiosity
- Respect Befriending Dragons community agreements during the session

- Gain new career development options for leadership of self and others
- A dragon hoard of tips, tricks, frameworks, and tools for career leadership
- Paths and perspectives for a more fair workplace rooted in anti-racism

Race + Gender Equity Toolkit - Beyond DEIB (full day workshop)

DEI 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 DEI changes to prioritize on your team?
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.

Culturally Appropriate Coaching

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).