Cindy Gross (she/her), Leadership & Culture Coach, CEO and founder of Befriending Dragons, is a citizen of the Delaware Tribe of Indians and Cherokee Nation, a cisgender white woman, tech industry pro, mental health advocate, systems thinker, anti-racist, lifelong learner and sociable introvert. Her friends describe her as resilient, courageous, inspirational, wise, inclusive and authentic. Some call her humorous, but she doesn’t see it.
Tell us about your business
I’m the founder of Befriending Dragons, a coaching and leadership development company focused on uplifting women and underestimated leaders in the tech industry. With a mission to create workplaces where everyone thrives, I employ strategies that build confident leaders capable of overcoming systemic challenges. Befriending Dragons is rooted in empathy, candor and equity, empowering leaders to challenge the status quo, embrace discomfort and foster inclusive, thriving communities.
Using frameworks like Gracious Space, Adaptive Leadership, Radical Candor and the Inner Development Goals (IDGs), Cindy helps leaders navigate challenges with clarity and confidence. Her lived experience, as a seasoned pro in the tech industry and a mental health advocate, informs her philosophy. Cindy’s commitment to race and gender equity equips leaders to drive meaningful change and create positive ripple effects within their organizations.
Befriending Dragons offers customized guidance to aspiring leaders who value growth, integrity, collaboration and team success. Cindy’s approach enables leaders to build high-performing teams, retain and accelerate talent and drive change for themselves and their systems. Befriending Dragons is dedicated to transforming workplaces by promoting systemic change, fostering courageous conversations and building collaborative cultures for sustainable impact.
What inspired you to start your business?
When I left Microsoft in 2019 after reporting harassment, I was so depressed. I had trouble focusing on anything work-related for more than about 2 hours a day. In 2020, still fighting depression and seeing my therapist 2-3 times a week, I launched my LLC, took my first coaching client and signed up for International Coaching Federation (ICF) training with inviteCHANGE. It was tough work to unlearn 25 years of tech industry ultra-logical, unemotional, fast decision-making habits. I had to learn to be present, stay curious and focus on only one thing, one person at a time.
A year later, I signed up for the next level of ICF training to complete my Professional Certified Coach (PCC) certification. I gradually came out of the depression. In the last 1-2 years, I’ve been able to concentrate for hours at a time, working whatever hours are needed to complete the tasks I’ve assigned myself. All without compromising on my self-care.
I’ve put into motion the whole idea of “Befriending Dragons.” Instead of trying to slay our fears, procrastination, imposter syndrome, self-doubt and inner critic. Let’s take the time to comfort that part of ourselves. Let’s get curious about the signals, messages and meanings that have gotten entangled. What happens when we befriend those lonely or fighting parts of ourselves, when we befriend our anxieties and instincts? Now we can separate the signal from the message from the meaning and make new choices. Choices that move us forward to become the person we want to be next. That’s what Befriending Dragons does for us.
What was the first step to starting your business?
I decided to stop trying to find myself or the perfect situation. I created what I needed to be who I needed to be.
What’s one mistake you made early on in your business?
I tried to do everything, all the socials, all the systems, all the audiences that were the unhealed versions of me. Then, I had to learn to truly focus on one thing at a time, one audience, one niche, one new system. I had to learn a new process.
What excites you about your work?
At the heart of Befriending Dragons is the belief that transformative change starts with empathy, candor and a commitment to equity. This belief is born from lived experience navigating systems that weren’t built for everyone. The philosophy equips leaders with the tools to challenge the status quo, embrace discomfort and create inclusive, thriving communities in the workplace and beyond. Through frameworks like Gracious Space, Adaptive Leadership and the Inner Development Goals (IDGs), Befriending Dragons helps leaders step fully into their potential and drive meaningful change.
How do you differentiate your company from other similar offerings?
Having faced significant challenges in the tech industry, from reporting harassment to battling depression, I know firsthand what it takes to navigate tough environments. This lived experience gives me a unique perspective and deep empathy for underestimated leaders. I help them transform their fears and doubts into strengths, fostering resilience and confidence. My expertise in frameworks like Gracious Space, Adaptive Leadership and Radical Candor, combined with my commitment to race and gender equity, equips me to guide others in creating inclusive, thriving workplaces where everyone can succeed.
Describe your company in three words.
Equitable. Leadership. Journey.
What’s your proudest business milestone so far?
I put in hundreds of hours of work to earn my International Coaching Federation (ICF) Professional Coaching Certification (PCC). Over 150 hours of training – more than a Master’s program! Well over 575 hours of coaching individuals and groups and improving my skills with mentors, supervision and peer coaching. I know I provided value for my earliest coaching clients, but WOW. I can be so much more useful to my clients today! As my coaching got more skilled, other areas of my personal and business life improved because those skills are really life skills!
Who’s a female entrepreneur that inspires you?
Lisa Mae Brunson, founder and Chief Visionary at Wonder Women Tech, social innovation architect, speaker and impact leader.
What’s a business myth you’d love to bust?
Willpower and desire aren’t enough alone. We also need vision, community, a system and the ability to take tiny steps, even when many of them will fail at first.
What advice would you give to other female entrepreneurs?
Build a strong dragon wing – a group that genuinely supports, sponsors and uplevels you. Surround yourself with people at similar business stages and those soaring at different heights. Seek and accept help, but remember you’re the Chief Dragon Rider – you don’t have to follow every bite of advice. They’re not in charge, you are. They don’t know what’s best for you and your business – you do. You’re the CEO – internalize that and act with that full agency. Be there for your dragon wing in meaningful ways without carrying their water or feeling like you have to please your supporters.
Anything else you want to share with our audience?
I’m here for you. If you feel pulled towards any of these types of growth for yourself or your organization, let’s talk.
- Empathy and Leadership: Transform your leadership approach by fostering trust, inclusivity and connection
- Community Building: Shift from silos to collaboration by fostering a culture of shared values and support.
- Systemic Change: Address deep-seated barriers to create equitable systems where everyone can thrive.
- Sustainable Impact: Move beyond surface-level solutions to drive real, lasting change in your teams and communities.
- Courageous Conversations: Learn how to navigate difficult conversations with Gracious Space, Radical Candor and Adaptive Leadership.
- Confident Leadership: Step into your fullest potential with the clarity, courage and skills to lead authentically and inspire meaningful change.
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