Leaving corporate tech for entrepreneurship means more than updating your résumé—it’s a deeply personal transition. This session offers a dragon’s eye view of leadership pivots, guiding you to define your next chapter, align with your values, and step into a leadership identity beyond old success markers.

We’ll explore three key areas:

- Untangle Corporate Identity – Recognizing how workplace structures shape leadership instincts and personal narratives.

- Step Into Your Next Chapter – Redefining success based on values, joys, and leadership superpowers rather than external validation.

- Build Your Flight Plan – Creating your personal leadership operating system, including decision-making frameworks, boundaries, interaction preferences, growth edges, and trusted guides—your dragon wingmates.

This session equips attendees with clarity, strategic tools, and an actionable framework for navigating leadership transitions with purpose and confidence.

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

Standing out and upleveling your career requires going beyond your subject matter expertise. That's just the table stakes to enter the room. You need to be strategically visible and show that you deliver impactful outcomes that align with organizational goals. Cindy Gross, a 25-year tech veteran who grew into a leadership coach, will dive into practical approaches to get recognized and rewarded for all the hard work you've done while laying out a path forward to the next phase of your work life.

As a woman who struggled to implement advice from people who looked and talked like those with the majority of the power, Cindy recognizes that the path forward is truly different for each of us. We need to assert our uniqueness - Cindy visualizes herself as a dragon in a herd of unicorns to claim that inner power. There are, however, common threads. We need to pay attention to and nurture relationships, create opportunities to share the impact we have, seek out sponsors who will say our name when we're not in the room, and craft authentic narratives that showcase us within the framework expected by the culture.

You'll leave with a "Monday Toolkit" of curious questions, awareness exercises, & evidence-based strategies that help you grow into the person you already know you can be - the leader of your dreams, recognized and rewarded for your work.

Pre-reqs
Curiosity, openness, & a readiness to create culture change.

Goals
Have new ways to demonstrate your leadership to yourself and stakeholders.
Be persistent and clear about your own needs.
Listen differently to your inner critic so you believe in your power and self-worth.

It's exhausting always being "the other" or "the only." No matter how kind everyone is, we spend extra energy preparing for the next reminder that we don't quite fit, we certainly don't belong, and we must protect ourselves. Join Cindy Gross, a 25-year tech veteran who grew into a leadership coach, to explore how we can advance the careers of people who often feel left out, worry they can't be authentic, & experience imposter syndrome.

Cindy was often the only woman in the room and the only Native American in the org. She has been told to stop calling out sexism because it tells people she is a woman before she is a techie, diminishing her influence. She experienced the all too common "you're not technical enough," "we won't lower the bar" for women candidates, and "grow a thicker skin" when she said "ouch, stop." Cindy will tie these personal experiences to data, published studies, and DEIB expertise. Both the individuals who are “othered” and the people leading them need mentoring, coaching, and sponsorship to help create belonging cultures where people want to stay.

You’ll walk away with a “Monday Toolkit” of actionable evidence-based strategies that open career pathways, improve workplace culture, & retain more women in tech. These actions help slow the outflow of highly skilled, highly connected women, people with disabilities, and people of all races and ethnicities who leave the industry long before they should have to – leaving a gap in organizations’ innovation & competitiveness.

Pre-reqs
Curiosity, openness, & a readiness to create culture change.

Goals
Apply mentor, coach, and sponsor skills as an ally to people who are "othered" in tech workspaces.

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.

Who Will I Be When I Grow Up?
Hint: It's never too late to choose!

Do you feel frustrated, drained, or unfilled by your work? Do you want to explore new possibilities, passions, and potentials for your life and career? Do you want to unleash your authentic self and become the leader you know you aspire to be?

If you answered “yes” to any of these questions, then this session is for you!

Join Cindy Gross, a certified leadership coach, ex-techie, and CEO of Befriending Dragons, for a fun and interactive workshop where you will learn how to redefine your identity and leadership presence with the help of coaching tools and techniques.

You will:
- Discover more about who you are and who you want to be, beyond your work and achievements
- Create a tangible paragraph, artwork, or image that expresses your unique personality, values, and goals
- Align your identity with your life and career plans, with clarity and confidence

You will also get to:
- Connect with other like-minded participants who are on a similar journey of self-discovery and re-invention.
- Receive feedback and support from Cindy, an experienced coach who specializes in helping women in tech thrive.

This workshop is suitable for anyone who wants to create more joy, meaning, and fulfillment in their life and work. All you need is curiosity, questions, and goodwill - and a willingness to let go of judgment.

Don’t miss this opportunity to choose who you will be when you grow up into your next phase - and start living your best life today!

How many Indigenous folks do you know who work in tech? Most companies don't even bother to report numbers because it is so low. Yet we're here - we bring a wealth of knowledge, experiences, and skills that contribute to innovation, creativity, and competitive advantage.

Cindy Gross, a citizen of the Delaware Tribe of Indians & Cherokee Nation, will tie her personal experiences to studies like the Kapor Center's "Native Tech Ecosystem" to illustrate why it's so important for tech companies to invest in, work with, and hire from Native communities. This includes actively seeking out Native candidates then letting us be authentic at work, incorporating data about Native people and communities in our projects, and investing in Native-led K-12 and college STEM education starting with access to digital resources often unavailable in Native communities.

You’ll walk away with a “Monday Toolkit” of actionable evidence-based strategies that helps you understand the landscape of Indigenous issues in tech, why it matters to you and your organization, and first steps you can take within your own scope of control. Wanishi and Wado.

Pre-reqs
Curiosity, openness, & a readiness to create culture change.

Goals
Practical steps to be more inclusive and equitable for Natives in Tech

This can be an interactive workshop, series of workshops, main-stage session, or keynote.

Negotiate Boundaries for Success
How to say no without feeling guilty

Do you wish you could say “no” to your boss and coworkers without feeling guilty or ruining your career? Do you struggle with setting healthy limits at work and in your personal life? Do you want to enjoy the holidays without feeling drained and resentful?
If you answered “yes” to any of these questions, then this event is for you!

Join Cindy, an ICF-certified coach, leadership expert, ex-techie, and boundary expert, for a fun and interactive workshop where you will learn how to create and communicate boundaries with your boss - and anyone else who needs them.

You will discover:
🐲 Why boundaries are essential for your well-being and success
🐲 How to identify and overcome the common barriers to setting boundaries
🐲 How to use my simple worksheet to create a boundary that works for you
🐲 How to communicate your boundary with confidence and clarity
🐲 How to handle pushback or resistance

Boundaries are not selfish or rude - they are a gift to yourself and others. They allow you to honor your needs, values, and goals while building trust and respect with others. They free you from stress, overwhelm, and resentment, and help you enjoy your work and life.

Pre-reqs
Experience in work environments where your boundaries aren't working for you.

Goals
By the end of this workshop, you will have one boundary that you can implement right away and take to work on Monday. You will also have the tools and skills to create more boundaries in the future, whenever you need them.

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.

This can be an interactive workshop, series of workshops, main-stage session, or keynote.

Navigate Work Culture with Confidence
How to deal with imposter syndrome, burnout, and microaggressions

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 issues that get in our way, including racialized and gendered systems
- 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

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

Goals
- 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

This can be an interactive workshop, series of workshops, main-stage session, or 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.

Goals:
- 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.

Comments/Notes:
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.

This can be an interactive workshop, series of workshops, main-stage session, or keynote.

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.

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

Goal:
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. https://www.leadershipeastside.com/people-of-le

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).