Finding direction (for us and the people we care about)


Cindy Gross

Befriending Dragons

Hi Reader,

I’ve been thinking a lot lately about the invisible loads we carry.

We all know someone—maybe it’s a colleague, a dear friend, or maybe it’s you—who is holding everything together at work. They are brilliant and indispensable, but they are also navigating a system that wasn’t built for them. They are tired, not from the work itself, but from the friction of just trying to lead authentically.

For a long time, the conversation has been "should I stay or should I go?"

But I believe what we really need is direction. We need a compass, not just an exit sign.

That deep desire to help—to be the guide I wish I had—is why I am focusing my work on The Befriending Dragons Leadership Navigation System.

This isn’t just about business strategy; it’s about human sustainability. It’s about ensuring that the people we care about don't just survive their roles, but navigate them with clarity, intention, and their health intact.

I am ready to help, and I’d love your support in reaching the people who need this most.

I am opening up space to support leaders in two specific ways:

  1. Deep 1:1 Navigation: For the individual leader who needs a confidential strategic partner to map their path.
  2. Organizational Cohorts: Partnering with companies to support groups of "Keystone Leaders" so they can navigate together.

Come say hi (and see the system) - I’m hosting a few 45-minute Strategic Briefings this week to walk through this approach. I’d love to see your face, catch up, and share how we can "befriend the dragons" in our professional lives. You can RSVP here: [Eventbrite]

How we can help each other You are often in rooms I am not in, and you see the struggles of friends that I don't see. I would be so grateful for introductions to the people who are currently looking for a guide:

  • Leaders navigating new or expanding roles who need a strategic partner to find their footing.
  • HR and L&D teams who are trying to grow leadership capacity but aren't sure how to support their senior talent.
  • ERG and affinity group leaders who are working hard to build inclusive cultures.
  • Conferences or podcasts exploring strategic leadership and the future of work.

If someone comes to mind—or if you are feeling the need for better navigation right now—please just hit reply.

I’d love to hear how you are doing and how I can support you.

Navigating with you,
Cindy Gross | Leadership Navigation System for High-Capacity Women in Tech
🐉 https://befriendingdragons.com

600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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Befriending Dragons

For senior women in tech who are operating without a map in terrain that keeps changing. I'm Cindy Gross — leadership navigation coach, 25-year tech veteran, and the person who helps high-capacity leaders separate what's them from what's the system. Subscribers get tactical frameworks, named patterns, and honest intelligence on the dynamics most people won't say out loud: scope creep, political feedback, survival mode, and how influence actually works. Built for leaders who want precision, not pep talks.

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