The benefits of leadership coaching in the tech industry – with Cindy Gross

Coffee ChatsSeason 3Episode 12
Simple Talk - Redgate Software Blog

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Steve is joined by Cindy Gross to discuss leadership coaching in the technology industry – what it is, how it works, and the many benefits it brings. Recorded on-site at PASS Data Community Summit 2025 in Seattle.

Cindy is an executive coach and Adaptive Leadership Expert with 25 years in the US tech industry. As a former SQL Server Master (MCM) and expert in cross-organizational navigation at Microsoft, she transformed her focus from complex technical systems to empowering leaders within systemic chaos.

Today, through Befriending Dragons, she guides indispensable Keystone Leaders struggling with burnout, equipping organizations with her Leadership Navigation System to befriend Leadership Friction and convert Leadership Debt into strategic leverage, thus ensuring critical talent retention. As a citizen of the Cherokee Nation and the Delaware Tribe of Indians, Cindy integrates the Cherokee principle of collective leadership, Gadugi, into her work.

Cindy’s LinkedIn: https://www.linkedin.com/in/cindygross

Learn more about Befriending Dragons: https://BefriendingDragons.com

Befriending Dragons’ schedule: https://befriendingdragons.com/meet

Cindy’s email: CindyGross@BefriendingDragons.com

Cindy’s Instagram: https://www.instagram.com/befriendingdragons