🎙️ Eat Your Own Dog Food: Shelley McKinley on AI, Ambiguity, and Owning the Grey Areas

Lessons I Learned in Law

Shelley McKinley, Chief Legal Officer at GitHub and Vice President at Microsoft, joins Scott to share career-defining lessons from two decades at the sharp edge of tech, innovation, and regulation.

Now leading GitHub’s global legal, policy, and trust teams, Shelley offers a behind-the-scenes look at the early days of GitHub Copilot, launched before ChatGPT put generative AI on the map, and shares what it really means to advise on emerging technology when the law hasn’t caught up yet. She talks candidly about navigating ambiguity, making smart bets in fast-moving industries, and how the best legal advice can’t be given in a vacuum.

Shelley’s lessons cover how to lead in-house teams with the right mix of legal and non-legal expertise, how to focus on high-impact work in a sea of meetings, and why building strong internal networks is a non-negotiable skill for modern legal leaders. Her reflections are sharp, grounded, and refreshingly honest, touching on everything from grunge music to paralegal strategy, Microsoft’s legal transformation, and the FUD-to-FOMO evolution of AI.

Guest Recommendations:
• Podcast: Acquired — Particularly the Spotify and Microsoft episodes
• Book: The Meditating Mother by Laura Kopchick — A quirky short story collection written by Shelley’s college friend (https://www.amazon.com/Meditating-Mother-Laura-Kopchick/dp/1962148157)

About Heriot Brown:
At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.

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