#148: C.J. Mahoney - Microsoft General Counsel, Former Deputy US Trade Representative, & Law Firm Partner

Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.

Today's guest is C.J. Mahoney, the Corporate Vice President and General Counsel at Microsoft. Before joining Microsoft, C.J. served as the Deputy United States Trade Representative (a position to which he was unanimously confirmed) and was previously a partner at Williams & Connolly. He started his career as a law clerk for Associate Justice Anthony Kennedy after graduating from Yale Law School where he was Editor-in-Chief of the Yale Law Journal and attending Harvard University. C.J. was also one of Jonah'sfirst legal supervisors when he was a summer associate at Williams & Connolly 15 years ago.

In this episode, C.J. shares valuable insights about the legal profession including:

🏙️🧩 How growing up in a small Kansas town where lawyers were well-respected influenced his decision to pursue law as a career path [1:59]

🎓⚖️ How his journey through Yale Law School and prestigious clerkships ultimately led him to realize he wanted to learn how to try cases rather than focus solely on appellate work [3:46]

🔄🌟 How his career path wasn't as linear as it might appear on LinkedIn, but rather involved being open to new opportunities and distinguishing himself from other talented lawyers [6:48]

📝💼 How his litigation skills proved surprisingly transferable when he moved to trade negotiations, particularly in synthesizing complex information and cross-examining experts [14:19]

🧠📊 How the ability to take complex facts and make them understandable is a superpower that has served him well across different roles [18:13]

✍️🔍 How writing things down and putting concepts in your own words is crucial for learning new areas and sharpening your thinking [18:44]

⚖️💻 How his perspective on litigation changed dramatically once he moved in-house and saw firsthand the burden it places on businesses [24:52]

🤝💯 How building trust is the most important aspect of managing people, particularly in creating an environment where people feel comfortable bringing bad news [27:12]

🌐🔮 How the intersection of AI advancement and political polarization creates unique challenges and opportunities for lawyers in the technology sector [34:11]

⏳🏆 How sticking it out through hard times at a law firm and building a strong foundation was one of the best career decisions he made [41:06]

This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.