S03E136 Leadership, Humanity, & AI in Law with Rory O'Keeffe

Episode notes

Legal leadership is most powerful when it sounds human. We sit down with Rory O'Keeffe, an Irish‑born lawyer who’s worked across criminal law, big projects, arbitration, and global tech, to unpack how in‑house teams move from being seen as blockers to becoming strategic guides. Rory’s journey reveals why curiosity beats certainty, how a blunt “no” kills influence, and why the best legal advice often looks like three clear options with honest tradeoffs. We dig into real stories: the temptation to backdate a contract and how to stop it without blowing up the relationship, the moment a single acronym derails a meeting, and the quiet damage caused by clauses that always get negotiated down. Rory makes the case for coaching over mentoring, building psychological safety so teams raise issues early, and using practical playbooks to cut contract cycle times by 20% or more. He also shares his approach to cross‑functional trust, asking simple questions, translating privacy and cybersecurity into narratives leaders can actually use, and giving the C‑suite decisions they can own. AI and legal tech are here, but the smartest teams choose tools with eyes open.