Real Lawyers with Kevin O'Keefe

Kevin talks with Cyndy McCollough, founder of McCollough Consulting, about moving legal marketing beyond AI experiments and into a shared roadmap. Cyndy explains why training first matters, how to pick one small pilot and measure it, and why a middle-out model beats top-down or bottoms-up alone. She shares practical wins—prompt libraries, email triage, event prep, competitive analysis and content strategy—that free teams to do higher-value work, drawing on a career that spans Microsoft and Oracle to leading BD in major firms. If you run marketing or BD and need a clear starting point, this conversation gives you the playbook.

What is Real Lawyers with Kevin O'Keefe?

Real Lawyers with Kevin O’Keefe explores how legal professionals publish to build influence and drive the business of law. Each week, LexBlog Founder & CEO Kevin O’Keefe sits down with lawyers, journalists, technologists and other leaders to discuss the evolving role of publishing in the legal profession—from blogs and newsletters to podcasts and beyond.

Presented by LexBlog, the network powering independent legal voices worldwide.