Cyndy McCollough on AI Roadmaps for Law Firms, Middle-Out Change and Piloting Wins

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.