Real Lawyers with Kevin O'Keefe Cyndy McCollough on AI Roadmaps for Law Firms, Middle-Out Change and Piloting Wins
Aug 28, 2025
Cyndy McCollough, founder of McCollough Consulting and expert in AI roadmaps for law firms, shares her insights on integrating technology into legal marketing. She emphasizes the importance of starting small with AI pilots to build comfort and measure success. Cyndy advocates for a middle-out approach to foster collaboration, contrasting it with traditional models. She provides practical tips on tools like prompt libraries and email triage, enabling teams to focus on high-value work, drawing on her rich experience from the tech giants Microsoft and Oracle.
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From Microsoft Layoff To Law Firms
- Cyndy joined law firms after a tech layoff and learned legal marketing from scratch.
- Early firm work required explaining basic web concepts to partners and adapting tech skills to law firm culture.
From Pockets To Orchestra
- AI efforts in firms are often isolated pockets without shared strategy.
- A coordinated roadmap and conductor-like leadership unlocks orchestra-level results.
Personal AI Comfort Test
- Cyndy removed Google from her phone and used ChatGPT exclusively to build comfort with LLMs.
- That personal experiment taught her practical limits and iterative prompting techniques.