Real Lawyers Podcast: Cyndy McCollough on AI Roadmaps for Law Firms and Middle-Out Change

Cyndy McCollough—founder and principal consultant at McCollough Consulting—joins Kevin to talk about moving firm marketing from AI dabbling to an actual roadmap. We get into training first, picking one small pilot, winning buy-in with a middle-out model, and the everyday use cases that free teams to do higher-value work.

Watch the episode below or subscribe wherever you get your podcasts.

Outline

• 00:00 — Intro and Cyndy’s background in legal marketing and tech
• 01:16 — What firms are asking for right now
• 04:30 — Competitive intel and research as fast, practical wins
• 05:21 — Event prep and follow-up that doesn’t eat your week
• 06:26 — Early admin wins like inbox drafting and summaries
• 07:48 — Why a middle-out change model works best in firms
• 09:18 — How to choose one small pilot with clear success criteria
• 11:03 — Training first, tool basics and setting expectations
• 22:38 — Building prompt libraries and simple standards
• 30:51 — Governance, an AI council and lightweight guardrails
• 37:16 — Three adoption models firms are trying and what sticks
• 45:09 — Where to learn more and how to keep momentum

Key Takeaways

• Start with training so people know what’s possible and what’s not
• Pick one pilot that solves a real pain, measure it and share the win
• Middle-out change beats top-down edicts and bottom-up chaos
• Prompt libraries and simple standards reduce rework and variance
• Email drafts, event prep and competitive research are fast wins
• Keep governance lightweight so it enables, not blocks
• Align BD and marketing workflows so AI helps both sides
• Momentum matters—make the first wins visible and repeatable