Redefining Law in 2026: AI Strategy and Commercial Insights with Rory O’Keeffe

Episode Overview

In this episode of the Time Technologies Podcast, host Awais Haq joins Rory O’Keeffe, founder of RMOK Legal and co-author of The AI Advantage, as he discusses the shift from criminal defense to tech law, the reality of "agentic AI" in legal practice, and practical steps for launching a successful legal consultancy in 2026.

Episode Timestamps

00:00 – Introduction of Mr. Rory O’Keeffe: Commercial and AI lawyer.

01:34 – Career Beginnings: Navigating the legal landscape in Ireland.

02:40 – Criminal Defense: Experience with high-stakes litigation and trial work.

04:44 – The Pivot: Transitioning from criminal law to corporate mergers and acquisitions.

06:55 – Transferable Skills: How courtroom experience aids tech contract negotiations.

08:54 – Entrepreneurial Shift: Moving from the partnership track to founding RMOK Legal.

10:35 – Workplace Culture: The importance of humor and levity in high-pressure law.

15:52 – Building a Consultancy: Three practical steps for legal entrepreneurs.

18:30 – Competitive Edge: Providing partner-level service without the "Magic Circle" overhead.

22:15 – The Future of Billing: Moving from hourly rates to fixed-cap and commodity services.

25:51 – AI in Practice: Why AI won't replace lawyers, but lawyers using AI will.

32:21 – Vendor Due Diligence: Critical questions to ask when choosing legal tech.

40:17 – Professional Ethics: Maintaining codes of conduct in an automated world.

44:00 – Testing Technology: Implementing pilot programs for mid-sized law firms.

52:05 – Agentic AI: The risks and realities of autonomous AI agents in 2026.

59:00 – Legal Education: Preparing the next generation for an AI-driven profession.

01:03:20 – Global Regulation: Navigating the EU AI Act and international data laws.

About The Guest

Rory is a Fractional General Counsel and former Accenture Director of Legal Services with 20+ years’ experience in commercial law, technology law, AI governance, data protection, cybersecurity, digital regulation and complex contracting. He supports high‑growth and enterprise organisations across the UK, EU and US, helping them manage regulatory risk, commercial negotiations, digital transformation and AI compliance.

He has led legal strategy for £2bn+ annual contract value portfolios and negotiated 150+ major technology, outsourcing, SaaS and digital services agreements valued £20m–£250m.

His focus: accelerating deal velocity, improving legal processes, and reducing operational and regulatory risk.

As Founder of RMOK Legal, he delivers embedded Fractional GC services that provide 55% cost savings vs. external counsel and 35% faster contract cycles. He builds scalable governance frameworks for AI, data, cloud, cybersecurity and digital operations, enabling confident, defensible decision‑making at pace.

Co‑author of the bestselling “AI Advantage”, offering practical guidance for boards and legal teams on AI strategy, risk and responsible deployment.

Host of the “Beyond The Fine Print®” podcast, providing actionable insight on AI regulation, data protection, in‑house leadership, digital risk and legal transformation.

Active in shaping the profession as a Trustee of The Solicitors’ Charity, Trustee at Activity Alliance, and member of the Society for Computers and Law (AI Committee), focusing on digital ethics, AI governance and professional resilience. Speaker at SCL, Data Protection Conference 2026 and more.

Actionable Takeaways

1. Strategic Use of AI in Legal Work

• •Acknowledge AI as a Tool, Not a Replacement: The mantra is that "AI won't replace lawyers, but a lawyer using AI will" [26:20]. Use AI to handle menial tasks like contract review, data sorting, and e-discovery to save time and costs [26:32].
• •Maintain Human Oversight: Always verify AI outputs. Determine your "tolerance level" for accuracy (e.g., 80% or 90%) and ensure a human lawyer provides the final audit to stay in line with professional codes of conduct [27:05].
• •Be Transparent with Clients: Encourage clients to ask how AI is being used in their matters and how it affects billing [27:34].

2. Practical Steps for Launching a Legal Consultancy

If you are looking to start your own legal practice or consultancy, Rory suggests three key steps:

• •Understand Boundaries with Regulators: Talk to your jurisdiction's regulator early to understand which activities are regulated versus unregulated [16:19].
• •Build a Referral Network: Establish relationships with boutique firms or specialists. This allows you to scale for large deals (like M&A) without having the overhead of full-time junior staff [17:55].
• •"Get Out of Your Own Way": Avoid the perfectionism and over-disclaiming common in traditional law. Focus on being competitive through technology rather than just replicating the "Magic Circle" law firm model [18:56].

3. Avoiding "Shiny Object Syndrome" in Tech Procurement

• •Start with Existing Tools: Before buying new software, ensure you have fully utilized tools you already pay for, such as the full suite of Microsoft Teams features like Planner [38:08].
• •Pilot Before You Purchase: Instead of a full rollout, run a "pilot" with a specific team (like litigation or tech) to test the tool on one or two projects [44:20].
• •Check the Vendor’s Viability: Ask who owns the tech company. If it is heavily venture-backed, there may be pressure for a quick exit or price hikes, which could lead to difficult data migrations later [35:09].
• •Assess Disaster Recovery: Ask about the vendor's support staff and backup plans. If only two people support the tool and both get sick, your business operations could stall [48:43].

4. Professional Development and Culture

• •Focus on "Right-Brain" Skills: While AI handles the "left-brain" logic and summaries, lawyers must double down on critical thinking, persuasion, and complex problem-solving [01:02:09].
• •Integrate Levity: High-stakes legal work is stressful. Using humor and "levity" during negotiations can diffuse tension and maintain team sanity [11:05].