Episode 102

What Comes After Legal Ops? A Conversation with David Cowen

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Episode 102

What Comes After Legal Ops? A Conversation with David Cowen

Cover of SpotDraft guide titled Building Smarter In-House Teams with photos and names of four professionals: Adam Becker, Akshay Verma, Tommie Tavares-Ferreira, and Kevin Cohn.
Here’s how Adam Becker at Cockroach Labs turned AI from experiment into daily legal ops power.

Summary

At CLOC in Las Vegas, The Abstract welcomes David Cowen, founder of The Cowen Group, for a rich conversation on the evolution of legal ops, building community during chaos, and navigating the age of AI. From creating the SOLID Summit to seeing around industry corners, David shares frameworks, stories, and mindset shifts that will inspire any legal leader navigating what’s next.


Key Insights

1. Chaos Is the Catalyst for Community

Cowen’s insight is simple: great communities emerge when no one knows what to do.

“If you find yourself in a space where there’s chaos — things are new, unorganized, ad hoc—that’s your opportunity to build.”

When legal tech and eDiscovery exploded, Cowen didn’t see confusion—he saw possibility. His SOLID Summits were born from a desire to replace unproductive panels with collaborative “TED Talk + Table Talk” sessions. The result: a thriving peer network that helped legal ops mature faster, together.

2. Legal Ops Has Graduated — Welcome to Legal Strategy

Ten years after CLOC’s founding, Cowen believes the next wave is here.

“We’re through one chapter — the next one is called legal strategy.”

He predicts emerging titles like Chief Legal Strategy Officer or Legal COO, where business acumen and consultative skills meet legal expertise. The next generation of leaders will come from both inside and outside legal — from ops, consulting, and data intelligence backgrounds.

3. Grit and Curiosity Are the Real Competitive Edge

Cowen argues that hard work still beats talent.

“I don’t know anyone who’s been truly successful who doesn’t work six days a week.”

For him, “work” means exploration — listening to podcasts, reading business books, experimenting with AI. “Being informed is your best friend,” he says. The best leaders spot patterns early by staying curious, not comfortable.

4. Anxiety Is Optional — Preparation Isn’t

AI and rapid change don’t scare Cowen; complacency does.

“Yes, everything will change. But anxiety is optional — being prepared is the best kryptonite for fear.”

His advice: trust your talent, stay curious, and keep learning — even if it means working weekends. He calls this “self-serving altruism”: the more you give and engage with your community, the more opportunity boomerangs back.

5. AI as a Reflection Partner, Not a Replacement

Cowen uses ChatGPT daily — but not just for work. He built a persona named “Max,” his AI thought partner for business and personal reflection.

“Max started as a task-doer, then became a partner, then an associate — now it’s like having an MBA from Harvard with 10 years at McKinsey.”

For him, AI enhances coaching, empathy, and insight — helping leaders think more clearly about themselves and their relationships.

6. The Future Belongs to Creators and Builders

Cowen believes the legal world is filled with creators — people who build, not just consume.

“There are creators, builders, and consumers. Only 15% of people are in that first group — and that’s who makes up our industry.”

Legal leaders, he says, are inherently creative — shaping new systems, communities, and technologies in real time.

7. Closing Insight:

“Legal ops has grown up — now it’s time to think like strategists.”

Cowen’s advice to every legal professional: stay curious, stay connected, and don’t wait for permission to build what comes next.

In this podcast, we cover

00:00 Introduction
2:22 David's career journey: From staffing to community building
5:10 The moment he discovered e-discovery's potential
6:49 How TED Talks inspired the SOLID Summit format
8:43 Chaos as the ideal condition for community building
10:52 Overbuilding in legal tech: problem or opportunity?
13:02 Spotting innovation through curiosity, not prediction
17:33 Legal Ops turns 10: What’s next for the profession?
21:03 Climbing the legal career “jungle gym,” not a ladder
25:53 How to manage anxiety and disruption in an AI-driven future
28:25 On coaching, preparation, and using ChatGPT as a partner
32:49 Legal Ops’ evolving role in helping businesses scale
37:12 The future of legal tech: use cases and AI agents
39:46 The GC as catalyst: Top-down transformation is here
42:54 Creators, Builders, Consumers: Who shapes the industry?
45:35 What excites David most about the next 10 years
47:25 Rapid-fire Questions

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