Episode 84

Why Lawyers Struggle with Communication with Briefly CEO Adam Stofsky

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Episode 84

Why Lawyers Struggle with Communication with Briefly CEO Adam Stofsky

Here’s how Adam Becker at Cockroach Labs turned AI from experiment into daily legal ops power.

Summary

Join Adam Stofsky, CEO of Briefly, as he shares how he integrated his passion for human rights advocacy and education with his legal training to found the nonprofit New Media Advocacy Project and a company that uses animation and AI to teach vital communications skills to lawyers.

Key Insights

1. Legal impact requires scale — and scale requires systems.

Early in his legal aid career, Adam saw how hard it was to help more than a few clients at a time. He explains that systemic change requires repeatable processes, not heroic individual effort. Tools, workflows, and narrative strategy help multiply the impact that a single lawyer can have.

2. Storytelling is not “soft.” It’s strategic.

Whether advocating in court, fundraising, or aligning teams, the ability to tell a compelling, emotionally grounded story shapes outcomes. Adam used media when he realized that lived experiences of clients were the most persuasive evidence — if the system could be made to see them.

3. Mission-driven organizations must still operate like businesses.

Grants and goodwill are unstable fuel sources. Adam argues that sustainability comes from revenue consistency, operational clarity, and clear prioritization — otherwise teams burn out. A strong mission motivates, but structure is what keeps the mission alive.

4. Hiring for alignment, curiosity, and capacity to learn beats hiring for pedigree.

Adam hires people who are comfortable with ambiguity and who demonstrate care and follow-through. He believes that small legal teams win when they avoid over-specialization and instead create a culture of shared ownership and scrappy problem-solving.

5. Leadership requires tolerating imperfect progress.

Scaling legal support means accepting that not every workflow will feel elegant — but it will reach more people. Leaders must shift from “I will do this perfectly” to “I will build a system that allows many people to do this well enough, repeatedly.”

6. Closing Insight

Legal Ops is the heartbeat of scalable legal service delivery. The work is not just about efficiency — it’s about structuring legal support so more people can access it, consistently. The earlier you design for scale, the more durable your impact becomes.

In this podcast, we cover

0:00 Introduction
2:30 Why Adam wanted to become a lawyer
5:54 Starting your career at Debevoise & Plimpton
7:28 Transitioning into human rights work
11:05 Founding the non-profit New Media Advocacy Project
18:23 Dealing with the challenges of human rights advocacy
24:02 Adam’s biggest accomplishments at NMAP
27:16 Living on a farm in Upstate New York
34:48 Founding Briefly
45:16 Helping lawyers communicate better
48:57 Lessons from creative professionals
51:59 Expanding Briefly’s customer base
58:06 Rapid-fire questions
1:01:04 Book recommendations

View AI generated transcript

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GUEST
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