AVAILABLE ON
Episode 34

From Prosecuting to Leading In-house at a Tech Startup: S. Michael Lee, GC & COO at Engaging.ai

AVAILABLE ON
Episode 34

From Prosecuting to Leading In-house at a Tech Startup: S. Michael Lee, GC & COO at Engaging.ai

Key insights

1. Identity as a Professional Mosaic.
Lee rejects the "melting pot" theory, advocating instead for a "mosaic" where distinct cultural and professional backgrounds—like his Korean American heritage—create a unique tapestry that adds value to the whole.

2. Strategic Persona Adaptation (Tai Chi).
Faced with jury bias against "aggressive" Asian American men, Lee developed a stern, logical trial persona. He views this not as an injustice, but as a "Tai Chi" moment—taking the force (bias) sent at you and reversing it to be more effective.

3., The "Master of One Thing at a Time" Skillset.
Trial attorneys must become experts in a specific case overnight. This "jack of all trades, master of one thing at a time" mindset is directly transferable to being a GC at a startup, where diverse legal and business issues arise constantly.

4. Networking via Reliability.
Half of Lee’s roles came from referrals. He emphasizes that doing high-level "free" work for professional associations or friends builds a powerful reputation for reliability and high standards, which are the primary traits employers seek.

5. Avoid the "Sticky Floor.
"
While people often fear the "glass ceiling," Lee warns against the "sticky floor"—creating one's own barriers by making excuses or waiting to feel "100% ready" before attempting a transition.


6. Closing insight

Your career is not a single track, but a collection of experiences that prepare you for a future you cannot yet predict; the key is to stop worrying about being "ready" and start focusing on being an indispensable operator who can master any issue placed in front of you.

In this podcast, we cover

0:00 Introduction
2:50 Honouring your connection to the Korean American community
5:53 Finding inspiration in your community to work in public service as a prosecutor
12:35 Applying lessons learned as a prosecutor to the private sector
14:05 Finding an in-house role after building your career in public service
15:52 Networking to advance your career
22:33 Dealing with layoffs at Blind
27:18 Taking on a new GC and COO role at Engaging.ai
29:20 Advice to lawyers looking for new positions
30:54 Book recommendation
31:40 What you wish you’d known as a young lawyer

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