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Ep 34: From Prosecuting to Leading In-house at a Tech Startup: S. Michael Lee, GC & COO at Engaging.ai
59 Plays9 months ago
How do you approach, accept, and move on from career transitions, both planned and unexpected? What does it take to transition from decades in public service to roles leading legal at tech startups and law firms? And how can you leverage your network to bounce back after an unexpected layoff?
S. Michael Lee, General Counsel and COO at Engaging.ai, has conquered many of these tense moments. Starting his career as the first Korean-American prosecutor in the Santa Clara County DA’s Office, he brought lessons learned from his experience as a trial attorney to his second chapter as an in-house counsel and—eventually—legal and business leader.
Hear Michael as he discusses why your network is essential to finding your next role, why you shouldn’t limit yourself or your job prospects, and the importance of honoring your roots in your professional life,
Annual Compensation Report: https://salary-report.spotdraft.com/
Read detailed summary: https://www.spotdraft.com/podcast/episode-34
Topics:
Introduction: 0:00
Honouring your connection to the Korean American community: 2:40
Finding inspiration in your community to work in public service as a prosecutor: 5:36
Applying lessons learned as a prosecutor to the private sector: 11:36
Finding an in-house role after building your career in public service: 12:57
Advice to lawyers in government service trying to move into the private sector: 14:37
Networking to advance your career: 16:57
Dealing with layoffs at Blind: 20:40
Taking on a new GC and COO role at Engaging.ai: 25:04
Advice to lawyers looking for new positions: 26:52
Book recommendation: 28:19
What you wish you’d known as a young lawyer: 29:02
Connect with us:
S. Michael Lee - https://www.linkedin.com/in/s-michael-lee-27ab86/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.
Recommended
Transcript
Jury Polling and Behavior Insights
00:00:00
Speaker
At the end of each jury, you would poll your jury, you would talk to your jury, ask them how you did and ask them about the case. And a lot of times jurors will stay because they want to talk to you about your case and about you and your closing argument and things of that nature. I found that a lot of jurors were actually, they found it off-putting if I was really aggressive. I interpreted that as jurors were afraid of the angry Asian man. If you're really aggressive,
00:00:30
Speaker
Then they're like, whoa, why is this guy so aggressive?
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Speaker
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Speaker
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Introduction to Michael Lee
00:01:32
Speaker
How do you navigate moments of career transition?
00:01:36
Speaker
expected and surprising due to opportunity or adversity. Today we have Michael Lee, the GC and COO at engaging.ai, an AI company powered by a one-of-a-kind AI UX engine that generates video-first digital experiences faster and cheaper than has ever been possible before.
00:01:59
Speaker
Previously, Michael was the Head of Legal at Blind, a platform for employees to share information anonymously with each other. Pretty cool company. Michael also held a number of other private sector roles. And before that, he spent more than 18 years as a prosecutor with the Santa Clara County District Attorney's Office. Had an extensive career in public service, which we will definitely be talking about today.
00:02:26
Speaker
Michael, thanks so much for joining this episode of The Abstract. Thank you so much for having me. I hope that I can provide some decent insights for you and your listeners. I am sure you will.
Cultural Heritage and American Mosaic
00:02:41
Speaker
Before we get started talking about transitions, I know your roots in the Korean American community are really important to you. Actually,
00:02:52
Speaker
may have been an episode with Juna Rho, which is a great episode, and her involvement in that Korean American legal scene that brought you to the abstract. Tell me a little bit about why your Korean heritage is so important to you. Yeah. Part of it is just because it is my heritage, right? If you're Italian American and you have Italian roots, then that's probably something that's really important to you.
00:03:22
Speaker
For me, I'm a Korean American. I have Korean roots and where my family comes from or where I was born is important part of who I am. Personally, I don't prescribe to the melting pot theory of American culture and society. I don't think that we have to lose ourselves in order to be part of America.
00:03:43
Speaker
I prescribe to the mosaic theory that we're all a distinct piece of tile within America. And we're next to other pieces of tile that are also distinct. And as you create a tapestry of tiles together, we create a picture, a mosaic, that's unique and that we couldn't be able to, we wouldn't be able to create on our own. So my Korean Americanness adds to the Americanness of other people. And their Americanness adds to my Americanness
00:04:14
Speaker
I love that. I've never heard that before. And Mosaic is also a lot more beautiful than a melting pot. It's a really great way to start this episode. I know that your heritage and the community also ended up being important to some moments of career transition, which we'll talk about. But let's go back to the beginning.
Unexpected Law School Journey
00:04:38
Speaker
Did you actually expect that you were going to have a career in law?
00:04:42
Speaker
I think you ended up moving towards the law. Well, in college, I was not thinking about law school. I thought I was going to go into international business and I didn't have like a very specific way of getting there to international business. But after I graduated from college, uh, it was a recession and my parents' truck cleaning was not doing well.
00:05:06
Speaker
So he laid off two people and he hired me for free, his dry cleaner for about a year. And during that period, he actually just sat me down and asked me to go to law school, something that was surprising to me. Um, and I thought about it, prayed about it and thought that, you know, why not? There's, it's not like I have a thing that I absolutely have to do in my mind. So I said, give it a shot. And it worked out really well.
00:05:36
Speaker
When you left law school thinking about what you wanted to do, I ended up becoming a prosecutor and spent almost 20 years in the Santa Clara County DA's office.
Inspiration from Historical Events
00:05:46
Speaker
What inspired you to pursue a career in public service? At the time I graduated from college, I was very idealistic and I really wanted to do something that was going to help protect society and contribute to our society.
00:06:04
Speaker
And I thought that being a prosecutor would be a way for you to do that. I was actually really moved by the Hawaiian American, Hawaiian Japanese American immigration experience versus the Japanese American immigration experience in California during World War II. As people know, there were tons of Japanese Americans in California, the West Coast in general, who were basically put in internment camps because
00:06:34
Speaker
concentration camps by any other name. And the Japanese Americans in Hawaii were not because they were more integrated into the society and into the structure of government. There were Japanese American police officers and nurses and people who were integral to the infrastructure of polling in society and taking them and putting them into camps would have been too disruptive.
00:07:03
Speaker
And it would have been hard for a cop to knock on the door of a fellow police officer and say, hey, I'm going to put you and your family in a truck because we can't trust you. And so I really do think that all of us, minorities especially, need to be integrated into the mechanisms of government and society so that we can make positive change.
00:07:27
Speaker
And I think so. So our audience understands you were the first Korean American prosecutor in Santa Clara County. Is that right? That's right. Ethnically, I was the first Korean American prosecutor in Santa Clara County, which was interesting. Tell us a little bit about that. I would imagine it might have presented some level of adversity, either your coworkers at that time.
00:07:51
Speaker
probably with juries as well, unfortunately. Tell us a little bit about how you navigated maybe some of that bias that you experienced.
Overcoming Bias in the Courtroom
00:08:00
Speaker
Yeah. I think people know about unconscious bias now, but in the early 2000s, it wasn't a war. My people just figured you have the bias that you have. And I guess from a jury trap perspective, because this is pretty easy for me to share. Yeah.
00:08:20
Speaker
From a jury trial's perspective, I had a challenge because I was very young looking as an Asian American as well. And at the end of each jury, you would poll your jury, you would talk to your jury, ask them how you did, and ask them about the case. And a lot of times jurors will stay because they want to talk to you about your case and about you and your closing argument and things of that nature. I found that a lot of jurors were actually
00:08:47
Speaker
They funded off-putting if I was really aggressive. I interpreted that as jurors were afraid of the angry Asian man. If you're really aggressive, then they're like, whoa, why is this guy so aggressive? And I thought, I'm a prosecutor. I should be passionate about what I'm doing. I should be passionate about what I believe. And I need to convey that to my jurors.
00:09:11
Speaker
But if I wasn't really aggressive, as aggressive as some of my Caucasian American colleagues, people were actually sort of scared. They were scared of that angry Asian man. So I had to take a different approach. And the approach that I decided to take was sort of like a stern logical approach. So I had a stern logical jury persona, really, where I conveyed my conviction
00:09:41
Speaker
the conviction that I had in the facts that I was presenting based on my ability to be logical and calculating and stern, right? But I wasn't angry, because if I'm angry, then they're scared of the angry Asian man. So I took sort of a bias, if you have, in society of Asian people being smart, being logical, and being able to show facts in a logical, scientific,
00:10:10
Speaker
meticulously organized a wet manner and then being persuasive because of those things. And that became a trail person instead of the typical passionate, strong, angry prosecutor that you might see on TV or stereotypically. It's really interesting. I'm curious
00:10:34
Speaker
Did you feel a sense of injustice in having to do that and having to sort of modify your behavior? Did you feel like wasn't that different from just maybe the need to act in a role like that? I mean, in some ways, if you're a prosecutor, you're a little bit of a sort of like actor, you're going to have a persona anyways. How did you, how did you reconcile that yourself?
00:10:55
Speaker
At the time, I was just thinking, what's the best way for me to convey my message and to convey my conviction to people who are listening to me? So I wasn't thinking of it in terms of, oh, woe is me, or I feel so syphilitic because I have to do things differently than my colleagues. I was really thinking about it in terms of like Tai Chi. You take the force that's sent at you and then you reverse it in order for it to be more effective, or you to be more effective.
00:11:25
Speaker
I should say. So I took it as a tai chi moment, take their bias, and then use it as a force for good. That's interesting. That's great. I like that saying. I've got another question for you on your time as a prosecutor, which is really, are there any lessons that you learned
00:11:48
Speaker
while you were a prosecutor that you ultimately now are still able to take today in the private sector and apply.
Skills Transition from Trial Attorney to GC
00:11:56
Speaker
Yeah, how does your time in public service informed the approach that you take today as a GC of a private company? Sure, that's a great question. I think that if you're a trial attorney especially, that each trial you have, you have to become a master of that trial. So trial attorneys are basically
00:12:18
Speaker
a jack of all trades and a master of one thing at a time. And that's really what you have to be when it comes to a GC at a small company. You can't know everything. It's just impossible. But you get confronted with questions from all parts of the law and they have to be integrated with business issues that you may not be familiar with.
00:12:43
Speaker
And because of that, you have to be a jack of all trades. And if each issue comes up, you have to be a master of one thing at a time. So that's, I think, a skill that really was a one-to-one carryover from my time in public service. As you were thinking, I mean, 18 years is a decent chunk of anyone's career. As you were thinking about transitioning into the private sector, thinking about moving to an in-house role, I'm curious.
00:13:10
Speaker
easy for people to convince people to hire you? Did they view that sort of public service as an asset? How did those conversations go? I think the vast majority of people just were like, well, why do you want to do this now? There were a lot of people who were not very receptive, quite frankly. Most folks are like, well, if you want to be civil,
00:13:40
Speaker
And so where's your civil experience? And I would tell people that I have regulatory experience as a regulator within the government because I was in the consumer protection group at the DA's office and that I knew how to do civil. But most people thought of that as government experience and as civil experience. And so it was hard for me to convince people that I had the ability to do what
00:14:10
Speaker
Quick announcement before I let you get back to the episode. Spotdraft just released our annual compensation report for in-house legal professionals. If you're wondering how your compensation compares to your peers across industries, years of experience, and more, make sure to check it out. Find it at salary-report.spotdraft.com or head to the link in the description. Now, let's get back to the episode.
Advice on Public to Private Sector Transition
00:14:37
Speaker
If you were able to give advice to someone else who maybe had spent a bit of time in government service and was looking to make a change or make a move, what would you tell them? Should they think more about networks? Should they think more about how they present their experience in the best light? Do you think they should go to a firm instead of trying to go straight in-house? What sort of advice might you have for someone in a similar position? So I asked a lot of people for advice.
00:15:07
Speaker
They basically said everything that you said outside experience, doing something similar. Uh, some said that you had to go to the last room in order to prove your, your worth and that you were good at what you did, that you're properly trained. And other people were like, why even do that? Just if you want to be in house, then you should just go in house first. Right. So I tried to do a little bit of all of that. I went into.
00:15:33
Speaker
uh, the civil part of the district attorney's office in order to learn to practice and learn what regulatory work was like. And I networked with people in order to try to, to, uh, to get inroads into becoming an in-house. And ultimately I applied to both law firms and in-house and got a job at a law firm, um, at an M.A. 200 law firm, a decently large firm.
00:16:00
Speaker
And I did IP litigation there for two years in order to get properly trained, per se, show everyone that I knew what I was doing and that eventually went in-house. So I would say, do what you can in this try. Stay where the opportunity lies because you just never know. You don't know if there is a friend at an
00:16:26
Speaker
at a company who knows you and knows that you're going to be good at your job, no matter what you do, and gives you a chance, right? And you don't know if there's a love from job out there that's going to be able to give you the necessary experience to show people on the in-house side that you can do civil, that you can be good at
00:16:49
Speaker
and give you a chance. Just do it all of you. Whatever opportunity there is for you to get trained, go ahead and take it. Let's talk a little bit more about the importance of network. How has your network helped you at various moments in your career? Were there those people who you knew someone and they stood up for you and they helped you get a job? Tell us more about that. Oh, absolutely. Half the jobs that I've had have been introductions from friends or actually
00:17:19
Speaker
know someone who I've worked with that I was trying to woo as a client or someone else who was just impressed by the fact that I was helping out for free and then during that period figured that actually this guy really knows what he's doing so I'd like to hire him. That those types of experiences are an invaluable part of trying to find a job and get
00:17:43
Speaker
And when you think about it, if you're going to hire a plumber, you might look at Yelp or one of the blogs, but you're very likely to just pick up a phone or text somebody and say, Hey, do you have a plumber that you can refer me to? And then once you get the referral, if you get one, then you also do your due diligence and check the review sites and stuff.
00:18:07
Speaker
But it's very likely that you're going to go with somebody who has a positive referral, or you worked with in the past, and then you know it's going to be good. That's just human nature. And that's how the world works, not just getting a plumber, but getting a job. Yeah, I want to double click on an idea that you have there, which is maybe offering some advice for free, or doing a little bit of advisory work. I personally have found that to be
00:18:37
Speaker
really helpful, both for finding potential job opportunities, expanding your sort of network, even consulting opportunities sometimes come along or build out of a relationship like that. So I'm a big fan of the try to respond to like pretty much every LinkedIn message that you get, try to take any call, whether it's, you know, a student who's looking for some career advice, or
00:19:06
Speaker
someone who wants to talk to you about a job opportunity and anything in between, the seniority of the person doesn't matter. I'm curious if you found that some of those advisory gigs or conversations have turned into anything much more material. Yeah. I mean, my first job out of the DA's office was at a law firm and it was a referral by a partner who I had worked for, or I should say worked with,
00:19:33
Speaker
It's the Santa Clara County Bar Association. She's a former president of the Bar Association. And I was an incoming president of the Bar Association. I had a good reputation for getting my work done within the bar. And I had worked with her and people around her so that they knew that I was good at what I did. Whatever task I was given, I was going to be responsible with.
00:20:02
Speaker
uh, implementation was going to be at a high, um, level that my standards were high. And what could be more powerful than that in terms of whether or not you're going to decide to hire somebody. I've worked with this person and he is good at his, at what he does. And when he says yes, even though he's not getting paid, you know, that it's going to get done. So he's a reliable person.
00:20:29
Speaker
And what are you looking for in employees? Someone who is good at their job, has high personal standards, is reliable, and who you can trust when they say something's going to get done. I know before your recent move to engaging, there was actually an unexpected transition that happened at Blind, as many tech companies have been
Coping with Unexpected Job Loss
00:20:53
Speaker
through. I've been through myself before. There was a rift.
00:20:58
Speaker
Um, I'm curious, tell us more about how you navigated sort of the emotion of that moment and then regrouped and started the job hunt again. I think actually you, you did that pretty well and you did that pretty quickly. Uh, so any lessons you would have from, from that experience for, for others. So when I got rest, I was surprised. I wasn't, um, I wasn't part of the committee that laid myself off. And, um,
00:21:27
Speaker
And I don't think that that's unusual because no matter what your position is within a company, you're still an employee, right? Unless you're the owner of the company. And so barring that type of situation, you're an employee and you might get risked. You just, just have to be realistic about that possibility of the company using it to meet while you cannot. But that said, it's nobody,
00:21:56
Speaker
feels good when that happens. So I think that you just have to be honest with yourself that you need help in terms of getting a job and reach out to everybody you know. If you have a good relationship with that person, then that person should know that you got laid off because you are looking for a job. If they don't know, then they don't know that they can help you.
00:22:22
Speaker
They might be that person who gets a call or has a conversation with a friend and finds and knows that there's an open position but doesn't know to convey it to you because they don't know that you got laid off and lucky. Yeah, I think that one of the good things about a lot of the layoffs that we've seen across the tech industry over the past couple of years
00:22:49
Speaker
is that the willingness of folks to be open about it and to talk about it, the fact that they were a part of 5% or 10% or some cases, unfortunately, 40% of a company that was let go all at once, it's I think really changed the perception of what that means. And people understand that there's often sort of wider economic or secular forces at play, as opposed to it being an indictment of an individual and their performance.
00:23:17
Speaker
I actually think one of the good things is that maybe the term layoff doesn't carry the same stigma. I don't know if that's what you experienced as well. Yeah, I absolutely think that that's that's the case, especially when in our industry in in tech and in startups within tech. It's such a volatile workplace that work environments are just so volatile that some companies just
00:23:47
Speaker
jump up in a J curve and then smash it to a cliff on the way up. And other companies seem like they're doing well and moving up slowly, but then suddenly some economic factor changes or the industry changes or some change happens within the leadership because there's a fight or whatever. And now there are a bunch of people who have been risked and
00:24:17
Speaker
are looking for a job. It just happens. And that's a, that's not an indictment on the person who gets ripped in. I think that's something that is more and more understood as we go on. There's still a bias. I mean, that's real there. It's easier to get a job when you have a job. It's going to be that way. But I think more and more people are coming to understand that just because you got
00:24:45
Speaker
Rift doesn't mean it's because you were the weakest link within the company. It could just be because the company did not need you or it could be just random, frankly, that they needed to meet their numbers and your number happened to be picked.
New Roles at Engaging.ai
00:25:04
Speaker
Yep. Tell us a little bit about the new gig at Engaging. And I know now you're taking on the COO role.
00:25:12
Speaker
as well. What are some of the challenges that you're excited to tackle in the first few months? Well, this is my third gig as a GC or head of legal. So that part hasn't been as difficult, I think. Now, but the third time you better know what you're doing. But the COO taught a job I've never done before. So going in and learning about
00:25:41
Speaker
some of the like PM processes and some of the background processes that I'm not familiar with is it's challenging, it's different, right? But it's part of the excitement of being in a startup that you can do these new things and you can stretch yourself and reach out to your network for advice and just do your job while also gaining new skillset. It's so many like big
00:26:11
Speaker
company jobs are about just being super specialized and staying in your lane. I really like the fact that small companies and startups are about knowing that boxes have to be moved and being able to sort of roll up your sleeves and move boxes when they have to be moved as part of your team. Yeah, I mean, it's about being a doer and a sort of operator just as much as it is about the
00:26:37
Speaker
Maybe the knowledge that you bring to the table, getting things done. Yeah. It's about who you are as someone who is creative and flexible, but also disciplined, right?
Embracing Opportunities and Overcoming Limits
00:26:50
Speaker
Yeah. We've talked a lot about transition today. Anything else that you'd want to say as we start to wrap up in terms of advice for those who might be looking for a new job right now on their own volition or been put in a position where it's a necessity.
00:27:06
Speaker
I think the best piece of advice I could give is don't limit yourself. Everybody's heard of the glass ceiling and the fact that other people put a ceiling on top of you. Well, I think that a lot of people sort of create a sticky floor for themselves. And by that, I mean they create their own barriers for jumping up and moving up within their careers or within a hierarchy.
00:27:36
Speaker
They say, well, I've got to do this first. I've got to prepare that way first. These things happen to happen before I can actually make that transition. And making excuses, just dropping things on the floor and making it sticky. They don't actually move their feet and start trying to move up that ladder. So I would say don't create a sticky floor for yourself. When you think you're ready, you just got to go. And sometimes even though you're not 1000% ready,
00:28:08
Speaker
You're not going to ever be 100% ready for every new transition in your life. Just get ready and go. I've got just a couple of hopefully fun questions for you left.
Career Reflections and Recommendations
00:28:20
Speaker
I'm a big reader. I travel all the time for work, so I'm always looking for books to read when I'm at 30,000 feet. What's a good book that you've read recently? I just finished The Babaverse.
00:28:36
Speaker
series. It's a science fiction series by a gentleman named Dennis Allen, I believe it is. I really enjoyed reading. Dennis Taylor, sorry. So I really enjoyed reading that series. It's a four-book series. I'd highly recommend it. Fun. I might get four flights out of it. Yeah, maybe.
00:29:02
Speaker
As we wrap up, just one final question for you that I like to ask a good number of our guests. If you could look back on your days as a young lawyer, maybe at the DA's office, just getting started, what's something that you know now that you wish that you'd known back then? That's a good question. I would say you don't know where you're going to be in 10 or 20 or 30 years.
00:29:31
Speaker
So don't act like you do, just whatever it is that you're doing, do it with an attitude that this might be preparing you for the next thing, even if you don't like it. And if there is some sort of opportunity that's like, ah, there's no way that I would do X, Y, Z in the future. So even though I'm interested, I'm not going to give it a shot. Give it a shot. It could be that five, 10 years in the future, you're actually going to be glad that you had
00:30:01
Speaker
had that prior experience. Well, Michael, thanks so much, especially as you're ramping up for a new job for taking the time to speak to our listeners today. We really appreciate it. Thank you, Taylor. I hope you have a great rest of your day. Thanks. And to all those out there listening, thanks so much for joining for this episode of The Abstract and we hope to see you next time.
00:30:30
Speaker
If you enjoyed this episode, I'd recommend that you give my interview in Season 2 with June Aro, head of Strategic Legal Initiatives at the UC Office of the President, a listen.
00:30:39
Speaker
We talk about how to build a culture of inclusion, ethics, and compliance for your organization. You can also subscribe so you get notified as soon as we post a new episode. And if you liked this one, I'd really love to hear your thoughts, so leave a rating or a comment. If you'd like to reach out to us, our LinkedIn profiles are in the description. See you all next week.