The GC-to-Board Playbook, with Executive Coach Anne Marie Segal

Anne Marie Segal spent 15 years as an attorney - at White and Case, a hedge and private equity fund, and her own firm - before becoming an executive coach to general counsel and senior executives across six continents. She knows what it takes to make the leap, and what holds most lawyers back from making it.

In this episode, Cecilia and Anne Marie get into the psychology behind lawyer identity, why so many high achievers stay stuck, and what it looks like to grow beyond the legal function, whether that means taking on a board seat, building toward a CEO role, or starting something entirely new.

Follow Anne:

@Anne Marie Segal on LinkedIn

segalcoaching.com

You'll hear:

• Why the GC role is expanding faster than ever and what the best ones are doing about it
• The mindset shift lawyers have to make before they can get on a board (hint: you are not the GC on the board)
• How to know if you have a fatal flaw blocking your next move  and what to do about it
• What AI is changing for junior lawyers, senior lawyers, and everyone in between
• The one question every lawyer should be asking themselves right now: what wouldn't you want to delegate?

00:00 Introduction 01:03 Anne Marie's "When Harry Met Sally" moment leaving law for coaching 04:06 The fear behind staying: money, identity, and worst-case scenarios 07:38 Anne Marie's career path: White and Case, hedge funds, and letting go 12:50 Shedding the lawyer identity without losing what makes you good 17:03 Why lawyers are uniquely valuable and what that actually means 18:45 The expanding GC role: 70% of Fortune 1000 GCs now own two or more functions 25:07 GCs and board seats: the mindset shift most lawyers miss 30:36 Fatal flaws and how to find yours before they find you 36:11 AI and the legal profession: what boards are asking and what students are getting wrong 40:53 Advice for junior lawyers: what wouldn't you want to delegate? 44:54 One thing every week: how to actually make the move 47:21 Lightning round: the book that shaped Anne Marie and what she wishes she'd known before law school

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⁠@Cecilia Ziniti⁠ on LinkedIn

⁠@CeciliaZin⁠ on Twitter/X

⁠@GC AI⁠ on LinkedIn
@gcai on X

⁠gc.ai⁠ website

Transcript

Cecilia Ziniti (GC AI) (01:03)
Anne-Marie, welcome to the show.

Anne Marie Segal (01:05)
Thank you, Cecilia. So glad to

be here.

Cecilia Ziniti (GC AI) (01:08)
Let's start with the moment when lawyers realize they're capable of more than being quote, just a lawyer. So you've spent your career now 15 years working with people who want to reach that next phase. Tell us what happened when you made that decision and then we're gonna bring it forward to the present and working with your clients.

Anne Marie Segal (01:29)
Sure. And I just want to make sure I'm clear. 15 years as an attorney and 11 as a coach. So footnote. ⁓

Cecilia Ziniti (GC AI) (01:35)
Love the precision, love the footnote.

Podcast for lawyers. So thank you.

Anne Marie Segal (01:39)
Yeah.

So, wow, there are so many ways I can tell this story about the transition, but it's similar to what happens with my clients, which is one day you say to yourself, after years of being happy or unhappy in the legal career, I think I'm done, or whatever comes to mind, right? But something that you feel, something inside you that needs to shift. And that absolutely happened for me. ⁓

I would say that what led me to it instead of what pushed me out of law was meeting coaches because I didn't really know coaches before this. joined a mastermind. I learned more about coaching. It was kind of a, I always say it's like a, when Harry met Sally, I'll have what she's having moment. So I toasted my friend that I wanted to be a coach and she said, oh, you'd be amazing. My friend, a career coach. And that was all I needed. I was on track.

So, yeah.

Cecilia Ziniti (GC AI) (02:39)
I that.

It must be, I think your point about that it's a moment, I have these moments myself, right? Of like the first time I used a pre-chat GPT version of GPT and just jaw on the floor, like, oh my God, everything has changed. I got funny, said this about moments. My first like real kind of professional office job,

Anne Marie Segal (02:56)
Right.

Mm-hmm.

Cecilia Ziniti (GC AI) (03:07)
was

as an intern at the Federal Reserve in the early 2000s in Chicago. I still keep in touch with the person that I was roommates with. She had a long career in tech. ended up as a VP of sales at just a really hot deck of corn. And I emailed with her last night. Now I want to a little side diversion because I think it's super relevant on this moment. I emailed her last night because I happened to be selling to where she had worked.

Anne Marie Segal (03:09)
Right.

Mmm.

Right.

Cecilia Ziniti (GC AI) (03:35)
And she says, that's amazing, I'm amazed by the growth and success. And she says, Tech and I broke up. My goal is to stay out. It's hard not to be part of the party, but I needed to make the change. And she's doing yoga retreats, and she's essentially a solopreneur, but quite successful doing what she loves. So I don't know what happened, but she talks about it as a breakup. You talked about it as a Harry met Sally moment.

Anne Marie Segal (03:47)
Right.

Cecilia Ziniti (GC AI) (04:00)
Is it a moment and then how do you help your clients listen to that moment if there is one?

Anne Marie Segal (04:06)
I think it often is a moment or it's a series of moments, but it's definitely marks in time, right? When I work with clients, it's like I sometimes say peeling back the onion, I know that's a cliche, but really you're hitting milestones. Like the first milestone might be, ⁓ my gosh, I don't have to do this for the rest of my life. Another milestone is when you realize that

A lot of people stick to being lawyers because they're afraid that they're going to fail at something else, but also that they're never going to make that kind of money again. And, you know, when I asked the question, what if you could make more?

You know, it's like I'm like.

Cecilia Ziniti (GC AI) (04:50)
I think that is right. it's, people talk about like abundance mindset, very hard. It is exceptionally hard because you've achieved a lot, like by definition being a lawyer, you have achieved a lot. And so it feels like this, it's almost like, like investing, right? Where it's like, you know, your husband or whatever, like, are you going to take some more risk? And this is something that I interview folks for GCI all the time. So we hire, we have about a third of our company is lawyers.

Anne Marie Segal (04:55)
Right.

Right. Right.

Cecilia Ziniti (GC AI) (05:17)
And we occasionally do have candidates pull out because they're worried about, because these are not purely practicing roles. Obviously they have a legal skillset, but you're working with people, you're working on AI, you're working in tech, we've got lawyers coding. But they have that fear. So what's behind it? And in that moment, is it like they should be so lucky and be your client? how does it usually play out?

Anne Marie Segal (05:44)
Well, I had it and they always say people become a coach because they had an amazing coach or because they wished they had and when they see what they missed, you know, it motivates them. ⁓ I would say the fear is in some cases ⁓ mitigated by thinking about the worst case scenario. I go through this a lot with clients like, OK, so what's the worst case scenario? You have to sell your second home in Paris, you know, or

Or like law firm partner, you know, or you don't show up the same way that you showed up all the time before. ⁓ You have to reinvent yourself. You have to take a step back for some period of time. Maybe it's three or six months, maybe it's a year and breathe and like get to know who the hell you are because you've been forgetting, because you've been pushing so hard.

You know, things like that are what come out of sessions, for example.

Cecilia Ziniti (GC AI) (06:44)
I mean, it's interesting this ⁓ abundance mindset kind of underlay of like, you know, I had a coach one time tell me that it's like, or maybe it was like working mom advice or something that was like, you know, instead of saying I have to go to work, it's like, I get to go to work. And so you said something like, okay, you have to reinvent yourself. One of my professional idols, of course, Taylor Swift, she literally has the errors, right? Of like, she gets to read it.

Anne Marie Segal (06:49)
Mm.

Bye.

Right?

Cecilia Ziniti (GC AI) (07:13)
herself, right? She gets to like the different phases of her life.

Anne Marie Segal (07:14)
Exactly. Right?

Cecilia Ziniti (GC AI) (07:17)
Okay, so you asked them so that I imagine that the Paris house question goes over like a lead balloon, but but but give us give us

Anne Marie Segal (07:24)
Well, I don't necessarily

say that out loud, but I ask them and they come to it. You know, I mean, a lot of coaching isn't me pointing fingers saying something, but it's like, so what would you have to give up? You know, and then it comes. Yep. Yeah.

Cecilia Ziniti (GC AI) (07:38)
Yeah. So what's, what's a,

give us a success story. Tell, tell us about, about that people you've seen had that moment. Obviously your, your self is a success story. So I'm assuming you're happy as a coach and you love it. Do you ever miss the, the, deal junkie stuff from, being at a hedge fund?

Anne Marie Segal (07:49)
Hmm.

zero. I don't miss it at all. No, I don't miss it. ⁓ I thought I would. I guess it's just I knew very clearly what priorities were causing me to want to shift, ⁓ which is in large part having more control over my schedule, which, you when I had my own law firm, so I was at White and Case and then the Hedge and Private Equity Fund, and then I had my own firm. And then I tried a smaller

Cecilia Ziniti (GC AI) (07:55)
You're zero! Not at all! Don't miss it at all.

Anne Marie Segal (08:22)
Kindler, Gentler law firm, which it turned out not to be. But, you I kept trying to take trips with my family and then be working till God knows when, even as a solo entrepreneur, solo practitioner. And I was just, I was done. Doesn't mean other people should be done. I don't mean that, that, that, you know, this is an evolution. This is just a transition for me.

Cecilia Ziniti (GC AI) (08:41)
So basically, that like, lawyer, our job is solving people's problems. ⁓ What made you open up to let go of that?

Anne Marie Segal (08:42)
Right.

Hmm. So when I did my first coach training, they asked what you wanted to be most for a client and I said, reliable. And everybody kind of laughed, you know, like you're such a lawyer, you know, ⁓ and it's true. ⁓ Michael Melcher, ⁓ who's a personal friend of mine, and one of the people I met as I got into coaching said, you know, lawyers who to become coaches are some of the best coaches because they know how to show up.

and then they have this emotional intelligence. So you need both pieces. And I don't want to say that being reliable is not important, but also I learned to not, as you said, not solve problems for people. So imagine if when I met you, I said, you know what? You don't sound happy at all as a GC. You should, and then I gave you my advice. It doesn't work that way as a coach.

Cecilia Ziniti (GC AI) (09:41)
Yeah.

Anne Marie Segal (09:41)
That's not what

coaching is about. It's about you learning what's inside of you and me facilitating that.

Cecilia Ziniti (GC AI) (09:46)
Do you ever get clients frustrated with the therapist thing of like, what do you think? you're right, because part of me, will admit, I'm perhaps not with you, but with other coaches or in general, where I'm like, can you just tell me what to do? I literally sometimes have that feeling. So what do you do in coaching when that happens?

Anne Marie Segal (09:52)
⁓

Right?

Right.

Bye.

It's interesting because usually the people who ask me to tell them what to do is on an intro call. And I'm like, okay, I've known you for five minutes. But I don't coach. I traditionally coaching is supposed to be all of that, you know, arc of the coaching call and, know, at the beginning, figuring out what you're going to solve on that call. And, you know, there's a whole lot of methodology around it, which

Some of us are very happy to learn because it's how we unlearn the lawyer piece. But then we, you know, I explained to people when I first meet them, I'm also a consultant in some ways without that title, you know, and so you tell me when you want me to jump in. I'll sometimes say, I'm hearing something. Can I give you what I'm hearing? Can I tell you, you know, what comes up for me? But just take it with the spirit of

as it's offered and not ⁓ that this is the solution. And almost, I don't wanna say almost always, 80, 90 % of the time it's right, but sometimes they're like, you know, that's really not it. But then it leads them to what it actually is.

Cecilia Ziniti (GC AI) (11:14)
Yeah, I think that's right. mean, I, there was a podcast with the chief product officer of Rippling and he basically was like similar question except for in a venture capital context of like, okay, and it's almost this idea of advice reflects the giver as much as it reflects the receiver, right? And so this, okay, here's what I've experienced or here's what I've done and just sparking that thought.

Anne Marie Segal (11:27)
Right?

Cecilia Ziniti (GC AI) (11:41)
But it's the advice that he gave in that podcast was that as an entrepreneur or just as a human, when you've got this kind of like board of directors type relationship with a lot of people is like figure out what you can ignore, take the good with the bad. Like the advice is about a moment in time of the giver's life but also of yours. So I think that's how I've looked at it. Is there any, do you ever not take on clients? Because you think that they won't want to see.

They won't want to see the light.

Anne Marie Segal (12:13)
absolutely. ⁓ I've never said to someone, don't seem coachable, but it's very clear sometimes that people are not coachable because they're like, what I'm doing is not working and I want to I'm almost pounding. I'm pounding the desk right now. This is the way they they go into it. You know what I'm doing is not working and I want you to tell me how to fix it. You know, that's not coaching. ⁓ So I I've

Cecilia Ziniti (GC AI) (12:21)
you

Yeah. Yeah.

Anne Marie Segal (12:43)
developed an intuition for that, ⁓ I steer clear of those clients or potential clients.

Cecilia Ziniti (GC AI) (12:50)
Wow. Let's talk one more question on the coaching, which is a lot of lawyers have being a lawyer as part of their identity. ⁓ Does that, how do people grow past that? And do they have to? And do they have to, get the big jobs, you know, the COO or even CLO, is there something that where they, like, is it an unlock?

Anne Marie Segal (12:55)
Sure.

Right.

Mm.

Cecilia Ziniti (GC AI) (13:20)
In other words, like obviously if you're gonna become a coach, you're gonna become something that's not a lawyer. You gotta move past that. But presumably there are people that can stay with that identity and that's just who they are. Is that okay? like, does it, give us the benefits of seeing yourself as more than a lawyer.

Anne Marie Segal (13:38)
Well, I'll go back to what you know is true, which is we're one of the only or maybe the only profession that talks about lawyers and non-lawyers. So you already kind of start there. ⁓ I would say you don't give up being a lawyer. Like, for example, I'm still a lawyer. I prep people for how do I talk to the board? How do I figure out what's material? How do I present myself? And of course,

That's because I've seen that in action and when it goes well and when it doesn't go well and I've had lots of clients tell me their experiences. And so I approach it as a lawyer in that sense. ⁓ But I do think you, it's not that you shed being a lawyer, it's just that you shed some of that crap that we're fed in law school and in our early careers, which is that lawyers, and this is where I started, are so different than non-lawyers.

and that somehow, you know, like we're almost a different species or we see things that other people don't see. You know, my husband didn't go to law school. My son didn't go to law school. He's 22. They're always telling me, I saw this in the news and this is what I think. And often they're right. You know, it's not like lawyers have a corner on that market. What changes is that lawyers need to think more expansively.

That's really it. So it's not that you're not a lawyer, but you are not only acting as a lawyer and seeing everything with the lens of being an attorney.

Cecilia Ziniti (GC AI) (15:11)
I mean, I think that's right. It's like, always used to tell my teams advising more junior lawyers, is like, you gotta be at least bilingual. So if not actually be a native of both kind of countries, business and law, you have to at least speak the language and, you know, least you're able to be a tourist. But what we're saying something deeper is like, it's both and, and I would agree with you that people who are not lawyers, ⁓ I've worked with many over the years that are basically better lawyers than most lawyers because,

Anne Marie Segal (15:26)
Right.

Cecilia Ziniti (GC AI) (15:39)
They can kind of see the wider picture. They can think creatively about risk. ⁓ one of our podcast guests, Matt Gipple, who is kind of a quintessential lawyers lawyer clerked, ⁓ you know, was very, was it Latham? ⁓ but he, asked him a similar question and he said the best kind of collaboration that he ever had was with an autonomous vehicle engineer where they were figuring out how to address a regulation that was brand new.

And the engineer had an idea that no lawyer had ever thought of and turned out to be like perfectly on point with the reg and a way to achieve both the compliance that was needed and the technical requirements. And I think it is interesting, you're right, that I think the example you use in your book is like nobody talks about bakers and non-bakers. And so I definitely, lot of lawyers love to cook and I cook but I don't call.

know, colleagues, non cooks or whatever. So amazing, good stuff. All right, so that's a good context for what's going on in legal profession. It's going through a shift. AI is taking on more work. can talk about AI. Big law firms have been restructuring their associate pipelines. I think we crossed $5,000 an hour for lawyers or even 10. But they're still in that, in these, all these shifts, which are happening at the same time. There's a question of like, how are...

Anne Marie Segal (16:37)
you

Cecilia Ziniti (GC AI) (17:03)
lawyers uniquely valuable.

Anne Marie Segal (17:04)
So lawyers are valuable when they can solve problems that are not only compliant, but maximize what you're trying to do. ⁓ I guess later we'll talk more about junior lawyers and that, but a lot of people want to be better lawyers. And what I find is to be a better lawyer is when you

have this expansive view. It's not that I'm getting better at the subject matter expertise. People who go to the general counselor, for example, I always say there's a reason there's a word general in it. You don't need to develop subject matter expertise in every single area. And if the board asks you a question, you don't have to, my God, I didn't get on the weeds on that. my God, they're gonna fire me. Which clients have said to me, at times they're afraid of that as they're going into board meetings.

You know, it's not... ⁓

That's not what lawyers bring most. They bring their training, even though I disparaged it a moment ago. They bring the way they look at things and see things from multiple sides, not even just two sides. Sometimes it's more than two sides. They understand the underlying issues for policy questions. Why did we do this? They understand bright lines. They understand just so many things that help us decide

how to act in a business context. So I would say that's a lot of what lawyers bring. Maybe you have more things, but that's what I see.

Cecilia Ziniti (GC AI) (18:45)
Here's a number that's exciting. So looked at some recent data, 70 % of senior lawyers at Fortune 1000 companies manage at least two functions beyond legal. Wow, that is a stat I did not know before I looked it up. So ESG, privacy, cybersecurity, compliance, government affairs, I've seen procurement. So the GC role, HR of course, the GC role is becoming bigger than it's ever been.

There's the CLO concept. I talked with Danielle Shearer, who's chief trust officer. ⁓ So when you look at GCs, what they're being asked to own right now, what they're owning, ⁓ why do you think that is, that the GC role is expanding?

Anne Marie Segal (19:28)
⁓ I would posit that it's because GCs are damn good at what they do. know, ⁓ I mean, if you want something done right, you give it to the GC. I mean, that's the way it is. And every successful business that I've ever ⁓ seen had the pleasure of seeing the inside of. So I would say that's why, you know, and then GCs themselves are realizing what you and I have been talking about, which is, you know, I don't need to settle.

Cecilia Ziniti (GC AI) (19:32)
Let's go, yeah.

Anne Marie Segal (19:58)
on just being the legal function quote unquote. So those two things.

Cecilia Ziniti (GC AI) (20:04)
Any, and I don't know if, know, obviously confidentiality and what have you, but any one of either your clients or folks you've seen in the press particularly jump out as a great example of a GC who either became a more than that or is managing many functions.

Anne Marie Segal (20:21)
present company accepted.

Cecilia Ziniti (GC AI) (20:23)
Ha ha

It is true. did have Malin Yen on the pod. She's fantastic. She became a ⁓ founder as well. And then now she is a very successful runs a very successful venture capital fund. ⁓ And similarly, she came from IP and very good example of like, okay, know, lawyers, you can just handle more and more and more and you, you, you do it effectively. So yeah, that's great.

Anne Marie Segal (20:29)
Mm-hmm. Mm-hmm.

Right.

What I see first usually is a bolt on kind of idea. You know, I'm going to add business development. Like in your case, remember you added business. You know, I added this different area. I add this different area. And then somehow they, they wake up. I had a client, I was talking to her and she was said, I need to expand my brand because I'm adding these different things and these different things. And you know, it was kind of like, it's not scope creep at some point. It's like just a new thing altogether. And that's when I said to her,

Are you trying to get ready for a CEO role? And she was like, how did you know? You know, at that moment of being seen, ⁓ she was afraid to say it out loud.

Cecilia Ziniti (GC AI) (21:29)
Yeah.

You know, isn't that fascinating that like I literally told someone of my friends, Amber Illig is now an investor in GCI, an incredible full circle moment. She was very interested in investing and in personal finance and venture capital and angel investing and started like a women's interest group of doing this at cruise. I, same thing. I'm like, Amber, I think you're a CEO. And she was like, wow. And she remembers that conversation. I still remember it. I was driving home and

I said the CEO, like you're a CEO thing and that was maybe five, six years ago and now she's like top one percentile of ⁓ TVPI, which is a measure for OVC and we, and she invested in us. So it worked out great. Yeah, it's like, and so I think telling people, giving people permission is a good thing. also, it really comes down to this like mentorship of, I'm always so interested in how people got into what they're doing and.

Anne Marie Segal (22:11)
Mm-hmm.

Excellent.

Mm-hmm.

Cecilia Ziniti (GC AI) (22:28)
I met someone who, ⁓ one of our sales folks, is he has specialized in selling software to healthcare and pharma and hospital systems and things like that. And it's because he had a son who basically was in the NICU for some time or special needs and needed something with his heart and spent months in the hospital seeing all the different machines. And he's like, I wonder who makes this machine and that machine.

Anne Marie Segal (22:55)
Right.

Cecilia Ziniti (GC AI) (22:56)
And it is fascinating that there's this just like, can have somebody tell you what you don't see, or you can have the world kind of reveal something to you. I love that.

Anne Marie Segal (23:06)
especially when you're someone who's pushing forward, know, the kind of overachiever personality or warrior personality, you know, because you just you don't stop and look around. ⁓ But but to some degree, it's it's developing an intuition for that. mean, I'm not sure I would have been able to do that. You know, 10 years prior to becoming a coach, five years prior, I don't know. mean, I remember there was someone at the Hedge and Private Equity Fund where I was working.

Cecilia Ziniti (GC AI) (23:12)
you

Anne Marie Segal (23:35)
And I went down and I said to him, I'm going to quit. I'm sorry, I really enjoyed working with you and everything. He said, I knew. I knew you were going to quit. I said, how did you know? He said, pulled your kids out of private school and put them in public school. And I said.

Cecilia Ziniti (GC AI) (23:50)
⁓

wow, look at that, that's hilarious.

Anne Marie Segal (23:53)
And I was like, well, there were other reasons. He's like, yeah, I know, but you know, that's my job to see trends. You know, we had a whole lot of conversations around this sort of thing, but it's just like, everybody else was totally shocked except Richard, you know? Yeah. So.

Cecilia Ziniti (GC AI) (24:06)
That's fascinating. Wow.

There are these people that just have that incredible intuition as well. Yeah, no, we've got a friend telling my, I've got a, 14 year old is a very good baker. And this particular friend is like, when is Al's gonna open a bake shop? You gotta encourage her to bake, open a bake shop, you know, do this, like get her to get her to the farmer's market. And he, and he kind of mentions it a lot. And I think she's gonna.

Anne Marie Segal (24:13)
Right.

Cecilia Ziniti (GC AI) (24:33)
think she's going to do it. Like literally to the point where we went to, we traveling and there's like a big shop in Santa Barbara called Three Sisters Bake Shop. There was something like that. And I'm like snapping the picture on Instagram and sending it to my kids. it's like, you know, see people that can see these seeds. You, you, you listen to them. That's amazing. The, the private school addition is fascinating. So what other trends should we be watching for? So we've got a lot of GCs on the podcast. ⁓ you, you talk to a lot of GCs this like taking on other functions is one.

Anne Marie Segal (24:34)
Excellent.

Bye.

Right.

Mm-hmm.

Bye.

Cecilia Ziniti (GC AI) (25:02)
Anything else that we should be out in front of from your point of view? Yeah, mean obviously AI is the big one, but there's probably either other trends or other things that we should know about.

Anne Marie Segal (25:07)
⁓ in terms of what GCs might be doing next.

Well, you know, one thing I think of right away is GC's going for board roles, which is in some ways an obvious crossover, in some ways not at all. ⁓ So I would say that is it a trend? mean, it's still an uphill battle in a lot of ways, but it's making headway. know, ⁓ the political climate.

Cecilia Ziniti (GC AI) (25:25)
Yes, okay.

Anne Marie Segal (25:45)
climate has shifted a bit. And I think with that, it's been harder for lawyers to get on boards. Boards are just not taking as many risks. ⁓ But that being said, you know, there's, they always need to, the way they choose a board, as you know, is they're replacing someone who's leaving. So they always need someone with that set of skills. And especially, it's not like, I'm a lawyer, put me on your board. It's like, I'm a cybersecurity expert, or I do crisis management, or I've

I've been through three or four turnarounds of companies or whatever as a lawyer, but just in general, right? ⁓ So that's definitely something to watch.

Cecilia Ziniti (GC AI) (26:29)
I mean, the stat that we pulled is 92 % of GCs interact regularly with their boards. That's right. I was corporate secretary in various of my roles. And it is fascinating now when I think about what I want from a board member. It really is that like, I'm going to call you and it's going to be a call that I want to make because I know I'm going to get value. I will get someone looking around corners, but I can see where.

Anne Marie Segal (26:35)
Mm-hmm.

Cecilia Ziniti (GC AI) (26:58)
the qualities that a great GC has of kind of like, I call you, you fix it, the solving problems thing. But also that you, that you're someone who's seen those trends, who can kind of help me ⁓ navigate an issue without me feeling like you're asking me for something. Like, I mean, I think unfortunately that's how it works. So a little bit the service mindset as well. But yeah, I mean, for me, like I, because I was involved in boards through you and through others,

Anne Marie Segal (27:17)
Right.

Cecilia Ziniti (GC AI) (27:27)
⁓ and then obviously as a GC, ⁓ I think she sees can make great board members. The thing that I, that I would not want in a board member though, that I think GCs have to move beyond is the, like, the always thinking about risk all the time, you know, and, and on that one, they're, the data is clear. Optimists live longer, optimist businesses do better. Optimists, ⁓ you know, network more, they see greater returns. mean, it's like the data is exceedingly clear.

And that is one thing that the like, you know, I think I told, I was evaluating, essentially which VC to go with for one of our rounds. were very lucky at our last funding round that we had, ⁓ we had a choice and I'm like, I don't think I want a board member around with nervous energy. Like I just can't, I'm not going to do it. And so, ⁓ is that the advice for DCs is to me move beyond the nerves or like who

who are the ones that make that great transition to becoming a board member or who seek out a board seat and get it.

Anne Marie Segal (28:31)
So

I don't know if it's always nervous energy. I some GCs are very calm, but yet they are, as you said, risk-oriented or downside risk-oriented. ⁓ are not necessarily thinking of... It's almost like, so when I ask GCs to create their value proposition for a board and I listen to them...

It's almost like they're anticipating that they're gonna be the GC on the board. I mean, the biggest mindset shift is you are not the GC on the board. There is a GC. You are a board member. Full stop, done.

So you have to have the entire gamut, range of what a board member should know and think about and be attuned to and you have your antenna out for all of it. It's not, you're not the GC on the board. That's the same for a CFO. It's the same for some other people. It's the same for a marketing person, but ⁓ it's kind of more insidious in GCs because that's where they...

You know, another myth is like that GCs somehow only add their value when they're acting like a quintessential GC. And so that holds them back too in the GC role as well as in the board transition. And a question you haven't asked, but is a corollary or it's kind of in your question is what keeps GCs off of boards? And in addition to everything I just said, I think it's also just they're taking that leap of faith.

and then really investing. So a lot of GCs are like, I want a board role. And they're hot for three months, and then they don't do anything for six months. And you know how that goes. And so you really need to let everyone know you are a future board member, a board candidate, and do everything you need to do to get yourself there. It can't be kind of just a wish. It has to really be a plan.

Cecilia Ziniti (GC AI) (30:36)
I love that. mean, we, in our classes, we teach classes on AI and we ask, you know, how many of you have a AI goal in 26 or 25 when it was last year? And we'd get 90 % of the people saying they do. And then the next question was how often are you using AI for illegal work? And you know, that number has shot up, but.

there were times I would ask that and ⁓ half the people would say never. And it's like, well, okay. And then it's like, what is it, a plan without a, or a goal without a plan is a wish or something like that? Yeah, think that's exactly what you said. There is some work to be done. I think one thing I've seen, and I'm curious your take on this, is that you see very high achieving folks who for whatever reason have some fatal flaw. Like they talk too much or they,

Anne Marie Segal (31:04)
Mmm.

Right.

Cecilia Ziniti (GC AI) (31:29)
you know, spacey or whatever. Like, cause there's people where I'm like, you know, that I've worked with even as vendors or PR firms or what have you, where like, they are good at what they do, but there's something that's like annoying. And so like, I had somebody last week, a guy on the pod and he said on his team, had someone who ⁓ essentially executive comms was her blocker. She was very good, but you know, the like,

ask a question, get an answer, like that was not, that was, that they didn't do that. And he set a goal for her and they worked on it and they did it. And then she got promoted to GC. And so I guess like, is there something like as a coach or as someone, like how do you get people to have that self-awareness about it? And I think, you know, for me it was, you know, I think it was the role where I did need to not be a GC anymore. I loved being a GC. I really did.

But what I loved was being closer and closer to the business and more closer to the entrepreneurialism. And so you kind of said, hey, you know, why does everybody else get to be a founder and not you? Why don't you do it? And that was a conflict of factors. AI came out and so it was literally like, was like, like you talked about moments where it was like handed down from literally like the heavens, this like once in a generation tech shift that made it possible. But I guess.

Anne Marie Segal (32:46)
No.

Cecilia Ziniti (GC AI) (32:50)
If people have a fatal flaw or like how do even know if you have one or is there an introspection process that is part of this board readiness that you talked about?

Anne Marie Segal (33:00)
Sure.

So this is one of the ways that a coaching relationship is so different than every other type of relationship. You know, we talk about level three listening, where you're not waiting for your chance to respond. You're not thinking about other things. You're actually really listening to the person. And so it's not exclusive to coaching. Sometimes you have someone like that in your life, but many people don't. Or if they do,

the person doesn't know anything about being a GC. And so they just can't benefit from it in the same way. But so for example, when I do interview prep, whether it's for a board position or a GC position or something else, sometimes if someone's talking too much, for example, one of your examples, I remember one time ⁓ recently I asked someone the interview question and she gave me the answer and it was one of those tough questions.

Why are you leaving your current job or something like that? And I read it back to her. So I typed it all out as she was talking and I read it back to her in this kind of monotone voice. So you said, buh buh buh buh buh buh buh buh buh buh buh buh buh. And I just kept going on and on and on and making it like, and then I said, what do you think of your answer? Because, and I said, do you feel like you answered the question? Do you feel like your answer was responsive?

Cecilia Ziniti (GC AI) (34:17)
Yeah

Anne Marie Segal (34:25)
Do you feel like it was convincing? So I'm not telling her it's not. And I even said to her, I'm just going to read it back to you, as if I was reading it out of a book or something, so you hear it without any of the inflection or anything. It's all a process of bringing awareness. And many people, when they hear their flaws, can change. And many people can't. And some of us are somewhere in the middle.

And, ⁓ but if you want to be on a board, you know, I say being a GC is like being in the Olympics or something, you know, and being on a board is kind like winning the Olympics or, you know, I mean, in the sense of like how good you really have to be to get to there. So, yeah, you're going to have to fix some things about yourself, everybody, not just the person who talks a lot.

Cecilia Ziniti (GC AI) (35:08)
Yeah. Yeah. Yeah.

want it at every

level. And I think it was a challenge because at Amazon, they were very disciplined about performance management. people talk about it wasn't quite stack ranking, but almost. And this idea of a fatal flaw that would prevent you from being a VP or AGC or whatever it is was very much a thing where, but it...

how good people are, like it's me at the company. I think about this a lot, like how much I can performance management, how good you got to be here in AI, you you think, okay, Cecilia, you're a CEO, you've reached the top. Well, guess what? Guess who I'm competing with? I'm competing with Claude, right? I'm competing with players with trillions of dollars. So I have to be that good. And everybody on the team has to be that good where, you know, the difference between a good piece of marketing and a great one.

Anne Marie Segal (35:59)
Right.

Cecilia Ziniti (GC AI) (36:11)
You know, Netflix, Reed Hastings points this out. It's not 10%. It's a thousand X. And so like literally this relentless, and this is where I think some of the self-awareness too of like, do you want to be in the game? Because it does require, you know, a level of dedication and focus very similar to Olympic training. That same CPO of Rippling talks about it where it's like, you know, this is the, there's a sport of business and you can win and you have to be nimble and adjust very quickly. And now of course AI has

has thrown into all of it, right? Where it's like, okay, if you're a very good athlete and then suddenly you're competing against people with an Ironman suit and you don't got the suit, you're going to lose. Like you just are. It's like if you're gonna do underhanded ⁓ free throws or something, like you're just not going to win. And so like, let's talk about AI. That's a good transition AI. So what are you seeing with AI ⁓ both at the board level and in the legal profession?

Anne Marie Segal (37:07)
What am I seeing with the AI? It's an interesting question. ⁓ So, well, so I recently heard a podcast that you were on and forgive me, I can't remember who it was with, you were saying, you can put it in the notes, you were saying, ⁓ you're explaining what GCAI does. And I was thrilled and enthralled because you just explained it so well and how it's...

Cecilia Ziniti (GC AI) (37:07)
What's your Yeah, what's your view? Yeah.

Anne Marie Segal (37:36)
different than just the kind of searches that you can do on your own and just the way that it works. I think, I know we're not here to promote your product, but I mean, think people who understand that, who understand like, we can't just have AI, you know, it's an LLM, right? You can't just ask it things and you're going to get the right answers. You have to really curate what you're asking. You have to be curious when you ask it.

You have to know the right things to ask it. You have to know the things to tell it not to do. know, like, well, it'll find whatever's most prevalent. So, you know, is this the current view? it, you know, is there any, you know more than me all the questions to ask. But I think that's a very important element of AI is the fit for purpose idea, which is what I knew J.C. AI was, but then hearing that podcast, I was like, wow. And she explains it so eloquently.

You know, I know why people are buying her product. I know why she has a thousand plus customers. You know, I mean, it was amazing. So.

Cecilia Ziniti (GC AI) (38:41)
And how about overall, you know, for companies like at the board level, it's, you know, we see a lot of boards talking about AI. We see, get a lot of legal teams reaching out saying, you know, we've got a CEO level initiative, board level initiative to AIFI everything. ⁓ Do you see anybody, I mean, obviously we, you know, we have a lot of exposure to legal teams using AI, but just in general and kind of the,

Anne Marie Segal (38:45)
Mm-hmm.

Mm-hmm.

Mm-hmm.

Cecilia Ziniti (GC AI) (39:08)
the world, are you seeing for companies doing this well? And then, you you've got kids that they're probably using AI for homework, what have you. Where does this lead? Put on your trend spotting hat. Where does it go?

Anne Marie Segal (39:17)
Mm-hmm.

⁓ So, yeah, the thing that AI does best is really tell you what, it kind of fills in your blind spots, right? It's very different. mean, I would say once you are an expert, I mean, the difference between a board member using AI and a student using AI, know, a board member using AI is like, either making their life

easier because they're ⁓ they're not taking so long to generate something or you know what is it that they haven't thought about so that they can fill that out you know that's the way I would see board members using it in terms of students my daughter actually doesn't use AI very much she's kind of you know she did it in a summer internship she's concerned and I agree with her that it's kind of bringing us all to like one conclusion it's kind of

It doesn't, it's really easy for AI to kind of flatten things out when you need a lot of nuance, but that's something you just need to be aware of. I don't agree that you shouldn't use AI as a result, but students, ⁓ I think unfortunately what I'm hearing is they're using it rather than learning, which is the other thing that worries me. ⁓ Where are we going with that? But, you know, again, it's just like any other technological advance. It's not like,

That means we shouldn't have it. It means we should be very clear about when and how and where to use it.

Cecilia Ziniti (GC AI) (40:53)
that. ⁓ Let's talk about attorneys, kind of like pretty new attorneys. ⁓ Say they're in their first five years of practice, this AI thing is a thing. ⁓ Let's say someone's in big law and they hear this and they're thinking about a move in house or they're thinking about their next move. Give us your, we like checklists, give us your checklist of what they should be thinking about and making a career move.

Anne Marie Segal (40:59)
Mm-hmm.

Mm-hmm.

In terms of AI or in terms of generally? Uh-huh. Yeah.

Cecilia Ziniti (GC AI) (41:22)
general. mean, think AI is kind of in the meme, right? Because,

you know, sort of like there's data around less juniors being hired. I talk with law firm partners, they say they're busier than ever. So I don't see that. But ⁓ just in general.

Anne Marie Segal (41:33)
Mm-hmm.

Right, so I had mentioned to you right before we started that when I heard that GCI was at Glock, sorry, at Glock, ⁓ that there was a keynote speaker, ⁓ Zach Cass. And what he said, and I think it was amazing to think about it this way, this is a legal operations conference, so the idea is, what is AI doing here? How are we thinking about AI? I didn't hear it, but I read about it afterwards.

⁓ What is it that we wouldn't want to delegate was the thing that sounded so interesting. If we have AI and we can delegate almost everything, what is it that we as lawyers don't want to delegate? the want is an interest. I don't know if that's exactly the word to use, but that's the way I think about it. It's not just what shouldn't we delegate. That just sounds so normative. But really, from a creative, open perspective, where is it that we bring value?

And so that's the way I would be thinking about it, even as a junior attorney. Like, where is it that I'm going to bring value to my law firm and then as an in-house lawyer? I always say, should I hire you is the essential question in any interview. And it's the same here. Like, if there are things that are, you know, they're not going to hire you because you know how to do NDAs better than anybody else necessarily. You know, I mean, some

places might, but those are the sorts of things that are probably going to start to get and are getting outsourced to AI. In fact, you might've mentioned that on your podcast, the other one. ⁓ So think about where, what, I sometimes also say, what's your genius? know, like what do you bring to the table? And that's not a precocious question for someone three years out of law school. Maybe it's first year, you're not really sure of anything yet, but you know, that's where you want to start to hone.

as you're moving up and as you're thinking about moving over to in-house. And it's obviously a different skill set altogether. So to understand what that really means, and that's another place that AI can be helpful. You just type in, what is the value proposition of an in-house lawyer versus a big law lawyer? And then getting into the details specifically about yourself. As an idea generator, there's nothing better. There's really nothing better than AI. It's not a thought.

necessarily, but it's a thought assistant kind of, but it's just really, really amazing in what you can get. bigger shifts as well. I was a lawyer for 17 years and now I want to be a baker. What do I need to be thinking about? And you kind of tighten up what your question is and give some more details. But I go through...

that exercise sometimes with people when they want a big career shift and like, what would you be doing every day? Okay, so you want to be a baker, you love to bake, but what does it mean to be a baker or own a bakery? Like what are all the things that you'll need to do on a daily basis? And you've seen this as you made the change, the CEO isn't just, well, now I lead it all, there's like so much else, right?

Cecilia Ziniti (GC AI) (44:54)
Yeah, I mean, think it's this like AI to draw out the reality of what it's going to be. And like, you you said sometimes people just need to be told what they told what to do or they want to be told, you know, or someone say you're a CEO. Well, OK, like AI can do that. And then it's like, all right, the next step. And I think in my case for entrepreneurship, the advice I give all the time, people are like, what's your advice? I'm like.

One thing every week, one actual thing, a foot in front of the other. So you're gonna be a baker, okay, like scope out a location, okay, start baking for friends, okay, make a baking blog, like this like, do the thing. And like, I think that's what's hard because I do think some people can get just lost in the planning or the dreaming or the wishing or the next year or the whatever, which is where like the actual act of like quitting the job to do the next thing, I will say that was one of the best, the best things that happened to me was like,

I worked with Amjad at my last ⁓ company and it was like, hey, you seem really into this legal AI idea. ⁓ Is your head really in this role? And I said, no. And then we found a replacement and I started the company. And so I think that's good advice. I love it. So I'm an associate, I'm checking boxes. You know what the path of the firm looks like. Although you can shape that too, right? There are people that have these really interesting niche practices and

Anne Marie Segal (45:58)
Hmm.

All right.

Cecilia Ziniti (GC AI) (46:16)
are able to build those and lean into certain cases. You also get random stuff like, you know, pandemic was a huge opportunity for people to step up. Or, you know, I talked with one woman at a firm who, ⁓ she just always, you know, gravitated whenever a client had a breach, she would be on that. And then now she has basically a cybersecurity breach practice specifically, not just cybersecurity, but like what to do with breaches.

and she's on the Rolodex of Kroll and all these others. And she's built that practice, it's a great practice, did not exist before she got into it. It was just kind of a generalized privacy practice. So you can do anything, I think is my, yeah.

Anne Marie Segal (46:51)
I'm thinking

about something as you're saying this, which is also you don't necessarily have to leave the law firm to go in-house to do what you want to do, because sometimes it's just moving to a different firm, because maybe her firm wouldn't have supported her in that, for example. Instead of, you know, heading your head against the wall looking for an in-house role that's going to match that, maybe it's starting your own firm or, right?

Cecilia Ziniti (GC AI) (47:06)
Exactly.

⁓ Exactly, exactly.

And then by the way, if you do your own thing, then you're an expert that the company that wants that is going to seek you out. And then you can go out that way. So I love it. All right, let's go to lightning round. A book person or a mentor that shaped how you think.

Anne Marie Segal (47:21)
Thanks Natalie.

book. you can't see the title. The wisdom of no escape by Pema Chodron. It's she's a Buddhist nun.

Cecilia Ziniti (GC AI) (47:40)
Wow, Buddhist nun, all right, good, love it. And then something you wish someone would have told you before you became a lawyer.

Anne Marie Segal (47:50)
before I became a lawyer. ⁓

⁓ before I became a lawyer, you someone did tell me, and I wish I would have listened, you're gonna, your personality is gonna change completely and are you ready for it? ⁓

Cecilia Ziniti (GC AI) (48:05)
⁓

wow, that's big, that's heady, I love it. right, good advice. Okay, so Anne-Marie, this is a great conversation. I'm so glad we finally got to do this.

Anne Marie Segal (48:08)
That was heavy. So.

Absolutely. Thank you so much. It's great to see you as well. I'm toasting your success from here in Connecticut.

Cecilia Ziniti (GC AI) (48:20)
Likewise.

Here's

thank you and I will link in the show notes and we've got a book on interviewing if you want more sort of tactical advice. She's available at Seagal coaching. You can look her up or find her on LinkedIn. That was my conversation with Anne Marie Seagal, the founder of Seagal coaching, executive coach to general counsel and senior executives across six continents, author of Master the Interview and know yourself grow your career. Whether you're leading a legal team, working inside one, thinking about philosophical issues around being a lawyer.

or building the tools that empower them, head over to gc.ai and see how the most forward thinking folks in legal are doing their best work. Follow CZ and friends wherever you get your podcasts. Thanks and we'll see you next time.