The Tolstoy Test for Legal Leadership: Ron Bell of Collective Health (ex-Yahoo, Apple)

Ron Bell shares lessons from nearly three decades in Silicon Valley. From Apple during its near-collapse, to Yahoo’s formative years building one of the Valley’s first scaled in-house legal departments, to leading legal and administrative functions today at Collective Health.

In this episode, Ron Bell, Chief Legal & Administrative Officer at Collective Health, talks with Cecilia to explore what it means to be a strategic legal leader in times of transformation.

The conversation spans the rise of legal operations, how AI is reshaping legal work, and why companies don’t want “lawyers,” they want value. Ron introduces his now-famous “Tolstoy Test” for prioritization, explains why legal leadership is a team sport, and offers practical advice on staffing, humility, ecosystem thinking, and adaptability in a rapidly changing world.

Show notes:

• The evolution of in-house counsel in Silicon Valley
• Early adoption of legal ops and e-billing
• AI as a value accelerator (not a lawyer replacement)
• Strategic thinking in M&A and build vs. buy decisions
• The role of adaptability in modern general counsel leadership

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⁠gc.ai⁠ website

Transcript

Ron Bell: 00:00 Companies are really not interested in having lawyers. Like they're just not. They're interested in what lawyers bring them, right? Perspective, answers, values, deliverables.

Cecilia Ziniti: 00:17 Welcome back to CZ and Friends, where we talk with legal leaders, operators, and technologists shaping how companies move forward. I'm your host, Cecilia Ziniti. Today I'm joined by Ron Bell, the Chief Legal and Administrative Officer at Collective Health.

Ron and I worked together years ago, literally at Yahoo, and I've always appreciated him as a lawyer, as a leader, and as a person. He brings judgment and perspective to complex situations without making them heavier than they need to be.

He's got an incredible history in Silicon Valley, including working for Apple, literally not just pre-iPhone, but pre-Apple being Apple, basically. He's got this rare ability to keep things clear, human, productive. He started off his career at big law, has seen incredibly high-stakes situations across all kinds of industries.

And he spent nearly three decades across big law, public companies, high-growth tech. He was the general counsel of Yahoo during a pivotal chapter. He helped build some of the earliest legal operations functions and trust and safety functions in Silicon Valley. And he's led beyond legal teams as well, with HR and administrative functions as well.

He's got a long view on leadership, value, legal teams, all of it. And I'm happy to say he's a friend, was literally one of my first mentors. I was a patent and litigation paralegal at Yahoo back in the early 2000s. And Ron is one of the people who inspired me to go to law school. So very excited for this conversation. Let's dive in. Ron, welcome to the show.

Ron Bell: 01:44 Thank you for having me. I feel like 20 years in the making, right? Exactly. We've known each other a long, long time.

Cecilia Ziniti: 01:50 Literally incredible. All right. So you've lived through some big transitions, including, I would say, the rise of in-house as a function. So Yahoo doesn't get a ton of credit for this, but I would say it was one of the first kind of tech legal departments in the Valley. What do you have to say about that? What is in-house as a function?

Ron Bell: 02:12 Well, I think it's changed a lot, as you said. I mean, before, like, sort of the mid-'90s, a lot of it was managing outside counsel.

And then I think really the rise of the internet and technology and Silicon Valley was a big part of that, sort of bringing a lot of functions in-house for the larger legal departments, more specialized, global, interrelated, and with a focus not so much just on getting answers, but on driving value.

How do you be proactive and help drive the business forward and anticipate what the issues might be, anticipate what the policies might be and how you can shape them? And then working as a team, right, across functional, not just legal, but other business functions to help drive results for the shareholders. So it was kind of a switch.

If you think about the law firms as being very driven by their relationships, you know, with the individual companies that they're working with. It was about being a full-time stakeholder and sort of an in-house resident consigliere and a business strategist.

So I think a lot of that was driven by a lot of different factors in the environment, but that was really what the change was, I think.

Cecilia Ziniti: 03:28 I still remember a little story when we were at Yahoo. Your group used to be called the deal team. So literally like a commercial transaction deal team.

Ron Bell: 03:36 Yeah.

Cecilia Ziniti: 03:37 And I remember that they went through a rebrand and you're like, okay, we're gonna name it something else to reflect what we do. Why the rebrand? And what did you rebrand to, if you remember?

Ron Bell: 03:50 I don't remember what we rebranded to exactly. I think it was transactions and business counseling or something similar to that. It was because I think legal functions often get seen in one dimension. And if you just think about all the things that we do, there's at least three components to it.

One is just the basic maintenance of keeping the business running, the stuff nobody finds exciting, filing all the corporate filings, so on and so forth. Then there's the protection aspect of it. That's the risk management, right? The litigation, maybe some policy making.

But the aspirational aspect of it, the part that's in service to the business, thinking strategically, how can we make these contracts more effective, more revenue generating, better terms, better relationships with our partners, that part sometimes gets short shrift.

And I think it's important to think holistically about that because I think that's one of the, frankly, one of the mistakes I think we make as lawyers is we let other functions define us as the naysayers, as the risk bearers, right? And I think it's important to speak that language that lets them from the outset see who you are and what you're about.

Cecilia Ziniti: 04:57 Along that vein, you were actually pretty early in recognizing legal operations as a function. So tell us about that. What did you do? And if you can give us maybe even like a from/to of like, so Yahoo at the time obviously had millions of users, had a very advanced subpoena compliance team. It had, you know, I think probably hundreds of entities globally.

So very complex. That was the environment. What were you seeing at the time? And then how did that translate to legal operations? Of course, at this time, CLOC, the Corporate Legal Operations Consortium, did not exist. Legal operations as a function, I don't think was a thing. So tell us about that.

Ron Bell: 05:37 Right. Well, it's funny you mentioned CLOC because one of the first inspirations was a meeting I had with Connie Brenton, who's one of the founders of CLOC. And she kind of took me out to breakfast one day and we were just talking about the complexity that all the legal teams were facing, right?

The fact that now we had to go faster globally, across multiple jurisdictions, at least in the case of the internet companies, the laws weren't really well defined yet, the rules weren't defined. But we still had the—and the departments were much larger and more complex to manage because they were often multinational with a lot of specialists.

She was kind of saying to me, I think there's room for a new type of function. And I just saw it all of a sudden. We just need—we can't continue to operate the function the same way that we have before. We have to adapt the function to the new reality, which is all of the things I just said, right?

And that means a professionalization of how are we interacting with our outside counsel? How are we developing our people? What systems do we have to support our lawyers in getting the job done? And how do we know that we're delivering value, right?

The from/to would be like at that time, despite the fact that Yahoo was an internet powerhouse, one of the leading companies on the web at the time, the bills were all paper. And so they would be passed around. And often they were like these bills that would say like Yahoo, you know, legal general.

And it would have litigation items on it, have transactional items, have IT items. It'd be passed from, you know, father to son, you know, mother to daughter, like the Talmud around the office. And of course, the problem with this—everyone had to sign off on their piece. And the problem with this is it took forever to get the bills paid.

Half the time the thing got lost on somebody's desk, or somebody would go out on vacation and it would take like three years to pay the outside counsel. So the outside counsel were also like, you know, come on, guys, you got to do better. And this was also around the time that e-billing was just taking off.

And so I had a conversation with our then general counsel, Mike Callahan, and said, I think we can do things a little bit different. And to Mike's credit, and Mike has always been a forward-thinking person, he immediately embraced that and said, yeah, we have to do better. Go out there, find out what's out there and figure it out, right? So that's what we did.

And so the transition was literally from being a paper-driven—you know, monks in cubicles with little quill pens—to suddenly being able to bring to the work we were doing as a department some of the same technology, some of the same thinking that we were putting out there as a company.

And it was really transformational because then all of a sudden Mike could say in real time, here's how we're doing against our budget, and here's what's trending, and here's what's not, and inform the decisions at the corporate level in a way that suddenly went from we're kind of flying blind or at least three to six months delayed, to really being able to know where we were putting our spend and how efficient we were being and where we needed to make changes.

And I think that was hugely transformational.

Cecilia Ziniti: 08:37 How have you seen legal operations? How do you think about legal operations today?

Ron Bell: 08:42 So I had the very good fortune to hire as my head of legal operations a gentleman by the name of Jeff Franke, who's one of the leaders in the legal operations field now. Jeff was kind of my not just my head of legal operations, but my chief of staff, right? He was the partner in sounding out like what are we going to do as a function?

What message are we going to deliver to the team? What do people need to know? Where are we seeing the problems, and so on and so forth. So I think of legal operations now as kind of being the heart and soul of the legal department, right? These jobs of being general counsel are kind of lonely jobs, right?

There's only so many people you can talk to about problems. Everybody's got an interest, sometimes a personal interest, especially if they work for you and whether they get X project or so on and so forth, that history, perspective. Having somebody you can bounce ideas off of and brainstorm who is really there to help you be a better, more effective leader is a rarity.

And legal operations functions have that idea. I think too often they get jammed into that niche of we just want to implement some software. And your job is to sort of manage and be legal IT. But really, it's the opportunity to be a strategic partner. So I see that as—it is almost like the operating system of the department.

Cecilia Ziniti: 10:03 How does that show up for stakeholders, right? So your example of e-billing, you know, that sort of feels quaint now, but obviously helpful in terms of running legal like a business and really thinking like, okay, how do you mobilize resources, get the right level of risk, staff, et cetera. Cool with you there.

Wondering, is this something where, you know, when I think about the goals of a great legal team? And, you know, when I see AI, I see stakeholders noticing, right? So one of our users had their chief revenue officer say, you know, Amy, what the heck happened to legal? Like you guys are just on fire lately. This is incredible.

And the answer of what happened to legal was they were using AI. So that's cool. But I guess wondering, like, how do you see that impact? And you've been very close with boards, with CEOs, obviously, you know, that consigliere thing. You know, is there a from/to story there in terms of the impact?

Ron Bell: 10:58 Well, I think if you're talking about AI or even just the legal operations function, like I used to sit down with Jeff every quarter and we would talk about what's coming up, like what board meetings do we have, what information do we need to get together, what do we need to make sure we have for finance, what are we anticipating in terms of our hiring and so on and so forth?

AI didn't exist at that time, at least in our universe, but like today it's a tool for efficiency, for getting things done, for getting answers faster, for speeding up the work that you do every day. Companies are really not interested in having lawyers. Like they're just not. They're interested in what lawyers bring them, right?

Perspective, answers, values, deliverables, right? And AI is a tool to accelerate that, not to replace, I don't think, the lawyers, although there's some people marketing it that way, and I think it's silly.

But I think it's to accelerate the value chain and enable you to do more so you can focus on the things that AI is not maybe as good at, which is the, okay, let me think strategically and how do I build out these relationships and what do all the stakeholders here need to know? And what are the company values and how are those going to be reflected in my work?

Like AI is a statistical engine. It can give you some great predictions and answers around things that might be statistically an average, right? But if you're trying to think outside the box or apply things specifically to your company, it's a complement. And that's how I think it's best used, honestly.

Cecilia Ziniti: 12:28 I agree. So you said something super interesting, which is that companies don't want lawyers. Some of the faithful listeners to this pod are my parents, but my dad once gave me career advice saying, hey, you know, he's an entrepreneur.

Hey, you know, the amount that I want to spend on lawyers and accountants in an ideal world is goose egg, like literally nothing. Right. That was an inspiration to me to do exactly what you said, which is to think about it in terms of value driving.

And I, you know, I still remember we had somebody on the pod, David Morris of Snyk, and he said, hey, you know, it was really an apex moment for me when my whole team got invited to some product retreat or got invited to, you know, whatever, as really like, hey, this is super important.

So I guess in that realm of strategic answers and guidance, you've been involved in some pretty big transactions. Obviously, Yahoo famously almost bought Meta like three times and didn't do it, and you know, almost was bought by Microsoft.

So in an M&A context specifically, any stories you can share about sort of really driving that value or, you know, legal being part of that analysis in a way that is value that would not just be something you could get from an AI today.

Ron Bell: 13:46 Sure. And I'll be judicious because of course privilege and all that. You know, there was one acquisition we were doing where one of the questions that was on the table was do we build it ourselves, right? Or do we acquire this company?

The legal piece of that, the mechanics of that, you know, were relatively easy in either scenario. The sitting down and saying, this is what it will take to build it ourselves, this is the time, these are the contracts we'd have to put in place, these are the relationships we'd have to establish.

These are the trust and safety issues we'd have to be able to address.

Versus the time to market of acquiring a company that had already established a substantial presence in the area in which we were interested in, who had a good culture that was a nice complement to who we were and how we saw the world, which was geographically located in a place that would make it easier, right, to work with them.

And they were in SoCal, we were in Northern California at the time. And looking at it from the perspective of, you know, either way as a lawyer, I think you get to a result. Thinking as a strategist, we would pick up all their patents.

We would have that time, we would accelerate our time to market in a way that wouldn't have been possible if we built it ourselves. And of course, there were engineers that wanted to build it. And God bless them, right? There always are. And sometimes that is the right solution.

But where you're talking about a more mature market, you're a new entrant, you don't have prior experience in the area, and there's a way to accelerate the transaction, accelerate the value, acquire some valuable IP, right, some expertise, like that's the part where I think as an advisor, in any function, honestly, but certainly in a legal function, you've got to say, are we looking at this the right way?

Right? Are we thinking about the chessboard the right way? What if we turned it around and thought about it a different way? That's a big part of being a legal counsel, I think, is helping the business place the right bets.

Cecilia Ziniti: 15:59 Do you ever have to temper yourself or your teams from the desire to be right?

Ron Bell: 16:06 Every day, at least for me. I have to remind myself that I'm not right. And I mean that like not like I'm deliberately wrong, but like there's a challenge that comes with expertise and tenure, which is if you're right enough, you start to drink your own Kool-Aid. And that's the most dangerous thing, I think, for a lawyer to do.

Because then you don't start asking the corner cases, what if I'm wrong? What if we did this a different way? What if we don't deliver on the way that I'm suggesting that we do it? Is there a more efficient and effective way to do it? Not just the way we've done it in the past, but could we use technology like AI to accelerate this process?

And would that be more helpful? I think it's really important as an in-house counsel, and particularly as a general counsel, to be humble and to say, I don't have all the answers. I know people who can help me get the answers. I'm gonna surround myself with really smart people who can help me brainstorm and think about the answers and often drive them themselves.

But I don't need to be the quote unquote the smartest person in the room, right? I don't need to be Sherlock Holmes. I need to be more like Columbo. I need to ask a lot of questions. I need to, right, come in in my rumpled raincoat, right? Like, I just have one more thing about the marketing program. It's just bothering me for my report, right?

And help people, smart people that you're working with who also have their blind spots and their passions and their interests, to come to decisions that they can feel proud of and that are the right answers for them after considering all the different angles.

So, you know, I don't find that I work with a lot of—and I certainly don't feel on my team I have people who are arrogant in any way, but I think as a lawyer, every time I have to remind myself you lose credibility if you are trying to be the smartest person in the room. Help other people who are equally smart as a partner in getting to the right answers.

Cecilia Ziniti: 17:58 You've used what you call the Tolstoy test. I am so intrigued by this.

Ron Bell: 18:03 I don't read Tolstoy, but you can fill in your favorite Russian novelist or any novelist.

Cecilia Ziniti: 18:08 Exactly, exactly. No, it's good. So tell us about that. What is it and does it relate to what you just explained?

Ron Bell: 18:14 Yeah. Well, the Tolstoy test is just a framing, right? For like everything that we do every day. There's—you can—every company, every company at any stage, public, private, is on fire a thousand different ways.

There are, you know, a hundred issues or more that you can spend your time on, most of which will not move the needle, some of which are essential, right? You got to do your corporate filings every year, your taxes every year, boring though it may be, you got to do it. Make your filings on time.

But you can really exhaust yourself and your business partners by trying to run down a lot of things that in the end don't really matter. And so for myself, I sort of came up with this benchmark, which is not I'm going to ignore everything, but how do I know if something is really important?

And the answer is if it's something that, if we get it wrong, is going to be so melodramatic, catastrophic, that it would make a great plot for a Russian novel. And, you know, the people who suffer, you know, who go to the "why, why did I not do it differently," right?

That person, if you're going to be that person, if your colleagues are going to be that person, if your company is going to be that person, spend the time on that, because that's 80% of the risk, maybe 80% of the value, right? Because it doesn't have to be a plot-negative story. Think in terms of, give it a little bit of perspective.

Not every haunting is a Ghostbusters-level event, right? You don't have to bring out the particle beams for everything. Take a step back and say, is this something I need to spend time on and what are the consequences of it?

And then you'll be much more focused and you'll also be less exhausted and your business people will appreciate you more because you won't be the lawyer who comes in and says, you know, there's a new state law every day, which there is, and we need to change everything tomorrow, which we may or may not need to do, right?

Provide a path, provide perspective, help guide it.

Cecilia Ziniti: 20:12 I love that. It kind of—I feel like now, you know, people talk about this as like main character energy, right? And it's like, okay, are you really the main character? Is whatever law, you know, one of the 16 new California laws, does it warrant main character energy? And the answer is probably it doesn't. But I love that.

Ron Bell: 20:32 It also helps you honestly think about other functions too, right? Because often the big dramatic legal issues can be marketing and communications issues as well, right? They can be board issues. So it helps you to sort of think about are there other stakeholders I need to bring along on this journey and get involved.

So it also makes it less of a lonely function, I think.

Cecilia Ziniti: 20:51 I agree with that. You've talked about using RFPs and about getting the right people in the right job. What is your advice on kind of staffing at large? And now let's take a step up. Like, so obviously you have legal, but you also have administrative, HR, other things.

Like, you know, if someone, a listener, is lucky enough to be in a position where they're deciding how to staff something, either a new litigation or any kind of matter, really any problem at the company. So I'm assuming you're, you know, you said you're a problem solver. Things come to you.

You know, it's a healthcare company that you work for today, Collective Health, you know, huge plethora of things that could be. What goes through your head in deciding who's the right person or team or resource for a job? And how do you get good at making those decisions?

Ron Bell: 21:41 Well, experience and falling on your face is how you get good at making those decisions. But also watching what works, right? Seeing what works for others. I think when you're staffing, I try to apply two rules. The first is kind of like a privacy concept, right? Minimum necessary information, minimum necessary staff.

More bodies does not necessarily make something more efficient or effective. The right bodies with the right experience, the right perspective—who's done a deal like this before? Who could benefit from doing this deal? Are we going to do something, you know, is this a line of business we're going to do in the future? Great. Who's going to be our expert?

Who's going to be our point of contact, right, for that? We've often used sort of a primary contact model for lawyers. So, you know, you have repeat clients, you have repeat businesses that you work with, transactions you work with. And of course, in that case, you might bring someone in.

But then it's also looking around like, are these cases where there are other functions within the legal or in the company that you need to bring along too? So privacy would be a good example, security would be a good example, international lawyers. Can I get their input? How do I get their input?

Let's say if I'm doing a deal early enough in this process or this procedure that I'm putting together or this contract, that it's going to make a difference, right? And then really encouraging people, you're not just there to play your instrument. You're there to be an orchestra and to have a symphony together that is beautiful to the ear, right?

And successful for the company. So encouraging collaboration, regardless of your level. Like I don't really care what people's levels are, right? Like it doesn't matter to me. Like at the end of the day, I want people to work together, be thoughtful, inform each other, keep each other up to date on things that matter within the business.

And so I also think there's a cultural component to staffing as well. Make sure that not only people have the right knowledge and mindset on how to do whatever it is that we want to do, but also on how to work together.

Cecilia Ziniti: 23:49 I was speaking with, well, actually, this person was from Yahoo, but a friend in finance. And I had been struggling with finance as a function because now as a CEO, I'm, you know, I would say I manage finance now, had never done it before. And the financial model was confusing to me. Anyway, I was struggling with staffing that.

And I talked with my friend and I said, hey, you know, how much would you expect that, you know, the stakeholder, in this case me, the CEO, would understand of the financial model and what goes into it and so on.

And the response was kind of similar to what you said, which is, you know, if I had to explain to you how to play the saxophone, like it would be laborious and it would suck and, like, or you know, someone explained to me how to play the saxophone, like all the different parts, whatever, like it would be a difficult exercise, probably not worth it.

But the advice from this person was, hey, but you know what good saxophone music sounds like. And when you're listening to it, you know, and that symphony concept is the same thing where it's like, as the leader, I'm assuming, you know, when you first took responsibility for HR, you hadn't necessarily done it before. How do you know what good music sounds like then?

And do you, you know, did you have to shed some of the legal knowledge? When did you kind of start wearing the hats? People use the hat metaphor, people use other metaphors, but how did that evolution happen for you? And what advice do you have for others?

Ron Bell: 25:18 Well, that's quite a question. Let's talk first about doing a function other than legal or taking that on, like the people function. First thing you got to do is remember it's a different function.

And we lawyers get really comfortable with the way that we operate and the way that we give answers and the way that we provide things. People is a whole different ball game. Obviously, there's a lot of legal components to it, but it's also emotion. Like compensation is not just a question of like, is it quote unquote consistent with market? It's also a psychological question.

Does this person feel motivated? Are they being compensated relative to their contribution to the company? And many of the conversations you're having are the softer skill conversations, which lawyers like clean answers, right? Like we like to say, this is the way to go, this is the way not to go. Being a chief people officer is often about the gray, right?

There's 20 different ways you can return to the office. None of them are illegal. Some of them have more friction associated with them than others, and there's a communication component. So it's relying on people who are in those functions to help you understand the questions to ask.

It's obviously looking at external resources if you have it. It's understanding the cadence of the function, like when do you do compensation decisions or promotion decisions or whatnot.

And then working backwards and trying to not ignore the lawyer part of it, but remember in that function, you're acting as a business person as well as a lawyer, just as the GC, you're acting as a business person and not just as a lawyer. But it's a little different when you're seen as the person in charge of people or something like that.

The larger issue, I think, Cecilia, independent of that, which goes to part of your question, is I think one of the most important pieces of advice I could give to somebody. I was at Yahoo for a long time. I think almost 17, 18 years, I lost track of it. It was a long time. So I was in one place for a long time, not in the same role.

And the benefit of that, I think, was that I got to experience firsthand that old saw about the blind man and the elephant, like one grabs the trunk and says it's a snake, and one grabs the leg and says it's a tree. And the answer is the elephant is all of those things. And companies are a lot of different functions and ecosystems, internal, external, and so on and so forth.

And so one of the best things you can do for your career to develop that mindset of service is to start thinking about who are the necessary stakeholders for every problem? Who's going to be concerned with this? Is finance concerned with this? Is the CEO concerned with this? Is the board concerned with it?

Outsiders, the investors, the regulators, like who is concerned about this? What would they want to know or what would they want me to do in this situation? And am I or my team doing those things, providing that information, thinking about how to draw that circle, and then doing that, right? And what are some examples?

I mean, as lawyers, we always see examples of things that didn't go well, right, elsewhere. But what can I learn from those examples that might illustrate how I do that? Because I think thinking in terms of stakeholders and ecosystems gives you a much better perspective. And it becomes much more important the more senior you become in the department.

And certainly for the general counsel, where you're leading a function of the company, but you're also a leader of the company. So you pull one strand and you have the world's best contract and it's airtight, but it slows down the commercial pipeline to a crawl, that has consequences, right?

As lawyers, we're always adding friction or we're speeding things up. So thinking in terms of ecosystems, I think, is also important. And that's true also in the people function.

Cecilia Ziniti: 29:02 One of the things you reminded me of is—so there was maybe two or three years ago. I don't hear about it as much now, but there was a trend around this sort of hating on middle management. So it was like at Meta, you know, it was like, okay, we're gonna have a span of control where any one manager is gonna have nine-plus reports.

And the idea is that the people doing the work should be doing it. And, you know, even now for me today, you know, I get to choose what kind of org I want. Is it gonna be flat? Is it gonna be more hierarchical? And you know, I've obviously had different models. I was at Yahoo, I was at Amazon, I've been at a variety of small companies.

But that kind of ability to see the ecosystem as you described is a little bit in conflict with that view as expressed. And you know, I think AI, other forces, return to work, the super high revenue per employee that a lot of these tech companies enjoy are all factors in that. But how do you reconcile that?

And do you share that sort of, I guess, at least expressed bias against folks in the middle?

Ron Bell: 30:22 It's a great question. First of all, I would say like, where does that come from? Companies don't tend to grow—you know, like when you read the business case studies, it's always like, it's always very efficient. You know, then the company did this and that and the other. I mean, the reality is like, we're doing X. Okay, I think we need an expert on that.

Let's bring someone in. Oh, someone left. Let's restructure and put the—and like, there's all these decisions that get made that sort of leave you with a hodgepodge. So every so often it is helpful to take a step back and say, okay, if I were starting from scratch and looking at where we need to go, does this make sense? Do I have the right people in the right roles?

Do I even need all the roles that I have? And what do I need going forward? And I think that's helpful for companies and for departments, independent of any bias against middle management.

But because many times people are trying to solve problems by bringing in other experts or other resources or amassing teams of scale because they perceive that'll let them move up and so on and so forth. There's also a need, again, to just look and ask yourself those questions, right? Because organically you might not get to the right place.

That said, I don't have a bias against middle management. I have been in middle management, and there are many middle managers who have worked for me. To me, it's really a question of how quickly and effectively can you make decisions and act. Are you overstaffed or understaffed?

And are you thinking sensibly, right, about how you're building your business? And I think sometimes these things are just shortcuts. If we're honest, sometimes these things are shortcuts, not even aimed at legal, but because the company as a whole hasn't been as attentive to that, right?

And I find functions at a company, especially one that's growing quickly, mature at different rates. If you invest a lot, like you're investing a lot in tech, I bet your tech team is awesome. But if you don't invest a lot in marketing, which you do, but if you didn't, your marketing team would be lagging.

And at some point, your marketing team is behind your tech team in terms of staffing and resourcing. So then the question becomes how do I restructure it to balance that out if it's important that I have better marketing, right? So I think these things are tools and shorthands. I'm not a big fan of things like middle management.

We don't need middle management, or we don't need no stinking lawyers. Like at the end of the day, I don't, you know, I don't know whether you do or you don't, but I know it's a question that a mantra doesn't answer.

It's maybe a rule of thumb, but you know, maybe you should look at the other fingers too every so often and think about if that's the right call for you at that time and in that place. And maybe it's using technology, maybe it's bringing in more people, maybe it's restructuring, whatever it may be.

Whatever makes you more efficient, effective, capable, able to execute, that's what you should be thinking.

Cecilia Ziniti: 33:09 I love that. I heard a podcast this weekend by the CPO of Rippling, the HR software company, and he said he's got a mantra, or at least somebody mentioned that, to your point about understaffing, he said, you know, you want your teams to be like a little bit dehydrated.

So they're like thirsty and motivated and moving fast, but like you can't obviously have them, you know, passing out. I guess like, do you see that? You know, at Amazon actually, I would say it pretty intentionally understaffed in-house lawyers relative to revenue. And the idea was that it would force focus on the most important things. Have you found that?

Ron Bell: 33:46 I think that's an excuse, honestly. I think people say it's gonna force focus on the most important things. Well, what they really want to do is keep the cost down and they see the legal function as maybe an adjunct to that.

Having said that, you know, look, every team—I do agree that it's useful for teams to be a little lean because it does force prioritization.

However, I would challenge the notion that legal teams as a general rule should be starved because legal touches so many other different functions that if you have, for example, a commercial legal team that can't keep up with the deal flow, you're not going to close the deals and book the revenue. And so, yeah, sure, maybe you can accelerate that with other tools.

Doesn't have to be people, it could be GC AI, for example, right? Could be helpful.

But make sure that your staffing is appropriate to the business need and making sure that teams that touch so many different functions and can be a huge value accelerant, strategic, intelligent execution, are not impeded in a way that literally makes them the molasses that slows down the whole operation.

Because what isn't fair is to understaff or under-resource and then look at the function and go, why can't you make this happen? Like, and that happens all the time, it happens all the time, right?

But philosophically, saying like, I don't want to start with a hundred people or a thousand lawyers, sure, start there, but then map it to what reality is and what you need to do. And not every function is different and not every industry is the same.

Cecilia Ziniti: 35:15 I see that across the board. I see that with our customers, I see that with us. You know, we obviously, because we sell to lawyers, everybody wants to negotiate our MSA, including a small deal.

Ron Bell: 35:26 And so it's been really interesting, and then you tell them afterwards, if you used GC AI, you would have negotiated this faster.

Cecilia Ziniti: 35:33 We are incredibly lean; our GC, she's amazing. You know, we—but these issues, it has surprised me how much, you know, it really is the day-to-day issues of like we've got the end of the fiscal year coming, of like, okay, legal is like a revenue driver in this scenario of like, you know, holding firm.

And then there's been the rise of the deal desk. And, you know, yeah, super fun. That resonated a great deal. I knew that middle management comment has always kind of sat weird with me, even though the proof is in the pudding in terms of Meta's revenue and how fast they've been able to move and the plethora of issues that they deal with.

But that was definitely something that I at the time was a little not sure about. All right. So let's see. You mentioned AI. So let's talk about AI. Heard of it. Yeah, let's jump into that. You've been in tech, you know, since forever. Literally at Apple in the '90s, right?

So I gotta ask the question, did you know then that Apple would be what it is today?

Ron Bell: 36:35 Clearly not, because I left and went to Yahoo. But I was there. I will say I was there through Steve Jobs' return, the launch of the original iMac, and the last, I think the last product that I worked on—I supported PowerBooks, printers, and displays.

And the last product that I helped contribute to, I shouldn't say worked on, because that's probably a little highfalutin, was the iBook, which was one of the first, if not the first, laptop with Wi-Fi in it.

Cecilia Ziniti: 37:03 Oh. Okay. So you left Apple, though, because it was, I guess, a time of rebuilding for Apple.

Ron Bell: 37:10 Apple when I started, which I think was—I'm not even sure. When I started at Apple, let's just go with that.

If you look it up on LinkedIn, when I started at Apple, the first day that I joined was the day that I think it was Wired magazine that came out with a cover that was the then multicolor Apple logo, surrounded by a crown of thorns and a single word: pray. This was my first day on the job. I mean, Apple was really struggling, right?

It had not—you know, it had the Macintosh, it had the early Macintosh, but there was a lack of focus. There were a lot of different products that were going on. It was a large company. It was seeing inroads into the education area, which had been an early strong point.

Laptops were not—I mean, Apple laptops were great, but they were more expensive than their comparable PC counterparts. And so, you know, it was a challenging, challenging time.

The company actually took, if I recall, I don't remember if it was a loan or a patent cross-deal, but there was a deal with Microsoft at some point in there, literally to get the money to keep it afloat longer. So we would see layoffs on the regular. So it was a really, really tough time.

But you could see after Steve returned and after the company began to focus on not a hundred products, but say four or five, you could see that discipline and focus returning, and you could see it beginning to move into the ascendancy. Could I have called out how it would be today? No.

Although it is funny that some of the execs I supported back then, including Tim Cook, are still there. They've done very, very well. Yahoo, on the other hand, was a young company that was lighting up the world as one of the formative portals in the internet space.

And, you know, so the—I made—I thought that was a technology that was worth pursuing from a career standpoint because it seemed to be a faster growth, more differentiated area than say hardware and software were. But, you know, who could have called it? Yeah.

Cecilia Ziniti: 39:09 It was—I mean the prayers clearly worked, right? $3.8 trillion later. It's incredible. The thing is, you can't know. I mean, this gets to your thing about decision making, right? Like you cannot know at the time.

And I had a mentor tell me, you know, hey, you live in Silicon Valley, you're gonna have a bunch of near misses, and you're—you know, this person is my mentor, so they were pretty positive. They said, Cecilia, you're really smart. So you're probably gonna have like eight near misses where like you could have joined.

We had folks from Yahoo who joined Meta very early, that left or joined Google relatively early, and you know, they own islands and whatever now. So I mean, separate from that, like, you know, this satisfying, incredibly rewarding career that's taken you here, like you've done okay. So let's go back—let's talk about AI.

So you're not—you've obviously seen tech very early. You saw the internet, you saw Apple, but you've seen concierge medicine, other innovations. What's your view on AI? And then what's your view on AI for legal work?

Ron Bell: 40:10 Well, I think AI is and has the potential to be one of the most transformative technical advances ever, right? Because it has the capability to interact and simulate some of those higher level thinking processes that previously we haven't. Like you haven't had technology that could curate marketing or edit your contract previously in a way that you could do today.

So that alone is a huge gain in efficiency. Sometimes, unfortunately, it will cost jobs in some cases. That's amazingly transformative. And then to move things between languages and cultures, right, on the fly, right, and rewrite your copy, like that's incredible.

I think we are going to see way more use of it in ways over time that make more sense. It feels like we're going through this period where everybody's like, you know, can AI do that? And they're like, sure, sure. It can absolutely do that. It can fly your car, sure.

We'll figure out, as we did with the internet, where the places where it's strong and the places where it is less capable are, and we'll apply it sensibly over time. And I think the place to apply it sensibly right now is as a tool to help others, right, rather than in all cases as a standalone tool to do something independently.

Maybe customer service, some of those things within a limited bound makes sense. But I think ultimately it's gonna be more of a tool. For legal, look, I think legal teams are probably a bit, if we're honest, enamored of AI and fearful of it at the same time, right? Like is it gonna replace me? Is it gonna take my job?

Is the ability of AI to spit out something that purports to be an NDA instantaneously gonna be quote unquote good enough that nobody feels that they need lawyers? I don't think that's the case. I think it makes the easy stuff easier, just like forms did before it.

It makes you a better, more effective attorney who can get more things done and make sure you're pressure testing things against perspective, right? Like have I thought of all the issues here? Is there anything I missed? Is there something that's unclear? Testing it against potential audiences. If I'm a board member looking at this, what questions do I have?

So I think it's a huge value accelerant for that. Where I think we will struggle a little bit is there's an entire generation of people who will come in and start using AI and won't yet have developed maybe some of those strategic chops to think about the higher level stuff.

And that's gonna be a challenge for the profession in terms of making sure that we're also mentoring people and helping them not to over-rely on the technology and to have good—just as calculators—before calculators didn't replace scientists, you have to have good math sense. Of course, you use a calculator, but also know that doesn't really make sense.

Like, you know, know when to question the answers and ask questions. I think that's something we'll need to focus on as a profession to make sure that we're helping the next generation be as effective and, using the technology, be even more effective.

Cecilia Ziniti: 43:12 Awesome. All right. Ron, you've seen the legal profession, you've seen in-house legal evolve over a long time. If you could leave listeners with one thought about being a great legal leader, what would it be?

Ron Bell: 43:28 Well, the first thing is adaptability. Probably the core thing is adaptability. The technology will change, the people will change, the companies will change. You were using the analogy of like you join a company and you don't know where it's gonna go and so on and so forth.

You don't really know what technology—I mean, the technologies, the companies that I have worked with in my career didn't exist when I graduated from law school. Don't be afraid of change, embrace it, but also be conscious on the parallel. Technology brings a need for change. Change management. Leadership brings a need for change management.

That is something as a leader that we need to focus very intensely on and help tell the story, bring along why this advancement makes sense, or this change in the department and procedure makes sense, or adapting our contract makes sense.

Help thread that narrative, help people with the change management, and help yourself not get locked into one vision of the world. Always be thinking about where's the world going, where's the puck going, and try to be there yourself.

Cecilia Ziniti: 44:30 Love that. All right, let's go to the lightning round. What is a myth about being a general counsel that you'd like to debunk? Or are there any myths about Silicon Valley, about GCs, anything?

Ron Bell: 44:46 First thing I learned as a general counsel is it's a team sport. No general counsel knows everything, and every general counsel has a lot of stakeholders that are counting on them every single day. The board, the CEO, the regulators, their direct reports, their other functional leaders. You are both the boss and you are not the boss.

Cecilia Ziniti: 45:08 The boss and not the boss.

Ron Bell: 45:10 And the sooner you realize that you actually, in a way, had more freedom when you were in that junior role when you first started in the department than you are when you're in the senior role, where everybody's looking to you for the answers that nobody has, and there are a thousand things on your plate, and you got to figure out your way.

And everyone has a claim on your time and a legitimate interest in what you're gonna say and making sure that you do it right, great responsibility. But as gentle Uncle Ben said, with great power comes great responsibility and great accountability.

Cecilia Ziniti: 45:41 I love that. All right. So book, idea, or mentor that has shaped how you lead.

Ron Bell: 45:47 Oh, that is a wonderful question. I would say, as an idea, you know, I had an interesting experience once, which was I was given one of those online photo assignments, like someone will post, like, take a photo of X every day, and it was like, take a gloomy, moody photo. And I thought, I know exactly what I'm gonna do.

I'm gonna go to a cemetery in Colma, which for those who are around here, is sort of this area outside of San Francisco where San Francisco has a lot of cemeteries, and that's where they are.

And I went to this really old cemetery with a lot of headstones and tombstones, and I was starting to take photos, moody photos, and I realized all of a sudden, I didn't know the vast majority of the people on the gravestones. The rich and the poor may have had bigger or smaller gravestones, but they're in the same place.

And many people in the cemetery had been buried there longer than they had been alive. And in the end, all of them would. And what I took from this is a reminder that accomplishments and fame are kind of fleeting, right? There were 12 Apollo astronauts. How many of them can you name? And they literally went to the moon, right?

And so the experience really reminded me to think about the long-term consequences of my decisions and the people I'm working with and the legacy I'm building and how I'm going about my life, right? Am I being a jerk? Am I acting with integrity? Am I growing people?

You know, our lives are short, and what lasts is the legacy that we build and how we treat others and the dreams we help to elevate. And I think all of us are candles. And I'm Jewish and we just got through Hanukkah. So you use the center candle and you light all the other candles.

So all of us can be the light to light everyone else and make our time here better. So that's how I try to think.

Cecilia Ziniti: 47:35 Wow. All of us are a light. Incredible, Ron. Thank you for joining me and bringing such an incredible perspective to this conversation.

Ron Bell: 47:43 Thank you for having me. I'm just delighted to be here.

Cecilia Ziniti: 47:46 What a delight. That was my conversation with Ron Bell, the Chief Legal and Administrative Officer at Collective Health, and who reminds us that we can all be the light, that great legal work is about judgment. He had so many nuggets of wisdom here.

I just—I don't even know how we're going to do the social post around this podcast because, you know, the boss and not the boss, be the light, recognize the elephant, all this incredible wisdom. Thank you so much.

Follow CZ and Friends wherever you get your podcasts to learn how legal teams are using AI to work smarter and better and implement some of the leadership things that we talked about today. Visit gc.ai or find me on LinkedIn. You can find Ron on LinkedIn as well.

He's very active on socials, so you can find his wisdom about AI, leadership, and everything else on LinkedIn as well. Thank you for listening. We'll see you next time.