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Unlocking Success in In-House Legal Roles: Lessons from Doug Luftman, ex-DGC @DocuSign
162 Plays1 year ago
If you’re an in-house attorney, how do you set yourself up for learning and growth throughout a long career? How should you define success? Is it being named the General Counsel of a high-growth company? Or are there other paths for an interesting and inspiring career?
Join former DocuSign Deputy General Counsel Doug Luftman for an in-depth conversation around mentorship, management, and fulfillment at work. We talk through how Doug positioned himself to take on executive-level leadership roles, including as General Counsel of two different tech companies. We’ll also explore how he learned to thrive in high-pressure, cross-functional environments where constant learning and growth were required. And, in what can be a challenging job hunting environment, he’ll share tips for managing unexpected career transitions and emerging stronger on the other side.
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Transcript
Introduction to Doug Luffman
00:00:03
Speaker
Welcome listeners to The Abstract. My name is Tyler Finn. I'm the Head of Community and Growth at Spotdraft, and I'm so excited to be joined today for our second episode by Doug Luffman.
00:00:19
Speaker
Doug has a long and storied career in Silicon Valley, across Fenwick and West, Palm, which she was at when they were acquired by HP, serving as general counsel of a number of high-growth technology companies that have been sold, and most recently as deputy general counsel and chief privacy officer of DocuSign. So excited to have you on the podcast, Doug. Welcome.
00:00:47
Speaker
Thanks, Tyler. Looking forward to our conversation, and thanks for having me here.
Reflections on 25 Years in Silicon Valley
00:00:52
Speaker
Me too. We've known each other for a while, so I think it'll be conversational. I give our audience a little bit of your background and your career, but any highlights that you would share off the back of some of the most interesting roles that you have?
00:01:08
Speaker
Oh, boy. I think you summarized a variety of the companies. I think it's more about being in Silicon Valley over the last 25 years and really seeing it going from consumer electronics and hardware companies to software as a service. And now, chat GBT and artificial intelligence and the likes. It's been pretty exciting being in the Valley over these over two decades and seeing where things are going and just being part of the history of Silicon Valley.
00:01:33
Speaker
Yeah, here at Spot Draft, we are paying a lot of attention to AI, chat, GBT, and seeing a lot of buzz about that in the market for sure. I wanted to start by going back to the beginning of your career.
Transition to In-House Roles and Tech Interest
00:01:45
Speaker
You know, you started as outside counsel at Fenwick and West. You actually did go in-house pretty early on and took on a GC role. And then, you know, throughout your career, you continue to pursue other legal executive positions at both private and public tech companies.
00:02:03
Speaker
Specializing in tech, the audience might not know this yet, actually. You were an electrical engineering major and undergrad. How much of the sort of specializing in tech was your interest in hardware versus a career choice and seeing tech as a sort of huge opportunity? How did you think about picking this sector?
00:02:22
Speaker
Yeah, I think it really came down to the dynamics around technology is that basically in the late 90s, it was the thing from the standpoint of impacting everything from the internet to consumer electronics to data, data centers and the like.
00:02:39
Speaker
And so, I think that's what really intrigued me about it, and one of the reasons why I came to Silicon Valley. I had the opportunity to look all around the country, and it just kept coming back to just this really exciting exponential growth and doing really new and exciting things. And also, I think the work philosophy and mentality in the Valley has been really refreshing as well, where sometimes it gets that cowboy culture, but in the same topic.
00:03:02
Speaker
It's really just this exciting environment where you kind of think outside the box and you're encouraged to. And it's not about risk elimination. It's about assumption of risk and really just going in with your eyes open and really just trying to make a difference.
00:03:14
Speaker
That's a great perspective to have, especially as the company's lawyer too, being willing to balance both the risk side and the opportunity side and innovation side.
Advice on Transitioning to Executive Roles
00:03:23
Speaker
You've served as GC for a number of companies throughout your career. How did you position yourself for those legal executive positions, I would say, not always with the GC title, but legal executive positions? What do you think?
00:03:37
Speaker
businesses are looking for. I'm thinking about this for those folks who are out there who may be contemplating wanting to make a jump to a GC or executive role sometime in the next few years. Yeah, I think one has to be careful all about the type. We hear about VP of Legal, which I suspect we may talk a little bit more about later, and General Counsel and the like.
00:03:59
Speaker
I think it's really more about looking at what you want as a career trajectory and saying, look, if I want to go from either a specialist to a generalist, being a generalist means you need to think bigger picture. You need to be able to connect the dots between different functional areas within a company, whether it's a product development, corporate compliance, sales and marketing, government affairs and the like.
00:04:20
Speaker
And then also, I think it's also about building an executive presence, right? I mean, when you write an email that is three pages long and exec is not going to want to read it, so you want to think about the audience you're engaged with and also kind of really better understanding where everyone is kind of coming from. And then really developing that broad skill set. I mean, it's not necessarily being a mile wide an inch deep, it's more along the lines of really picking those areas that are truly your specialties.
00:04:44
Speaker
and really refining those, and then where you may not have as much depth, knowing where your limits are and knowing where you need to develop until you build enough of the skill set to show that you can basically tackle all the things that a company needs. It's funny you say three pages, not being what another exec might want to read.
00:05:02
Speaker
I was at an event recently where we were talking about working with finance and CFOs, and the same thing was said there, which was three bullets, not three pages. Because if you have three bullets and then three pages afterwards, they're probably only going to read three bullets.
The Role of Managers in Growth
00:05:17
Speaker
I wanted to talk a little bit today with you about how you've evolved from sort of role to role and managers that you've had in the past who have been willing to let you grow, offer you new opportunities, perhaps versus those that have not given that same level of opportunity and where you've had to look outside and think about finding new opportunities.
00:05:43
Speaker
And so, how have you thought about that throughout your career? How does that interplay with that concept of being a specialist versus a generalist that you were just talking about? Have you approached it? And then maybe after that, I'm going to ask you about how you think about it in the context of the teams that you've built to and giving your new team. So with regard to this, I think it's a couple of different dynamics. I mean, let's talk about maybe the company overall and then getting into specifically the manager characteristics.
00:06:11
Speaker
From the company overall, I think what you're always looking for is a work culture and a company culture that basically encourages professional development, growth, and the like. Really, often I think people look at companies just from the standpoint of the name. There are many companies out there that you could probably name that basically the work culture does not fit the public persona or that it is a very difficult place to work. I think it is very important when you are going into your next opportunity or even in the current opportunity, re-evaluate
00:06:41
Speaker
What dynamic you're actually working within and seeing whether or not it is actually helping you? Career-wise be constructive or whether or not it's actually holding you back I think the second part which is I think what you were you were asking about as well is a manager is I've had this really fortunate opportunity throughout my career to have very dynamic very supportive managers and and mentors and
00:07:00
Speaker
where there were basically a desire to get additional skill or additional insight. There's also people beyond even legal that you can actually go to and colleagues and peers within the same company or even outside the company where there's obviously professional networks and even just colleagues that you interact with. I'm just sharing best practices. And so I think there's a variety of opportunity really to get insight. And I think the important thing of all of it is just be curious
00:07:24
Speaker
and really not be afraid to ask the questions about how other people do things. Because if you think that you're doing everything perfect, you're not going to grow. There's always an opportunity for self-improvement around that. And then I think from the standpoint of staying somewhere versus leaving or just where there's opportunity, also making sure the environment you're in, you're well-respected, you respect others as well. And so it's a mutual kind of relationship. And then you just have a very collegial type of environment wherever possible.
00:07:53
Speaker
Yeah, I think that in the sort of current market conditions, folks are finding that having that great manager, someone who wants to provide them with opportunities for growth, just nice people to work with is maybe weighted more heavily today than it might have been two years ago, right? People are willing to stay even if the salary isn't quite where they want under the title isn't because they know that those are the things that maybe matter the most.
00:08:18
Speaker
I think there's a great point, Teller. I think this also goes to the second part of your question regarding how do I look at managing myself? I think it's one of these things that you want to manage people the way that you want to be managed as well and really make sure that you extend that respect and empower them. I think one of the things, especially in the challenging environments that we see today, is being very, very transparent with your team. Where you know things,
00:08:42
Speaker
You shouldn't, as much as you can or you're allowed to share, where you don't know things, acknowledge that it's an uncertain dynamic. And with that, really say, look, we're all in this together. And I think the most important thing is that basically feeling like your team members feel like you have their back. That if there is a problem that you were there to support them, whether it is emotionally supporting them, professionally supporting them, really just being empathetic as it relates to what's going on in their lives, it may be a struggle. And I do think that the
00:09:08
Speaker
pandemic was actually a very telling time where people shared a lot more of what was going on. And you've got an inside view into the world because everything was on Zoom. And so you were able to really kind of get a little bit closer to people, ironically, even though you were remote because they were challenged with things of kids coming on calls and pets interrupting conversations. So you could be a little bit more casual. And with that really being empathetic, saying, look,
00:09:31
Speaker
Yeah, I've got a kid as well and sorry that they came on. I haven't joined the conversation if it's appropriate. Just keeping it real that we're all in this together with regard to whatever we're facing, whether it's the pandemic or whether it's the financial situations in the markets or even if it's just things within the company itself.
00:09:49
Speaker
Yeah, with work and personal life melting, I think a little bit of grace can go a long way. Before we go a little deeper on this, actually, why don't you maybe contextualize for the audience some of the teams that you've built?
Building and Supporting Teams
00:10:00
Speaker
Because you've built some pretty decently sized ones over your career. We'd just love to sort of hear like, you know, a few places where you've been GC or DGC or an exec, what are some of the team sizes that you've built up?
00:10:13
Speaker
Yeah, I've built everything from just having a couple of people on a team to most recently a doc assigned. I had a team of approximately 30 people. Really building the team, the part that I thought was always really exciting about building a team was never should be about empire building and just saying, I've got X number of people and therefore it's good. It's really more the collegiality and the dynamic and the interaction between all the individuals.
00:10:35
Speaker
see how they professionally develop, whether they stay at the company, whether they stay within the legal group or go to the business team, whether they leave the company and get to a higher level type of opportunity. I think it's just exciting to really work on building an organization where you are making a difference, helping them professionally grow, even potentially personally grow, and mentoring them wherever you can and really trying to make it a great place to work.
00:11:00
Speaker
I want to talk more about that mentorship concept, actually, and how you've thought about that in your own career. You thought of CEOs or you've interacted with boards before, board members as mentors. Do you feel like you turned more to other GCs or other executives? How have you really sort of tried to cultivate those types of relationships throughout your career?
00:11:26
Speaker
Yeah, I think it's actually always important to try to get every angle that you can. It is getting insight and mentorship from managers, getting insight and insight from even people who report to you, getting horizontal mentorship from people that are basically comparable either within the legal group or even outside the legal group.
00:11:47
Speaker
and really just trying to get a sense in different ways and I think by doing that as well as obviously as you suggested before CEOs and boards just hearing what makes them tick and what's important to them and what's not and even getting constructive feedback as to you know hey I just did a presentation what resonated what didn't resonate if I could do it over what what should I consider and I think
00:12:05
Speaker
The more you're kind of curious about how to always have self-improvement and also being genuine and sincere and also finding the right people to get feedback from, I think it's invaluable because then what you can do is that based on the type of individual comes in, you then can kind of tailor and change the lens as it relates to kind of how you convey that information to someone.
00:12:24
Speaker
Yeah, that horizontal mentorship is a cool thing to bring up, actually.
The Value of Mentorship
00:12:28
Speaker
I'm thinking about this, and I've been in companies before where they've actually established sort of programmatically opportunities for that to happen, where you may be a relatively junior salesperson, but you get matched up with the chief people officer or with the head of cons. And one, I think there's a ton of signaling value to that, right? To have executives signing up for it. But to your point, it goes both ways, right?
00:12:52
Speaker
that junior sales leader may learn a lot from working with the CFO or having the chance to have coffee with the CFO every couple of months. The CFO probably learns a lot too about what people are really thinking boots on the ground within the business. Yes, totally agree. I think it also grounds you because if you're just talking to the people that you know what they're going to share with you,
00:13:15
Speaker
Maybe validate your presumption, but it doesn't necessarily give you more. I always like it when I talk to someone that is maybe one, two years out of college or law school, and some of those questions they ask are really reaffirming of things that you probably have forgotten about.
00:13:32
Speaker
early on and from early on rear and you're able to really share some insight as to, okay, with the next five, 10, 15 years, here the dots you may want to connect or here are the things you may want to consider and either learn from my successes or learn from my mistakes and really just, you know, really help develop other people because I think giving back is always enormously important.
00:13:49
Speaker
Yes, thank you for being here today and doing a little bit of that. I want to express a little bit of an opinion and see how you react to it, which is that success is not becoming a general counsel or another executive.
Motivations in Work Environments
00:14:03
Speaker
You need to think a little bit beyond the title and what really motivates you when you get up every morning. Hopefully you have a job that actually makes you want to jump out of bed, not crawl.
00:14:13
Speaker
And over the course of your career, what type of work environments or quality engagements make you want to work really hard? What are the things that you've weighed as you think about what motivates you?
00:14:28
Speaker
Yeah, I think especially in the tech space, it's about the growth of the company. It is about the type of technology or products or ecosystem or industry. Over time, you start developing either a broad brush type of expertise across multiple industries that you can kind of utility player, which is often kind of how I operated,
00:14:49
Speaker
Or there are others that say, you know what, I just want to be just in FinTech or I want to just be in medical devices and the like. So I think there's that element of understanding where the company fits in the overall ecosystem and then do you like that type of environment. Because every industry has potentially a very different personality to it and a very different potential business kind of motion to it. And so you got to make sure you kind of align there. I think an equally important piece is really the sophistication of the leaders,
00:15:17
Speaker
and the executive team that you can be working with. Because I think with that, you're going to be working very closely with them on a regular basis. And if you don't like the people or if they are either too, you know, having a personality that may not align with yours or a different work philosophy and the like, there's going to be potentially additional friction and there's just no need for that additional friction. And what you want to do is really make sure that you're going with a very sophisticated team that, you know, that will help row the company with your help as well.
00:15:46
Speaker
And I think the third factor is resources. I think that's something you have to kind of consider when you're going in. Do you want to be the type that go in and be the first to turn it on the ground and roll up your sleeves? Or do you want to have it that you can actually build out an organization and being able to do additional things? And I think depending on where in your career and where your interest level, it can vary as it relates to which you choose theirs.
00:16:06
Speaker
Wouldn't follow up on that, on the concept of sort of learning whether or not you want to work across industries and be a GC at a life sciences company and then a GC at a, you know, sports company. And then how do you think about figuring that out?
00:16:22
Speaker
How did you sort of think about that as you tried to figure that out throughout your career? Was being at the law firm early on and getting to work with different types of clients really helpful? Was it just taking a few risks early on in a few different roles? How did you think about that choice to either sort of specialize in one industry versus bouncing around a little bit and trying new things?
00:16:45
Speaker
Yeah, I think it's a couple fold. One is understanding the trends in the market. I think that if you talk about certain technologies that were around 20 years ago, they're either not around today or they're commoditized today or they are struggling today. And so there's cycles around all the different industries in the light.
00:17:03
Speaker
So I think one aspect is not just being a good lawyer, but also understanding the ecosystems that you're working within or that you're interested in, and really just keeping track of basically their trajectory. Because there's always kind of a beginning, middle, and potentially an end to a lot of industries, or at least a revolution as to each industry when new disruptive technologies and business models come in. So I think that's one dynamic. And then I think the second one is talking kind of what we were talking about before about mentorship and being curious.
00:17:29
Speaker
It's talking to other people. And then if you're not in a specific industry and you have a conversation, they go, yeah, that industry is pretty tough. It's all about, you know, it's all about basically, you know, very, very thin margins or it's very, or it's very cut throat or it's very adversarial or it's, you know, very slow moving.
00:17:47
Speaker
you know, whatever it may be, knowing what that dynamic is and then evaluating does that fit where you are in your career, in your cycle in your life as it relates to, do you want fast-paced, middle-paced, slow-paced, more dynamic, fluid, or more structured? And I think that helps kind of navigate you towards really where you want to head.
00:18:05
Speaker
Yeah, I think it all probably comes back to relationships there and even being willing to do some cold outreach maybe even to folks within a given industry to learn a bit about it before you make the lead. The flip side of this sort of comment that I made earlier though that it's not all about the GC title is that sometimes titles actually do matter.
Impact of Legal Titles
00:18:27
Speaker
And you even previewed early on, right? Like GC versus DP of legal versus head of legal. We see a lot of these float around. Reporting structure, I think too, right? Like CEO versus CFO. If you're thinking about taking on your first GC or VP or head of legal role, what are some of your thoughts around those titles? Is it title that matters? Is it reporting structure that matters?
00:18:55
Speaker
There are other responsibilities you should be looking for. Run with that a little bit and don't be afraid to be a little pull-up. So I think there's a couple of different things in what you just asked. The first is let's just talk about titles. I think titles, and let's even throw in reporting structure as well, is very helpful as it relates to how either the executive team or just generally the organization either perceives legal or perceives the type of individual that they want to bring on.
00:19:23
Speaker
And again, I'm talking much generalities, and I think then anyone that's looking into these opportunities should then evaluate whether or not the generality fits basically the reality. But again, it's just intended to be little buckets to fit it in. When you see something like head of legal or VP of legal, what that often suggests is that they're looking for someone a little less senior
00:19:43
Speaker
And they're looking at it being maybe a little bit more on the side of operational. And often when you see those titles, you often also see them reporting into the CFO because they're looking at it as somebody coming in and working really to take outside counsel costs, bring it in-house delay. When you see GC and you see reporting into the CEO, it is a recognition that the legal function is more of an executive team member is going to attend the executive leadership meetings.
00:20:09
Speaker
and is really viewed as a peer to the CFOs and the COOs and head of HR and the like. And so again, generalization, but I think that's part of the conversation that one needs to have. And they also need to be comfortable with the reality of if they do go into that type of situation, they need to be comfortable with
00:20:25
Speaker
Hey, if you're a VP of legal, there is a chance that someone's going to be put above you later on if you don't establish your executive presence and the like. Or if you have a GC, you need to really step up to that executive role and really step into the fold of really understanding the expectation. And so I do think
00:20:43
Speaker
title and basically who you report to does influence the perception of what sort of work you're going to do. And I think it's important to have that kind of conversation very early on, either before accepting a position or even while you're in the position as to career development, how it moves from that title or reporting structure and really make sure that there is a clear alignment and expectations.
00:21:02
Speaker
Yeah, that makes a lot of sense. I think it also probably would inform those who might look at or apply to a role that's a VP of legal role, but know that even if you negotiate that title up to the GC title, what's really important is how are you being perceived in those interviews? What's her responsibility? Are they wanting to hand you? Are you going to be to your point at the exec team meeting? Or are they saying, okay, fine, we'll just throw you the GC title.
00:21:30
Speaker
we're actually going to pursue this exactly how we originally intended, which may not be a bad thing for the business and the stage that it's at, but for folks who are interviewing and want to make that sort of jump to think about. Yeah, definitely. Okay, enough about titles. Why don't we dig in for a few minutes into sort of the substance of being a legal leader? I think you've really thrived over the course of your career working with sales teams, go-to-market orgs,
00:21:57
Speaker
product teams as well, working on innovation issues. How have you built trust with those sorts of teams over the course of your career? Has it gotten easier over time? Has the perception of legal changed at all? What have you really done to forge strong partnerships with those other functions?
00:22:17
Speaker
Yeah, I think there's a couple of probably elements to it. I think the first is recognizing that not everyone has interacted with a lawyer in the past, or if they have interacted with a lawyer, they may not have had the most positive experience with lawyers in the past.
Integrating Lawyers with Other Teams
00:22:30
Speaker
And because of that, I think one of the first things you really need to appreciate in engaging with people, whether it is senior executives, whether it's peers, or even whether it's even more junior individuals, both largely outside of legal,
00:22:43
Speaker
is making it clear as to what you bring to the table. Because I think in the end, having a lawyer on staff, presume the first question is, why do we have a lawyer? And in fact, the biggest compliment I think that someone on my team got was, why do I have a lawyer at this meeting? And what that did is, it opened up the opportunity for them to say, well, look, I'm a product attorney.
00:23:05
Speaker
And I'm here because in order to give you product legal advice, I need to understand the product, the technology, your roadmap, the ecosystem, and then on and on. And so it provided that opportunity to really then explain the role and explain how you're curious about what's going on. And most importantly, that you care about what your client or your business partner is doing.
00:23:26
Speaker
rather than it being this ivory tower because ultimately if you were removed from basically the business and either sit in your office or at your home and you're really only engaging just to answer a question, what ultimately happens is you get into this ivory tower where suddenly you appear to be the tower of no, where you only stop deals from happening or that you just don't understand the context around what the advice is that you're giving and people go,
00:23:50
Speaker
You know, so-and-so just doesn't get it, right? And you wanted people to think of you not as a lawyer, but really as their business partner that just happens to have legal expertise that can then look at things through a legal lens. Absolutely. You know, oftentimes also help apply the advice maybe from the ivory tower too, right? From outside counsel to the business and where the business needs it, basically.
00:24:13
Speaker
More recently, you took on a couple of other functional areas that you had experience in, but that were newer for you to own wholly or fully government affairs. You were the chief privacy officer at DocuSign, which is a cool title that I want to ask you a couple of questions about. What drove
00:24:30
Speaker
that and that sort of like expansion in your role, expansion in your team. Was it like a real need within the business? Was it your hope to take on new issue areas and be both and it came together nicely at once? How did you actually think about that?
00:24:45
Speaker
Yeah, and I think this is one of the reasons why I went to DocuSign and begin with, which was it was that opportunity really to kind of stretch into not missing new areas, because I've done a lot of these areas before, but really start connecting all the dots together and really build out an infrastructure for it. But at the same time, I think it was also need-based. And so what I think ultimately happens, whatever company you go to, is you go in with this evaluation as to how can I make a difference? And what are the needs within the company? And is the company receptive to those needs? So for example, at DocuSign,
00:25:15
Speaker
There was a huge need for government affairs during the pandemic. And so we made a recommendation to the CEO saying, you know, there's going to be a lot of public sector need and there's going to be a lot of things that are going to have to be kind of navigated. We need to have some focus in that area of actually building out a government affairs function in order to engage with the public sector. We also had obviously public sector sales as well.
00:25:35
Speaker
And so it helped with basically having a voice and a focus in that area, both internally within the company, so they start thinking about government affairs as being something that will help with lead generation, the business, but also in advocacy and legislative reform and policy and everything in between. Compliance, I think it was a similar one.
00:25:53
Speaker
where compliance was decentralized throughout the whole organization. And we said, you know, it probably makes sense to centralize it. We don't feel passionate that we have to own it, but right now it feels like legal might be the best place for a lot of the compliance function just because we think five steps ahead and we're already doing parts of it. And so let's have that conversation. And then, you know, in the year, in two years, if it makes sense of a compliance somewhere else,
00:26:16
Speaker
then let's have that conversation as well as to finding a different owner down the road. And I think similar with privacy, it was in a similar fashion where we were dealing with a lot of data issues and we were already offering up part of the privacy regulatory compliance piece. And we said, look, we really should be thinking about this holistically as data governance. And so we ultimately double clicked on that and then built out a team both from a strategy standpoint and an operational standpoint to tackle that as well.
00:26:44
Speaker
Yeah, I think, so we actually, we did another episode with Megan Niermeier and her legal ops lead Brenda Perez in which we talked a lot about the limits, but also sort of like the limitlessness potentially of what the legal department could own. Just a little bit of a follow-up for you there. Are there other places where you sort of seen throughout your career that legal may identify the sort of issue, right?
00:27:08
Speaker
and say, we need to build out either this function or this team or a new process or program. But where you've said, we don't think that actually legal is the place to own it or legal will take it on for a shorter period of time, but then ultimately we really think it needs to be handed off to another business owner. Yeah. Have you dealt with that too? Well, yeah, definitely. I think that finance and legal are probably two of the major parts of the organization that often see horizontally and cross-function across the whole organization.
00:27:36
Speaker
And I think because of what you see where things are working really well and where there's opportunities for further enhancements. And so I think this actually goes to some of the stuff we were talking about before about professional development as well, which is I share philosophy, which is if you see a problem, you don't just kind of look the other way, right? Even if it's not a legal problem, you say, it's not legal for hate, not my problem. What you try to do is you try to own it to a certain extent until you find an owner.
00:28:01
Speaker
and really kind of convey that to others. And so, you know, over my career, I've seen areas where whether it's new product introduction, whether it's new geo introduction into new new countries, whether it is operational processes, where you go, you know, it is far from truly a legal issue.
00:28:17
Speaker
or a legal role to do it. But ultimately, in the end, for us to get to the legal advice, you need to have the business strategy. You need to have the decision-making process to come up with that strategy. You need to have the process of implementing on that strategy. And so what you often see is that lawyers are kind of helping facilitate it. So what I see really, again, back to the leadership, back to professional growth, is I think there are opportunities for lawyers throughout an organization when they see something that isn't working well.
00:28:44
Speaker
to actually step up to the occasion, especially as you want to be perceived more as an executive leader and say, look, I'm going to help build an ad hoc, a cross-functional ad hoc kind of tiger team.
00:28:55
Speaker
Yeah, I openly acknowledge that legal doesn't necessarily fully own it, but I want to help facilitate it. And let's have a conversation either on the call or back channel that really should own it. And let's just lean in together and let's just get to basically done. And what I've seen is that actually first addresses potentially fundamental issues within companies that potentially blow up. I think second, it shows your executive ability for things. And then third, it builds that cross-functional rapport
00:29:24
Speaker
of saying, hey look, let's go do so-and-so because this person can actually help on a special project or a very complex issue. And it doesn't have to be about whether it's a business or a legal issue because I think a lot of things, especially as we work in the house, blend together. I think it's about what are corporate problems or challenges in your organization and let's lean in to kind of help. That was a lot of credibility, I'm sure.
00:29:44
Speaker
Yeah, I am curious about one of those areas, and my background is quite a bit in privacy.
Data as Intellectual Property
00:29:50
Speaker
That role that you took on as Chief Privacy Officer, how do you think about the Chief Privacy Officer role evolving? And then you did have a lot of deep experience throughout your career in IP. And I'm curious, do you see any parallels in the rise of privacy and where you see privacy headed? You're drawing on from your experience working on IP issues as well.
00:30:14
Speaker
Yeah, I think it's twofold. I think first, privacy overall has been very heavily a compliance function, a very complex compliance function with regard to the evolving regulatory landscape. I think what that is actually evolving into it. The second point is it's more of a data governance question and a data strategy question.
00:30:32
Speaker
And so to your point about my background being that I have an electrical engineering degree, I started my career at Sun Lake and West where I was doing IPs before getting to be more broad. That data is almost like that new piece of intellectual property that's out there where data actually helps with stickiness of product differentiation and data helps with developing new services. And again, back to kind of artificial intelligence.
00:30:52
Speaker
Well, you don't have artificial intelligence. And so what I think is happening is data is becoming a very ubiquitous additional subject matter within companies that by controlling and having an understanding as to where your data is coming from, what you're doing with internally and where you want it to go, you're actually able to really create a further differentiation for your company and your products. And because of that, that's one of the reasons why basically privacy was brought under my remit is because privacy was one of these areas where it's kind of one part of that
00:31:21
Speaker
two-sided coin of data with regard to ensuring that you want to make sure that not just you do the right thing with data, but also that you have a data strategy where you then work with head of IT, trust and security, the product and the business, and also work with the audit committee on the board level and the like to ensure that basically there is a clear end-to-end data strategy for the company.
00:31:44
Speaker
And that was going all the way up to the board level for you, the governance committee. I am curious about that. The board was really concerned with not just sort of the compliance aspect, but also the data strategy piece too. Well, I think at a lot of different companies, it's starting to elevate up to that level because it's about need of breaches and the current sort of my data breaches. So that's around information security. It's about compliance, which is basically more of that kind of privacy kind of lens of things of
00:32:11
Speaker
What are we doing with the data and are we going to make sure that no regulatory authority is suddenly going to name you in a complaint or in action or the like? Then I think it's also the business end that if your company uses data a lot, or at least data is becoming increasingly important,
00:32:26
Speaker
what are you doing with the data and have you greased the skids to be able to use data the way you want, which may bleep back into your commercial agreements and whether or not you've got the adequate permissions, whether it is the messaging that goes out in marketing literature, whether it is in the click wraps on sites and the like, whether it's the third-party vendors you bring in that you're using their data and really holistically looking at it. And so I do think that the board, from the standpoint of that big picture, just knowing that somebody's helping connect the dots
00:32:51
Speaker
and that it's clear who is the owner of each of these different pieces. And if there is one clear owner, legal helping facilitate connecting the dots and ensuring that there is an owner or legal taking on that responsibility.
00:33:02
Speaker
Let's talk a little bit more about legal tech and maybe how data is going to be leveraged in the future, or even a little bit in the present today to drive tech solutions for lawyers.
Evolution of Legal Tech
00:33:14
Speaker
Not just because I'm at Spot Draft, but I was excited to learn that you are kind of a legal tech nerd. And it's something that you've tried to leverage all throughout your career across your different GC roles or different teams.
00:33:27
Speaker
How do you see legal tech evolving? What do you think is sort of most essential about it? Where do you think that the legal tech landscape is headed? Basically, I am a legal tech nerd, so thank you for letting me do that, Tyler. I appreciate that. Where I see legal tech is that there's been probably at least three phases today with legal tech.
00:33:51
Speaker
I think the first was that, again, late 90s, early 2000, you had separate corporations building their own legal tech internally, having their own IT groups, building out the system because there just wasn't anything commercially out there. And so the problem with that is how do you scale that, right? Because you're not building value by having a second IT group that is literally building tools that is only for the legal organization.
00:34:13
Speaker
I think that evolved from internal tools to then commercial tools of the first generation, which were really clunky. And you were usually picking the best of the worst just to kind of get something out there so you didn't have to support it. And at the same time, you really use things to be more optimal and more efficient.
00:34:29
Speaker
What's exciting is I think we're actually in that third phase. I think there's a lot of companies such as Spotdraft as well as others where there is this next generation of the technologies, next generation of the people that are actually designing it, knowing what legal needs, both internally as well as outside counsel, and being very sophisticated with it.
00:34:48
Speaker
And so I think what we're getting to is this point in the legal tech evolution where legal tech is no longer just this kind of weird little area that people just kind of hold their nose and just use whatever's out there, but rather it's becoming strategic tools that are not just value generators for the legal department, but I think we're also becoming product differentiators or company differentiators because if you can
00:35:10
Speaker
pull up an agreement very quickly, or if you can respond to something more decisively than your competitor, you're able to get into maybe a new market quicker, or you're able to build a product more quickly, or you're able to give insight to the board or the CEO more quickly in order for the company to move more quickly, which is, I think, what we all want.
00:35:29
Speaker
In other words, it's not just about the legal team, right? It's about the whole business. I sure hope that we're beyond the first adopter, first mover stage from where I sit. I want to start to wrap up our conversation, which has been really great, by talking a little bit about the people that you've worked with and the teams that you've built.
Retention Strategies and Leadership
00:35:52
Speaker
As we have talked about, the environment I think has changed a little bit over the course of the past couple of years. But retention is sort of always a challenge, especially with really talented folks. What are some of the things that you've done over the course of your career leading teams to grow as a manager and to focus on retention?
00:36:14
Speaker
Yeah, a couple fold. I think first being genuine. I think if you come in and you're approachable and people feel like you're trying to do the right thing, they get a little bit more, should we say, people give you a little bit more discretion that if you goof on something or if you do something that rubs someone the wrong way, they're like, all right, you didn't mean it. It was just a misstatement and the like. And so I think that's the first part is being genuine and the like. I think in addition to that is really
00:36:41
Speaker
Often you hear that there's two schools of thought. One is you're the most intelligent person in the room and everyone around you acknowledges that and that's one approach. The approach that I subscribe to is you want to surround yourself with people that are the brightest and best around you and just put you to shit because I think what that basically reflects is first a confidence in yourself that you know that basically you are who you are and where you have strengths, great, where you have areas of opportunity,
00:37:10
Speaker
Acknowledge that as well and you surround yourself with people that will give you their insight and be you know further value and tell you when you're wrong or tell you when there's Alternative ways of doing things and you want to really ensure that you have that kind of team. I've been very very fortunate through my career I'm really finding up those types of brilliant people that are willing to work with me and I could sarcastic say tolerated me, but but the worker
00:37:34
Speaker
and really empower them. And I think the second part is, if you actually go in with this high octane kind of group, which I usually call my legal rock stars,
00:37:43
Speaker
Yeah. The other thing you have to recognize is you can't just put them in this very, very narrow box and say, look, I know I'm giving you only tactical stuff and that's it. And I think you also have to balance it with empowering them to present to the CEO, empowering them to present to the board, empowering them to drive strategic projects and make sure that when you do give them those opportunities, back to the mentorship piece, is you want to make sure that they do it when they're ready.
00:38:07
Speaker
and that they're also prepared to succeed in doing that. And I think by being transparent, you say, look, I'm not not giving this to you because I think you're going to muck it up, but I want to make sure that you look like a rock star in front of this executive or this individual. And so for that reason, let's hold off for three months, but I promise you, let's work on it and let's have a conversation. And I think in one-on-ones, yeah, with a team, which sometimes people may roll their eyes saying, oh, another one-on-one,
00:38:35
Speaker
I think the important part of that is actually to ensure that there's at least a structure or at least a forced opportunity for you to discuss things with your team. And often I think everyone loves the evaluation process you have for performance reviews every six months per year. And my philosophy is that you should never go into a performance review where your team doesn't know where they stand or where they're strong or where there's opportunity.
00:39:02
Speaker
that to be really a validation of what's going on. I think all too often people are surprised by basing the feedback because it hasn't been this ongoing dialogue through a whole year. And so I'm a big proponent of really making sure that people know where they're just hitting at the park, where there's opportunity for further growth and the like, and really leaning in with people. I mean, that's part of the role of being a manager is really to make sure that everyone's successful. I agree. Continuous feedback is always better as someone who's done a little bit of managing, but mostly been managed.
00:39:31
Speaker
Also, it really resonates with me that one-on-ones are important and keeping those on the calendar because that's the opportunity for that continuously. The flip side of retention, though, these days is also that it is a bit of a top market and there have been some layoffs at large tech companies.
00:39:52
Speaker
And so, I guess, just curious for those who may be going through unexpected career transitions, if you have any advice for those folks. Yeah, sure.
Advice on Career Transitions
00:40:04
Speaker
So, I mean, I think that the key thing is it's not a reflection of you as an individual or as a professional, because of any layoffs technically are because they eliminated position. And so, I think that's the first takeaway. Second is that it's not, I mean, some people, unfortunately, find a new opportunity immediately.
00:40:20
Speaker
and others, sometimes it takes a little bit longer. And that's also not a reflection of the individual, but rather of potentially the opportunities that are out there, of your network, of other situations and dynamics going on. And so I think there's also the
00:40:36
Speaker
Surround yourself with people that understand these to 9x and any share of you So at least you don't feel alone because I think there's more recent it in some really good studies around just People that kind of isolate themselves and basically they have more health issues and the like I think it's important to say look you really reach out to family friends colleagues and just have conversations and validate what you're experiencing what you're feeling and And just you know
00:41:02
Speaker
really powering through the dynamics of looking for the next opportunity. Looking at it is very much that. Is that next opportunity potentially is a better opportunity than you currently have? That next opportunity gives you a new experience and using it as a way to self-reflect as to what that new thing that you want to do is. If you have free time, do additional things. Learn the guitar or improve your golf game.
00:41:26
Speaker
or actually take courses or really lectures. As I was watching this video here, hopefully people take little gems away from it and just really using it as an opportunity for growth.
00:41:37
Speaker
I think that's great advice. Yeah. As someone who went through a layoff last year and now I'm lucky to be sitting here and interviewing you and having a sort of like great job and next adventure. The thing that I took away most from that experience was how supportive people were. And, and even the people who I didn't expect to reach out. That was even, that was almost even more rewarding to, to experience than, you know, the call from mom or former boss.
00:42:04
Speaker
It was very cool to see how many people wanted to help, and the only thing I can say to that is hopefully that all of us can also pay that forward, too. One fun question before I let you go, because we can't end by talking about layoffs.
00:42:19
Speaker
We asked this of our first podcast guests, so I'll ask it again to you. I think it's kind of a fun question. What's the best swag you've ever gotten from a tech company? And also only if you want to, what's the weirdest or the worst?
00:42:36
Speaker
Boy, the best swag, I think, was a golf club, which was actually pretty cool. I mean, it was one of these things where, you know, you put in your business card and you got chosen, but that was actually pretty cool, getting a nice kind of driver. And then I think the, boy, the worst one, boy, where to start on the swag? I don't know.
00:42:57
Speaker
It's like those things that you wonder why give it out and are people actually going to use it? I'm certain it was one of those anything with some sort of flashlight in it that you never know whether to use it. Of course, we've had the power outages around here recently, so maybe it would have come in handy. But generally, instead of some sort of lighting element to it, I always was wondering why I need a lighting element.
00:43:21
Speaker
Um, I'm taking notes as the person, it's podcast in charge of picking what our swag is at, uh, at events around the country. I will not be asking the team to, uh, to pull together little key chain flashlights with our, with that tip.
00:43:39
Speaker
Well, Doug, this has been so much fun. I really appreciate you hopping on and taking some time out of your day to speak with our community. He's got so much great advice to share from your career. Thank you so much for taking the time.
00:43:56
Speaker
It's absolutely a blast. Thank you for the opportunity. Again, I hope that people get a couple of nuggets out of this and look forward to continuing the conversation with you and others. Again, it's just great to share ideas with other people and they get facilitating this. Absolutely. To our listeners, thank you so much for joining and listening to The Abstract today. We hope to see you next time.