The Wellness Esquire Podcast

"Being Yourself Takes 0% Energy" — Jonathan Cullen on Ditching the Lawyer Mask

• Ariella Cohen Coleman

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Jonathan Cullen spent 18 years as General Counsel at Pfizer Canada before walking away to build a full-time coaching and consulting practice for lawyers and law firms. In this episode, he sits down with Ariella Coleman to unpack what it actually takes to lead — and stay yourself — inside a profession built on formality.

Jonathan shares the early-career moment he decided authenticity wasn't optional, even when it landed wrong. He breaks down "touchdowns and fumbles," the weekly team ritual he built around admitting mistakes first — his own — to make it safe for everyone else to do the same. He opens up about his son Tristan's six-month hospitalization as an infant, and how that experience permanently changed his definition of urgency and his tolerance for making hard calls.

The conversation turns to what law firms consistently miss: curiosity. Jonathan explains why firms that never ask about a client's culture, decision-making structure, or definition of "winning" end up delivering technically correct advice that still misses the mark — including his own story of winning a case in court, only to find the business disappointed by the outcome.

He and Ariella also dig into the built-in tension of the billable hour, why "principle-based advice" builds more trust than a flat yes-or-no, and why the best leaders are the ones you barely notice — until the exact moment they need to step in front of their team.

About the guest: 

Jonathan Cullen spent 18 years as General Counsel at Pfizer Canada before recently leaving law practice entirely to launch a full-time coaching and consulting practice. He now works with lawyers and law firms on leadership, business development, and professional growth — bringing an insider's view from nearly two decades of sitting on the client side of the table.


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Host Info: Ariella Cohen Coleman

The Wellness Esquire: a bold new path where wellbeing, happiness, and authenticity drive performance and success. https://thewellnessesquire.com

Ariella Law, PC: strategic legal support for entrepreneurs, growing companies, and mission-driven organizations — formation, contracts, compliance, and fractional general counsel, delivered project-based or by subscription. https://ariellaw.com/

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SPEAKER_00

What a fantastic conversation with Jonathan Cullen. Until very recently, Jonathan was the general counsel of Pfizer Canada. When I saw that he had made the leap to go out on his own to coach and consult with lawyers and law firms to help them thrive, I was so excited for him and all the people he's going to impact, and I knew I had to have him on the podcast. Jonathan is such an incredible example of someone who has climbed to the top of success and has done it while being entirely himself. His casual, goofy, practical joking, kind self. We talk about Jonathan's early decision to always be himself because pretending to be someone else just takes way too much energy. We talk about how leading with curiosity, kindness, compassion, and humor actually leads to better business outcomes and deeper relationships. We talk about how sharing our mistakes is a gift to those around us. We talk about what Jonathan learned from 20 years as in-house counsel about what firms can do to improve their relationships with businesses and help their business clients achieve their goals, and how individual lawyers can step up their games to be the leaders and trusted confidence their clients and colleagues are looking for. I know you're going to absolutely love this conversation. Be sure to follow and reach out to Jonathan through the links in the show notes. Enjoy the conversation and remember to please rate and subscribe. It's so nice to see you. It's been a few years. Quite a few years.

SPEAKER_01

I know. It has. Yeah, yeah, it has. And thanks for your uh understanding on rescheduling. It worked out actually.

SPEAKER_00

Oh, it's this is getting very funny. I feel like most of my uh podcast recordings begin with someone acknowledging like the way I am about rescheduling, which is like it happens, who cares? We all need to reschedule when life happens. Um, but it's become really interesting to me because of the volume of guests who even when I say, don't worry, reschedule as many times as you need to, I don't care, still carry guilt. And it says so, and it's not like I don't experience that ever, you know, when I'm rescheduling for somebody else, but it just says so much to me about the the unnecessary guilt that so many of us carry around on so many levels, and and the things that we really should learn how to let go, because it just it doesn't matter. And by definition, we can't have a zillion priorities, and all of my priorities can't be the same as yours. So it's all good.

SPEAKER_03

All right. I appreciate that. I appreciate that. Thanks for having me.

SPEAKER_00

I'm delighted to have you. I uh when I saw your post that you were shifting from you know practicing and doing some coaching on the side to just taking the coaching full time, I was thrilled. And you know, it's not that I know you so well, but I I I remember our conversation from I don't know, half a dozen years ago or so, um, so so fondly. And uh and you know, there's a quote that I love um from my my Angelou about uh, you know, people will forget what you said, people will forget what you did, but they'll remember how you made them feel. And I I you were one of the first people that I felt in in the lawyer world that I was starting to be more open in myself with, right? And just acknowledging this exact thing I'm doing right now isn't quite right. I'm starting to figure out who I am and how to turn that into what I want. But boy, does it feel scary to tell people who I am and how do I how do I do that in this industry where we're often not encouraged to be totally authentic and vulnerable? I think that's shifting. Um, but uh so I've just held you in this fond space since then, and I I love seeing that you're you're now gonna take your your eunus, which is really wonderful, uh, just in the little bit that I know to more people. And so I think that's great. So I'm glad we're gonna.

SPEAKER_03

Yeah, thank you. I appreciate that.

SPEAKER_02

I and I agree with you on the uh authenticity part of the way I looked at it has always been it just takes too much energy to pretend to be someone else. You know, I don't have that kind of energy, and I would rather, you know, being me takes zero percent, and then whatever percentage I've saved, I can actually put it to doing something good, you know?

SPEAKER_00

Yes, it I I agree a thousand percent. It's uh it's much less exhausting to just be you. Were you always comfortable in your professional world just being you, or did you have to yeah, this is a really good question.

SPEAKER_02

Um I think I made an early commitment to myself um when I was in private practice at a large law firm and to to do that, to be myself. And it didn't, it wasn't always having a positive effect, but I was okay with that because you know, like all good things in life, there it's rare that there will be no sort of like side effect that has that you have to manage, you know. And I was very lucky, I think, because early in my practice, I think people appreciated that uh who I was brought with it some good things, and maybe the things that didn't necessarily fit, they it was okay, you know, and and I was uh I was lucky to have found that pretty early. And it's funny, as I do full circle and I'm happy to talk about it, but uh many of the people that I began my career with learning from and have you know stayed in touch with, and that would be something I would highly recommend for people, as I launch my my new coaching and consulting practice now, uh many of them are reaching out and uh either supporting me or seeing how we could work together. So it's just sort of a full circle for that. But but yeah, early on, I I definitely made that commitment to myself. And I think the important part is like to make a recommitment of that, you know, whenever you get sort of like, okay, like for me, if I use the example of me, I'm not a super formal person. And as you know, our profession tends to lean towards more conservative, formal, and for good reason, I understand that. Um, and I certainly have my moments where I can, you know, do that, and it's definitely appropriate sometimes. But uh, I also always thought that like we are in a service industry, we we work with human beings, we don't work with you know companies. Companies don't make decisions, people make decisions, and so you're dealing with a person on the other end, they have their stuff that day, they have their personal stuff, they have a spouse, they have a dog that's sick, they there's all sorts of stuff. And I always thought, you know, developing a real relationship with people, um, understanding the troubles they're going through. I just always felt that resulted in a honestly a better business outcome, you know, and also made your day more interesting and you develop real relationships. So that was always my approach to it. And uh I do, you know, over time, uh, yeah, there's some times where it it's challenging. And I like humor. I'm I'm rarely, I'm usually the first person to sort of make a joke about something. I I again I also find that's disarming in a moment that can diffuse tension. Um at the same time, humor is definitely one of those hit and miss where like you're gonna fall flat sometimes, and you know what? So be it. It's okay. I would rather, again, to go back to what I said, I'd rather just be me. So yeah, over time I have a question. I'm like, is it okay to do this this way? And especially like when I've taken on new leadership roles with like new groups of people that don't know me, and it's so tempting to sort of like look at the audience you're speaking to and think, How can I please them? Uh, as opposed to a little bit of a nuanced, like, how can I understand them, you know, better? And I always leaned toward understanding, and then that didn't actually change who I was and what I was doing, it was just leaning into curiosity about people. And uh I think if you do that genuinely, people see and believe that you are truly interested in them as people in whatever profession, including a legal one, you get a lot of leeway to be yourself. Like if you if you don't do that and you are just sort of like shaping the universe, bending it to your will, and not really trying to understand the people being affected by it, they're not going to be so pleased when you are, you know, sort of feeling free to be yourself. So I think it's sort of a little bit of a give and take.

SPEAKER_00

Do you remember that in that early phase in your career when you made the decision to just be yourself? Was there an incident that you were facing? Like how how did I at that point in my career had no insight into just I was so afraid of so many things? Yeah. And a lot of that was, you know, innate people pleasing that I've done a lot of work to, you know, make go away or at least a lot quieter. And I so did something happen that just made you go, oh, I have to decide right now. I'm either gonna be me or somebody else.

SPEAKER_02

Yeah, yeah. There's a few. One I can think of. I remember I had to do, I think I was a I was an articling student, and you know, both trying to integrate into a culture of a firm and also trying to find yourself. You're, you know, quite young, and there is a competitive element to it. And I remember I was doing a presentation on a subject uh that I was quite passionate about uh to probably one of the practice group I was wanting to apply and and to work with on a long-term basis, though, it was intellectual property litigation, which is what I ended up doing. And I made a presentation and I I could tell like it went well and you know, things were going well. And then I to this day, I don't know why I did it, but at the end, uh I think they asked any other comments, you know, from me or whatever. And I and then I made a joke about, and it's it was Montreal winter, and I think I made a joke surrounding, you know, never eat yellow, yellow snow or something like that. And I I don't know why I said that and like where it came from. It must have been something I'd heard, you know, earlier in the day or whatever. And like everybody laughed, of course, but afterwards I was sort of on my way home and I thought about like, wow, that could have gone poorly. And I'm like, who am I who am I gonna be? You know, am I gonna be the person that that continues to sort of try to lighten the mood a little bit and on the chance I might alienate people and definitely hit the wrong note, and I've definitely done that over time. And so yeah, I thought about that, and to their credit, I'm positive they all they thought a combination of like, you know, who's this Yahoo, but also that was kind of funny. And uh as an aside, somebody that was in that meeting that ended up being a long time mentor of mine. Uh, I had lunch with her like last month when I started my new career, and uh it was just a reconnection. And uh she told me she still has like framed or whatever at her home now a uh a sort of practical joke I sent around by email. Um, and she still has it, and that's 20 plus years later. And she said it kind of um, you know, emphasized and described exactly who I was. And I remember the practical joke, and I at the time I sent like a PDF document or something that crashed the emails of the, I don't know, hopefully not firm Y, but like of at least the local unit because it was so large, the PDF. I'm like, my God, these days, like 20 years ago, I guess that could happen. These days it certainly wouldn't. But uh, so I thought, okay, that was a career modifying event. But in the end, she remembers it super fondly that it was really funny and still has it, you know. So so be it, that was the result, you know.

SPEAKER_00

That's amazing. And uh in part I love the story because I think all of us have had at least one, if not many, experiences of saying something, doing something, and then spending the rest of at least a day just being like, oh my god, why did I do that? I'm such an idiot, that's so embarrassing. What's ever like how is this going to impact? I've destroyed everything. I'm a moron.

SPEAKER_03

Yeah.

SPEAKER_00

And just wondering, you know, how how is everybody gonna take this? Was I as ridiculous as I think I was? What do I do next? And then just figuring out like how do you recover from that? And sometimes it's a big deal, and sometimes it really wasn't. We're just panicking.

SPEAKER_02

Yeah, that's right. Yeah. One of one of my general learnings in life is yeah. Well, it's funny. Uh something I can't remember where I heard this, and it certainly wasn't in the legal space, but somebody I heard say, people are not thinking about you as much as you think they are. You know, that you you are the center of your own universe, but you're you're not the center of anybody else's, just by definition. And we tend to sort of overanalyze those events. And when it's happened to me or members of my team, you know, like over time, I always try to like put it in context. Like that was 36 seconds, you know, over the course of thousands of hours of positive, you know, events that you've put out into the universe. And another piece is always like to ask other people, you know, I I think that was a big deal. I think I I screwed that up. What was the impression in the room? And invariably, like, you're gonna get something a lot less impactful than you imagined, you know, just because of how we are so critical of ourselves. So, like having that um safe space with a few people in your life and career to ask, like, can you honestly tell me if that was as bad as I thought? And if the answer is yes, which is entirely possible, so be it. At least you got an honest answer. And I always like when I would hire people, like when I used to, you know, sort of go through the CVs and interview people for roles on my team. I wanted people that had experienced stuff like that, that had made, you know, quote unquote a mistake or, you know, stepped on a landmine or done something different. Because guess what? If I'm hiring someone who hasn't had those, they're all gonna happen on my watch, you know, like it's gonna happen. I would rather the people that um, you know, I still remember one of my friends when I used to litigate, uh, we went to court, you know, for one of the first times. And uh the before he says his first words ever to a judge, he hit his head on the microphone that was leaning over and it made this giant reverb in the whole courtroom. That was his introduction to the court. And I remember thinking, I looked at that and I'm like, I'm gonna learn from that, I'll duck. You know, like I'm not hitting that. So the other part is of it, I always think when you have a screw up uh or something you view like that, not your shining moment, you should share it. You know, like he told me, like, I hit that microphone, didn't I? And I'm like, I laughed at him and then I said, I'm not gonna do that. So the fact that he was willing to kind of like eat it and be embarrassed, and and then I ended up having, you know, being better. I think a lot of leaders who are open and vulnerable, it we don't talk enough about like why, you know, why that's good even from a business perspective. The more you share about what you've done that could have been done better, even if you're embarrassed, it's a gift, right? To tell other people, like you're you're sharing the things that they don't necessarily need to make the same error, or you know, they may have their own view and do it differently. But uh yeah, I was always a big fan of sort of sharing screw-ups like that.

SPEAKER_00

I I love that. And that was actually gonna be one of my questions for you. And we're gonna back up in a minute and kind of go to your beginnings. But since we're on the topic of mistakes right now, anyways, and you're you're so focused on leadership, which again we'll get more into. Can you talk just a little bit more about like how good leaders can handle and respond to their own mistakes and to other people's mistakes?

SPEAKER_02

Yeah. Yeah. If I start with the last part, other people's mistakes. I think like one of the worst things you can do is really unless it's like company ending, which it never is, um, the worst part is like to begin with the sort of negativity about it, you know, and to make the person feel worse than they already do, because it's pretty rare that people are you know having a blunder and then just not even being aware of it. So because you have to think like just the human psychology of it, if you have a behavior and you get punished for it, you are not necessarily as you know unlikely to repeat the behavior, you're definitely less likely to uh admit to it or share it. So by you know, as a leader, by sort of coming down hard on someone who's made a mistake, you might be lowering the chances of it happening, you know, again, but you are definitely lowering the chances of them telling you about it, which is uh it's gonna be worse, you know. So that was always my view is to begin the conversation about like, okay, like tell me about what happened. Tell me about what you perceive as the impact, you know, like what really happened. And then you can get into like, could we have done this differently? And that's more like a little bit of thought process together. What could we do differently next time? Once that conversation starts like that, people are generally open. You and you haven't said anything negative about it yet, you know. And I tend to ask the question like to make it a sort of self-reflection exercise, like what rather than telling the person they should have done X, to ask, like, well, do you think you would have done it differently in retrospect? You know, and that just the very exercise of thinking about it, you know, the neurons are firing and you're making new connections, and you are in that moment creating a better result for the future. And I would usually to make sure, and you do as a leader, it's a balance of like bringing people forward and shoving them a little bit. And there is a moment where you have to make sure that the person is accepting accountability, you know, for mistakes like that. But you can you can have that at the end of the conversation as opposed to the beginning, completely different vibe. Um, and then yeah, in terms of your own mistakes, because they definitely happen. Uh, my own approach was like, I'll give you the example, like we would have weekly team meetings over the years, and uh, I would always like to start with the uh touchdowns and and fumbles of the week, which is a you know North American phrase that didn't always translate to some of my international colleagues, so I would adjust it, but as a concept, you know, successes and failures. And when I started that concept, of course, I had to start because nobody wants to be like jumping in and you know talking about everything they screwed up with their manager and the team. So we started small, me first, and then also talking about personal stuff, like things I could have done better on the weekend, you know, whatever. And it sort of lightens the vibe and everything and gets people in the habit creation of talking about failure, because that's not a habit that organizations have, and we tend to sort of move on as fast as possible. So to get in the habit weekly basis, talk about things we could have done better, uh, and then it starts to trend into you know work-related things, and then I always had plenty to be honest, that I could have done better. So I was always happy to admit that. And the the evolution I saw in people, they were often surprised. I was willing to admit certain things that I didn't have to, you know, like they didn't need to know some of those things. Um, maybe also surprised in what I viewed as something I could have done better. You know, some of them weren't outright failures, but maybe something that in retrospect I could have, you know, even done even better. Maybe it was a success, but I thought, oh man, if I just done that, it would have been a success on a different order. So I like surprising people and they were surprised by those. And then it starts where they start sharing some of theirs, other people start adding on. And like the you know, best moments are when someone shares something and other people learn from it and we all do better from it. Uh completely different mindset about uh learning from failure, and that is definitely something in our profession that we are allergic to, right? Like it's and I understand it, like we're taught how to be, you know, have the right answer and be as close to perfect as possible. And anything, any admission that you are not delivering that sort of eats into your ego, but also eats into your image as someone who can provide the you know the right answer. So I get it, but there's but you know, in a lot of ways, if we want to be more than just the technical sort of lawyer, you want to demonstrate in your company or your firm, your organization a leadership behavior that has to be part of it.

SPEAKER_00

Okay, so let's back up a little bit. Maybe a little more than a little bit. So I I think you knew you wanted to be a lawyer by the time you were in third grade.

SPEAKER_03

Yeah. Yeah, yeah, yeah.

SPEAKER_00

Entirely based on law and order, or was there more to it?

SPEAKER_02

Yeah, I a good question about the early days. I don't I suspect I was not yet watching that TV show, but I for something it drew me. My my brother, like if you watched my brother and I when we were kids, we would get uh you know, the toys we would get at Christmas, probably sort of you could guess what we. were going to be. I I liked to argue and he liked so to sort of construct. And he's a landscape architect and I'm I'm a lawyer. So like that we we sort of like you you could see what happened with that. And so over time it was just something that you know it I got drawn to and yeah I I I enjoyed sort of the culture of it. I watched a lot of TV shows and read books about it and always had that in the back of my mind. I did a degree in psychology uh took you know some wandering time off in between degrees and some people in my circle said you know you always liked law you you did some courses in in you know before before university in that and uh I thought yeah okay I'll give it a stab and my very first day very first class I was like this is for me like I I knew I liked it I liked uh I liked the ability to persuade people to a position which is really hard in life you know everyone's these days especially so ensconced in their sort of world view and to to open up a whole toolkit on how you can change people's hearts and minds towards issues is a really important thing in life. So I liked that aspect of it. I liked the impact you could have on society. I liked you know fighting for someone else trying to understand someone else's point of view. I am competitive I have to admit I liked that's probably why I went towards litigation I liked you know the win and uh as I progressed in my career the definition of what win was you know changed over time. Uh so yeah I I really uh I was drawn to that and I uh yeah started then started practicing after law school at uh uh at the time Ogil v Renault that became Norton Rose uh in Montreal and uh I did intellectual property litigation for a little bit and then uh I wanted to learn more about a business you know being closer to a business and being closer to business deciders and made the leap to to Pfizer where I uh stayed for 18 years.

SPEAKER_00

You mentioned your view of winning evolved over the years. Where where did do you view winning and success in the same way or those different terms for you?

SPEAKER_02

Yeah yeah great question um yeah I mean I I think one of the things I learned in business definitely is um you know there are many components to your business strategy and you have to really start with the highest level like what are we trying to achieve as an organization and then it's like what are you trying to achieve in this particular context and the legal component poof it was very rare that the legal component was like close to 100% of the the the driving force behind it. It's it's a tactic often that supports a business outcome. So you could almost have like a business outcome that's like fully divorced from the the legal outcome depending on what you're trying to achieve. So you know success and winning the legal matter can often be not the same thing. And that that is you know when in-house counsel are working with their firms that's something that I always viewed as the in-house responsibility to sort of explain to your counsel if you're working with outside counsel like what winning or success actually looks like for the business. And uh it can it can really vary like if you take litigation for example I remember distinctly winning a litigation and the business being disappointed and I was like I I don't understand what's happening and one of the tenants in business is like once you set your budget and you you don't want to have surprises up or down like you don't want to have a huge variance where you're obviously bringing in less revenue than you anticipated but bringing in a lot more revenue than you anticipated although in theory sounds good it also signals to the overall business that you're you don't have a good handle on your budgeting your prediction ability is low you may have sandbagged it where like you underestimated on purpose and you over deliver to look good. So actually delivering a win that brings in unanticipated income on some level which blew my mind was problematic. And so that literally was is the best example I can give where we had a physical win in court a court decision and you know we were able to maintain I believe it was a patent case and the outcome was in part I'm sure it was a passing you know thought but in part at least was troubling so right away that is my greatest example of like you have to understand what the business is trying to achieve when you're delivering legal results and sometimes you know um aiming like in negotiations aiming for like especially in negotiations like where you want to land for a win might really depend on the goal of the business. Sometimes the goal is we want to develop a relationship with this you know other company we don't want to crush them into the ground so let's you know be light on the negotiation. If you didn't have that context you would imagine this you know landing on a particular place in a negotiation was a loss you know so you to spend some time trying to understand what your clients are trying to achieve is just absolutely important.

SPEAKER_00

And what about your own personal view of success?

SPEAKER_02

How has that changed from you know around law school to let's say now yeah for me that's an easy answer because uh for a long time and it's understandable a long time like your your success is your personal success you know like I got this degree I got these grades I um got this job I was promoted I achieved this outcome and that's fine and that's how you sort of build up like there's there's no other way but I discovered in um whether it be like informal management uh you know managing without authority which is extremely difficult or managing people or sort of leading a larger group uh I just discovered a lot more personal and professional satisfaction when people in the group or as a group achieved something positive both because I guess on a human level it's just so rewarding to see other people succeeding with your support and then at a professional level it's harder it's like if it's just you and you have you know outcome you know A, you you can you can work all night you can power through you can go heads down on the computer you can you know do the research you can pres prepare the perfect presentation and you'll probably do well because it's all up to you. And that is quote unquote easier because it's at least a large portion under your control. Once you start working with people God bless people but they're messy you know and to get a group of people or even a small you know or or an individual to trend in a certain direction that you think would be beneficial and to land on an outcome that you're trying to achieve but at the same time to give them a large you know birth to sort of do as they think is the right thing because I was always a fan of like help set the direction but leave the pathway a lot up to them because most of the time they'll find a better way than you to get people to land on outcomes that you know you think are good, I I started to realize wow that is so much harder and it's so much more rewarding both at the personal and professional level that that to answer your question started to be my changed definition of success which means like if you're really really doing a good job as a leader you're almost invisible right like you're in the background there's not a lot of credit going to you when you become visible is when you need to protect your team and you sort of step in front and you know take the splatter and uh I I always felt that was a super important part of the job that when you know you get out of the way for their successes but when they need help you need to sort of step up and uh and protect them. So yeah my definition completely evolved over time and I and I really it just changes you as an individual as well.

SPEAKER_00

I assume it was when you went to Pfizer and not prior but correct me if I'm mistaken that's when you started to understand that lawyering isn't all there is to sort of that or practice that the practice of law isn't all there is to being a good lawyer that especially in the context where you now were in there's all these other considerations as you've talked about with business but also so much with with management and also as we've touched on with leadership and these are not things anyone really talks about certainly not my experience in in law school or really in in any amount of you know the training that we go through how did you start to wrap your head around oh wait I'm good at the law part but that's actually not gonna allow me to be really good at this job.

SPEAKER_02

Yeah no that's a good insight um I think my answer is it was kind of phased like phase one was I've always been very intellectually curious which is absolutely one of my weak points it can be a strong point but I I like to learn a lot about a lot of different stuff. So um you know these days with Instagram like good luck like I'll go down a rabbit hole real fast you know so I have to I have to temper myself on that that being said uh being intellectually curious has has always been a strength for me. So I did have little pieces early on in my career even at a firm or in law school where I wanted to know more about how something worked you know regardless of where it fit in. And of course like when you're early in your legal practice you have to spend a lot of time on the legal stuff because you need to get really good at it you know and to when you're when you're much more junior if you look at a courtroom with the person next to you who's talking about the golf game with the judge and you're like what do I bring to the table I always brought I was more prepared than that person. Like I I'm not gonna have the experience the seasoning or the relationships or the smoothness I might hit my head on the microphone but I'm gonna be more prepared I'm gonna bring you know better cases and all that stuff. So that the I use that intellectual curiosity in that way at the beginning and then later I think when I joined a company 99% of the time you're working with non-lawyers so I did bring like okay I'm curious about what does a pharmacist do at a company? Why, you know what is a you know this person's role I didn't even understand people's jobs you know so I spent a long time a lot of time trying to first you know that phrase first seek to understand. I did a lot of that and then just through that act of just getting to know people you are diversifying your your universe of information. But I didn't at the beginning explicitly think about how that would change my practice although it's I'm I think it certainly did. I my turning point was I think when I wanted to compete for uh my first leadership role as the general counsel at Pfizer Canada I recognized I had gaps in people leadership experience um all sorts of stuff so I leaned into the curiosity I already had to say okay how am I going to self-learn this stuff? You know there was there was uh training available at the organization which you know was great but I I thought I really need to double down on this because it's not the lawyering skills that are going to get me this job. And it's not and it whether it be that job or you know something similar wherever I ended up going, I thought I'm really gonna have to learn a whole different skill set. So my own way and everybody's different uh I just sort of uh leaned into okay if I I want to learn about for example managing people what are the different sort of uh spheres I can do that in so I did a lot of mentoring I did a lot of sort of learning about you know what other people in the organization did how they managed people and then I did tons of like self-learning in terms of podcasts, books. I did a lot of uh free online courses just went back to school by myself and and I started to realize wow all of these skills that are super important in a company that are agnostic to your role you could be you know government affairs or a medical person or whatever they are important and oh wow uh it's all been done before and someone really smart wrote it down or recorded how to do it and it's all out there you know and then I thought okay well I'm just gonna absorb as much of this as I can and do it my own way like to go back to your earlier point. I'm like I'm not gonna become them and be a manager like they're gonna be I will try it my own way and stand and fall you know on my own. So then I sort of thought what are the subjects I want to do this with you know what will be important for my broader learning so I dove into you know management leadership negotiation strategy you know uh supply chain stuff literally I took supply chain courses which like at the time I thought yeah like the these are things that make a difference for my particular organization. I should know more about this um and then I the other part was I was surrounded by smart people who knew a lot about this stuff and I just had literally a list I'm like who should I have lunch with who should I have coffee with and just ask what how do you do your job how can I help you what does that look like so I did a lot of that and I basically like read myself into the job and to understand it. And then I and then when it started I I took a risk and managed people in a way that I did not have a model for like I didn't have an individual who was a model for me. I had my uh patchwork of learning and I just said I'm going to take the patchwork put it together in a single unified approach and just go for it.

SPEAKER_00

Are you able to kind of characterize or summarize the key points of that model and and the parts that you think allowed you to be so successful?

SPEAKER_02

Yeah maybe if uh if I had to I think the first one is to like think first like a business person if that's the role you're in if you're in a business organization. So if you're in a nonprofit to think you know if I was the leader of this nonprofit how would I think so I always sort of thought I'll be a lawyer second and a member of this organization first. And if you think that way then that lens is super helpful. So that's piece number one. Second was to lean into what I said before about people, you know and to to spend time getting to know uh members of my team my members of my you know fellow uh management team uh really at like a level and it's different for everybody but at a level at least one level below like the surface you know and often more than that and I always thought like for example on the team if you don't know the names of the kids of your team members you don't know the thing that they care much more about than their jobs. You know so if that's silly not to know those things. And I don't have the world's best memory so I deaf I took notes and I'm like in my first meetings with people if I didn't know them because many of them I already knew but if I didn't know them I would ask like could I please ask you know uh you've got two kids would you mind what are their names and they would tell me and I would tell them I was honest I'm like I'm gonna write it down because I I it's important to me but I'm you know I'm horrible at remembering so I I also took the approach of I'm going to admit when I don't know something and not I'm not good at it. And at the beginning that's scary because that's like 90% of stuff. So you're constantly saying like I'm gonna do this because I don't know what I'm talking about. And there's a balance there of like they appreciate the vulnerability but you also have to give some sense of strength and direction. Like people don't want to follow like a you know a sinking ship. So in areas I was confident about I think that's another sort of element of it I didn't hesitate. If I knew something was the way I wanted to do it the way it was going to work I just went for it. And as long as I you know explained things to people I think people appreciate going along on a journey when they get an explanation so as part of that overall approach so first you know business first um a human approach with the people and then I really like the element of like strategic thinking like how do the pieces all fit together and I think that's something that I was okay at on challenging the team members and the organization too like how not to be narrow when you're thinking how do things connect with you know resources how do we how do we connect all these things the people the issues the challenges um and then creative you know use of resources um I I always appreciated when we're constructing advice like legal advice to think about realistic use of our resources how do we you know put first things first and really put our focus on the high level stuff. So I was very good over time I got better and better and I ended up being I think pretty good at really minimizing the work on the stuff I thought didn't matter.

SPEAKER_00

And that takes a little bit of courage when there's someone else saying no no no that matters you know the small thing matters and you have to make a call to say and protect your team to say we are not going to spend energy on that you know so that was a little bit of my approach I want to talk more about the the people part of this and I I I want to talk about how you think about the role of compassion and empathy with your team and and understanding everyone as individuals um and and part of what I want to get at with that is I know you you have a kid I think a son with Down syndrome and I wonder how that's helped you and if you don't want to talk about it left and no no worries but how that helps you understand that everyone you're working with has a very different kind of brain. Yes and their success in in part will depend on you understanding and respecting that they need to receive communication differently perhaps or convey it differently and you know you write down your colleagues kids' names because you know that's one of your challenge points how do you how do you think about all of that?

SPEAKER_02

Yeah yeah first of all I'm definitely proud and happy to talk about my son his name is Tristan he's uh he's 14 now and I'll start with that like um when he was born he uh he was significantly ill and and I was off work while he was hospitalized for for six months so you it's an opportunity to reevaluate like number one where does work fit into your life uh absolutely but even within work I had a much better understanding of what an urgency was like when you are dealing with your child dying and you have to make decisions about that you can't go back to like that email is urgent to respond to by the end of the day it has to be like really high bar. So I came back from that experience um I think weirdly paradoxically much more empathetic towards a lot of things and on the flip side having no patience for BS you know like and and just not willing to engage on the system for the sake of the system like I I I and I and you know to connect back to my earlier comment about where does your job fit in your life it also probably stiffened my back a little bit to not be worried about making hard decisions for fear of what it would do to my career. I I was at that point for for many years and I think it's a good point to be at where I want to make the right decision for the organization, the people and in my role at Pfizer like a healthcare organization, patients like the patients we served was always always always number one in my mind. And I after my experience with Tristan I had no fear of losing my job because I didn't you know pander to some decision somebody else wanted I was very confident in making decisions I thought were correct. So that that was sort of like one thing that it that was probably that that was the main thing I think that that the experience with him shifted in me. And then in terms of like the empathy with individuals it it did, you know, if I give you the example of one example of when uh he he was hospitalized and I was in a a a room with uh it's different now at the hospital you he was at the Montreal children's uh the room at the time had multiple patients in it and I remember um there were kids that would have seizures constantly and And the if a parent had to leave the room, you you were actually there and could comfort other kids who are having a seizure. And it just sort of like make it forces you to be beyond yourself and to think about other people, even if you're you're not having a party there, you're like, I wasn't there for you know positive reasons that we had our own troubles, but it does open your eyes to other people are dealing with things, other other people are suffering, everybody's got something in their lives. So it definitely taught me that that everybody's got something going on, and 99% of the time you are not aware of it. And in our profession, or in in you know, often in large companies where there's just professionals doing a good job, people hide it, you know, people try to be just to get through the day, first of all, but they also don't want to look vulnerable or weak, or or some people legitimately just don't want to talk about that at work. That's totally okay. But I think one of the things I learned was, you know, you start a conversation. Hi, how are you? How was your weekend? I always, and I didn't succeed at this all the time. I'll be the first to say that. Um, I always tried to do my best to listen properly to what the actual answer was that may include the words being spoken, but are also including people's body language, the way they said the words, if they're looking at you, what's in the background, do they have their camera on, other contextual clues? And if if the answer is like, hmm, that deserves further inquiry, then you've got to find your happy place as a manager or as a leader, like how how much do you sort of push on that a little bit, you know, given the person and your relationship? That's where like having a good relationship with your team members or or colleagues, it doesn't start in a crisis, it should start on a regular basis so they feel comfortable having, you know, maybe a conversation. And there's definitely a separation between work and uh your home life, and and I respected people's privacy. And if they didn't want to talk about something, good, I'm glad that they felt confident to tell me that. At the same time, the person is trying to work and they're going through something, and it would be wrong, I think, for as a manager to ignore that completely. So I got pretty good at cueing in on sort of people's, you know, reaction to that question. And often they would, you know, want to just skip by it and move on. And I think having the confidence to sort of pause and just taking a few minutes from the conversation to dive into that a little bit. And if you do that consistently with honestly, with everybody you meet, uh, I'll just start with as the person doing it. It can be it can be draining, uh, to be honest. And that's why I think a lot of people don't do it as a manager or as a colleague or friend, you know, or family member, to be the one to absorb other people's psychic energy sometimes, it can be challenging. So you actually have to find a way to help others while you know not setting yourself on fire all the time. And that was another learning for me. Like, how can I help people without sort of sh taking on their challenges, you know, um permanently, sometimes temporarily, you do. Um, but that was a learning I had. And I I like I said, I I was not always effective in it, but I think just being aware of that made me uh better at my job.

SPEAKER_00

What led you to decide I am done practicing law? I am gonna take my leadership and business skills and all this insight that I have that got me here and just go full time and and spread it around.

SPEAKER_02

Yeah. It was definitely not a single moment. I'll start with that. It was uh over a long period of time, um, and trying trying out, you know, a lot of the aspects I just talked about and in a different capacity with people. I I helped in, you know, for years, I helped people in my own time um, you know, work through problems and things like that. And all credit to my to my wife, she's like, you know, that's a job. I was like, man, yeah, maybe. And my first thought was that could be my you know, post-retirement career 2.0. Like that's where I sort of started thinking about. And it was easy to think about it in that way because it was non-threatening to my current existence, you know. It was like, yeah, one day. And it wasn't even like a maybe one day, like I'll have a tomato garden. Like it was like, yeah, I could easily, you know, when I'm retired, I could switch into uh helping, and I and I thought about lawyers as well, like helping other lawyers. And I I liked the idea of a way to contribute to the profession in a different way in the future, like you are doing with this, you know, podcast, you're contributing to the profession in a way that probably our bars and bar schools didn't think about at the time, but you are, you know, so it was something I thought about. And then uh, you know, over time I started to realize as I was talking about before, the part of the job that I really liked was the human aspect of the individual. And I also, you know, the flip side of it was I also enjoyed really thinking about organizationally like strategy and how legal services and legal advice can really fit into an organization and how do we work with our outside counsel and how does that work? And I just liked thinking about the issues in a little bit of an abstract but then practical way. So those like the sort of the coaching individual side and the the larger piece, I really thought about a lot and applied it my current role with my team and with the organization and did my best and didn't always succeed because that's you know, not all my ideas were good ones, and not all of them should have succeeded, but I liked the concept of trying out new ideas and I had wonderful management and and team members. I can only say good things about the the the legal division advisor, amazing people gave me a lot of um encouragement to try these new ideas, and and um I I liked that. And then I I think that maybe if I if there was a turning point, you know, it came on many dog walks, uh in part with my wife and in part alone, and and just thinking about you know what was important to me in my career, what I truly enjoyed. Um did I I think I asked myself the question, what if this wasn't a future career 2.0? What would if what would it look like if I did it sooner? Which was a bigger change. And I I like, you know, for big changes in life, I kind of like to just try on the idea like a t-shirt, you know. So I wore the t-shirt for a while, and through that prism, I would say, like, okay, what would today have looked like, you know, if I was doing it differently? Um, I always liked being entrepreneurial within an organization all the way back to when I first practiced at the law firm. I liked beginnings, I liked starting something, challenging what stuff looked like, um, setting up something that might sort of last longer than me. I liked that idea. And and then I thought I started to think a little bit on the business side. Like, was there a, you know, if that's one thing I learned at Pfizer was like how to think like a business person. And I started thinking, is there a market for this? Do people even need this? Um, you know, do law firms need help in you know designing their professional development or um you know how to acquire and and develop clients? Like, do they even need this stuff? So I started to think about it a lot and observe the market and do my own sort of thinking about it and a little bit of light research. And then I started to land on, yeah, I think there is a need. Um and then I thought I thought, well, what could I do to advance this while at the same time, you know, being good at my current job? That was very important to me, which is challenging, but I I definitely managed to do that. Um, what I did was I took a coaching certification uh last year, and I thought, you know what, if if if I decide to stay in my current role and and career trajectory, this is only gonna help. This will be great. Like I'll be better at my job. It'll give me another tool and toolkit. Um, and if I decide to do something else, this will help. So I like that kind of thinking where it was like a win-win. So I did that. It reinforced to me, number one, that I wasn't terrible at it, I but it also showed me some new skills and concepts that I just didn't know and you can't get without that kind of training. I liked it. I liked being in the milieu of like talking about the concept with other people. And the one thing I did observe was I had thought about it more about as a business than other people, like who are in the same cohort as me, and they were maybe a little bit earlier in their journey of like learning, coaching, and things like that, which is fine. But I I thought, yeah, this this could be uh an actual business. And then then began the dog walk phase number two with my wife, where I told I told her I was serious, and she's like, What? So she was like super the most supportive person ever to be a thought partner with. But when I flipped over to yeah, I'm like, I might set a date on it, then we began the freakout phase because you're going at the end of the day, you're going from stability to instability. Uh, you're going from what I think a lot of my peers would kill for as a job, and took me a lot of building of blocks over time to get to where I was. And uh, I'm not I'm not the kind of uh climb the mountain, you know, for the next role type person. I really like being thinking about the role I'm in and what happens after that, you know, what whatever happens. So I wasn't too concerned about like what is this gonna mean for my career trajectory. I liked being in the present moment of what I was doing. So thinking about like what would my day-to-day look like really appealed to me. And then uh I kind of put a date in the calendar mentally and said, okay, by this date, I'm gonna work towards that and see how it goes. And I started working towards it and building up sort of the business concept and reaching out to some people and pressure testing the, you know, am I crazy question? And it wasn't so crazy. And then I then I started feeling like I am gonna do this, and then I started feeling all the the thing that hurt me the most was thinking about leaving my team. Uh, and I felt like uh a little bit like I was abandoning them. Um, I loved working with all of them. I felt like I was abandoning the especially the Pfizer organizations that I support in multiple markets. That really sucked, and I didn't like that feeling. But uh sometimes you got to do what's right, you know, for yourself and your family. So that was sort of the process.

SPEAKER_00

How does it feel now?

SPEAKER_02

Great. Honestly, uh, I feel very good. I think it was the right decision so far. I know it's the right decision so far. We'll see what the future brings. But as of today, I feel like I'm doing what I thought I would do, helping helping people. Uh, I do see that there's a market. Uh, I've I'm working with a couple firms on you know various things, like sort of my overall uh approach is sort of in four buckets. I help people coaching one-on-one, mostly lawyers, but not all like professional services uh across the board are pretty similar. Um so coaching one-on-one, even group coaching could be small groups of people. Um, the third third box, um, I you know offer uh presentation time, training to organizations. Um, mostly, I think my sort of like core approach is like if I'm talking with a law firm, you know, what is what do your clients really think? You know, because I spent 18 years in that role of hiring law firms, deciding which ones we use, how do we deploy their resources, which ones we want to work with, which lawyers we like. So that, you know, thinking I think is valuable, hopefully. I'm sure it'll become less valuable over time, but as of right now, I still remember some of that stuff. So I I offer to help uh law firms with that. And then box three is uh any help they they need with their professional development program as a system and helping either create or design that with them, you know, how to train lawyers and what what are the skills they need as they work their way through their career. And then uh fourthly, just how firms seek out, acquire, and maintain their clients, you know, uh a lot of them in their business development programs uh miss the mark a little bit. And I've seen what works, what doesn't work, at least from my perspective. There's all sorts of ways of doing it, but that's another way that I help. And so far, there's an interest across the board. I'm uh I'm enjoying it. I'm trying to also um pace myself, you know, um, being a solopreneur, you are uh you are the IT department, you are the janitor, you are everything. And I have definite limits to my skills in all of these areas. So I'm trying to make sure that I'm not spreading myself too thin and that when I like, for example, if I have a person who has a one-on-one coaching situation who's trusted me to sign up with me and to give you know me some of their time every month, I'm a hundred percent committed to them in that moment. I don't want to be distracted by anything else. So that's important to me as well. And I'm taking that from my experience, you know, in my previous role of just making sure that I I'm present in front of the person, you know, that honestly, if you're doing that in whatever your job is, if you're present with the person you're working with, then you you'll probably succeed.

SPEAKER_00

Do you have uh a tip or or you know a go-to method for making sure that you're you're present and also you just not it's one thing to know that you want to not be stretched too thin, it's another thing to actually follow through with that.

SPEAKER_02

Yeah. Yeah. On that last part, just because I'm in early phases of my you know new business, um I'm I'm uh willing to explore all possibilities, you know, people reach out with different opportunities. And I think I I owe my my family that's you know want worried about we're gonna eat cat food, you know, soon. Uh I definitely owe them the the you know exploration part. But uh I I think I'm actually, you know, to the benefit of the people I work with, I think I want to make sure it's a good fit, you know, and I and I have had conversations with people and I'm like, you know, I'm not sure this is the right fit between your organization and what I'm offering. And I'm I'm even though that's hard when you're um beginning a new business, I'm definitely able to say, like, I don't, I don't, let's, let's see if this works later, but right now I don't think so. And I think I'm doing the right thing for them and for myself. Uh, you know, and the on the presence piece, um, I think it's a practice I developed over time that I'm pretty good at compartmentalization. So when I look at my calendar, for example, like you and I talking today, I have I block time before and crucially after, um, to, and it it varies by the task, but to mentally prepare for whatever that is. So for this event, you know, I didn't know what we were going to talk about, which is the best way of having a discussion like this. I love it. Thank you for that. But I also just steeped myself in what you're bringing to the universe, our prior conversations. Um, I didn't think too much about like what you would ask me because I like to sort of think about it in the moment, but just to sort of be present in what you're trying to achieve, the goal for your audience. So that's five minutes just sort of sitting there. And your physical environment, you know, like I close all the other things on my computer earlier, uh, just making sure I'm comfortable, all those things. I've always done that, which means you got to be the master of your calendar a little bit. Because if you say I'm going to block a little bit of time to do that, if you have the bat classic back to back, you are going to look less effective in every meeting, you know, versus fewer meetings and look more effective and be more effective. So that's like, you know, one tip I would have for people. And just I I take time to think um in advance quite about quite uh quite in quite in advance about things. I have a presentation to a law firm coming up, and I was you would maybe you'll laugh at this. I had a dentist appointment this morning, and I don't know about you, but I weirdly I kind of look forward to the dentist as long as like everything's cool and I don't have to have have a lot of drilling going on, but I closed my eyes and it's entirely possible I fall asleep, like you know, with kids and stuff like that. That's you know, okay if you're lying down, your eyes are closed. But I also this morning, like weirdly, I was thinking about this presentation I was gonna give, and I came up with three or four really good ideas. And I'm like, geez, I gotta remember this because I can't like jot anything on my phone while I'm sitting on this chair. But I I often use just sort of moments where not moments where you're by the pool with your family, like you should I'm not advocating that, but moments where you're otherwise occupied, but your brain is very alive and you can think. And I use those moments to sort of do a deep think on stuff, and I, you know, exit that thing and I got in the car, and I'm a big fan of technology, so I, you know, uh dictated into my AI, you know, like some ideas and I like work on this while I'm you know going somewhere else and just sort of churn through those ideas. Um, I'm a big fan of that, and the people you work with benefit from that. Because if you just I I think if you just sit down in front of your computer and say, okay, I have an hour blocked to think about this article or this you know presentation, yeah, it's gonna be okay, but I've always gotten better ideas walking the dog on the treadmill, whatever. And if you have some method of triggering those ideas and capturing them, there's something to me about like a variety of locations and contexts that I just come up with like better ideas sometimes. Uh so anyway, so as a little trick, like if you then arrive at your computer and you are your brain and your document is a bit pre-populated with um things that spark creativity, I get excited. You know, I'm like, okay, uh, that idea at the dentist, I really want to dry dive into it, and then you get sort of a you know, a much more interesting thing. So part of the presence is like to create an environment and a context that excites you to be there. If you're gonna be bored doing whatever you're doing, uh, you're not gonna bring yourself to be present and you know, to really focus on what you're doing. And that was another, to go back to your earlier question, it was another reason I wanted to make this change in my career. It's exciting for me to help people in this capacity. And it's exciting, whether it be an individual, you know, making a one of the biggest reasons I felt it was time for me to move on was I was lucky enough to work at an organization that I think has made at the organizational level has made a dent in the universe. You know, if I think about the COVID pandemic we all lived through and uh the work we did at Pfizer, I was very proud of that. And as a team of thousands of people, we put a dent in the universe and I I felt good about that. And then when I, you know, as I help individuals, for example, if you make a dent in the universe or they make a dent with your help of the universe of a single person, holy cow, is that impactful? Like you've changed someone's life, you know, like I feel good about that. Uh, that's something that I really appreciate and was a driving force of you know, me wanting to try something new. And then the flip side of the consulting with law firms, I felt really good about like doing a full circle and coming back to help law firms and help the profession that I grew up in. Um, and I often was as a client on the side of I could see so many things I would do differently or better if I helped you, and I did sometimes if I could in the firms that I had a really good relationship with and worked with them, I would put my time to help, you know, meet their associates and help develop them because I saw so many opportunities for them to do that, and I really liked the idea of it. So, bottom line, I like you know putting a new version of a new dent, you know, in a different universe. That was one of the reasons I wanted the change.

SPEAKER_00

Do you have another couple of minutes? If you do, I'm not rushed, yeah. Because I also want you to, if you can, summarize maybe your top one or two items that you feel like you did keep seeing at law firms that you thought, if only, you know, of course every firm is going to be different. There's no blanket statement, but across the board, what do you think a lot of firms could understand to improve?

SPEAKER_02

Yeah, no, it's great. Um, I think one of the things is like because it's a paid service, so you make a request of a firm and they, you know, appropriately answer your request, there's often not a lot of space for the firm being curious about the client, you know, about how the organization works, the culture, the decisional framework, who are the deciders, what you're actually trying to achieve. Uh, I remember working with some law firms for years, and then they would talk about two individuals thinking that one reported to the other just because of. The relationship they viewed, and I laughed. And I'm like, holy cow, they do not, they're their peers, yeah, their jobs are totally different. And I realized they don't understand like our decision framework at all, and you know, and it had been years we're working together. So I think the one thing I would advise law firms to do is to just ask, you know, to be curious. Uh, what can you describe your company's culture to me? And I I remember going to a firm event with uh two other colleagues from Pfizer at the time, and I asked, it was an event where there were multiple firms, so it wasn't, you know, I can't uh I won't pin this to any one in particular, but I I asked, like, just could you uh describe your firm's culture to us, you know? And uh to be honest, they they could not, you know, and in fairness, they were young associates and they they they struggled to describe the culture of the places they worked at. And then they asked us, could you describe your culture? And all three of us in unison gave the same forward answer. You know, it was a very clear culture at our organization, and it wasn't one of those dusty things on the wall. So, you know, my response to them was also because you don't know our culture, you don't realize the um uh filter through which I give legal advice. Like, and the purpose of the organization was breakthroughs that change people's lives, patients' lives. So the people taking the medications, it's all about patient. My advice is filtered through that. I am I would be willing to take a very high legal risk uh in the situation, for example, if someone was dying of cancer and they were told they have two months to live and they needed a particular medicine and there were legal risks in providing that. I was willing to take a much higher risk because the outcome is an individual whose health is in jeopardy versus our legal risk as a as an entity. So that was uh that framed our advice to the organization. But if the people at the law firm don't know that that's how we think about it, they'll just think, well, your legal risk is high there, you shouldn't do it. So I think that's number one is be curious about the culture of your organization, be curious about how decisions are made, who makes them, how much, and you could just ask the in-house, you know, in instructing counsel, how much authority do you really have? And it's funny because you may not want to ask it that way, but it's all, you know, we're all human beings. The individual at the company who does not necessarily have a lot of authority but is the connection to the law firm probably doesn't want to admit it because they're going to think, well, then they'll just go over my head to my boss, to my colleague, you know. So, but then to protect your own ego, you're getting a worse outcome, you know. So you can have an honest conversation. Who is in a circle around you that helps you with decisions? How can I help, you know, inform all these people so we get a better decision? There's a way to approach it with like without bursting the bubble of the person working with you, but to get a better decision. Often that is not explored for um call it sort of uh, you know, reasons not to offend people, but I'm all about better outcome, you know. So so asking about the decisional framework, and even like, for example, I a lot of the uh tactics I think that law firms in a good way do to try to give value to their clients, newsletters, um, maybe even there's there's some podcasts out there, like sharing legal information. This is good. This is sort of like I view as kind of layer number one. Um, layer number two gets much more personal, and I'll flip it around. Like I was just thinking about something this morning. Uh, if you're a you know, a litigation outfit, you do litigation for you know, like you're a boutique or something like that, you do mostly that. And you have a client that of course has litigation, but you don't know much more about the rest of their business, you're probably not the right group to be giving advice on that. Litigation is like such an expensive, unknown thing. It's you know, it could be really costly out of nowhere. The relationships usually that in-house counsel have with their litigators is is a challenging one. And one way to add value, for example, would be if the firm were to say, listen, um, we know we don't advise you on X, Y, Z matters that are more maybe opinions or giving advice, but would you be open to like we could train your in-house team on how to think like a litigator that in that situation to help your business? So that might mean negotiation skills, that might mean, you know, kind of analytical frameworks, risk taking, uh, persuasion. Like, who doesn't, as an in-house counselor or general counsel, who doesn't need persuasion skills? So I would love to see law firms take their strengths, you know, whatever that may be, and instead of saying, or in addition to, here is some subject matter information, how about flipping it around and say, can I help teach you some skills that might you know be beneficial for you in your day-to-day practice? To me, that's like something out of the box that I've not been ever been offered and would love. And even I think I even talked about like um, you know, because I'm I'm a former litigator, so I'm biased towards that, but I always felt like it shaped me into who I was, you know, and uh I thought, okay, if we can learn those kind of skills, it would be useful across the board. So I think the overall to answer your question, I think if the firms think about the needs of the organization of the people there a few layers deeper than we are now, there's lots of opportunity for exchange of value. And by exchange, I mean what I just described someone from the law firm coming to teach, you know, um a particular skill. And uh we, you know, that's nowadays we all all the lawyers are taking, you know, professional credits, and you do you sit through a presentation and you learned about substantive law area, and that's fine. But if you flip flip the script and let's say I was a manager at a company and I were to reach out to a law firm and say, hey, uh I two things. I've got someone on my team, I'm trying to get them to work on their presentation skills, their influence skills, uh, all these things, public speaking. Would you mind if they come to present to your team at the law firm a little bit of an overview about what's going on in our industry? Like that's a reversal that I don't see very often. And it would be like a win-win-win across the board. What law firm would say no to that? You know, so why not ask? If you're the law firm, would you guys mind? I know it's some use of your time. Could you have one hour, you know, someone on your team, if you want to have a junior person develop their skills? Just teach us about your company, about your industry. What are your challenges? Uh, that would be cool. I would have said yes to that for sure.

SPEAKER_00

What are your thoughts on if uh how the billable model, billable hour model impacts the relationship, the curiosity or lack thereof, the exchange or lack thereof?

SPEAKER_02

Yeah. Yeah, it's a challenge right from the start. I mean, uh, let's just be honest, like they're kind of diametrically opposed the interests in the model, like the the firm is its interests lie in more hours and the client in less. And that's that's that's the obviously the tension. I think there's a place, even like even if you stay within the billable model and you don't exit it towards you know, some other you know, model, which of course there are many that exist, and many of them are good. But even if you are within that model, there's so much space for like um building trust, uh, making sure that the client is satisfied with the work and the approach, all the way from like just honest conversations at the beginning. Like, what am I gonna bill? Who's gonna be billing this? What are things that I have a lot of leeway on that I don't necessarily need to bill? Let's talk about uh it all starts with a conversation, you know, and even like uh the approach of the in-house council and the outside council seeing each other as colleagues as opposed to a client uh provider relationship, which they are right, we are all in the legal profession colleagues. That mindset of okay, I how do I explain to my colleague here how we're gonna work together and what's a win-win. Um, and if you set that out from the outset, I think nobody's gonna feel like they're getting hosed along the line. And then I do think it's okay as things are going on, if there's pain points and something comes up, there should be like uh it should be the norm that there's an honest conversation, like either, you know, what's going on with this, uh, you know, there's a lot of hours in this matter, and I didn't think we that was gonna happen, or the quality of the work. So the the culture of honest conversations, I think is super important in that. And also like uh the best relationships I've had with law firms are, you know, okay, we're in the billable model, we're looking at, you know, like specific matters and what they're gonna cost, but to step back a bit and ask like the law firm, what are you guys trying to achieve over time as a firm? Do you want to get more into this specific area, these markets, these geographies? What are you trying to achieve as a business? And I will keep that in mind and try to help you because when I give you work, I will know what you're you want. And if you have that conversation, if someone says, I'm looking to get, we're looking to get more and more into antitrust uh in this, you know, this market, if I can deliver some work in that area, it's disproportionately valuable to the firm, right? So maybe they view that as a bigger exchange of value than a particular matter that's just you know something they do every day. But it I won't know that unless I ask, you know. So if they say we're really looking to get into this particular litigation space, and I can offer them something in that space, I'm giving more value than you know is otherwise expected, that that is a balance. So in you know, just negotiation theory, you sort of have to put everything on the table and move the pieces around a little bit so it's open conversations. And then at the end of the day, I mean, this isn't like a shocking thing to say, but the law firms have to really avoid surprises, you know, like uh getting that huge bill when you didn't anticipate or uh sort of budget for it. That was one of my learnings when I started managing legal budgets was first of all, even in large companies, the legal budgets are are not large, you know, like they are they are understandably they uh businesses are in the business to make money and they put their resources towards things that make money. And typically, you know, legal, legal disputes and things don't fit in that category. So you have a very finite bucket of stuff. So the amounts of money that like get attention are relatively small compared to the revenues of those organizations. So you can spend a lot of time diving into like small amounts, and the firms might sort of be surprised because they view your organization as a large behemoth or whatever. And I think it's it's incumbent on the in-house person at the beginning to say, like, okay, generally, this is you know, you certainly don't have to sort of give your annual budget or whatever, but like just to give them a sense of the scale of how much work you're really anticipating that year. So that as the firm works towards things, they'll go, okay, time out. I I should speak to my client because if I go down path X, it's definitely gonna you know change the nature of it. So I do so honest conversations, um being creative together, being you know, uh goal-oriented for both entities, what are we trying to achieve? And then if I'll be much more accepting and you know, quote unquote forgiving of a firm that is uh maybe high on the billing side, if I'm seeing a lot of value out of it, they're developing my team, you know. And I, you know, as a last point, I always expected out of my firms that if we make a request that isn't like clear or it seems too open-ended, or they there is a risk that it'll be misunderstood and end up end up being a matter that gets sort of super billed, they have to tell us that's not a good question. I I want to be corrected, I want to be like educated. If they say, why don't you ask us this? I think this is gonna be a better result. What do you think? Like having you know the firm just blindly follow your instructions and then you get a huge bill, that just doesn't work, you know? And so honor that's part of the honest conversation category.

SPEAKER_00

Is that maybe part of how you'd think about um so my my question, my next slip question was actually gonna be, you know, is we've covered you know a number of ways that firms can improve. Um and so what about a couple of ways that you routinely see that individual lawyers can improve, whether they're at a firm and you're struggling with these communications, perhaps, or in-house? What are the things that are keeping them from becoming the leaders that it seems like they want to be, and also from developing those relationships across colleagues?

SPEAKER_02

Like, yeah, yeah. Yeah. I mean, I think part of it is viewing things at on different dimensions, you know, like the dimension of okay, if I if I'm working with these multiple stakeholders, I've got my clients, I've got my team, myself, the firm I'm working with. Each of these dimensions requires, even as one problem is working through it, requires a little bit of thought and a little maybe a little bit of a different approach. And overall, you should feel like you are uh at the center. You're the the hub and you're the master of the situation and how this problem moves through. Okay, you know, how do I deploy my resources? My my client needs X. Um, you know, you should be the person to be thinking about. Is I start with, is this even a legal issue? Should I take control and deploy my you know legal resources, or should I challenge that this is probably something that we can solve without deploying legal resources? Because I was always of the view that in most organizations, um, certainly at a law firm, but in companies, your legal resources are some of your most specialized, um uh unavailable and expenses, expensive resources. So you have to make like have that in mind before deploying them, which means I always start with the assumption or the question: can someone other than a legal resource deal with this problem? Or can we have the lightest touch from a legal resource touch onto it? And then you have to have the self-awareness that there are other, you know, um experts and service providers and colleagues that are also expensive. You don't want to offload it to, you know, um an equally expensive and and uh challenging resource. So anyway, so start with uh, and it isn't a lazy starting point, I don't want more work. It's more like I am the guardian of highly expensive resources in the organization, should I deploy them? And the answer is often uh a light version of no. It could be I can help with this problem, but I'm not going to fully own it and really give it the most expensive kind of review. So part of that is I think the individual at the beginning asked themselves that. That's the in-house version, the law firm version. If I'm an associate and I'm getting an ask, I think to make it the most efficient way is like, uh, do I fully understand the question and the context of the question? Because the worst case, and I've I'm absolutely guilty of that over time, is you know, you beaver away on something and you get this perfect answer, and uh you've been, you know, climbing up the wrong tree the whole time. So clarity on what you're trying to achieve, clarity on your role as part of the team. It is, I cannot remember ever working on anything in the last 20 years where my sole effort was the reason for success. There's always someone else. So, how where what's your role in the team? How do you best deploy those resources? And then, you know, if you do land on yes, I need to deploy legal resources, then I go through like all sorts of levels of like, is it is there someone internally that knows that is this is their day job, that they're an expert in this or they can help, or someone on the team. If you're a team leader or manager, part of your responsibility is to develop other people. Is this going to be an interesting development opportunity for another person? Should I give it to them? Should I help them? And then if you do, you know, delegate it to someone, what's your role and helping them with that? Then if you decide, no, this one is actually appropriate for me to do, how do you prioritize that? And where does it fit into your day and what resources do you personally use? And then if it's something that I always view it as way too technical and expert for us to handle in-house, and has to be an and important for the business, then I will deploy outside council resource. And I, in order to do that really effectively, then to go through am I being clear with them on what I need, what's the timeline and what's the deliverable and all that usual stuff. And then to go back to our previous conversation, like what's the benefit for the firm? Is this something interesting to them? Can they deploy an uh you know a younger associate to learn on it? So my point is at every layer of all of this, and I haven't even gotten to the client, at every layer of all of this, you're thinking about what's the most effective way to use resources at many levels. Uh, and then once you make that decision, which all of this thinking probably can happen in 10 seconds, but once you make that decision, then how do you engage with your client on it? Like, you know, tell them the plan, you know, like this is what I'm proposing, uh, this is how I plan to manage it. And as an in-house counsel, you know, you have to think it's weird, eh? Like, I didn't go into law thinking I'd say no to my clients, but it I I would say a variation of no quite a bit, meaning like challenging, is this really something you think the company should spend legal resources on? Can we can we come to an answer without that? Um, one of my approaches was called principle-based advice. And can you, rather than just answering the legal question, can you together, client and lawyer, develop a principle that they walk away with and use on their own and uh take risks on their own as long as it's within the universe of that principle? So you have to decide your risk tolerance as a lawyer. Are you willing to have your clients go out and take decisions you are unaware of, you know? And in business, one of the key elements is speed. Can you, you know, out competing your um competitor a day too late is losing, you know? So can you do things faster? One of the main hits, you know, as many of the people listening to this on the legal profession will, especially in-house counsel, will know is we're too slow. You know, we slow things down. We are barriers, we're blockades, you know, and so the principle-based advice concept is to address a little in part that, like the speed aspect and to transfer some of the risk taking to the clients. And that requires trust, that requires conversation. So that in all of those decisions, even if you decide, okay, I'm not going to do this, but I'm going to leave it to my client, that I think, in my opinion, can be done within a framework, not within a hope and a prayer. So, you know, sending them off on their own without your overall framework guidance is a recipe for disaster. But I always enjoyed that, like giving your clients a measure of autonomy is a sign of a maturing lawyer, uh, a sign of your excuse me, a sign of your trust in them over time that you've built, a sign that you know the organization and what the limits and tolerances are and where we can play a little bit, take risks. Uh, that was something that took a long time for me to develop over time, but is something that I highly deployed, you know, um later in my practice and really enjoyed that.

SPEAKER_00

Amazing. I could talk to you all day. Is there anything else you're you're yearning to share that we have not covered or only touched on a little?

SPEAKER_02

Yeah, I'll I'll I mean, just to last thing I'll say maybe is just in the space that you cover a little bit with you know, wellness in our profession and uh on many levels. Um, you know, my only thought for people is uh just given where I am in this moment in my life and my career with making a a change, you know, a big change. And my thought for people is like it doesn't have to be as dramatic and scary as completely changing your career, you know, leaving a job, things like that. But I think change is good. People are often afraid of change, it stresses them out, it you know decreases their wellness sometimes. But uh, you know, change is always the thing that creates something better after, you know, and if even if something hits you, you didn't anticipate it, you didn't create it, it's gonna be a change. The times in my career when I've had the most opportunity to do something different and cool and fun was when something was changing, you know. So I would just uh invite people to number one, both um welcome change and work within it, see what's on the other side, take advantage of the moment, and then second, create changes, you know, in their their lives and their their career. And it can be small, you know, but uh take something from what we discussed today and try something new in your practice, you know, and that that could be a small change that precipitates something bigger. So that would be my my closing thought.

SPEAKER_00

I love it. Thank you so much. I again I could I could talk to you all day. I loved this conversation. Thank you for putting out into the world so much really valuable wisdom that we we really all need. And I'm I'm excited to see all of the the dents that you're gonna have in the universe uh through your individual firm and and lawyer uh clients.

SPEAKER_01

Thank you. Thank you. I really appreciate it, Ale. Thank you so much.

SPEAKER_00

Thanks for listening. I hope you got a ton of value from this conversation, and that you will check out the links in the description to learn more about the guest and the wellness esquire. And I hope you take even just one minute to do something for yourself today. Maybe right now. Drink more water, say no, call a friend, do something that makes you happy, have a 30 second dance party, find something to make you laugh. Also, be sure to subscribe and send the podcast to a colleague. And if we're not yet connected on LinkedIn, please fix that. I'd love to know you. See you next time.

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Ariella Cohen Coleman

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