Denise Baker | Leading a Law Firm: Hot Topics, Tough Calls, and Leadership Lessons

Elise Holtzman: Hi, everyone. It's Elise Holtzman here, a former practicing lawyer and the host of The Lawyer's Edge Podcast, where I sit down with successful attorneys, legal marketing specialists, business leaders, and authors to talk about how lawyers and law firms can grow and sustain healthy, profitable businesses.

Hi everyone. It's Elise Holtzman here. Welcome back to another episode of The Lawyer's Edge. Today's episode is brought to you by the Ignite Women's Business Development Accelerator, a nine-month business development program created by women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers and supporting the retention and advancement of other women in the profession. Registration is now open for the 2025 Ignite cohort and early bird pricing is available. To learn more about Ignite, visit thelawyersedge.com/ignite.

I'm excited to welcome my guest today, Denise Baker, who is a co-managing partner of WeirFoulds, one of Canada's oldest and most prestigious law firms. In addition to her role managing the firm, Denise provides advice on complex municipal and land use planning law issues appearing before multiple courts and tribunals in addition to participating in mediations and negotiations to effectively resolve disputes before they ever get to court.

She chairs numerous land use and municipal law-related committees, including being a past chair of the municipal law section of the Ontario Bar Association, speaks frequently for organizations like the Law Society of Ontario, the Ontario Bar Association, and the Ontario Professional Planners Institute and she's been teaching land use law for years.

Denise is repeatedly recognized by Best Lawyers in Canada and in the Canadian Legal Lexpert Directory in the field of municipal law and she's also ranked by Chambers Canada. Denise, welcome to The Lawyer's Edge.

Denise Baker: Thanks, Elise. Thanks very much for having me here.

Elise Holtzman: I'm excited to have you. You and I met as faculty members for a conference put on by the Managing Partner Forum at the end of last year. As a managing partner with plenty on your plate, including the multiple things I just mentioned, your teaching and your chairing and you're doing all sorts of things, practicing law, why do you invest time, money, and energy in attending a conference like that? We can all list things that we get from going to conferences, but for you, what do you get out of it? Why is it important for you to make the time to do that?

Denise Baker: Yeah, that's a great question, Elise, and certainly one that you think about every time you sign up for a conference to say, “What is it that I'm going to get out of this? Why am I spending my time there?” That particular conference that we were at the Managing Partners Forum, it was in October in Chicago, the one thing that really drew me to that conference first and foremost is it was a conference for women managing partners or women in leadership roles.

The one thing I loved about it is it was the same type of issues that managing partners of any gender would deal with, but from a woman's perspective. I think that's really important, because as they say, it’s the old adage, but it's true, it is lonely at the top so it's really important to make those connections and get those perspectives from colleagues in very similar situations that you can then consider and reflect upon and where appropriate, implement into your firm. That conference in particular was highly valuable for the work that I do for WeirFoulds.

Elise Holtzman: As you mentioned, there was a lot of discussion at the conference about all of the things that managing partners are concerned about working on. What are some of those things? What do you think are the key issues you're facing in your firm? What are some of the key issues that you think law firm leaders generally are facing these days?

Denise Baker: Leadership right now is a difficult road. I think there are a lot of moving pieces and so a number of the key things that certainly we're grappling with, we're still grappling with the back to work situation, and it's not so much “Back to work, I need you in the office so I can see your face” issue but it's the back-to-work issue of “How am I satisfied that the six-year lawyer that we all expect to have a certain skill set back in 1995 has the same skill set or at the same level today?”

We worry about how they're being trained. Are they being trained? How are they coping with a virtual platform for litigation, for example, or how are they getting out to meet clients and, and make sure that we're properly servicing our clients?

All of those issues that are around, I would call “back to work adjacent” type issues, not because again, like I said, we need to see people in the office, but we need to ensure that the lawyers, we have a duty, in fact, I would say that the lawyers coming in behind us are properly trained.

I think that's one big issue. Somewhat related but also independent is the new talent coming, the younger generation that's coming up behind us. They have a different work ethic, a different drive, and probably rightly so, have a more balanced approach to how they want their life really to be led.

We have to properly find ways to motivate them. I just think back to when I was practicing, and sometimes you didn't want feedback, but they want feedback, they want constant feedback. It's important that we provide them that type of feedback that the statistics would show they're less likely to stay in one place for their whole career.

Selfishly, training lawyers and onboarding lawyers is very expensive. You want your good people to stay. How do we make sure that we're properly motivating them and meeting their needs, and ensuring job satisfaction, really at its basic level? I think that's another emerging issue.

Elise Holtzman: Some of the issues you're talking about, making sure they're properly trained, making sure they're getting the feedback, making sure that they fit into the culture with people from other generations who think a little bit differently than they do, then you mentioned technology.

It seems to me that so many of these things are related, especially with AI coming along. Because, to your point, if AI is supposed to start taking over some of the roles that maybe first, second, and third-year associates have occupied in the past, they don't spring from the ground as fourth or fifth-year associates.

You can't give everything over to AI and then say, "Oh, great. When it gets to the point where you would want a fourth or fifth-year lawyer to be involved, we can just have them involved." Well, how are they learning that first through third-year stuff and the judgment and all of those things? I'm curious whether you are starting to see that, whether you guys are using that technology, and what role technology plays in terms of your growth.

Denise Baker: Technology is probably one of the key leading issues. Not only those issues that you mentioned, their impact on the workforce, and those sorts of things, but this technology is extraordinarily expensive. How do we ensure that the law firm itself is suitably profitable to be able to invest in these types of technology pieces? That's one side of it.

I'll tell you this at least, I just came back and I did the Harvard Leading Professional Service Firms course in Boston last week in January, and one of the sessions was on AI. I've never been one that says, “Oh, AI is not coming,” or anything like that, but I hadn't embraced it at all into my practice. One of the courses when I did that program down at Harvard was on AI and I'm going to tell you my mind was blown, just completely blown.

I've come back and I've just been playing around with it on weekends and on even aspects of my own practice and speaking to some of my young associates who are doing some work and saying, "Well, why don't you try this? Why don't you try Copilot or even ChatGPT and those sorts of things? Try this and see if it's saving you time." We're starting to roll that out.

I had a report provided to me and a client saying, "Can we meet on such and such a day?" So I was like, "I'm going to try to throw this report." It was a public report. You can Google it. It was a publicly available report. I pumped it into ChatGPT and I said, "Can you summarize this report for me?" And I do land development so I looked at the report and I was like, "First of all, this is amazing, a summary of one page, look how knowledgeable I'm going to sound and everything. It's so great."

Then I looked at it and I said, "There's something wrong with this report." It didn't talk about the impacts of wind on the building or the impacts of the building on wind, however you want to look at it. So I went back and looked at the report. Of course, there were wind issues in there. But I knew that because I've been practicing law for over 20 years. The question is if our young people are just saying, "Hey, summarize this report," and then they go in and talk to people and they're missing that issue, that's a big issue. It's a very expensive issue if you miss it.

So developing that judgment is the critical piece. How do we do it, really? I think in some respects, you know when the calculator first came out and you calculated it but then you still added it up just to make sure that it was actually doing what is right? I think we're in a little bit of that stage where you want to say, "I'm going to still read the report and make sure nothing's missing but we have to make sure people aren't lazy, that they're still doing that exercise."

That's the only way to develop the judgment. You're still going to have to read the cases. AI cannot read the cases for you. You're still going to have to read all the documents and learn to craft a cross-examination. But I do worry about shortcuts, people taking shortcuts.

Then we also have to hire for different skills. Asking AI the right question is important. One of the interesting exercises we did when we were down in Harvard, we were trying to solve a problem. One of the people said, "Well, I asked AI what questions I should ask AI," and I thought, "Oh, my goodness. That was a brilliant concept." I didn't ask AI that. I was still trying to solve the problem. So I just thought we really have to make sure the prompts are right and that the young people are skilled in that area.

A new area of law, I find it tremendously exciting. I'm all in now. I was hesitant before but I think it's coming and it's here to stay so we have to weave it into our practice. Then I think the last piece of it is over the last five years, we've seen such turmoil in the practice, and there's been an unsettledness and the market has changed. It was going gangbusters in COVID, and then it slowed down, interest rates were high, money became more expensive, there's great uncertainty in the market these days as you guys are seeing in the States and we're definitely feeling in Canada.

People are a little bit uneasy and I'm finding it's more difficult conversations, more time needed to be spent with people one on one and making sure people of all ages are properly motivated, making sure people are doing all the things that they need to do in order to have a successful practice. I think that's another big part of what we're seeing in the industry.

Elise Holtzman: Managing partners are in this strange situation where, unlike other sorts of companies where somebody is managing and somebody is doing the work and somebody is designing the products and someone is marketing the products and someone is selling the product, managing partners are in a situation, all lawyers I think, private practice lawyers are in a situation where they're supposed to do everything.

When you get to the managing partner role, it just becomes even more critical that you manage your time well because you're wearing so many different hats. I notice many law firms are starting to get into a co-managing partner framework for the management of the firm. I know your firm is doing that as well. You have somebody with whom you're managing the firm. What made you as a firm decide to use that framework? Have you always had it? Is it something fairly new? What's the reasoning behind that?

Denise Baker: The co-managing partner framework came up actually during COVID. COVID was a lot. That was massive in Toronto, everywhere but in Toronto, we were out of the office for a really long period of time, so.

Elise Holtzman: Yeah, I don't think everybody necessarily realizes that I remember Canada, we were shut down here, but you guys were really locked up tight. I think you guys had a lot more restrictions on you even than we did.

Denise Baker: Yes, and can you imagine at the beginning of that, when they first shut us down in March of 2020, thinking like, "Oh my goodness, like what is going to happen? Did they shut the courts down? We do a lot of litigation at our firm. What was going to happen? How was I going to make sure that all 250 of our employees were going to be able to put food on the table, to be honest with you?"

It was a very unsettling time. I was sat on the management committee. I was not the managing partner at the time. I did sit on the management committee and I think it just evolved through there. It became a much bigger job than traditionally having everybody in one office and being able to see everything. It did evolve from COVID. One of the beauties I would say of it is because, as you rightly noted, we do still practice law.

My co-managing partner is Wayne Egan. He's a securities lawyer while I'm on the land development side, I'm a litigation lawyer. One of the great things about it is if I'm in a lengthy hearing or a lengthy trial, Wayne runs the firm on his own. I don't have to worry about those sorts of things. If he's got a significant closing or any other parts of what securities lawyers do, then I run it. We provide that backup for each other.

I think that really helps to make that our clients are well-serviced as well as our partners and employees. We also have a really good COO, a professional management and a professional management team of excellent CFO who all sit with us on the management committee to make sure everything moves forward and in addition to Wayne and I, there are four other members on the management committee.

As the COO runs the operations of the firm, generally on the staff side, Wayne and I don't have it very strictly, like, “You do this, Denise, and you do this.” We have somewhere he takes the lead on or I take the lead on. But again, it's just nice to have somebody to bet around ideas with. It's a lot. Trying to practice and manage 110 lawyers and 130 staff, it's a lot.

I have to tell you, I would strongly recommend the co-managing partner framework if you're also practicing. Because I think that's the key piece. If there's still a practice element to it, for me, it's been a game changer.

Elise Holtzman: Are there other tips you have in addition to having a co-managing partner, somebody that you can share the load with, and as you say, back each other up? How do you manage your management responsibilities along with a busy practice? Do you have tips for other people who might be in a similar situation?

Denise Baker: My nature is to want to know everything about everything. I think maybe that's the litigator's nature like, “You need to know everything if you're going to cross-examine on it.” You can't know everything. You have to have a lot of faith, so you've got to put trust you hire good people. Spend the time to hire good people, we have a great COO, a great CFO, and I'm in constant contact with them.

They're implementing management decisions, but how they're implementing it necessarily, I don't know the nitty-gritty of, and being okay with that, I think it was learned because it's just our nature to want to know everything. I think that's in part the same with the things that Wayne is taking on. If we've decided that's something that Wayne's doing or I'm doing, the other one stays out of it. You really have to stay out of it.

That all goes hand in hand with not just delegating, but complete delegating. Here it is, but I'm not keeping one foot in. It undermines the people who you've delegated the decision to and you really want to empower them to make those decisions. It's hard, I can tell you, it's difficult, but it's necessary. I have three children too, so I could manage the firm like 24/7 because there's always something to do, something to think about, something to strategically think about, but you have to put your faith in others.

Elise Holtzman: What I hear you saying is in part that it's not just about what you do or what you don't do, it's partly about who you become, how you change and shift your mindset and shift the way you show up. It's a conversation that strangely, I've been having a lot in the past few weeks with several of my individual coaching clients who are in roles like yours, senior leaders, managing partners of the firm, huge rainmakers, that sort of thing, and when they want to grow and they want to continue changing in their roles even though they're so accomplished, one of the questions I've found myself asking lately is not just what do you need to do or not do, but who do you need to be. How do you continue evolving as a leader, as a rainmaker, as a human being?

See, you mentioned this idea of being willing or able to let go a little bit more. I'm curious if there's anything else that comes to mind as you think about how you've changed, how you've grown since you've taken on this role, what if anything comes to mind for you?

Denise Baker: So I think that's a great question. I think it's one that everybody should reflect on more. I will say the one thing is I listen more now than I ever did before. Because I've learned that maybe, I was going to say even as a leader, but perhaps the better phraseology is especially as a leader, this notion that we know everything in real-time, it has to be dispelled. My instinct was to react to something with a response. Whereas now it's listen more, speak to Wayne, is it a big issue that we have to involve all of management? What are their ideas? Because perspective is everything.

You take all those inputs in, you listen to all those inputs, you take them in, and then come up with a response or a plan of action as opposed to wanting to always immediately react. Listen more, take a beat, and then respond, I think are something that I personally, in my evolution, my leadership journey, is something I've really, really focused on. Some tastes are better than others, I'll be honest. But I think that's the second one, is that listening more.

Elise Holtzman: One of the things that you and I worked on together for the Managing Partner Forum Conference that I mentioned was a people management issue. You mentioned having 250 partners and employees. That's a lot of personalities. That's a lot of needs and desires and opportunities and complaints and everything else.

One of the issues that you and I discussed at the conference with the people in attendance was this idea of troublemakers, toxic partners, people that have a lot of influence and a lot of power in the firm, but are also really challenging to deal with. I suspect that every managing partner would have at least one story of a situation like that.

If I recall correctly, you were the one who came up with this idea to talk to the managing partners about it. Tell me why that's something that you thought was important for people to have some down-and-dirty discussions about.

Denise Baker: The why to that was exactly as you said, every managing partner that I had spoken to in my experience said, "What do you do with the partner who has a huge book of business, but who knows they have a huge book of business and perhaps their behavior isn't always ideal, what do you do with that? We presented that problem as a bit of a case study in that Managing Partner Conference to share that experience. What are people doing in this situation?

The one thing I did learn was there, also everybody had that one person either past or present. Wanting to get some ideas from people, share those stories and how did you deal with them? Share the solutions. Because we can all share, that's venting. But how do you deal with it? Particularly in a day and age where, Elise, I don't know when you came up, but certainly, when I came up, the idea of people, of partners or lawyers yelling in high-pressure situations wasn't unusual.

Probably, you were just like, “Whoa, that seems a bit much,” and moved on. That kind of behavior is no longer acceptable at all in the workforce. If you think back on it, you're yelling, like who would yell? It just seems so bizarro. But if I'm thinking that, this next generation is thinking it's completely inappropriate and they're absolutely right. But now maybe that partner, let's just say they're towards the end of their career, they're now trying to relearn all of these types of, I don't want to say it was ever acceptable, but it was much more prevalent.

Now it's completely unacceptable. They're undergoing a journey as well. How do you ensure that that toxic behavior is dealt with? Because the law firms often just don't deal with it. That's been the go-to for lawyers. Like maybe if we just don't talk about it, it'll stop. But that behavior needs dealt with because historically and today, it's very expensive behavior.

People leave, associates leave. Staff people leave. You have to replace them. They leave again if you don't deal with them properly. That type of behavior can't all be done in the name of client service, because that's often what we hear. Well, we just have to serve our clients, right?

Elise Holtzman: Yeah, exactly. All that matters is getting the client what they need, and if you're not doing it the way it's supposed to be done, I'm going to yell, and so it'll get done that way. Then we present this face to the client that everything is fantastic over here, where there's a lot of turmoil going on. There's also this issue, especially in today's world—and I think this is a secondary issue, but I think it's still important—is the publicity surrounding these sorts of things.

Now we have websites like Above the Law and things like that that come out and they're tabloids essentially for the legal profession. These things show up and it does create distress in clients. Like, “Is this the kind of firm that I really want to be with?” and, “Oh, my God, I don't want to see my lawyers being written up in the paper about this sort of thing,” and also even for attracting talent. The law students read all of this stuff.

I mean law students today, one of my kids happens to be in law school at the moment, law students today know far more about law firms and other organizations than we ever did. They have access to all sorts of things that we didn't have access to. It does become a reputational issue so all of these things are negative.

But as you and I are saying, people have gotten away with a lot, especially when they were the founders of the firm, or they've been at the firm forever, or they are on the management committee, or they have a ton of business, and everybody's afraid, well, maybe this guy, and it's not always a guy, but often a guy, especially because they tend to be senior leaders, he's going to pick up his toys and his clients and go to another firm.

Denise Baker: Right, and that's scary if you have your rainmakers concentrated in a few people. That then does become scary. But I think you have to ask yourself when you're grappling with these issues is what are the impacts of that behavior on your culture. I will say this, I think it involves having very difficult conversations, one-on-one conversations.

Sometimes people who've been able to behave like that for a long period of time don't actually realize the impact of that behavior on other people. It's so ingrained in them until it's called out to them. Then sometimes they actually become some of the greatest lawyers and the behavior can be modified because it's now been pointed out, really pointed out to them.

Lawyers are not much different than any member of society. If you walk around behaving a bit like a jerk and then somebody says, “By the way, you're behaving like a jerk,” you're like, “Oh, wow, maybe a bit more mindful of your behavior and the way you're presenting yourself to the world.”

I think calling out that behavior as leadership is integral to preserving a strong culture going forward because, like you've said, and like we always say, most days, reputation is all we have. If that reputation gets ruined, particularly in the media, it's difficult to come back from.

Elise Holtzman: I love your optimistic view of this because I think that that requires a lot of self-reflection and self-awareness and people being willing to say, "Oh, yes, I've engaged in bad behavior." Some people are, obviously, it sounds like you have experience with that and, of course, some people aren't.

But I think that if I recall correctly, the consensus in the room was, as a managing partner, you really just can't sweep this under the rug to the extent that people have swept it under the rug for many, many years and people have gotten away with bad behavior, there's so much of an emphasis on culture, so much emphasis on talent retention and training and reputation that I think the women in the room were saying, “We can't just turn a blind eye to this and be willing to sweep this under the rug any longer.”

I think as challenging as some people find the generational differences, as you point out, in many ways, we do have the younger generations to thank for that because they're not willing to tolerate it the way that we were. We went into it just thinking, “Well, this is just the way it is.”

Denise Baker: That's right.

Elise Holtzman: Especially, I have a feeling I've been out of law school longer than you have, but I graduated from law school in 1990, back then, it was like, “Suck it up, just deal with it.” Especially with women getting into law firms even more and more, that was the last thing you wanted to do was to complain that somebody's being mean to me. That was not going to play well. I think that one of the things that we can say that this younger generation has done for us is turn the light bulb on for us, that these sorts of things won't be tolerated.

Denise Baker: You know, I completely agree. You didn't say, I graduated from law school in 2002, and then you most certainly didn't say so and so is being mean to me, but what you did do is you left. You either left the profession, you left private practice, or you just left that firm and went and found another one. None of which are good solutions for leadership people, the people who are left behind.

That's part of our job as leaders to stem that leaving because that is not good for your firm. I think, as you said, law firms are unique, particularly law firm partnerships because sometimes partnership agreements are making it very, very difficult. A lot of times people are like, "Well, why don't you just fire them?" Well, that doesn't exist and they're a partner, they own the firm. If it's a partner whose behavior is challenging, that's very difficult.

It's not a corporate culture where you can just say, “You're out.” I think that's why maybe I am optimistic about appealing to people's rational senses. It's all about persuasion in a scenario where you either need a majority or 75% to get somebody out with toxic behavior.

Elise Holtzman: Meanwhile, managing partners are put in this position of figuring all of this out on the job. It's not like anybody taught you. It's not like you took Managing Partner 101 in law school or anything like that. So I think that it's really good advice for people who are pursuing leadership, who are stepping into leadership roles, because there is this shift that happens.

It's less about the individual contribution and the doing, doing, doing and dotting the I's and crossing the T's, and all of a sudden, it's about the kinds of things you've been talking about, managing these personalities, understanding the economics of a law firm, how do all of these pieces fit together, worrying about the retention, worrying about the hiring, worrying about serving the client, and being able to handle all of that while still creating a culture where people want to come to work. It's a pretty challenging job that you and your co-managing partner have taken on.

Denise, as we wrap up our time here together today, I want to ask you a question that I ask all of my guests at the end of the show. There is a phenomenon called the curse of knowledge where experts sometimes forget that what is so obvious and natural to them is not at all obvious to others. Now that you've been doing this job for a while, I would say you're an expert on being a managing partner and certainly an expert on your firm, when it comes to managing a firm on a day-to-day basis and also managing it into an uncertain future, what's a principle or piece of advice that may seem obvious to you, but you think is important for leaders or emerging leaders to hear?

Denise Baker: Outside of having previously said leaders need to remember to listen more, I would say leaders need to remember to celebrate the accomplishments. Leadership generally, maybe lawyers in particular, we can focus on the negative. That can be just our default position. But celebrating accomplishments, celebrating people who have achieved great things maybe one day or one week or celebrating the year-end of the firm and the success of the firm, it's so important. I think that celebration piece really pays dividends, maybe even more so than the negative side of that.

Elise Holtzman: Yeah, I love that. We do have that tendency. Partly we self-selected into law school, but we're also trained to look for the problems. That's our training, we're issue spotters, we're supposed to be doing that all the time. I love that reminder to be positive, to celebrate the wins, to celebrate the people, and to continue to create that culture that you want to have. Denise, thank you so much for being here with me today. It's been such a pleasure.

I want to thank our listeners for tuning in as well. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action, and make things happen. We'll see you next time.

Thank you for tuning in. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action, and make things happen. We'll see you next time.