Caravel Law's Jackie Dinsmore on what being influential means to her

'If what we do every day influences changes across the industry, then that to me is success'

Jackie Dinsmore, Managing Partner at Caravel Law, reflects on what it means to be named one of Canadian Lawyer's Top 25 Most Influential Lawyers. She also shares insights into her approach, including the importance of empathy and tenacity, that illuminates why she made the list. Click here to nominate for 2024, nominations close on April 19.

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Top 25 Most Influential Lawyer- Jackie Dinsmore, Managing Partner at Caravel Law Greg Greenberg [00:00:07] Hello, and welcome to Canadian Lawyer TV. I'm Greg Greenberg from Key Media. And today we're speaking with Jackie Dinsmore, Managing Partner at Caravel Law and one of Canadian Lawyer's Top 25 Most Influential Lawyers. Hello, Jackie. And thank you so much for joining us. Jackie Dinsmore [00:00:23] Thanks so much for having me. Appreciate it. Greg Greenberg [00:00:26] So first off, congratulations on the recognition. Can you tell me what does it mean to you to be, quote unquote, influential? Jackie Dinsmore [00:00:35] Well, first, let me say I'm extremely honored to be recognized in this way, there are so many terrific lawyers across our country. So when I received the news, it meant a lot to me. If what we do every day influences changes across the industry to make it better for lawyers and clients, then that, to me is success. I couldn't do what I do without my incredible team behind me. And I think that's also key. Some people have heard Bill Gates say that he surrounded himself with amazing humans that couldn't do things that he could do. And that's how Microsoft became the success it is. And I feel the same, I wouldn't have been nominated for this award if it wasn't for the incredible team I had by my side. So I think you can be a little influential if you can convince others to see things differently, to see that there's a better way of doing things. And the legal industry is notoriously scared of change. You've seen traditional law firms perform the same way for so many years. So I think being in a position to influence change in an industry that needs it so badly, is so important. And I'm so grateful to be given the opportunity to be influential in that way. Greg Greenberg [00:01:42] And can you share some of the highlights of 2023? What work have you been most proud of? Jackie Dinsmore [00:01:48] Sure. So when we started as a firm called Cognition back in 2005, it was a brand new concept. And it took a bit of time for people to really understand what we were looking to accomplish, and how we were going to do it. The idea of supporting big firm trained lawyers, in house experience counsel, as fractional counsel to startups and in house legal departments was relatively novel and new. And then coupling that with a low overhead model where we didn't have the mahogany panel boardrooms, and the fancy artwork and the corporate jets and this stogies, to help clients save on costs was really foreign to the industry. So I think I'm really proud of the fact that all of those things coupled with the use of technology, and being forward thinking in that way, has really changed the legal services industry for the better. And people really believe in us. Now it took a little bit of time. But you know, we now represent some of the biggest and best companies in Canada. In the past year, we've grown to over 100 lawyers, which makes us a considerable force in the industry. But I think I'm most proud of our NPS score. So for those of you don't know, Net Promoter Score, we have one of the highest if not the highest in the industry in the country. And that shows that we're doing things the right way, with our clients really eager to give us a good score on our customer service and our unique legal services. So I'm really proud about that Greg Greenberg [00:03:12] You mentioned change. And somehow, we're still recovering from the pandemic, finding the balance between returning to the office and working from home, how have you managed this new work in reality, this new change. Jackie Dinsmore [00:03:27] So it really isn't much of a change for us. I mean, our model has always embraced remote working. And I think that that's one of the things that made us stand out. And it made us a bit different. In fact, we were one of the first firms to offer this. So the pandemic didn't really change how we worked, the rest of the world just kind of caught up. So you know, as a way for us to reduce overhead, we had a small office where our admin team worked. But our lawyers typically worked at home or at the clients office. And this achieved a few things it helped us cut down on commuting time. So they became more productive. And it gave our lawyers some flexibility with their family to work from home. I read somewhere that there's an 89% dissatisfaction rate in the legal profession, people, a lot of lawyers don't like their jobs. And so to the extent that we can make the profession better for them, this was one of the ways and also forced us to become really forward thinking about technology so that our lawyers could be prepared to work from home. And we were also one of the first firms to have our lawyers work at the client, which meant that they really became embedded with the client became kind of knowledgeable about the team more quickly and became part of the organization. And as a result, this became really valuable for both the client and the and the lawyer and made us a really unique and interesting practice like we are today. Greg Greenberg [00:04:53] Well, it sounds like you have a very tight bond with your employees as well as your clients. Why is empathy important in law? Jackie Dinsmore [00:05:01] That's a great question. I can't stress the importance of empathy enough in our profession. And I think it's been lost over the years a little bit. When I'm working with a client, I always try and put myself in their shoes. And I actually have walked a mile in their shoes. In some ways I worked at Blake's, a big Bay Street Law Firm, then was Assistant General Counsel in house at Torstar. And as a result, I experienced a lot of the things that they experienced the issues that they have trying to do more with less budget, juggling the different priorities thrown up at them by the business units, managing internal business politics, managing external counsel and their spend, trying to provide more practical business minded advice rather than 20 Page memos or a redline document that no one can read anymore. So these are some of my own experiences that I could then help me or or with my clients. And so I think that's part of the reason why us as a firm has been successful because we we hear our clients and we listen to them. Also, as a woman in the industry, I've emphasized with many lawyers who are trying to juggle the expectations of their home life with a very, very busy career and the demands of that profession. And it's tough. So if you can understand where they're coming from, and they feel heard and listened to, they'll trust you to help them. When I first started my career, I wanted to work for a charity in house for a charity or for like the Children's Aid Society, because I thought, okay, that's how I can help. That's how I can really deliver value and feel like I'm doing good, doing good in the world. I never landed there. But I feel I ended up in a role where I'm making a positive contribution, and I am helping not only clients, but individual lawyers, and I just love that aspect of my job. Greg Greenberg [00:06:50] Well, you're not only altruistic, but you're also tenacious. And what I'm talking about is, in your bio, you have a quote, which deals with the lion and the gazelle, can you talk about it? Jackie Dinsmore [00:07:01] So the quote goes like this, every morning in Africa, a gazelle wakes up, it no must run faster than the fastest lion or it will be killed every morning and Africa lion wakes up, it knows it must outrun the slowest gazelle or it will starve to death. It doesn't matter whether you're a lion or a gazelle, when the sun comes up, you'd better be running. I just love that quote. So what does it mean to me? I guess what it means to me is it doesn't matter whether you're on top of your game and achieving all the successes in the world, like a lion. Or if you're just starting out, or perhaps have just experienced some failures, you still always have to kind of keep the same mentality, which is keep evolving, working, running, making things better all the time, I see folks who have reached kind of the pinnacles of success. And, you know, they tend to kind of get lazy, they're like, Okay, we found something that worked. Alright, then now I'm gonna go sit in my arm chair, and we don't have to evolve or do anything better anymore. And that that can be the worst for not only your team and your organization. You know, as the saying goes, the rolling stone gathers no moss, so nothing should ever be good enough. It can always be better no matter how, what position you're coming from, or where you are in your success. And so that's, that's what that quote means to me is, as always keep evolving, running and doing things better if you can. Greg Greenberg [00:08:25] Okay, and then finally, going forward, any predictions for the future of your practice? And of the law industry in general? Jackie Dinsmore [00:08:34] Well, I mean, I can't answer that question without talking about AI and legal innovation. At Caravel, we have a Director of Legal innovation, and she's every day exploring the use of technology and in law, in particular AI. And I love watching this unfold. And I may be in a minority here, but I don't think it's going to replace humans, I think it's actually just going to be a supplement to what we already do great and help us do better. I'm not that pessimistic. I think that humans will always need place in law. And that goes back to your kind of empathy question, I don't think computers can have the same empathy. I see in house legal departments being expected to do more with less, I think continuing to do more with less, I think they will be subject to more KPIs around how they drive revenue for the business. It will always be about saving the business money. But I also see them as drivers of financial results, like some of the other departments in the organization. And I think they're going to end up using a lot of analytics to do that. kind of help them refine their their internal operations and make the client experience better. I think the client centric approach is just going to become more magnified and in house legal departments are going to be expected to be the drivers of that. At Caravel, we will continue to embrace technology, rather than rejected as we've seen some Additional law firms do will continue to grow a team with terrific humans and will continue to spend spent, like spread the message wide and far that our industry doesn't have to be so rigid. And that, you know, we can embrace the entrepreneurship way of thinking in law, and really use that that way of thinking to better the profession for both lawyers and clients. So I'm really excited to see what the next set 20 to 30 years are going to bring in our profession. Greg Greenberg [00:10:31] Well, it's been exciting speaking with you, as well as a pleasure. Congratulations again on being named one of Canadian Lawyer's Top 25 Most Influential lawyers. Jackie Dinsmore [00:10:40] Thank you so much, really appreciate your time. Greg Greenberg [00:10:43] And thanks to everybody for joining us today, and make sure you stay tuned for more award spotlights. I'm Greg Greenberg for Canadian Lawyer TV.