Ep #51: Innovation, Leadership and Redefining Your Practice with Founder of Flex Legal, Erin Cowling

The Joyful Practice for Women Lawyers | Founder of Flex Legal, Erin Cowling

Something I’m increasingly seeing in the legal world is lawyers considering their careers and wanting to do things differently. They want to try on different hats and figure out how the skills they’ve developed could be applied elsewhere. And this week, I’ve got the perfect guest on the show who is a true role model and inspiration for exactly this. 


Erin Cowling is the founder of Flex Legal; a freelance lawyer company that matches freelance lawyers with law firms and in-house legal departments across Canada on an as-needed basis. She started out as a commercial litigator, then went freelance herself, and eventually ended up growing so much that she’s now got a team of close to 60 freelance lawyers, paralegals, and law clerks. 


If you too are wanting to stray from the traditional law firm model and create new opportunities for yourself and others, listen in this week. Erin is talking us through her journey as a lawyer, entrepreneur, and leader in law, and how she straddles all of these worlds at the same time. You’ll hear some of the challenges she faced in solopreneurship, the opportunities that have presented themselves, and how she took Flex Legal from an idea to a successful reality. 


If you enjoyed today’s show and don’t want to miss an episode, be sure to subscribe and follow the show. And if you haven’t already, please leave a rating and review! Your feedback will help me create a podcast that’s tailored to your needs and goes straight to the heart of what matters to you. Click here to learn how to subscribe, rate, and review.

What You’ll Learn from this Episode:
  • The background story of Erin’s entry into law. 
  • Erin’s takeaways from working in commercial litigation and how she’s applied them.
  • How being a highly sensitive person has turned out to be a strength for Erin. 
  • Why Erin decided to transition out of traditional law. 
  • The values that guide Erin in her practice and personal life. 
  • How Erin took Flex Legal from an idea to a reality. 
  • Some of the challenges she faced as she was building her business. 
  • How Erin taps into community and support networks as a solopreneur. 
  • The opportunities Erin experienced that she didn’t expect.

Listen to the Full Episode:

Featured on the Show:
  • If you enjoyed today’s show and don’t want to miss an episode, be sure to subscribe and follow the show. And if you haven’t already, please leave a rating and review! Your feedback will help me create a podcast that’s tailored to your needs and goes straight to the heart of what matters to you. Click here to learn how to subscribe, rate, and review.
  • Want to get in touch with me? You can do so by clicking here or reaching out to me on LinkedIn
  • If you are interested in learning more about the work I do with lawyers, click here and send me a note, I would love to hear from you.
  • Flex Legal: Website | Blog | Instagram
  • Erin Cowling: Website | LinkedIn | Twitter
  • ELLA – York University
  • Radical Candor by Kim Scott
Full Episode Transcript:

You’re listening to The Joyful Practice for Women Lawyers Podcast episode number 51.

Welcome to The Joyful Practice for Women Lawyers Podcast. I’m your host Paula Price, lawyer turned certified executive coach. This podcast was created to empower women lawyers just like you to create a life and practice you love. Join me every week for a break from the hustle so we can focus on you, what you truly want, and how you can create it.

If you’re over the overwhelm, done with putting out fires, and ready to create a life and practice that brings you more joy, you’re in the right place. Ready for today’s episode? Let’s dive in.

Hello, my friends. Welcome back to the podcast. Paula here, and I just wanted to say a quick hi before I drop you into my podcast interview with Erin Cowling. Erin, for those of you who have never met her, is the founder of Flex Legal. You’ll learn more about Erin and Flex Legal in the episode.

But I just wanted to give a special shout out and thank you to Erin for being my guest today. I think she is amazing. I love what she shared. I think all of you who are tuning into listen will really enjoy hearing her journey as lawyer and entrepreneur. I think you’ll find her story to be inspiring. I think you’ll learn a lot from her about finding your path and creating new opportunities for yourself and for others. I just think you’re really going to enjoy hearing what she has to say.

So with that, I’m just going to drop you into the episode. Say goodbye until next week, and I look forward to reconnecting in our next episode. Hope you enjoy the interview. Talk to you soon. Bye for now.

Paula: Hi, everybody. Welcome back to the podcast. I am so excited to be introducing you to today’s guest. Her name is Erin Cowling. You may know of her. She has a company called Flex Legal. We’re going to talk all about that. Erin is a mother of three children, the founder of Flex Legal, you may know her from her blog. We are just delighted to have her here today. Welcome Erin to the podcast.

Erin: Thank you. It’s so great to be here.

Paula: Wonderful. Erin, can you tell us more about what it is that you do?

Erin: Yeah. So I am a recovering lawyer, I kind of refer to myself as that, and an entrepreneur. So like you mentioned, I have a company called Flex Legal. We are a freelance lawyer company. So we match freelance lawyers with lawyers, law firms, and in house legal departments across Canada who may need assistance on a as needed basis with their legal work. So instead of hiring a full time associate or another lawyer to join their department, they reach out to us and we match them with an experienced lawyer to assist on a as needed basis.

I also freelance as well as a lawyer. But as my company grew, I went from freelancing probably 90% of the time and working on my company 10% of the time, and it’s completely flipped. The company is now mostly taking my attention, and the lawyer part of me is shrinking a little bit

Paula: So fabulous. Erin, I’m excited to have you on today for a number of reasons. One of the reasons is that I think you have all these different hats that you’re wearing, and you can offer these different perspectives. So you started out, and we can get into this more. I’ve done a bit of research. I’ve listened to some podcasts. I’ve been on your blog. I’ve been following you on LinkedIn for a while. So I’ve seen that you have a background as a commercial litigator.

Then you moved into the freelance, and then your freelance started to grow so much that you’ve now got a team. How many lawyers are in your team? I believe you have more than lawyers.

Erin: Yeah, so our main focus is freelance lawyers. We have oh, I think we’re close to 60 freelance lawyers now across Canada. We do have a few law clerks and paralegals to assist when that need comes up as well. But our main focus is the freelance lawyer side of things.

Paula: Incredible. What I love is that you’ve got the lawyer hat, you’ve got the entrepreneur hat, and increasingly, you’ve got that leadership hat. So I’d love for us to be able to talk about that because I know that a lot of lawyers out there are thinking about their careers. They’re looking at doing things a little bit differently. You, I think, are such a role model and inspiration for that. I think what you’re doing in terms of having your team of freelance lawyers is that those lawyers too are doing law differently. Differently from the traditional law firm model.

So, Erin, I’m going to ask you a question about your very beginning entry into law. In one of the stories that I heard you tell, you traced your initial reason to going to law school—one of the reasons, not the only reason—to a time when you were cleaning out a basement. I believe this was at your university residence, and a book fell on your head, and it was the LSAT prep guide. That you started to read it. That you loved the logic game section, and that that was one of the initial sparks that led to you becoming a lawyer.

What I would love to know is what were the skills that took you from that moment where the book kind of landed on your head? This is maybe an ah-ha moment or a signal from the stars that this was destined to be to where you then ended up, which was in commercial litigation at a Bay Street law firm.

Erin: Yeah, it’s interesting journey. You’re right. It was a LSAT prep book left behind by a previous tenant, and it hit me on the head. Before going to bed every night, I would do a couple of the puzzles because I really enjoyed them.

When I applied to law school and was accepted, I loved, loved law school. I am a lifelong learner, and I think that’s one of the skills that has helped me transition through my legal career is I love to learn. I love new opportunities. I can’t learn enough. So law school was—I have an undergrad in English Lit and a minor in women’s studies and religion. So to change my education focus from those subject areas to law, it just it made me really excited.

I think the skills that helped me go from the English undergrad to becoming a corporate commercial litigator on Bay Street was I think I’m very analytical. I’m very practical. I’m very logical. Hence, I love the logic problems. I think all of those skills really help in litigation. I am great at seeing a problem, seeing a mess, and seeing through the messy pieces to get to the solution.

Being a litigator is just like that. It’s almost like a treasure hunt without the map. You have to figure out how to get to the treasure. When you find that ah-ha argument where you’re like yes this will work or you find that case, it’s the best feeling in the world. I think those are the skills I kind of developed through law school was learning how to be analytical, read a case, and understand how to pull out the stuff that’s important for your client and applying the facts of the law to the facts of your client’s case.

Paula: Erin, I love that story. I love that idea of the treasure hunt without the map. As you’re describing that, I can totally see it. I’m also a former litigator. I can totally see it and how it applies in the actual practice of law. Then I see it at that meta level, right, that you’ve taken in your career, almost like it’s the treasure hunt and there was no map. Flex Lega. Somehow you have created that. I’m excited that we have the opportunity together to chat about that today.

One of the things that you mentioned in your legal path is after you were working on Bay Street, you moved into an estate litigation practice. Which you described at one point as being, I think you were there for eight months, and you said it was seven months too long. I’d love to know what your takeaways were from that experience and how you’ve applied them going forward.

Erin: Yeah. So it kind of relates back to the first question you asked me. I’m very practical, analytical, and logical, like I said, and clients aren’t necessarily that. Clients bring another component into litigation, and that’s the emotional, the human side of things. So if I could be a litigator where I didn’t have to deal with people, I think I would be the best litigator ever. If it was just facts and it was just the law and there was no complicated emotions involved, I would still be a “regular” litigator, probably on Bay Street somewhere excelling.

But I am not. I find the emotional side, the conflict that comes with litigation very draining. It just was not suited to my personality. I think that’s one of the things I learned in estate litigation. I learned a lot about myself. I learned a lot about estate litigation. I learned a lot about how many unhappy people there are out there. I just was not in the right place, and I’m not the right person to help them. There are people out there who are great with this. I am not one of them.

So I think I took away from that role in that time to really understand who I am. There’s certain things I think you can change about yourself and there’s certain things you can’t. I think at my core, there was just a disconnect between me working on really emotional conflict filled cases all day and my ability, my emotional bandwidth, to kind of deal with that.

So which sort of lead into the freelance world and Flex Legal. Because as a freelancer, you don’t deal with the end clients. You’re only dealing with lawyers. The lawyers hand you the problem, the legal issue all wrapped up in a little bow, and you get to deal with the analysis of the legal issue.

You don’t have to deal with the “my sister hates me because Daddy loved her more” or whatever the issue is between the sisters and brothers who are fighting over the dead parents money that I never have to deal with, again. I think I learned to really listen to my gut and learn to listen to who I am as a person and what my career should be to fit who that is.

Paula: Absolutely. Erin, I just love that you are pointing that out. That you’re emphasizing that because you’re not the only one who has experienced that. There are a lot of really, really bright, talented lawyers out there who do not find that situation that you described, right, where there’s really high emotional struggles on the part of the client. That may not be the environment where they thrive.

So I think being able to identify that and then move forward in a way where you’re not putting yourself in that position, day after day. You’re able to focus on your strengths, but also in an environment that is conducive to your own well-being and professional growth. So I love that you highlight that because I know you’re not the only one. You’ve just articulated it in a really clear and beautiful way. So thank you.

Erin: I think for a long time that people who recognize that kind of blame ourselves because we think well, are we just too weak to handle this? Are we not smart enough? Like we see litigators who love the emotion and the conflict, and they love the how—And you just somehow think you’re less than those people. But we’re not less than. We’re just not in the right role for our skill set and our strengths.

Paula: I love that you said that, Erin, because it’s true. I mean I see it in my own children, for example. My son is, I think he’s kind of a little mini litigator in the traditional sense because I don’t think you have to be super aggressive or anything like that to be a good litigator. But his wiring is in that nature. Versus if I look at my daughter, she’s very sensitive. Conflict just is something that she works so hard to avoid.

So when you’re in an environment where you’re surrounded by people who thrive on conflict, I mean, I’ve worked with lawyers, I’m sure you have to, who thrive on conflict. They love the battle. They love the fight. If you’re not energized in the same way that they are, I know for myself I started to think, “Well, is it me? Is there something I’m doing wrong?” But sometimes it’s just how you’re programmed. You’re just wired differently?

Erin: Yeah, exactly.

Paula: And it can be a strength. I was gonna ask you this question a little bit later on, but I’d love to know. I mean, I think you described once, and I’ve been to courses on this, this idea of a highly sensitive person. I don’t know how far you’ve gone down that road in terms of the actual meaning of it, but how have you found that being, you know, sensitive? Like how has that turned out to be a strength for you in the way that you’ve built your career?

Erin: Yeah. For a long time, I didn’t see it as a strength. I saw it as a huge weakness. Because I even pulled out one of my report cards from like grade one. Like I don’t know how many report cards I’ve had where the words are Erin’s too sensitive written on it. So for the longest time, I saw that as a weakness, as a criticism, as something I needed to change. Even all the way up to mentors on Bay Street and in estate litigation. It was like you’re too sensitive. Just build up that shell. You’ll get used to being numb. It took me a long time to realize like—

Paula: Sounds appealing.

Erin: I don’t want to be numb. I don’t want to be numb to people’s pain. Yeah sometimes I want to turn down the intensity of it, but I think it is a superpower. When you when you’re asking a question, I’m trying to think of an example. But one time I can think of is, for example, when I’m in court or I was in court. Because I’m highly sensitive to other people’s emotions and  I’m hyper aware of subtle things that they’re doing, and I can pick up on stuff that other people might not necessarily pick up on. I can tell when a judge is pissed off, or I can tell if they’re not liking that line of questioning or my argument a little bit sooner than some people. So I can see opposing counsel going on about something, and I can just see the subtle things going she’s not liking this. She is not happy with you right now. But then opposing counsel is just oblivious to this.

So I feel like those of us who do are a little more aware of other people’s emotions, and where they’re coming from and pick up on those subtle things. I think we have an advantage in some situations. Like if you walk into a room you can, well at least I feel this way, I can read people’s emotions and pick up on them a little bit better, which, in turn, I think makes me more empathetic to those around me. Which can be, once again, it’s a double edged sword. It can be a great thing and maybe not so good thing.

But I think as an empathetic person, you can help your clients a little bit better. So when I’m saying clients, I mean our lawyer clients. I’m empathetic to their needs. I’m empathetic to our freelance lawyers’ needs. How can I help them? So yeah, it’s definitely a strength, but it’s something I’ve had to learn over time as a strength and something I can use to my advantage.

Paula: Totally. I remember taking it was like a weekend course on the highly sensitive person. The woman who was instructing the course was talking about how it really is a strength. It’s a superpower. And how as an evolutionary tool within the human population, that it was almost like you’re the canary in the coal mine. Right? You sense before other people what is about to happen?

I wonder in your founding of Flex Legal, for example, you found a market right? A need for lawyers to have assistance, right. They get help from your lawyers. Do you think that your heightened sensitivity played a part in that and be able to identify that there was a need here and that you could help people?

Erin: That is a good question. I don’t know maybe. I think really what happened was it slowly grew over time. I had one person. When I started freelancing, there was one law firm I was working with. I think that I could see that just being able to offload a little bit of work now and again was having such a positive impact on that person’s practice. So maybe in a way because I could see that she was happier that she could offload a little bit of this.

That’s where the wheels subconsciously were turning, right. Where there’s probably other lawyers who aren’t quite ready to hire a full time associate, and maybe I can help relieve some of that stress by drafting that factum for them are doing that little bit of research now and again without having the overhead costs of payroll every week.

Paula: Yeah, yeah. My next question for you, Erin, I think ties up nicely with this, which is the idea of what the values are that guide you in your practice and your personal life. What I was hearing there was almost like the value of relieving stress for other people. I don’t know how you would articulate that as a value per se, but what is it that motivates you in your practice?

Erin: I just think life’s too short, and that’s kind of my mantra about everything. I don’t really know where this came from and whether it’s…We’re only here for so long. If I can make other people’s lives a little bit more enjoyable and less stressful and less crappy then I will consider my life successful and less crappy as well.

I think about death a lot, which sounds creepy. But I know there’s certain cultures that really focus on death. They do have, it’s slipping my mind which cultures they are, but it helps them enjoy life more. I think maybe it was in my 30s where I started having this kind of fear of death.

I think it came around the time I had my first child. Because before you have children, death is death, whatever. There is no one really relying on you. Then all of a sudden, it kind of hit me. Well, if I die, I leave these poor things without a mother.

So then I got into this downward spiral. It just makes me—I think that’s where I think life is too short. But it’s not a negative thing, thinking about death. It makes me appreciate life so much more. When you appreciate life in the short time we have here, you just want it to be better, and you don’t waste your time on things that don’t bring you happiness.

I think that’s what really helped me make the decision to get out of traditional law. Why put up with this? It’s scary to transition to something different. But if something’s not working in my life anymore, it’s like no. I’m not going to put up with this. I use that also when deciding which lawyers to bring on to Flex Legal. If I see red flags and I see like this is going to be a difficult person, no, I’m not gonna deal with that. If this is gonna be a difficult client, no, I’m not going to deal with that.

So I know these aren’t really values. I think more this is more like a mantra or an outlook on life. But I think life’s too short is really helped me the way I’ve built my business and the way I’ve built my career. But I think if we’re talking values, honesty and integrity are like way up there for me. If I have to trust people at their word, trustfulness—Trustfulness is the word. If you say you’re going to do something and you don’t do it, I’m sorry. Like you’ve lost a lot of trust from me. I think people who are honest and have a lot of integrity and follow through, those are the people that I want to work with.

Paula: I love it, Erin, and I don’t think it’s creepy at all to think about death. I’m sort of moved in a way because yesterday was a day that I celebrated the life of somebody in our family who passed away on May 3rd. We’re recording on May 4th, may the fourth be with you day.

I completely resonate with how you describe that. That it’s a reminder that we are here for a finite amount of time. How are we choosing to live our lives in a way that brings us the most joy? That allows us to create the impact that we want to have. It really helps to focus, right, to focus on and ask ourselves the questions of what that is. If it’s not traditional legal practice and it’s something else in this case, then that’s what it is.

I love what you say about the people that you work with, right? I mean, we know that. We know that at that gut level when you’re working with somebody and you trust them and you know you can rely on them. Things are going to come back the way that you expect them to, and they’re going to show up. Like that’s such a different energy versus when you’re working with somebody you don’t know. Are they going to show up for the meeting? Are they going to do the thing they said they would? It’s totally unsettling. So I think that’s totally, I can relate. I’m sure our listeners can too.

You mentioned a few minutes ago, Erin, that you went for—I love this. Like, here’s Erin starting her freelance practice. It’s you, and then next thing you know, you’ve got a team. You’ve got a team that has continued to grow over the years. I think you’ve mentioned—Are you at 50 or 60 now?

Erin: Yeah, in between those numbers.

Paula: So that’s a lot of lawyers who are part of your team. So I would love to know like how you took Flex from an idea, like sort of something that was in your mind’s eye, to what it is now.

Erin: Yeah, I’m not a startup. I’m not one of those fail fast type of companies. It’s not like I woke up one morning going I’m starting this company. I’m getting investors. I’m going like crazy. This was really what people call a side hustle. Because I was freelancing, like I said before, a majority of the time and then Flex Legal was growing on the side.

You know, I had three young children. I was enjoying the freelancing. I don’t have an MBA. I don’t have a business background. I was learning as I go. Like I’m a lifelong learner. I was reading business books. I was setting up my own website. I was figuring out how to set up my own business number, all that kind of stuff. So it was a slow process that really fit my lifestyle at the time.

How did I do it? Really just slow and steady wins the race. I know there’s the big entrepreneurs out there who say don’t I did it all wrong. That’s not how you do it. You go all out and put all everything into it, but it was really just…It’s completely bootstrapped. Any money I made it went back into the company at the beginning.

Just I was very careful about who I brought on. I wasn’t ready to bring on… You know, I could have had a thousand lawyers in that first year. Enough people applied and everything, but I wanted to be very particular about who joined Flex Legal to make sure that they reflected the same values I had about the company and having excellent work, honesty, and integrity and someone I could rely on. Just as the lawyers came that I thought would be a good fit so did the work.

The work mostly grew through word of mouth. There was no marketing and advertising budget at the beginning. It was just me going to every lawyer event possible banging on doors, saying “Do you know what a freelance lawyer is? We can help you.” So that takes time. So it’s been seven years of slowly growing it to where it is now where it is my main job is running the company.

Paula: Yeah. Erin, I think that’s a story that everybody needs to hear. You have a blog post that you’ve been doing, and I was just on your website a few minutes ago. I think it goes back to 2014. Anyone who’s listening who wants to read some incredible blogs, they should go there. You should go there. We’ll put links of this to the in the show notes.

One blog post that I remember reading is one that you wrote about overnight success. Does that ring bells? I think the takeaway was that people were coming up to you and saying, “How to do this so quickly?” I believe your response to that was, “Well, actually, I’ve been doing this for years.” Just like you described Erin it’s like you start out and you keep going and you’d shift directions. You read books, and you learn, and you try and experiment.

What I love about you sharing that is I think for a lot of lawyers, they have been trained to be lawyers. The business side of law, maybe it is a focus in law school now, but when I went through it wasn’t really a focus. Yet, whether you’re in a law firm, or you start your own law firm, or you start a firm where you’re bringing other lawyers in, there is a business component to it. Whether you know it or not, you’re marketing, right. When you’re working for somebody, you’re actually marketing.

So I think how you’ve described it is so helpful because it shows that it’s not a one and done thing. That it’s an evolution. The way that your organization has evolved just shows that when you show up, like you said, you showing up, right? When you show up, when you have your values intact, when you put one foot in front of the other, after a certain number of years, you end up building something. It’s really neat to see how you’ve built up Flex Legal over the years.

We haven’t even talked about the three young kids, right? You’ve got a whole other life on top of that as a parent. I’ve got two, and I’m looking at you in awe thinking how do you do it with three? So I just love that you’ve shared that. I think it’s a story that just shows what sort of innovation and tenacity and putting one foot in front of the other—on top of your skills, let’s not discount those—can lead to. So thank you.

I imagine that your road was not always super smooth sailing. What kind of challenges did you face? Like as you’re going through the many years of building your practice, building your business, what were some of the things that you experienced that you found challenging?

Erin: Yeah. There were many times where I’m like I’m just walking away. I’m gonna fold this company and give up and go because I am done. So I want anyone who’s listening who thinks it was just all rainbows and unicorns, it was not. You know you pick the wrong people to do business with. You pick the wrong freelancers. You pick the wrong clients.

You learn from those situations. You learn to read the red flags a little quicker. You try different services that aren’t necessarily the best services to offer. You figure out what you’re good at, and just focus on that I think has helped. Yeah, it was lonely, I have to say, at the beginning, being a solopreneur and not having…Sure I had all my freelancers, but they’re all across Canada. They’re not really running the company with me. Then I brought on a small team of independent contractors who helped me. But, once again, they weren’t focused just on Flex Legal.

I think the best thing that’s happened is hiring full time staff to help and actually growing it that way. That has helped immensely in just helping me work more on the business instead of in the business, as they say. I think the challenges really are, if you speak to any entrepreneur, it’s all of that. It’s not being able to shut off. It’s working 24/7.

It’s worrying about your company. Am I going to pay this?  Oh, we had a slow month. Oh, we have a really big month. Oh no, we don’t have enough freelance lawyers. All of that comes along. But I have to say seven years later, I’m glad I am where I am. I’m not thinking oh, I should have closed it when I wanted to back then. I’m glad I stuck with it so.

Paula: I think we’re all glad you stuck with it. I’d love to know. So I am a solopreneur as well. One of the challenges that I find sometimes, not always, is that I feel a little bit isolated or lonely sometimes. I have my own strategies. I reach out to people. I connect with people. In the pandemic, wherever we are in the pandemic world, most of that is on Zoom or phone calls. It’s very little in person. I’m just wondering how you deal with that. Like as a solopreneur, how you go about creating a community or support or what that looks like for you.

Erin: Yeah, I have such great different little support networks, either within the legal profession. I have some lawyers I hang out with and I chat things with, but I also have in the entrepreneurial world some great people I can rely on. I joined an accelerator for women entrepreneurs called ELLA out of York University. I did that last year. I met some great entrepreneurs there. We’ve kept in touch.

I belonged to a business book club before the pandemic. We would meet once a month with other women who own small businesses, and we’d read a book, a business book, and catch up and talk through the pain points in our businesses. Really everyone’s pain points, no matter how different your business is, I feel like everyone’s pain points are kind of the same. Like how fast should I grow? I have issues with my employees. I don’t know what to do about this. So I feel like it’s nice to have people who understand what you’re going through.

That’s why I make sure that I kind of straddle both the entrepreneurial world and the legal world. Even the lawyers who are law firm founders, which is even better because they too are the entrepreneurs and the legal world as well. So really, it’s just surrounding myself with people who kind of get it. Even if I can’t walk down the hall and talk to somebody like I could when I was in a law firm and say I’m having a crappy day, I can pick up the phone or I can text and say oh my god. This client just did this to me or whatever, and they’re there.

Paula: Absolutely. I completely resonate with what you’re saying. I have some friends and colleagues in my network where I feel like that, right. They get it. When I call them and say, here’s what’s happening, we’re on the same page. I don’t have to explain it. Whereas sometimes there are other people that are in your social circle, your professional circle who you adore, but that piece of it is just not on the topic for conversation because you kind of almost have to be in it to really feel it.

Question for you, Erin, is managing a team. So for lawyers, for example, who are starting a solo practice, and then they find they have all this work. So now they’ve got other lawyers coming in. Then they’ve got the support to help the lawyers, et cetera. They go from being maybe solo to a few people, multiple people, and you’re now at 50 to 60. When it comes to managing your team, how do you try to lead? Like, what are some of the skills that you embody as a leader?

Erin: I think one of the things that’s important when you’re a leader and you’re growing your team, especially for lawyers who are starting out, is to kind of let go. I know it sounds counterintuitive.

Paula: It’s so hard, right?

Erin: For lawyers to do so, but otherwise, you’re just going to work yourself to death. If you have a team and you’re not letting them do their job, it’s counterintuitive. It doesn’t make any sense to be doing that. So that is something I’ve had to learn to do as well is let them do their job and trust them and open lines of communication.

So let them know that you’re there for questions. But ultimately, the responsibility for their work lies with them. you have to give them the tools to do their job and the space to do their job. Don’t fix their mistakes. It’s almost like raising—I don’t want to say raising children. I don’t want to make my employees sound like they’re children, but you know what I mean? Like if you keep going in and fixing the work for them or going in and solving the problems, they will never grow as employees or grow as lawyers or grow as associates.

So just letting go and giving them the space. Will they do the work the way you do it? No, because they’re a different person. But is there only one way to do the work? No. They can do it their way too and still come to a good result.

Like I said, I don’t have any management courses. I don’t have a MBA. I don’t have anything like that. So I try to read books to help me with this. I learn on the go. I find conflict hard. So when it’s to give feedback that is not necessarily positive, I’m still working on that. It’s hard for me, even though I know it’s very important. People want feedback. People want to know when they’ve messed up, and they want to know how they can improve.

So that’s something I’m trying to work on as leader. It feels weird saying that, but as a leader to be more comfortable with giving feedback when it needs to be given. I’m okay with giving the positive feedback. It’s the harder stuff. I’m actually in the middle of reading a book called Radical Candor.

Paula: Oh, I’ve got that book too. Yeah, yeah.

Erin: I’ve read like two chapters, but I’m like hopefully that’ll help me be a little more candid in my feedback. Yeah, I think I answered your question.

Paula: Yeah, it’s beautiful. When it comes to that letting go piece, because I know that’s hard, right, especially for lawyers. That’s something that comes up in conversations that I have with clients where they really want other people to do things the way that they do them. There’s a certain format they follow.

How do you deal with that? Like when you’re giving the assignment or when the assignment’s coming back? Like, do you have kind of an internal conversation or a barometer for when you would choose to give feedback, and when it would be something where you’re like, “No, I’m, I’m letting go of this. It’s something I don’t want to do anything about.” How do you handle that?

Erin: Yeah, I think especially when it’s my—I don’t want to say my business. It’s now our business. It’s Flex Legal. It’s an entity of itself. But at the beginning, it was my baby. I would write emails a certain way. I would respond a certain way to clients, and not everyone writes the way I do. So at first it was I would try—And I did it wrong, of course. I’d be like rewriting that person’s email. Well, that doesn’t help, right.

So then I would just look at the email and go, there’s actually nothing wrong with the email they’ve written. It’s just not the way I’ve written it. Is it still respectful? Yes. Is it honest? Do they have integrity in there? All the values that I put into Flex Legal. Are they responding on time? Those are the things I need to focus on that are important. Would they use the word, I don’t know, regards instead of cheers when they’re signing off? Like I need to let go of those little things. It’s the big picture stuff that I’ve learned to kind of focus on.

Paula: I love that, Erin. Again, it just shows how you you’ve got your values as almost like that’s the guideline. That’s what drives the decisions that you’re making in your practice. I just love that. It is hard. I’ve had that experience too where it’s really just looking at the work and saying, “Okay, this is not at all how I would have done it, but it’s still getting the job done.” It means I don’t have to do it.

Erin: Yeah. Exactly. That’s the key.

Paula: Sometimes that’s just like that’s key. One of the things I wanted to ask you about. We were talking before about challenges that come up, right. When you’re on this entrepreneurial journey, and you’re like oh, this is really hard. This thing came up. What are some of the opportunities that you weren’t expecting that came to you through this process?

Erin: Well, I think this. Like being guests on podcasts and being asked to speak on panels and being asked to mentor people through different organizations. One great opportunity that came up was I was the regional alumni advisor for the University of Ottawa Faculty of Common Law for a few years, I think three years, because the dean at the time, Adam Dodek, was looking for someone on the ground in Toronto to help kind of mentor new lawyers who graduated from University of Ottawa and moved back to Toronto. They just didn’t have anyone on the ground to kind of help with career advice and stuff like that.

He found one of my blogs and asked me out for coffee. We’re great friends now. I had that role for a few years. I don’t think that would have come up if I had stuck with my traditional practice as I started out as a lawyer.

Paula: So fabulous. Erin, do you still do that? I saw that you offered coaching for lawyers. Do you still do that?

Erin: I do. But not associated with the university. there was a change in the dean and certain things changed. So that role I don’t believe is with the university more. Hopefully, it’ll come back. Not necessarily with me, maybe with someone else. It was great while the time, but it took up a lot of my time.

But from that I realized that people were still reaching out to me for career consulting and advice. Even though I was no longer with the university, I develop the skills and I developed the kind of know how. I thought well, I could still be helping these people. So yes, I do through my Cowling Legal website, I do offer legal career consulting as well.

Paula: That’s amazing. You have so much to offer. I love how that is one of the unintended benefits of you doing what you’re doing, right. Like you are out there creating something that didn’t exist before. You’re innovating in how you practice law and how others are now able to practice law. Not just the team that you have a Flex Legal, but the lawyers that you serve, right. So you’re doing it from both angles.

This now creates for other people a model that didn’t exist before, right? So they can look to you and say, “Well, that’s new. That’s different.” It’s inspiring, right? It’s inspiring for others to look to you and say, “Okay, well, she did this thing. If I keep going, like Erin, if I commit to it one day at a time, it doesn’t need to be this overnight thing. It’s that slow, steady progress.” I imagine a lot of micro decisions that you make every day that eventually lead you to where you are today and will lead you forward. Exciting to think about that’s gonna be like.

Another question I want to ask you, Erin, was about money, compensation. There was a study that you were involved in. It was funded by the Women Lawyers Forum through the Canadian Bar Association. It was all about pay equity in law firms.

I wanted to bring this up with you because I think that for women lawyers, probably lawyers generally, but for women lawyers in particular that conversations about money. That if you’re a solo practitioner, for example, setting your rates and feeling confident with those rates. If you’re in a law firm, maybe it’s negotiating your salary. Or if your partner is it are you are you being compensated fairly in relation to other partners?

I would love to know from you what your take is on how it is that we relate to money, any challenges that you’ve maybe experienced or you’ve seen other people experience, and your thoughts on what we can do to be more confident in relation to our value and the compensation that we’re asking for, and, ultimately, I guess obtaining?

Erin: Yeah, I think we need some more transparency around this. I’m all for being transparent about. So for Flex Legal, our freelancers set their own rates. Like it’s up to them what they want to charge. But if we see a lawyer coming in and quoting way below the other lawyers, we will reach out and say no, you should be charging more. For your age and stage, you’re a little below. So we try to be as transparent as possible.

When I did my hiring for a full time employee, I put the salary on. I don’t understand. This is like something that really bothers me is those job descriptions where they’re like, whatever. They don’t say. So people could go through the entire hiring process, get to the very end offer, and then be like, “Oh, you’re paying me like a hundred grand less than I thought that this this role was.”

So I think we need to be a bit more transparent and less… There’s this taboo around talking about how much we make. I grew up in a family like that. You don’t talk out how much you make. You don’t talk about your salary. I think that makes it difficult for lawyers to talk to other lawyers and figure out whether or not they’re actually being paid what they should be being paid.

Whether it’s a gender thing, which I think through this study it was clear that women were being paid less. But oftentimes, we don’t know it because there’s no transparency. The more we can talk about this, if male lawyers can talk to their female counterparts and tell them what they’re making and putting it all out on the table, I think we can make some progress in the pay equity realm.

I don’t think we’ll get there overnight. I think it’ll take some time. There’s so many other factors that go into it, like bonuses, and maternity leaves or parental leaves, and things like that. But I think transparency will go a long way in helping this issue.

Paula: So great, Erin. Going back to what you said about some of your freelancers setting their rates lower than others, and that you’re now having a conversation with them. How does that conversation unfold? Like do you find that there’s resistance? Do you find that they’re open to that? What’s your sense of that?

Erin: Yeah, some of them just have no idea because they just don’t know what people are charging. So they’re like, “Oh, really? That’s what I should be charging?” I’m like yeah. They’re like, “Great. I’ll charge that then.” So when we onboard new freelancers, we always—You know, some of them are very set. They’re like, “This is what I charge. I’m not gonna go any lower.” That’s fine. Or I’m not gonna go any higher. But sometimes it’s really just we just don’t know. Because it’s not like you can google some of this stuff.

Was it the Canadian Lawyer Magazine, it used to do this survey about hourly rates across Canada? I found that was helpful like for sole practitioners, for people who are who don’t know what to charge. But I think lately, they’ve been like, it’s just it’s not been as helpful. They haven’t been given hourly rates or whatever.

But so I find it’s the informal situations like the Facebook groups of women lawyers saying, “How much do you charge for a will?” It’s good to know this. I like seeing that collaboration. They don’t see other women lawyers as competitors. They see them as someone they can help and say, “No, you’re charging too little. Or I’m charging more because I’m in Toronto, and you’re in small town wherever.” I think I love seeing people being helpful with each other and giving that information that’s been so hard to find sometimes.

Paula: Yeah, I love that Erin. I think what you said initially about money being a conversation that we often don’t have. Like you, it was something I was brought up to think oh, it’s taboo. We don’t talk about money. We don’t talk about Bruno, for anyone who’s watched Encanto. It’s not a topic of conversation. Yet, I think we do ourselves a disservice by not having those conversations, by not being open about those conversations because we can learn so much from each other by having them and by increasing our comfort level around those conversations.

So thank you. Thank you. Thank you. Erin, we are at the end of the questions that I have for you today. Although, I would love to ask you more and more questions because frankly, I’m just loving talking with you. One question that I have. The last question that I have is there anything that we didn’t cover today that you would like to add?

Erin: No, I think we’ve covered everything. Like I love meeting new people, and I love meeting other lawyers who are doing interesting things in law. So feel free anyone listening who wants to reach out. You can find me on my websites, or I’m on social media on Twitter, LinkedIn. I think Flex Legal’s on Instagram. I am not personally. So yeah, feel free to reach out. I love learning about what people are doing in the legal field and in the legal tech field and thinking of nontraditional ways to practice law.

Paula: Beautiful. I love it. Erin, before we wrap up, we talked about this for a moment before we started recording, which is that you have two different websites. There’s the Flex Legal website, and then there’s the Erin Cowling website. For anybody who goes onto those sites, can you just give us a bit of background in terms of how to navigate them?

Erin: Yeah. So the Erin Cowling website, I think can get there by erincowling.com or cowlinglegal.com. They both direct there. That was my original freelance lawyer practice website. So it has evolved over time from me being a freelance lawyer and trying to sell my services to really just my own personal place to kind of talk about—Like I have a blog, like you mentioned, that goes back to 2014. Just talk about issues that have come up in law or entrepreneurial stuff and women in law. So that’s kind of my place to be me. You can see my legal coaching and consulting on there as well. It’s my speaking engagements.

Then Flex Legal’s really more the business side of things. So it’s the freelance lawyer side it, but it also has resources such as legal networking events. If you’re looking, we do a monthly post where we put all the legal networking events which are now starting to go back in person. So if you’re looking to network other lawyers, we have that. We have posts on just law society updates or freelancing, ethics of freelancing, all that kind of stuff you can find there. Also, obviously, our team of lawyers if you are looking for assistance with a freelance lawyer.

Paula: Super. Thank you so much, Erin, and thank you, thank you, thank you for being here today. It’s been such a delight having you here and we’ll have to have you back.

Erin: Well, it has been—You’ve made this very easy. I get nervous doing these. So thank you so much. It’s been a pleasure being here.

Paula: Oh, it was such a treat. Thank you so much, Erin.

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