Welcome to Powerful Leaders, No Apologies.



Show Notes

Beth and Debbie talk with the Editor-in-Chief of Legal IT Insider, Caroline Hill, about her journey to becoming a powerful leader.

[07:54] What do journalists read and listen to?

[15:21] Stop apologizing!

[26:38] What is your leadership superpower?


  • Transcript

    Debbie Foster (00:03):

    Welcome to the Powerful Leaders, no apologies podcast, the show about women who are ready to own their power and change the world. My name is Debbie Foster.


    Beth Thompson (00:12):

    And I’m Beth Thompson. Our guests are fierce and fabulous women who are making a difference in their personal and professional communities. Are you ready to be inspired? If so, stay tuned and also check out our website at affinityconsulting.com/powerfulleaders. Here’s the show. Debbie, can you believe that we are now at episode five of our podcast? Time is flying by.


    Debbie Foster (00:41):

    Time is flying by. It is flying by. And I know I say it every time, but we’re still promising the hats, like the hats are going to be here. It’s just taking a little longer than we expected,


    Beth Thompson (00:50):

    Hopefully by the ALA conference in Seattle. Yes, I think that’s got to be our goal. Right? That’s good.


    Debbie Foster (00:56):

    That’s a good goal. Yes.


    Beth Thompson (00:57):

    Well, Caroline, thank you for joining us. We are so excited to have you as a guest today and I’m sure our listeners are going to love the accent that is so vastly different than mine and Debbie’s welcome to the podcast. We would love for you to introduce yourself and tell everyone all about your amazing life and career so far.


    Caroline Hill (01:20):

    Oh, thank you. Well thank you Beth. Thank you Debbie. Thank you for having me. Glad that I’ve got the right accent. So yeah, I’m Caroline Hill. I’m the editor in chief of Legal IT Insider, which is a global legal technology publication. I’m based in the uk but our coverage is literally global. So we’ve got a big audience in the US where I’m going to be spending some time this year, which is exciting. And yeah, very happy to tell you anything about the career to date, which has been quite varied.


    Beth Thompson (01:50):

    Yeah, we would love to hear about it. Why don’t you just give us a little glimpse into your career path?


    Caroline Hill (01:56):

    So I started out as a lawyer, so I didn’t really know what to do. I think perhaps a lot of Lawyerist. I studied law because I wasn’t really sure what I wanted to do. I was good at English, so I ended up studying law. And when I was at law school, I actually wanted to be a journalist, but I went to my careers advisor and I said I want to be a journalist. And they said, gosh, that’s really competitive. So I didn’t pursue journalism at that stage of my career. Instead followed the legal route. I didn’t qualify straight away. I actually started practice at a criminal law firm in a seaside town in the uk, which was very challenging. Can you dive into that in any more detail if you’re interested? But it was very male heavy. I was very young, it was very tough.



    Certainly a teeth cutting environment. And then moved on to do some court work, some outdoor type work for ra, which is now Gowling wg. After the merger we represented them running off to the world of justice and doing applications. They were based in Birmingham and then know what, I should probably qualify as a lawyer cause I still wasn’t qualified. And then so I went to Nor Rose where I got my training contract. And it wasn’t long after that I thought, do you know what, I really do want to be a journalist. And then I began, and if you want to come back to this, this is one of my funny stories, but I began a career at Legal Week and that sort of led that began my journalism career and then became the news editor at Legal Business and then took over this publication Legal 19 Insider in 2014.


    Beth Thompson (03:29):

    Wow. I definitely want to dig in a little bit to the early days in criminal work. I’ve been a reader for a long time. In fact, I have a hard time not calling it the Orange Rag because that’s what we’ve all called it for many years.


    Caroline Hill (03:44):

    I do call it the Orange Rag. Yeah,


    Debbie Foster (03:46):

    I always love that name and I would love to get the story of how it became that. But as Beth asks you her next question, I meant to say something about this at the beginning, but your LinkedIn kind of experience bio says Caroline Hill has worked in the legal sector for around a hundred years. The best thing she ever did was ditch a city lawyer career for her first passion writing, albeit mistakenly thinking she’d work less hours. I thought that was a really clever way to describe what you do now.


    Caroline Hill (04:22):

    Oh my Goodness. Do you know, I always forget that I wrote that a long time. But it does sum up. I feel like I’ve been in the legal profession for a hundred years. I have actually mean it was at my age away, but I did a really long time ago. I’ve been in the legal professional a really long time and it’s true to an extent. So when I was at Norton Rose, I was working all hours, but slightly begrudgingly. I’m sure the partners that I worked for at the time would remember that I wasn’t a hundred percent cut out for that kind of environment. But now I don’t begrudge working hard. And because we do all of the different time zones very often, I mean, I’m an early riser, I typically start at five anyway. And then quite often with the US we’ll be working late. Yes. But I do it with passion, I suppose that’s the difference.


    Beth Thompson (05:12):

    Well, and we appreciate, we know that it’s a late afternoon, early evening for you now, so thank you for taking the time. I mentioned earlier that especially in the early days it was a male dominated field. What were some of the challenges or obstacles that you encountered during those days?


    Caroline Hill (05:32):

    So when I joined the criminal, I only, there was one other girl and the rest were all men. And I mean, gosh, I don’t want to be judgemental, but to be honest, this is how old I am. We didn’t even have computers on our desk. We had to use a dick phone. I would have my clients come into the office and I would say, hello, this is, my name is John Smith. And I definitely didn’t do anything until we’ve seen the CCTV and then it was actually me. But I had a really good experience and then I’d have to take the tape down and get it typed up. And to be honest with you, there wasn’t an awful lot. The secretaries at the time, I dunno, maybe it was me and probably was me, but I just didn’t know how to manage myself in that environment.



    I think that they didn’t really, I felt that everything was more difficult. It was more difficult to get my tape done. I wasn’t tough enough to be perfect. Well, I mean it was a very tough environment. I think things have changed the more as you’ve got now, more women who’ve gone through that, stuck it out and you’ve got more senior women. But at the time there was actually one other, but I never really saw her. But I didn’t have any role models in that environment. All of the senior people were men. It was really challenging to be honest with you. Although it was super fun and exciting.


    Beth Thompson (06:41):

    I can imagine you’ve got many, many stories. That’s exactly what I was going to ask you next is when you don’t have role models in your work environment, where do you go? Where seek them out. I’m sure you’ve had mentors or role model since then. Were you able to find any then or did you just have to figure it out and then later?


    Caroline Hill (07:02):

    I actually just left mean to be honest with you, there were other factors, the pay to be frank with you. But I did leave. And one thing that I think if I’d stayed in crime, I think maybe I would still be doing it now because it really was a passion thing. I felt I absolutely loved the work. So yeah, I think it is so important. And since then I have sought out mentors. It’s so important. There are some women who I have turned to who really inspire me and on your worst day you can go and say to them, Hey, how did you handle this? And it does make such a difference, doesn’t it? And seeing faces like yours, which is why now I’m trying to do as much work as I can to try and help promote women to stand up, be counted. Because as you know in technology that we still have a diversity issue.


    Beth Thompson (07:53):



    Debbie Foster (07:54):

    A big one. I’m really curious when you talk about people that inspire you and how you’ve kind of traveled that journey to find those people. I sometimes wonder, I’m really envious of the journalist career. I’d love to feel like I was a really great writer and I think I can write things that sound good, but that’s not my passion. That’s not what I love to do. I don’t love telling the story, but I don’t really want to write it down. But I am curious as a journalist, what do you read, what do you listen to? What inspires you from a content production perspective that is outside of what you produce?


    Caroline Hill (08:35):

    Yeah, so I mean obviously we have to read all sorts, we have to read and there’s an ever growing amount in terms of the relevant work stuff. So the different publications, the blogs, the press releases, all of that I read constantly, but I don’t think probably that’s what you’re talking about. But obviously that takes up a lot of time just reading, staying on top of what’s being written and what’s been said including outside of the industry. But in terms of reading and being inspired. So I actually don’t read about leadership stuff. I read, I’ve, one of the books I think I’ve read that really impacted me, the two actually. One was Atomic Habits. They’re more about how to run your life and how to run it well and how to look almost how to look after yourself. So one was Atomic Habits and the other one was a book called Breath, which is written by a journalist and it talks about breathing properly and the importance of that and centering yourself.



    So I think I read books that help me cope almost more in terms of the volume. I’m a mom, busy schedule. The things that I find most impactful I think are things that really help me to manage myself and get the best out of myself. So those two books are amazing. Atomic habits, I dunno if you ever read it, but love it’s correct little changes. And for me that was so impactful. Cause I think the temptation is, oh, I’m going to change everything and I’m going to do everything a hundred percent better. And actually that’s not realistic. But you change something much smaller and just change one thing tomorrow and do it a little bit better. And then incrementally then over a period of time there’ll be exponential change. And that’s the point of view of that book. And that’s amazing. And then breath is so simple, but if you read it, it’s so impactful because you just, it’s the most simple thing that we do every day. But actually in perhaps situations, you know, talk to women about public speaking, but actually centering yourself and being able to compose yourself. It’s all about breathing. So for me that was one of the really impactful books.


    Debbie Foster (10:37):

    I do one more journalist question. When you read, do you have a mental red pen? Are you like, oh mg did that person seriously just write that sentence like that? Do you read with a red pen in your brain? I


    Caroline Hill (10:53):

    Do. I really do. I do. And also I hate my own typo. Even if I’m sending a text message, if I notice notice, I’ve put a typo, have to go, oh sorry, I meant I can’t it. Yes, you do notice, right? So I can’t read things like books, et cetera, that I think mean everyone’s got their own personal way, their personal likes. But for me, if I think something’s not written well, even if it’s a good story, I can’t read it. So yes I do.


    Beth Thompson (11:27):

    So is writing a book in your future? Or maybe you’ve written one already. I don’t know the answer to that.


    Caroline Hill (11:33):

    Yeah, no, truth be told, I have written a children’s book and it has sat I’ve, I wrote it in 2020 I think. And I dunno why, but I haven’t done anything with it. And then, so if anybody wants to be my literary agent for Children’s book Message Me,


    Beth Thompson (11:53):

    We hope we can make a connection for you so that you can get, I would love to see that. One of my friends from high school literally just had a children’s book published last year, so it’s never too late.


    Caroline Hill (12:04):

    Wow. Yeah, no, it’s funny. It was a real passion thing and I finished it and it’s quite a long and I quite love it, but I just haven’t had, this is perhaps a what should you do better, but I haven’t made the time. But I think hopefully I’ll start making the time to re-look at it and maybe do something with it. But no, in terms of other stuff, I don’t really have time. But I think in the future, who knows,


    Beth Thompson (12:26):

    Well stay tuned for that. So before we move on and switch gears to apologies and women and that kind of thing, are there any times in life or in your career that people have counted you out and it motivated you? Either it motivated you or it stopped you in your tracks. Let’s talk about that for a moment.


    Caroline Hill (12:47):

    Yeah, I mean, I don’t know if you should name vers, but I already have, but it was not anyone’s fault. So when I was working at Rako, so I was doing their court work, it was myself and this other chap and it was a bit of an unusual setup in that they didn’t have a London office at the time and we were their London office and we would rush off to the courts and do applications. And we were pretty good actually. We used to do really great work. I applied for a training contract and I knew a lot of the Lawyerist, but I got rejected for the training contract, which was at the time so hurtful because we were, and I’m sure there were good reasons, I probably did a really bad interview, whatever. Anyway, but at the time I was like, oh my goodness.



    So then I thought, right, what do I want to do? So I went for a training contract at Norum Rose and before I went for the interview process, I took on board all of the things that I think I probably didn’t do as well because they got obviously put you through lots of different tests and including a group environment, how do you react in a discussion? And I kind of worked out what it was that they were looking for. And so in that one with Rose, I was like, right. So I took the lead and I’ve got a hold of a clock and I’m like, right, let’s keep an eye on the time folks. And all the things that perhaps I hadn’t done before, but also before the day, the big training contract assessment day, I was just literally rocky. I went for runs every day and by the time I got there I was literally felt like nothing could stop me. That kind of thing. It really, really genuinely motivated me, that kind of feeling of failure, of wanting to make sure that that didn’t happen again. So it was really powerful and I was lucky I’ve got the training contract.


    Beth Thompson (14:22):

    Well I think that’s a great example of learning from a failure or maybe something that you knew that you could have done better differently, really assessing it kind of a postmortem to figure out, okay, what can I do differently or better next time? Yeah,


    Caroline Hill (14:40):

    There were reasons, I’m sure that, so there were obviously reasons, but rather than taking it as a defeat and thinking, oh I’m rubbish or what, just thinking, okay, what can I, turning it into a positive and saying, okay, I know that I could done this better. I know I’m being more quite analytical about it and thinking, okay, well how do I take that and how do I take it forward into the next experience and how do I make sure that I do that better? And I remember being really clear but also making sure that you are feeling the best in yourself. I really did. And I do like to stay fit and do physical exercise and look after yourself. Cause I think then you can be really bring your best game.


    Beth Thompson (15:21):

    No, absolutely part of the focus other than we really love to empower women. We spend time talking about the fact that as women we do a lot of apologizing. And so I have a quote that I would love to read you and get your input on. This is from lady by the name of Elena Fernandez. Don’t know who she is. She said, stop apologizing for believing your beliefs, feeling your feelings, choosing your choices, dreaming your dreams and being who you are. That’s pretty impactful. Would love to get your take on that quote in particular, but just in general women and apologizing when we don’t necessarily need to apologize.


    Caroline Hill (16:09):

    Yeah, I think women do do that. And we’ve got the expression, particularly group of my girlfriends got the expression, sorry, not sorry. Which we use quite a lot. And it’s a reminder if somebody says sorry, not sorry, I think we have to remind each other that we don’t have to apologize. And I think that there’s lots of things I think that we are sometimes expected to act in a certain way still. So I love people, I guess I’m an extrovert and I get energy from people, but I’m not sorry if I have to my job. Sometimes you have to put yourself out there and not be liked. And I’m not out there to be liked. I’m out there to do a good job. And do you know what if I do something that means that I’m not liked as long as I’m doing it ethically and as long as I’m doing the right thing, I don’t actually really care if you like me or not. Sometimes I say that and actually I secretly do, but still I feel like I’m not, and I’m not sorry for doing things that are, I dunno, not ladylike, whatever. And I’m not sorry for swearing. I will regularly drop here.


    Debbie Foster (17:12):



    Beth Thompson (17:13):

    It. Sometimes that’s just the best word to use. There’s no replacement for it. So


    Debbie Foster (17:18):

    That is so true. So I have a question that I’m really curious about. I remember the first time that Affinity was in the orange rag and I kind of felt like you guys will maybe get the reference the movie, the Steve Martin movie, the Jerk when he finds his name in the phone book and he is like, we’re famous. I remember feeling that way. This is a big deal. And I’m wondering, you I’m sure are pitched a lot of stories and successes and products and services and ideas from people all over the world about legal technology and if I were a betting person, I’d say at least greater than 50% of the people pitching you are men.


    Caroline Hill (18:10):



    Debbie Foster (18:10):

    Fair. Okay. Yeah. So my question is, do you ever feel like someone’s talking to you in a way that they wouldn’t if you were a man or in maybe a more challenging conversation about an opportunity that someone might feel like they have to be featured in your publication, which by the way is a source of truth in the industry that your publication is. If it says it in there, it’s true. That’s the thing. Have you ever had a situation where you feel like the game is no longer fair? You feel like someone is asking you to print something, publish something, or assert themselves in a way that you’re like, hang on, no.


    Caroline Hill (18:56):

    Do you know what? No, I mean no, actually no. And I do believe that maybe that comes down to a little bit of self-belief and I feel privileged to say that because I was very lucky to have, I’ve had sort of a lot of belief in me over the years, so I don’t want to seem too cocky about it. But I do think that you can either have belief because of your parents living in you and then just you are lucky or because you’ve worked on it really hard. But I do think that there’s certain element of expecting to be spoken to a certain way and now as soon as I get off this podcast, I’m setting myself up. Oh, ok.



    But I think that if you believe that you have a right to be at the table, you don’t even question it. Why the hell should you question it? And I really mean this from the bottom of my heart. I’m not just saying this, you believe that you and I believe that of all women and all people actually, I think that we believe in equal rights across the board and in terms of all types of diversity. And then I think that there’s a people sense that you doesn’t have the tolerance perhaps I do not have the tolerance force for that. So I mean I’m sure I have had some slightly more, I’m sure. Yeah. Anyway, probably different conversation altogether I have had sort of some bad, but not normally in people being pitched pitching to me. No, maybe I’ve just really not observant. Maybe I just don’t pick up on the signs.



    Or actually I have had, when thinking about it, I have had a situation where I was going to write something that someone didn’t want me to write. I did sense that that was a male female thing. I kind of sensed that they were like, oh little girl this, that they really, really desperately didn’t want me to publish something. Actually that was one of those times when I did feel like they sort of tried to patronize me and go, oh, I thought you were this, but actually you are this. And that’s when I think the expletives that came out of my mouth then and I had the biggest tension. And I perhaps tantrums wrong, but I was absolutely furious beyond all furious. So yeah, I dunno. I think it’s about believe in your, believe yourself and don’t tolerate that.


    Beth Thompson (21:10):

    And I suspect that if you were a man and that same individual did not like what you wrote, they would not have responded in the same manner and spoken to or written the same type of feedback to you as a man. They would’ve handled it probably very differently.


    Caroline Hill (21:28):



    Debbie Foster (21:29):

    I think that’s part of, we are really careful to not be man bashing because we all work with amazing men and not just amazing men who are just in their own amazing, but amazing men who recognize the important role that they play in getting women at the tables where they are. So it’s more like an awareness. We have some tradition, especially in legal that has kind of infiltrated all of the different areas of legal, whether it’s in a law firm or a legal service provider or a publication or a software company or a consulting firm or whatever, where there still is some of that tradition that is left that in some situations where I have had that I would describe to be exactly kind of the question that I asked you, I’ve been able to go back after and sometimes even in the moment where I say things that I regret where I’m like, that actually wouldn’t have happened like this. And I think that kind of awareness is so critical. But circling back to your point, which is a bit of a recurring theme through our conversation so far, is how are you taking care of yourself? So you show up as your best self confident in where you are in your life. And that comes across loud and clear in an email, in a phone call. You know what I mean? I feel like that’s kind of what you said.


    Caroline Hill (22:58):

    Yeah, no, and can’t agree with you more about the not man bashing and I and about the inspiring men. And I think that that’s so important to that. Men can be really much part of this whole supporting woman and that’s not a bad thing. Sometimes I think, oh, should we rely on men’s supporters to be, but actually having champions, whoever they are, is a good thing. Making people feel involved and not excluded. But don’t get me wrong, that life is not a smooth sailing. Certainly not for me. Sometimes it can be more like a rollercoaster where there are days when you feel like you’re smashing it and then there are some days when everything feels like it’s going wrong. But I do think that looking after yourself is really important, but also just understanding that some days you’re going to be running and some days you’re just going to put one foot in front of the other.



    And actually that’s okay. I think that as women, we kind of think that we have to be perfect as well. And actually that’s the most toxic word, which yes, hopefully we’ll bring out a game and we’ll I’m sure that we’ll smash it on many occasions. But actually there are sometimes just, I’ve been through times in the last couple of years when I’m like one foot in front of one foot in front of, yeah. So I do think looking after yourself and being positive thinking, I’m a big fan of it. I know that I think it’s probably more acceptable in the US than it is in the UK where we still get this kind of, oh that.


    Beth Thompson (24:23):

    Yeah. Before we dive into our final question, you know have talked about self-care and you talked about running and how that helped you to pump yourself up. What are a few tips that you have for folks when it comes to self-care and taking care of yourself? Maybe even other than the physical, right? What are some things that we can share?


    Caroline Hill (24:42):

    I had to think about that before. So obviously exercise is really important. So now I’ve stopped running cause I’m getting older and my knee hurts, so I go to the gym. I think it’s really important to look after, take care of yourself so that look after your physical self and you look when you look in the mirror and you’re just like, yeah, you recognize that you’re taking care of yourself and all of those sorts of things. And breath breathing, I’ve said obviously, but I think it’s also about working out. So I tell people, just be brave. So you sort of challenge yourself, develop some sort of things that puts you outside of your comfort zone. I advise people with public speaking, I’m like, just stand up. One of my frustrations with creating panels or getting people to speak, women don’t stand up, so I’m always just stand up.



    This isn’t necessarily a self-care thing I get, but it’s like just stand up, put yourself forward. If you’re in a meeting and there’s someone been speaking and then they say there are any questions, be the first to speak, right? Don’t wait until there’s that, oh well now can I say my thing? Be the first. Put your hand up, be counted, be brave. It can be really challenging. It can be. But then you’ll start to get this sort of, it becomes a little bit like, Ooh, I’ve done that and that was not too bad. And then that was awesome. But also don’t try and be perfect and don’t be afraid to be vulnerable sometimes I think. And I think that sometimes over the last couple of years I’ve had quite a lot of stuff going on in my life and I’ve said to people at times, Hey, I could just deal with some support. And I have had the most incredible team around me who have just been wonderful and who look after me when I need it and I look after them. So I think it’s about being vulnerable and make sure that you’ve got a good support team around you. And don’t be afraid to say, Hey, I’m not having a great day today cause and look after each other for me. That’s been invaluable.


    Beth Thompson (26:38):

    No, I think those are really great tips As we wrap up, we always about your leadership superpower. As women, we don’t really toot our own horns very often, so this is your opportunity to toot your own horn and share with us what do you believe your leadership superpower is?


    Caroline Hill (26:57):

    I dunno, it sounds like a superpower. I think my superpower is resilient. Do you think that’s a superpower?


    Beth Thompson (27:03):



    Caroline Hill (27:05):

    Yeah. I think I’m really resilient that no matter what happens, I’ve got really big shoulders and no matter what happens, I will show up and I will give my best something. Stories curves us and I will, but I will be there and I’ll also be there for that other people.


    Beth Thompson (27:22):

    Great. Thank you so much Caroline. We’ve enjoyed the conversation. We appreciate you taking time out of your beginning of your weekend. I guess it’s going to kick off here really soon and we appreciate you.


    Debbie Foster (27:34):

    Thank you so much. It’s real, really inspiring.


    Caroline Hill (27:36):

    Thank you so much. It’s a lovely session with you.


    Beth Thompson (27:42):

    That’s a wrap. Thanks for listening to Powerful Leaders. No apologies. Be sure and subscribe to our show and help us spread the word by sharing our show with your network.


    Debbie Foster (27:52):

    And check out our show notes at affinityconsulting.com/powerfulleaders for resources and ways to connect with us. See you next time.


    Debbie, here we are, episode four. I feel like we’re becoming pros, although now that I’ve said that, who knows what’s going to happen in this episode. But oh Lord, it’s, it’s fun so far. Still enjoying it. How about you?

    Debbie Foster (00:46):

    It’s been really fun, and every episode I leave that episode just with a nugget or two or something that inspires me to think this is a cool thing that we’re doing. I’m mentoring someone right now, and she sent me a message right before we got on this that said, I just finished listening to your podcast and it was so inspiring. When’s the next one coming out? And I thought, you know what? Why we do this, right? This is fun. So it’s, it’s been a blast.

    Beth Thompson (01:13):

    That is great. I had someone text me last night asking, oh, send me the link to the second podcast. I’m like, well, Thursday, it’s not out yet, so it will be out. I’m really excited about this episode. Judy, welcome. It’s been a long time. It’s great to see you again and to know that we’re both still in the legal industry after probably, I don’t know, 12 or more years ago that we first met. Super excited to hear your story and how you came up in the ranks in this legal industry and in particular technology space and now as a CIO. So we would love for you to tell us your story. How did you get started in legal and you know how you got where you are?

    Judith Flournoy (01:50):

    Well, first let me say thank you for inviting me in Debbie and Beth. I think it’s terrific that you’re doing this and giving people voices that others can hear. It’s such a powerful opportunity, and thank you for doing that instrumental, I think, in helping people grow in terms of their own career. So again, thank you for that and thank you for inviting me. So I started out my career not at all thinking I would ever be a cio. It wasn’t a thing I had in my mind. I’m going to be a chief information officer for a law firm bar from it. And in fact, I didn’t get into technology until later in my life. And I worked for a consultancy. Actually, the consultancy is how I ended up working in a law firm because that consultancy was a small consultancy in Los Angeles that did work for law firms in the Los Angeles and Century City areas.


    And one of the projects I happened to work on for that consultancy was for Rose in Century City. And it was a large project, and fortunately it was a successful project, and I made a reputation for myself as a can-do kind of person. There were some issues with some technology that the firm was using, and I was in contact with the firm, including the chairman of the firm due to that particular issue. And shortly thereafter, I was offered a job. And so I took my first job working for a law firm, not in the role that I thought I really was qualified for, but one that they wanted to give me. So I started with pro hours, a network manager, which I really was an engineer so early in my career was very technical. I was the one in the data center. I was pulling things apart, putting things back together again learning all kinds of things about different technologies.


    And my staff used to make fun of me because I was most known for all the acronyms I knew and all the technical terms that I knew and understood. And we would be having conversations and I would throw out some technical component piece of information and my staff would look at me and laugh. So let me just state now for the record that my staff today wouldn’t want me anywhere near a data center. I am not the technical person in the room. I am so fortunate to work with really qualified, smart, brilliant people that do that work every day and make me look really good. But I started out in that role, very technical, and then moving into working for a law firm in the early 1990s. So there you go. I’ve been around for a little while, probably more than 15 years. Yes. But we won’t go any further into that. And so I’ve been in this industry ever since. I love the industry. I love working with inside of a law firm. I love working with Lawyerist and I love legal technology because I think it’s very unique, and that’s how I started my journey.

    Beth Thompson (04:26):

    Wow, that’s great. The son of a great leader is surrounding yourself with amazing people. So you’ve done that. I’m curious, you said this is not what you thought you would be doing. What did you think you would be doing when you looked ahead at your adult life?

    Judith Flournoy (04:39):

    I thought I would be a professional musician.

    Beth Thompson (04:41):

    Okay. That’s a good segue, I think, into what else we really wanted to talk about. I’d love for you to tell us your journey. You’ve been able to do both then, right? Music and working in legal tech. So tell us about Legal Bites.

    Judith Flournoy (04:53):

    So interestingly enough, some years ago, 15 to be exact, I was in a conference room in Los Angeles and around the table, and one of the people at the table was Frank Gilman that time working for Alan Mackins, who was a CIO for Alan Mackins. And he was starting a band of legal technologists, basically CIOs. It was going to be an all CIO band. And I raised my hand and I said, gee, I’d love to do that. What do you need and do you need to be a really good musician? I don’t read music. What’s the expectation? And so he got laid out what his vision was for this, and he was going to write all original music about legal technology, and he said, let’s do this. So we ended up forming a band and started playing at the ITLA Conference, the International Legal Technology Association conference 15 years ago.


    All original music written by Frank, where he sings Lead and with a number of other musicians up there with us. And the band has changed over time. So there’s different musicians that have come and gone through the years, but it’s been a fantastic experience. So to your point, yeah, I get to do something I never thought I’d do. We played not on the main stage, but on a different stage at the Country Music Hall of Fame when ITLA was at Nashville some years ago. So to say that I was actually playing at the Country Music Hall of Fame at a point in my life was pretty amazing to be able to say that.

    Beth Thompson (06:20):

    That is amazing. And I believe you’re going to be playing at the opening reception for ITLA Khan this summer, right?

    Judith Flournoy (06:26):


    Beth Thompson (06:27):

    Look forward to it. We’ll be there. Debbie and I will be there.

    Debbie Foster (06:29):

    Be there. We will be there for sure. So Judy, I’m curious, as a CIO of a large law firm, I know you probably don’t have a typical day, but if you were thinking about your day in the life when it comes to leading your team, what does that look like? Are you focused on strategic big picture and your team is really focused on kind of the day-to-day or how does it work in a large law firm as a CIO?

    Judith Flournoy (06:55):

    Well, it’s certainly evolved over the years. So when I started out in this business and the different roles that I’ve taken on over time, my responsibilities and focus have changed. So as I mentioned previously, I was very technical early on and then moved more into what I would characterize as a strategic leader, not focused so much on the day-to-day operational aspect of the work and tactical aspects of the work. So right now, today and leading up to where I am today, I’ve led teams that are responsible for a broad variety of areas within the law firm. So I manage a team that handles the systems operations side. So that’s the plumbing I handle, managing the team that is a cyber security team, which is extraordinarily important in business today. I’m also responsible for the records and information governance team. I’m responsible for the practice management team, and they’re working mostly on projects that are in service to the practice and service to the client and legal, innovation, legal process, innovation.


    And I’m responsible for my IBS characterized as the application side. So what people use, the software they use, the tools they use and how they use them. And then I’m, these days, I’m also very involved with the firm’s client service and innovation committee. So my day-to-day is very focused more now on the innovation and service to clients. What should we be doing? Thinking about experimenting with exploring, what should we be doing in terms of communicating with younger attorneys associates, how do we engage with them? How do we understand what their needs are? They’re a very different generation, and they’re largely more technical than the predecessor generations that are in law firms today. What are their needs? And they’re a little bit unique, and that really changes my day. So I spend a lot of my day, most of my day in meetings these days in teams or Zoom, prior to Covid lockdown, I was in an office with everybody else and wandering the halls and going into conference rooms. So it’s made that transition over the last couple of years to doing this virtually, which thankfully works for everybody because it provides some more flexibility in terms of where people are and how they contribute and how they show up.

    Debbie Foster (09:05):

    That’s quite a list of things. That was, as you were rattling that off, I was like, whoa, that’s a big job. That’s a really big job. Whoa, that’s an even bigger job. Those, that’s a lot.

    Beth Thompson (09:15):

    And you’re in a band, and I think you do some volunteering with ITLA too, right? I know you’re probably on multiple committees.

    Judith Flournoy (09:22):

    Currently I’m volunteering for the talent council. So we are in the process of identifying, interviewing, and identifying the next group of candidates who will run for the board of directors. So that’s my current volunteer activity for ITLA. But I’ve been involved with ITLA for the most of my career, and I will openly share that. I give full credit to ITLA and my peers in ITLA for having lifted me up through the years, giving me opportunities to learn, giving me opportunities to lead, helping me learn how to communicate and build consensus. All of those things have been through my volunteer experience, through ITLA, and it’s been a fantastic organization to be a part of. And anyone who’s listening to this podcast, if you are working in legal operations, if you are working in a law department, if you are working in a law firm and your firm and or other entity is a member of ITLA and you are not participating, I highly encourage you to do so. It’ll be well worth your time, and you’ll get more back than you put in.

    Debbie Foster (10:18):

    And Judy, I think this was actually on one of the episodes of our podcast, but someone talked about the best way to learn how to be a leader is to lead other leaders. And that’s kind of what a volunteer experience ends up being, is working alongside and leading other leaders are leading with other leaders. And it can be a really magical experience in the volunteer community.

    Judith Flournoy (10:41):

    It really can.

    Beth Thompson (10:42):

    Yeah, for sure. I was just going to say, I think with that plug for ITLA, we’re destined to get joy on now. We just have enough Joy on,

    Debbie Foster (10:49):

    We have to get Joy on. So I think it’s also a great segue into, aside from ITLA, what is inspiring you podcast books that you’re reading, what kind of helps you take things to the next level as you continue on your journey?

    Judith Flournoy (11:06):

    Great question, because I’m all over the place. I’m one of those people who will read multiple books simultaneously. Oh, I don’t know if that’s good or bad. So I may not necessarily finish one sort of cover to cover in one, if you will stretch, but I’ll go, I’ll bounce around. So I’ll go from fiction to non-fiction. Right now I am reading a book called The Age of AI in Human, the Human Future by Henry Kissinger, Eric Schmidt of Google, and Daniel Hucking Locker who’s the dean of MIT’s Schwartzman College of Computing, this book, honest gosh, who could have known in this book, they talk about chat, G P T. Wow. And if anyone’s paying any attention to the press right now, and the 10, was it 10 billion of Microsoft is just invested in this company, OpenAI, if you haven’t paying attention to this, you should. So in this book, they talk a lot about this technology and its potential impact on the world, how it will impact not only businesses, but private industry and people and individuals, and how different ways AI can be a positive impact for us, but that we should have an awareness of its impact to us as humanity.


    So it’s a really good read. It’s one of those that you’ll pick it up, read a little bit, put it down, think about it, pick it up a little bit, put it down. And then the other one that I recently read, which was recommended to me by my colleague, Guy Wiggins, who’s my director of practice management, is Cal Newport’s book A World Without Email. And I don’t know if you’ve heard of this book or read this book, but it talks about what’s happened. He characterizes it as the hyperactive hive mind, where we are spending so much time in our inbox that it’s very difficult to do focused work, let alone to complete things. Cal Newport is really trying to encourage people through this book to think about other ways to interact, communicate, and execute, versus doing all of that in the inbox. So highly recommend that book for certain. So those are the two books I would recommend,

    Debbie Foster (13:06):

    And that his book Deep Work is one of the most impactful books for me, has really changed how I think about deep work and shallow work and what really moves the ball forward. And it isn’t shallow work, hot tip. It is not shallow work. So I can’t imagine a world without email, but I’d love to. Yes. So I’m totally picking that book up.

    Judith Flournoy (13:26):

    Yeah. Oh, I’m really trying to utilize teams a lot these days with my teams in particular, and using the chat feature in teams for everything that doesn’t really need to be in the inbox. So we’re really trying to push that both within the administrative departments but also within the practice areas. We’re trying to get people to move a little bit of that stuff out of the inbox.

    Beth Thompson (13:46):

    We’re doing the same. We’re doing the same. And you know, mentioned chat G P T earlier, that has been a topic in our teams virtual water cooler channel. Just this week actually, people were all buzzing and chatting about what the uses were for it and how many people are using it. And yet it’s fascinating. So

    Judith Flournoy (14:05):

    Is Indeed. Sure. So on the podcast side, I really like Law Nets Law Next, I should say, that’s the Bob and Brosy podcast. So if anyone’s familiar with Bob, he’s such a influential, impactful facilitator. Yes, he gets the right people in the right conversation in a way that really gets you to think. And then I like the New York Times Daily podcast because I want to know what’s going on in the world. So not just legal technology, there’s a world outside of my <laugh>, my job.

    Debbie Foster (14:36):

    Hard to believe sometimes. I love Bob. Bob’s a great friend and just a great industry thought leader. I love reading, reading and listening to anything that Bob does.

    Judith Flournoy (14:47):

    A hundred percent.

    Debbie Foster (14:48):

    So the next thing we wanted to ask you about obstacles and challenges along the way. Anything stand out as something that was just hard or where somebody didn’t give you the shot that you wanted to take? Or where you raised your hand for something that you were like, oh, I don’t know. I hope this works out. I, I’d love to hear a story like that.

    Judith Flournoy (15:09):

    I’ll see if I can do this for you sequentially, Debbie, because if So let me first start with this. I raised my hand when Proscar offered me the assistant director of IT position in New York City. I was a California native, didn’t think I would ever leave California. Did not think I was really prepared to take on that much responsibility at that time in my career. But I raised my hand anyway. When the offer came, I gave it some thought and I took the chance and I went and I did it. And I am so glad that I did. So I’ll say that’s the time that I raised my hand. And when it was not the most comfortable time to do so, I’ll also cite an experience at Proskauer. This is around the time that my then director of it, Rubin was leaving to go work for another entity.


    And at that time I was the assistant director of technology for Proskauer, and I was speaking to another director about the opportunity that was opening up with Lynn’s departure, and I won’t name who she was, but she said to me, and I’ve told other people this story before, she said, you’re not politically savvy enough. You’ll never be a director. And at the time, these are the thing, these are the conversations you have in your head later, right? You’re like, at the time, I didn’t even know how to respond. I think I just remembered thinking to myself, really, and what does that mean? But I didn’t have the wherewithal at that time in my life to say to her, what does that mean exactly? Can you explain to me what it means to be politically savvy? So if there’s any nugget of information out of this is when someone tells you something like that, that you can’t do it for whatever reason they’re telling you, you can’t have the fortitude to ask them what they mean.


    Just ask them what they mean. Just simple. What do you mean by that? And have them explain to you, because you can’t then go to whatever you need to do to address that. Whatever that shortcoming is that they think you have, if you don’t know what it is. She was not my direct supervisor. She was someone that I did not work that closely with. I knew her, she knew me, but at some level, she felt that I was not ever going to be able to rise to the position of a director. Fast forward, I ended up taking another job at another firm and took the director’s position when I went to work for Kelly Dry in 1997. And when I went to work for Kelly Dry in 1997, 1 of the things I learned from that experience in terms of the interview, and maybe this is something that your listeners can take away from this, is ask what problem they need solved. Because oftentimes during an interview, you’re telling them your story. They’re asking you questions, what have you done? Where have you worked? What’s interesting to you? Where do you want to be in five years? Kind of the standard questions. What you want to do is the interviewee is you want to ask what problems are you looking to solve? And how can I help you do that? Wow. And I honestly believe that that’s the reason why I got the job at Kelly Drive, because that’s the question I asked them.

    Beth Thompson (17:57):

    Great advice.

    Judith Flournoy (17:58):

    And then the last story I’ll tell you is this, sometimes in your career you will work with people where you will not get along. It happens. I was working at Lo and Loeb, I’d been there for eight years. My coo, retired gentleman who hired me retired and a new COO came in, and my new COO and I were like, oil and water, no matter what I did, just wasn’t ever going to fit. And I came to that conclusion after two years, took two years for me to do this, to come to the conclusion it wasn’t a good fit. And so when I decided to leave and made the decision to do so, no harm, no foul, right? We both left. It’s okay. No, I’m going to go do something else. You’re going to do something else. But I’ll tell you this other part of the story, which isn’t so much about that didn’t work out.


    It’s what happened next. And this is the power of networking. This is the power of remaining connected. This is the power of the people that, so when I left Kelly Dry in 2004 and moved back to California for family reasons and went to work for Lobin Loeb, I remained in contact with my chief human resources officer and my executive director. And we remained in contact for all those years. And every time I was in New York for business, whatever that, whatever the case may be, I would either have lunch or breakfast or something with Molly or Tom and I was in contact with them In 2012 when I decided to brush up my resume, I was sitting at breakfast with Molly and I said to her, I’m dusting off my resume as time for a change. And she said, why don’t you come back? And at the time when I was sitting there with her and thinking to myself, how would this work?


    And I said, well loud, how would this work exactly? Because you have someone that’s sort of the head of it right now. So what does it look like? Because I knew the entire team at Kelly at that time. So we had a chat about it, and then I talked to Tom, the executive director about it, and ultimately decided to make the decision to come back to Kelly Dry and haven’t regretted it once. So that’s the other part of the story is you can go back and you can do things and not have regrets. What you have to have is clarity about what it is you want to do. So I knew coming back to Kelly Dry that it wasn’t the job. It was when I left that what I needed to be focused on in the nine, nine years, I’d been away, what I’d learned, how I had developed as a leader, my skillset had evolved, and that meant that the role of a Chief information officer needed to evolve with it. And that is how I think I’ve best served Kelly Dry in the year since I came back, since I’ve been here since 2012, is I didn’t come back as the C I O I was when I left. So hopefully that’s helpful to your listeners.

    Beth Thompson (20:25):

    Yes. And as you’re saying this, I’m thinking and who’s not politically savvy to be able to navigate these relationships and to be able to go back. That’s amazing.

    Debbie Foster (20:35):

    Is amazing. Thank you for sharing those stories. I think that comment about the interview, I would love to be interviewing someone and have them say to me, tell me what problems you’re trying to solve. That’s such a powerful, turn it around and really get some insight into what that potential job might look like for you. I love that. I love that. So let’s switch gears and talk a little bit about apologizing. When we decided to name our show, Powerful Leaders No Apologies. We had done a lot of reading and research about women and apologizing, and certainly I don’t think anyone disputes the fact that women apologize more than men. In fact, I don’t think I’ve read anything that says, actually, I don’t think that’s true. Everything I’ve read says that is a fact, and there’s a skit that Amy Schumer is in where they’re on a stage, I think three or four women on a stage, and the skit is three minutes long.


    And it says, I’m sorry, like 80 times I went to speak and you were speaking, oh, I’m so sorry. Or I got up and I stepped on your toe, and I apologize you that I stepped on your toe. And it’s this whole dynamic around apologizing, and it’s something that as we’ve talked to our podcast guests about, what really resonates with them about not just stopping apologizing, but understanding that when you apologize for what you’re about to say, it is nowhere near as empowering as if you just say what is on your mind. We don’t need that entree or that filler word of, I’m sorry to really say something that we want to say. And I’d love to hear anything, any experiences that you have had around this concept of apologizing or maybe people who have been on your team that have apologized when they didn’t need to apologize, just kind of general thoughts on that.

    Judith Flournoy (22:31):

    Well, I think it’s true that, and as you said, everything you’ve read points us out. Women tend to apologize, and we do that by out of nature. It’s just kind of written into our D N A. I’m going to tell you I’m sorry first, and then I’m going to tell you what I need or what I want. But I’ll tell you, I’m sorry first because I feel like I shouldn’t ask you or tell you what I want because I shouldn’t, because I’m a woman and you know, should drive all of these things, make all of these decisions, but I’m also going to raise a counterpoint. And I think that sometimes apologizing is appropriate. And so I feel like when we talk about not apologizing, we have to be very careful when we’re providing guidance to individuals who we find apologize too frequently is to also let them know that there are times when apologizing actually is appropriate.


    That there are times when you may do something that inadvertently upset someone without you even realizing it may be after the fact. You may be in a conference room, a table full of people, and there’s a subject matter expert at the table, but someone else at the table has sort of taken over the conversation, and at the end of the meeting, you walk out of the meeting and you think to yourself, oh my gosh, I should have said to the group, and let’s hear from Jane, right? So you want to go up to Jane afterwards, and you don’t necessarily want to apologize. You don’t want to say, I’m sorry, Jane, I didn’t call on you, or I didn’t include you in the conversation, but you do want to let Jane know that you recognize that as the person who was facilitating that meeting, that it would’ve been in the best interest of the group for Jane’s voice to be heard. That’s a way of apologizing without saying you’re sorry. But I do think there’s an importance in recognizing, to your point, Debbie, that you don’t need to lead with, I’m sorry. First, you need to lead with the strengths of your argument of what it is you want to do, what it is you want to say, what it is you believe in, stick to your gun, stick to your instincts, and the people around you will let you know. If you’ve overstepped, they’ll let you know.

    Beth Thompson (24:30):

    Yeah, it’s a valid point. And I think it certainly then makes the instances where you are apologizing and you’re doing it when there’s a need for an apology, it will mean a whole lot more. It will. If it’s used infrequently,

    Judith Flournoy (24:43):

    It will. By the way, I’ve had to apologize to people in my career in different scenarios, and it was appropriate at the time that I did it.

    Debbie Foster (24:51):

    I think piggybacking on your comments about that, it’s the sincerity. It’s like it’s not just a throwaway word when you apologize, it’s sincere and it’s meaningful, and you’re explaining something that happened, not explaining away something that might have happened the wrong way, but that people are more likely to see you see that vulnerability and say, that’s a leader, a leader isn’t afraid to be vulnerable and kind of throw it out there and say, I kind of stepped in it there. I’m really sorry about that. Which is different than I’m sorry, but I have a great idea. Yes. No, you’re not sorry that you have a great idea.


    So Judy, for our last segment, one of the other things that we love to give people the ability to do on this show by asking a very specific question is the whole tooting your own horn thing. We’re all really good at something, but sometimes it’s hard to talk about what we are really good at. So we have this question about what is your leadership superpower? What is the thing that you think I’m the right person for this job because I have this superpower that makes me a leader that stands out or is something that I’m really proud of and something that my team really recognizes in me?

    Judith Flournoy (26:11):

    I think the first one is curiosity. Because I am as curious as I am, it tends to lead me to some things that people don’t necessarily anticipate or see. And I see them oftentimes before they do that helps me lead my team in directions they may not have known that they needed to go in. So that provides for strategy. So therefore I become a strategic thinker, if you will. It means I can sometimes be innovative as a result of that, but more importantly, I think that one of the strongest characteristics I have is that I’m empathetic, and I think that being empathetic in a world that’s complicated, where the work is sometimes very hard, where people put high demands on you, where you have demands outside of the workplace, I think being empathetic and understanding where people are at in the moment there is helpful to them and to you and to the team by at large. So I think that maybe being empathetic is my strongest of all.

    Beth Thompson (27:05):

    Both are great. Thank you so much. We have really enjoyed our time with you. I think our listeners are going to get a lot out of this conversation and the advice you’ve shared. We appreciate you very much and we can’t wait to hear the band at ITLA.

    Judith Flournoy (27:19):

    Looking forward to it, and I so appreciate your time today. Thank you for inviting me to the conversation.

    Debbie Foster (27:24):

    Absolutely. Thank you for joining us, and we are looking forward to seeing all of our listeners on the next episode.

    Beth Thompson (27:34):

    And that’s a wrap. Thanks for listening to Powerful Leaders. No apologies. Be sure and subscribe to our show and help us spread the word by sharing our show with your network,

    Debbie Foster (27:44):

    And check out our show notes at affinityconsulting.com/powerfulleaders for resources and ways to connect with us. See you next time.