Welcome to Powerful Leaders, No Apologies.



Show Notes

Beth and Debbie talk with Chief Information Officer, Judith Flournoy, about her journey to becoming a powerful leader. She credits her success to creating and surrounding herself with a powerful network of support. 

[11:06] What is inspiring you right now?

[15:09] Obstacles and challenges along the way

[26:11] 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 slash powerful leaders. Here’s the show,




    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.