Proven Not Perfect
Proven Not Perfect
Seizing Power and Growing Confidence with Maggie O'Brien, Managing Director, Co-Head Chicago, J.P. Morgan Private Bank
Maggie O’Brien is Managing Director - Co-Head of Chicago at J.P. Morgan Private Bank. She is a Daniel Burnham Fellow member of Leadership Greater Chicago, the region’s premier civic leadership organization. Complementing Maggie’s offer as a corporate and community leader, she is a mom and wife, committed to the love and advancement of her family. This conversation is ‘real’ and ‘raw’, getting deep into the reality of a PROVEN woman leader who navigates her journey with resilience, mindfulness and authenticity.
Maggie never expected to be pulled over on the side of a road for our conversation about female empowerment, but as she puts it - "such is the life we lead." This unplanned moment perfectly captures the reality of being a working woman balancing career ambitions with family responsibilities.
From the earliest days of her finance career, Maggie questioned whether she belonged in the room. At 23, walking into meetings with manufacturing executives, she wondered why they would ever listen to her advice. This vulnerability around confidence, especially for women in male-dominated fields, becomes our central theme. The conversation reveals how women often need significantly more certainty before taking risks compared to their male counterparts - a hesitation that can hold us back from opportunities for growth.
The turning point in Maggie's confidence came after successfully turning around an underperforming team, giving her tangible proof of her capabilities. Yet even successful leaders face setbacks. Her most valuable leadership lesson came from a failed turnaround where feedback revealed she'd been perceived as a "bulldozer" who hadn't taken time to understand the team before implementing changes. This taught her the essential principle that "you've got to get people in the boat with you before you ask them to row."
For women whose confidence has been shaken, Maggie recommends cultivating a personal "cheerleading squad" - trusted friends who genuinely see your value and can remind you of it during difficult times. This becomes increasingly important as leadership positions become more isolated, with positive reinforcement growing scarce.
The parallels between professional confidence and financial empowerment are striking. Women approach money decisions with similar caution, yet 80% will need to manage family finances at some point. For young women entering finance careers today, there's reason for optimism as technological advances make work-life balance more achievable, but representation remains critical - we need to see women who've successfully balanced career advancement with family life to believe it's possible for ourselves.
Listen for practical wisdom on developing self-advocacy, overcoming imposter syndrome, and finding your own power outfit (Maggie's is a hot pink Veronica Beard suit) that helps you own your presence in any room.
Drive, Ambition, Doing, Leading, Creating... all good until we forget about our own self-care. This Village of All-Stars pays it forward with transparency about misses and celebration in winning. We cover many topics and keep it 100. We are Proven Not Perfect™️
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I'd love to hear what you think!
Maggie.
Speaker 2:Chandra. Okay, you were supposed to be at home. You're not at home. I'm seeing a car behind you. What the heck? What is going on? This is feeling not perfect.
Speaker 1:Yeah, life happens. I got called down for an unexpected meeting Thought I left with plenty of time to get home to do this with you and pulled over on the side of the road because there was traffic and you know, such as such as the life we lead.
Speaker 2:So that's it, I swear um, you can have made this up. It's exactly, it's supposed to be right. So I don't want to lose a second of your time and I also want to keep you moving. But, um, first I have to say hey, girl. Hey, I said that I wasn't going to say that the audacity to have multiple children, a growing corporate career and, quite frankly, you and I bonded immediately because we also had the privilege of husbands who recognized our potential and, in some ways I won't say sacrifice, because I truly don't believe that was the case for either of them they chose unconventional approaches to support us and their belief in us and our families. And, girl, I don't even think I realized at the time how incredibly blessed I was in that. I mean, have you ever thought about that?
Speaker 1:I I've thought about. I think about it all the time and I think about it again recently because I just said yes to a little side job. That means a lot to me and I'm passionate about, but it means more time away and this morning was one of those examples. So you know who's carting around the four kids to the baseball and the soccer like that's my husband and he didn't blink an eye. It was like, ok, we're going to miss you, but if you want to do it, go for it. And I feel very, very lucky that I have that support.
Speaker 2:It's so good, All right.
Speaker 2:So look, I want to start this.
Speaker 2:When I thought of you, Maggie, immediately I thought of the fact that, well, when I thought of you, Maggie, immediately I thought of the fact that, well, talking to Maggie, who has this wonderful position of influence and leadership in the financial industry in an amazing city I think one of the best cities in America for an impressive and world-renowned company with a very vocal and present leader, like all those things line up to you so immediately I started thinking about all these questions that kind of went down that lane of finance and blah, blah, blah. I think it hit me very quickly when teasing this out with you that the conversation for us, very much aligned and adjacent to finance, is empowerment of women in their careers, and I think that it lines up so neatly to just being empowered in general and how that goes along with having options in life and taking risks that are calculated and seizing opportunities without being held back. And so does that resonate for you? Is that okay? Can we just kind of take that journey? Because if so, totally totally, yeah, totally.
Speaker 1:I mean I think you know, yeah, for women, for women in particular, the taking risk thing I think is a really big topic, like I more and more see how much more willing the male gender is to kind of lean in and take a risk and try for something, and how much more sure women feel they need to be before they do something. And I think, um, you know that's, that's something we should all be aware of and kind of embrace and then maybe push ourselves a little bit to step outside of the comfort zone. Um, because I think I think we're ready for a lot more than we sometimes realize we are, you know. So, encouraging everyone to kind of lean in, I think, is I've just seen so much of that recently that if that was one, one message I could convey is going to push, push ourselves to lean in a little bit- I love that.
Speaker 2:So let's let's take it back a little bit. When you started your career in finance, did you fully appreciate the power and position you were bringing just with your offers that you walked in the door with, or was that a process of becoming the proven leader that you are?
Speaker 1:No, I had no idea. I um, I mean gosh, I started in a training program so my first job was just to learn, to learn the job I was eventually going to do. The job I was eventually going to do was be a commercial banker for companies, Um, but at age like 23, I was asked to go out and bring in business, go get these companies to come work for you, and I'm like why would they work with a 23 year old woman who has never run a manufacturing plant and doesn't know anything about their business? You know so. So, no, I mean, I entered the workforce feeling like you know, I don't know anything about the real world.
Speaker 1:I've been a student, you know my entire life and um, have no idea what I brought to the table and probably brought. You know much less than I do now, just given the experience. But I think it's a, it's a learned thing as you go about um life. I think that's the other thing is, it's very easy still to focus on the stuff you don't have or the stuff you feel you aren't as good at, and, um, I wish I had learned earlier on to like lean in and appreciate the things I did have and did bring to the table, you know, even at 23 years old, with those business owners.
Speaker 1:Fine, I didn't have the experience, but you know what, Like, I always called them back. I was very reachable, I followed through on every commitment. I didn't know the answers to most anything, but I'd find them out and I'd come back, you know, and in the end that was a value to people, you know, and so, but it took me a long time to figure that out and have the confidence that, like that, what I was bringing was enough At some point, too, you realize that something is becoming a theme, and that is you're being consistently pulled into rooms and situations to do what you do.
Speaker 2:And I think it was that piece that really started to get me to say, well, hang on here. If they're seeing something to keep pulling me in, I might own actually stopping, pausing and figuring out just what that is right and asking the question why why am I here? Asking the question why why am I here? What was your evolution to the place where you went from? I'm doing a good job, I'm working hard, I'm being pulled in the room to, I know who I am, I know what I offer and I know what I'm packing Do you remember that?
Speaker 1:Hmm, yeah, I do. It took, I think. I think I would call that. I'm sure there's been a number of them, but I think the moment that comes to mind most readily is because I felt like for the start of my career, up through that first management job, like while I, while I was ambitious and I wanted the next thing, I also just constantly felt like I really had to prove myself. You know, that first management job, and you feel like, oh God, I'm like younger than the other people in this room and I'm the newest manager and I have to like be extra, extra good in order for these people to take me seriously. And, you know, you just feel kind of like an imposter, the whole. I mean, it's a very real thing, the imposter syndrome, like you feel like you know, I don't know like should I be here? Did I earn this? I be here, did I earn this, whatever?
Speaker 1:And I think, I think you know that first assignment I had as a leader and manager was a very big turnaround situation.
Speaker 1:In retrospect it was probably smart of the firm because there was very low risk in putting me into it. There was nowhere further to go down, right, but we ended up having a hugely, a hugely successful turnaround and, you know, by a year in, like that team had become the top ranked in in our system. And um, I think that's when I finally was like, okay, you know what, like I, I haven't accomplished. Like it's like I felt like I had a resume, you know, it's like I have a tangible accomplishment under my belt. And so now, like, if I feel like people don't think I'm qualified or aren't taking me seriously, like I had built enough, like in an innate kind of sense of accomplishment, and felt like you know what, continuing to give yourself, like the positive reinforcement that like no, we haven't achieved what we're trying to yet, but that doesn't mean that you don't belong in the role and it doesn't mean that you shouldn't have confidence in the meantime.
Speaker 2:I think that when I reflect on this generation, as I spend time with, you know, my oldest child's peer group, they bring a clarity about what their magic sauce is. That is unbelievable to me, because I know for sure that it took me a while to be able to articulate that, and I think they have almost the flip situation going on, because, where I didn't have that articulation early on, I just knew that I was going to work hard, I was going to learn everything, I was going to listen intently, I was going to watch, I was going to. I just knew that I was bringing a mindset to it. They, however, come in with all the things that I think I would begin to unfold Right, and so, if anything, it's the reverse situation.
Speaker 1:They're coming. Are they being taught that Like? How do they? How Like? Are they being taught to give that thought, or do you think that's?
Speaker 2:I think it's. I think I think we raised them. I feel like my peer group has raised this generation to have all the deposits that maybe we didn't have. And the other thing too, I think that we've spent I certainly did, you probably too giving them the opportunity to try so many things so that they're even as younger people they have an articulation of oh yeah, I tried, I tried that. I'm not good at that, but I am good at that Right, there's so many opportunities for them to sort of see what fits where.
Speaker 2:I feel like the generation that raised me, you know, with multiple kids and being a working woman and pursuing higher education and you know mom and dad and great, great upbringing and all the things. But still their thinking was well, they're the kids, we're the adults and you know, and they'll figure it out. Right, they'll go outside, they'll play, they'll figure it out. Whereas we're a little bit more sort of I felt like we were a little bit more strategic on behalf of our children. Now, the flip side to that is, I think, when it doesn't work, their resilience seems to be a lot more fractured than mine was for sure.
Speaker 2:I feel like my peers right, because we skimped our knee and nobody was home to like put the bandaid on it right. So you know, you just did it, whereas I feel like this new generation. Sometimes they skin their knee and that resilience takes a little while. So they have that self advocacy to begin with and it's the pivot to figure out outside of that. I mean, when you think about self advocacy and you think about your own success in leadership, how did you develop an articulation of self-advocacy and really owning your offers and being confident bringing those forward, and did you ever have a situation where it didn't work out so well?
Speaker 1:There have been tons of situations that haven't worked out so well, I think for the, I think for the self-advocacy part, like to me, I think I think self-awareness is so huge and I feel like very, very fortunate that early in my career I worked for a company that did a lot of training and a lot of the training would be around learning like who you are and how you operate. You know, so like what's your? You know, you've heard like Myers-Briggs personality tests, things like that. But you basically start to realize like, oh, I'm the way I am and there's actually and there's people who are totally different ways, but these my strengths and those things really resonated with me, like I have learned a lot from various different assessments. They're all very consistent. I'm a very specific type of person. But what also resonated?
Speaker 2:with me is are you e-s-t-j?
Speaker 1:yeah, totally, totally, 100, seven ESTJ all the way, okay, okay, yeah, so, like what you learn, you know, so, so, but like there are really good things that um come from an ESTJ personality right, like you get things done, you are efficient, you are results oriented, you are all the stuff and um. And then there's things you're not as good at. Like you're, you can come across as less empathetic. You, um, you know people can feel like you're kind of like a bulldozer, um, you know, and so but I, I think once you kind of learn all of that and you figure out what your strengths and areas for improvement are and you know that, then it becomes much easier to articulate to others and to self-advocate, because you are, you're describing what it is you bring to the table. You can, you can humbly admit what you don't or where you, you know where you focus on improving. But I think, I think self-advocacy is best when you, when you understand, like these are the things I'm good at, these are the things that I enjoy, and you kind of can lean into that, things that didn't go well, I mean, I can tell you that, the one that I always use when asked about this, and there's a million and 10 examples, but I think the really stark example is so I had a series of leadership jobs.
Speaker 1:After that first one I talked about, and because I had, you know, done this turnaround thing, every assignment I was getting we had talked about this. I remember when we were at Kellogg together, every assignment I was getting was another turnaround. Okay, so in assignment like four, um, it was another turnaround, the last one they had. Only, I mean, they yanked me from it after a year. I was like I at least want a year to enjoy the work I did. But no, they throw me into the next one. We were still getting our MBAs. I had a ton on my plate, right, three young kids, new job, getting an MBA.
Speaker 1:And so I just kind of went in and it's like I know the playbook, I run the playbook, I know how to you know, you got to turn all these things around and you got to come in and blah, blah, blah, and so I just got to work like right away and like six to nine months in, like I had not seen the shift that I would have expected or that I had seen at that point in time in my other assignments, and like I don't understand like I'm doing all the right, the same things Like how, why is it not working? And and so I think it was like nine months. I'm like I can't get to a year in this and not figure out why this isn't working. So I asked my boss to like try to suss it out for me, and she went on like a listening tour of team members and what came out which was really really like hard feedback to get at the time, but I've learned so much from it it was like you know, basically Maggie came in here like a bulldozer and didn't get to know any of us or understand our business, or understand our team or our approach or whatever. And it's all business all the time with like all this, you know, criticism, we never have fun, we don't do anything, you know nice, and blah, blah, blah, so, so like that was really hard to hear, um, but I it has been probably the most valuable lesson ever because you can see exactly how it happened. That's the potential downside of my personality type, especially when you have other factors and stress and things going on. So I will never make that mistake again. Every new job I've gotten since I go in and it's like 90 days of learning before we're going to take action.
Speaker 1:And I I think it was the lesson was you got to get people in the boat with you before you ask them to row, you know? And um, anyways, I went, I went back, right, I mean I think that's exactly right, that's exactly right. And I mean I went to that team, um, which I I also am proud of this Like I went to that team and just kind of fell on the sword. I was like this is what came out of, you know, our understanding here. And I'm very sorry, like I, I, in retrospect, I wish I had come in here differently. Blah, blah, blah, asked for a reset, started doing things differently and then, like then, within a few months, things started turning around and we had a great year. So, like it all worked out.
Speaker 2:You know, that has kept me very humble ever since I tell you, I have a similar story, as you know, and I think that is a priceless story. Right, because we can fall into this place of like rote behavior, like I do. This. It comes out on the other end and it's so easy, especially when we're super, super, super busy. But unpacking that, I think, is it becomes a superpower, right, because you understand people and you understand the system and the problem solving. You can marry those together.
Speaker 2:I truly believe that's what amplifies some of us to great heights of influence and opportunity and privilege to lead, and some of us get start to get sidelined. Right, because we forget that it does not mean we still get it right. Right, because I think for me, it becomes every new assignment, every new team, every new, any community. Right, it becomes a new opportunity to understand the culture. I think that's that's a takeaway from your, your learning too. It's understand the culture. And then, when you understand the culture, I think it's easier then to figure out how to advocate for yourself and how to increase your confidence. Have you ever, have you ever found that your confidence was shaken and you needed to figure out how to pull it back up again? I mean, have you ever run into that in your journey. Oh my God, yes, um, what do you do? How do you get past that?
Speaker 2:Because I think that you know it's, we blow past some of those things sometimes, but I believe that you know, in particular in this time where systems are being shaken and rocked, and you know, and some people are straight up, brand spanking new out of school and they're trying to figure this out, right, what would you tell them? What kind of nuggets would you share? And they're trying to figure this out, right.
Speaker 1:What? What would you tell them? What kind of nuggets would you share? I mean, I think the most important thing you can do, um, and I have learned this over years and, looking back, I think I did this not intentionally, it just kind of happened, but now I do it intentionally I think you need to have your own little group of cheerleaders and like, because what I found is, and these jobs, you know, these jobs get lonelier and lonelier Right and, and at some point you're in a big enough job that, like I don't know, I don't really expect my boss to tell me all the things I'm doing. Well, I don't get a lot of praise. I and he's for sure going to tell me about the things where we're falling short, and that's fine, I've kind of come to expect it. But it is kind of nice to be built up every once in a while.
Speaker 1:So I I have my little group of you know, I have a little group of cheerleaders, right. They're just people who, like, have come. I mean they're friends of mine, they're you right, they're people who I have gotten to know, I have relationships with, and they also think the world of me, you know, and they, they like I would call you or anyone else in this little group if I need like some pumping up honestly and they'll do it Like. So I think you know, I think that's really important and I think like innately. You know, early in my career I had a really, really difficult stint in a job with a very difficult manager who was just so like I felt like I got berated every single day and you start to be like, oh my God, like I thought yeah.
Speaker 1:I thought I had gotten to where I brought value but, apparently I suck, you know, and but I became very close with a couple other people on the floor during that time. We'd grab coffee. They just felt so bad for me, you know, but they'd kind of help bolster me up and so, anyways, I think I think it kind of happened organically, but but now I can put words to it and it's like you need your own little personal group of cheerleaders, I think. And you know, listen, sometimes you're a young professional, it could be your parents, it could be your, you know, college friends. My husband is like we talked about that earlier. He's like my biggest cheerleader you up, when maybe you're beaten down or not getting pumped up by really anyone else.
Speaker 2:So I'm going to say the bold leap, that this conversation on empowerment is very much aligned to the products that you sell and the things that you do in your core business every day. Am I wrong there? Because there's a whole new conversation around women and women in our relationship with finance and risk taking and investment, that I think all of these, some of these same themes of what you learn and what sets you apart in the end, are kind of right in the same lane. Am I off on that?
Speaker 1:No, no, no, totally, it's all. It's all the same things I mean there are. There are trends, both on, like, on the client side of things, and how women think about, or what they do or don't know about, um, wealth, money, all of that stuff, and then, um, it's totally, totally, and in many households, like that just hasn't been their role, you know. But but 80 percent of women are going to have to run their family finances at some point, because we are outliving men, there's divorce, there's other reasons, and so we know that that population is hugely important.
Speaker 1:We talk to them differently, like we have events that are specifically aimed towards the female demographic. For exactly that reason, the conversations are different, their concerns are different and their and their risk parameters are different, which also leads into kind of the the working part of the finance industry and how, women being more risk averse, there's less of us in, you know, investments and areas like that. So, and just like, when we make a recommendation, we always want to be very thorough about all the reasons it might not work, Whereas a male will just give his recommendation and because so? So we're learning all of these things as we go, but a lot of the same themes, you know, apply confidence, risk taking, feeling empowered, feeling self-assured, being able to self-advocate, all of that. All of that aligns with the financial side of things too.
Speaker 2:Wow, do you think that there is a shift or a change in the career lane of women in finance for all our girlies that are? You know it's graduation season If you're listening to the podcast in time of taping, and you've got a whole new breed of Chantres and Maggie's that are coming out with finance degrees and otherwise, and they're bright eyed and bushy tailed. What would you tell them as they start to walk into their career? That you wish you were told? Or, because you see the trends and the movements, you want to tell them just to underscore what they may already know?
Speaker 1:I think I certainly hope that, yes, there will continue to be more and more women in finance. I think I think, generally speaking, there's a few things that are really hopeful in that regard, and one is how, um, some of the advancements that have just been made in society whether it's ability to work remote or, um, even something as easy as, like, your groceries can be delivered by Amazon fresh right, like your grocery shopping can be delivered to you Like, there's a lot of things that that, when you look at why yeah, you look and you look at why a lot of women end up opting out of the workforce, it's, it's usually because they or finance, in particular, when you had to be at a desk all day long and, like they have to run these things in their household. There's a lot of ways to do that now that aren't as time consuming. It's not to say it's like perfectly easy, but it's much easier, and I think because of that, many more people will choose to balance it than, um, than completely opt out. I the thing that we need to just get better. They, we, you need to see people like you to know that you can sit there.
Speaker 1:You know, and I think, like when I started, um, there were women in leadership. They were few and far between. There were women in leadership. They were few and far between, but there were women in leadership For whatever reason in the world I was sitting. They didn't have children and that just was their personal situations.
Speaker 1:But I interpreted that as okay, you have to choose, like either you're doing the family thing or you're doing the big job thing, but like I didn't see anyone who was doing both, you know. And so I do think part like I want there to be more examples for these young women to see and be able to say, okay, that looks like me and what I want and I can do that. So, so we're doing really well at the entry level, like it's much more equitable, the male female breakdown. But then as you, as you rise up the ranks, it's still, it starts to dwindle and shift and by the time you get, you know, to my level or elsewhere, you're, you're not, um, you're, you're not anywhere near 50, 50, you know, and so, and I think that impacts the aspirations and choices that the people coming up, you know, make.
Speaker 2:So I think that's good, and I think that's an important point too, because seeing yourself, seeing someone that can just let you have that visual reassurance of what you imagine is possible, is actually possible because it's been done before. That is so important. I also think that somehow being clear as clear as you can at the moment that you're in right now on what it is that sets you apart, that makes you different and what's important to you, what your values are, I think is really, really important because, just kind of double clicking on what you said, there are so many tools that are available now to allow you to extend your bandwidth, extend your productivity. It's increasing the amount of choices that you can make, right, and so what are you going to do with that? How are you going to, how are you going to position that? That's, that's right on, all right.
Speaker 2:So, look, I got to get you on your way because you're still driving places. That's what you do, but I have rapid fire for you. I want to ask you a couple of questions, and you know you gotta, you gotta, you gotta make this go. Your favorite, your favorite app or tool that keeps you on track? What's your favorite app or tool?
Speaker 2:email oh, email, oh, it scares me, it frustrates me, it does overwhelms me it.
Speaker 1:It enables, yeah, yeah, but you know what it is without it. Like I'm doing this all the time. I'm in the car, I'm between the games, I'm between the meetings and, like, my email enables me to keep up with the job and, like, keep things moving even when I'm all about. So I couldn't.
Speaker 2:Yeah, it's like a lifesaver, all right. So then now, this is such the great question for you. Inbox zero dream or reality.
Speaker 1:Dream that's been a dream for years. No, I can't. I can't do it. There's so much I can't do it.
Speaker 2:All right, and then this is the last one that I have to ask you, because I know that one of the things that we bonded on when we walked into Northwestern University Kellogg was I was like, okay, she has some style, I see her, I see her. What's your power outfit?
Speaker 1:Oh, veronica Beard, I have two of them. I have a pink, full pink power suit like hot pink, and I have a orange like coral orange, and they have the great Veronica buttons. And yeah, that's another thing that took confidence. I used to dress in all black but I just was on two panels. Reason I wore the pink suit and the orange suit. So I've decided to really own the feminine power thing.
Speaker 2:Yes, True story. You wouldn't know this. That's on my shopping list this weekend. Absolutely no way. Oh, do it Because I love her and, yeah, I feel like I need to bring more color into my life.
Speaker 1:Have you seen the orange? The orange would look so good on you. Oh, I'm going, and they have a vest. They have a vest part and the normal blazer, so I have them both there, you go.
Speaker 2:I'm there, you're the best. I love you so much. Hugs and kisses to your family and I look forward to talking to you very soon. Thank you for sharing with Proven Not Perfect.