Honorees talk about the unconventional opportunities, challenges and pitfalls they encountered during their careers and the steps they proactively took to overcome them and find unexpected, career-enriching success and new paths to forge a satisfying career marked by innovation, notable performance and expanded business expertise.
Among the things you'll learn:
- How to spot and get out in front of potential internal, organizational and professional headwinds that can slow career advancement to executive management and the C-suite.
- When to take an international P&L role as a means of acquiring more business expertise and laying the groundwork to access potential leadership opportunities at the company's headquarters that you might have been overlooked for without the addition of an international role.
- Learning when to pivot, either a business you are leading or your career.
- Lessons learned: women who have faced the glass cliff talk about why they accepted a difficult role, what they learned from leading a division or company in crisis and what they'd do differently in the future.
Holly Sraeel (00:09):
Welcome back to Payments Forum and our special portion of the program to honor women of influence in payments. Right now we're going to talk about taking on new leadership assignments, knowing when to pivot and how to avoid the glass cliff. My name's Holly Sraeel I'm Senior Vice President of Strategy and Content for Live Media at Arizent and American Banker. With me today, Ankita D'Mello, Principal Product Manager for Wise to my left and Dorothy Conroy Rule, Managing Director of MUFG. Please join me in welcoming these women to the stage. We're going to have a candid conversation on how women can take calculated risks to advance their careers by accepting new leadership assignments that sometimes don't appear as if they will take you to the top. We'll also look at the importance of pivots and what steps you can take when you face career challenges. But first I want to give a couple of data snapshots to the audience that we're well aware of, but that clearly we need to focus on.
(01:08):
Still. In 2025, women hold still only 10.4% of CEO positions at Fortune 500 companies flat over the prior year, female CEOs lead 8.2% of S&P 500 companies. As of last year, women's average tenure as CEOs is 5.2 years compared to 8.1 years for men. There are over 79 female CEOs and private companies with revenues over a billion dollars in 2024, and women make up less than 20% of executives in FinTech. Clearly, we still have work to do. So let's get started. Dorothy, I want to talk to you first about at what point in your life did you decide to pursue a career in the payments business? Was it a known ambition or did you have a career moment?
Dorothy Conroy Rule (02:00):
I think we were chatting earlier. One of the first things that I did was count the money at my brother's ice cream truck, and I loved counting money. So you sort of take it back through Then those are things where you want to be relevant in a space. When I first got out of college, I ended up working at Citibank and a woman had taken over this cash manager. It was a new concept then given kind of my many years in the industry. So I saw her as a woman, a strong role model, and wanted to be part of this new and innovative thing in cash management. I had some experience previously where I was actually in high school and college and I would wander into the Treasury Department at Avis Renta car where I worked because I finished my work early. There were times there where there was a lot of paper going on and a lot of reconciliations and things that I ended up, because I had been taking some computer classes, ended up automating and saw the value that information could bring.
(03:09):
Previously, they had waited for monthly statements to come and I ended up calling all the banks and there was something, I think it was called an electronic coupler or something where it was a printer where it had a modem attached to it and where I would get daily statements. So I was in the very, very early days of some of these innovations and those are the things that made me really take interest in this thing called cash management. Later on that I ended up running and launching the first internet application actually for Citi in my career there. So I think that was probably the start.
Holly Sraeel (03:43):
Ankita and what about you?
Ankita D'Mello (03:44):
Yeah, it's a great question. I think something you'll often hear from product managers in general when they talk about how they start their career, it's always by accident because nobody really knew what product management was. So I think for me, even with payments in general, I think it was all one big happy accident and if I could go back and connect all the little pieces in my life, I think they somehow ended up making sense, which is really cool. But I think even now as a kid, when I think about when my parents gave me pocket money, my sister would describe me as a loan shark because she would always run out of money and I would lend her mine and then hound her for it for a month after. So I think in my own way I was always pretty nerdy about money. I always really liked it.
(04:35):
I liked the concept of budgets. I would have a spreadsheet for my $10 of pocket money. So clearly I was obsessed, but I didn't start out in payments. I actually started out in management consulting and I had a career there. I then switched into the beauty industry. So we're going to get it to unconventional moves, but really I think that how I ended up in payments was by looking back at all of the moments in time that I felt like I did my best and I tried to connect all of those experiences together and that was how I eventually ended up at WISE where I've now been for five years. So yeah.
Holly Sraeel (05:17):
Okay. Before we get into how you make decisions to take new assignments that may be viewed somewhat unconventionally, can you talk a little bit right now about what thrills you most in what you're doing at this moment?
Ankita D'Mello (05:32):
To your question?
Dorothy Conroy Rule (05:35):
Sure, I can take that. I think in terms of innovation is what thrills me. I like to solve problems. I'm known as a fixer I over the industry. So the idea of pulling different things together, working as a team and being on a team is doing the best possible job you can in your own position. So everyone knowing where they fit in, organizing groups around that and the people aspects of innovation, doing something new, solving clients' problems, I think it's also exhausting when you're doing something new. I teasingly say at work that making 10% on growing an existing product is easier than your first million dollars that you make in a new product because you're trying to, there's a ship and you're the little boat little guy on the boat trying to make things move. So that aspect of convincing management to take a new risk to go for something different in the innovation aspect and pulling together and building a team to do that is what I find most thrilling about the job that I do.
Ankita D'Mello (06:42):
That's awesome. I'll add to that. So I think the innovation part is always super exciting. I think for me personally, what I find the most thrilling is when I do something really difficult. So I think we've talked about this in the last couple of panels, which was so nice to hear, but I think the thing that keeps me going almost or keeps me staying at Wise even is the complexity of the things that you have to do in payments are sometimes so hard, and once you've actually done it and you've got that under your belt, it's such an awesome feeling and you almost get addicted to that. So I think that's what I find the most thrilling for now, at least.
Holly Sraeel (07:33):
Addicted to feeling thrilled. So let's start getting into some heavy lifting stuff. Let's talk about, Ankita, you can go first. Let's talk about when you first took a calculated risk, something that you pursued a role that might've been perceived as unconventional, linear, or even career suicide.
Ankita D'Mello (07:55):
Yep, for sure. So I'll talk about a time at WISE actually where I went through that experience. So I joined Wise First in their office in Singapore. So I was a product manager. I was based there and I was actually asked if I wanted to move to the US a few years after I'd been there to help set up the product management team out here. And if I'm going to be honest, there had been challenges with finding the right people. Our North America team also had a lot of challenges going on, and I wasn't really sure if I was the right person. Even I knew nothing about the North America payments industry. All my expertise lay elsewhere. So I really didn't feel like I could do it. I don't know if anybody else in the organization felt like I could do it. It was probably that maybe they just asked me and I ended up being an okay-ish candidate.
Holly Sraeel (09:01):
okay-ish.
Ankita D'Mello (09:04):
But something, and I don't know what it was, something at the bottom of my heart was maybe just do it and maybe prove to yourself that you could do it and prove to everyone else that you can do it. And it was calculated in the sense that I knew that it was going to be a really huge challenge, and I knew that if I ended up doing well at it, that it would be such a huge milestone in my career. Now, whether or not I was going to succeed was the question that I had to go and see whether I could actually make it happen, and I will say that it was probably one of the best career moves I made in my life.
Holly Sraeel (09:46):
Good for you, Dorothy.
Dorothy Conroy Rule (09:50):
Yeah, I think it's really important to be comfortable with ambiguity and to look at things where it might not be natural moves. I think for me, it was a time where I was running a business in the transaction banking side of the business and kind of really had done a lot of different things from payments to liquidity and reached a point where it was somewhat the same every day. I knew that at the time there were 14 banks that the Fed had come to and said, if you don't get your derivatives of confirmations in line, the Fed is going to shut you down. It was public information out there. So because I had had straight out of college worked in derivatives when it was new and different, I realized that given my client skills and my background as a product manager, I could do a lot to solve this problem.
(10:42):
So there was no role in that. I went to the head of operations. Everyone in the front office thought I was nuts to take a job in operations and want to pitch for that. So I really pitched myself and believed that I could make a difference and sold management on that You have a problem here and that I can really help you. So they created a job for me. It was just a sole job with an individual contributor, and I had a big team before, but it was something that I felt like was really important to do for the business. I also, I didn't know what a hedge fund was at the time.
(11:22):
So a friend of mine had worked as a COO at a hedge fund. So I took two days from work and I went and followed her around for two days to see what she did. I tealy say that I make things up for a living with respect to that. So once I kind of figured out what a hedge fund was, then I went and visited the hedge funds and said, you need us there. Because most of them didn't want to sign up for electronic confirmation. They wanted to keep it in paper at the time because it was a hassle for them. They had to do maker checker and they had to log on to things. They didn't want to do that when it was kind like a man and his dog kind of shops at the time. They were really tiny, but I explained to them without the banks on the other side in this fed letter that had come out, if we weren't there then they weren't going to have people to trade with.
(12:09):
So through sort of a lot of convincing, so I ended up building a whole team around it. Not a lot of people, just a few. But it was very successful that it became like an industry standard, this operational client service management, client relationship management. So other banks, other groups like Goldman ended up having these roles similarly. So I felt I created an industry change with respect to electronics and moving from this paper to electronic, an industry change of having this new role that became ubiquitous across banks and then ended up getting moved out of operations myself and my team back into front office role on the trading floor because folks saw it was so valuable. So it was a time where you saw a problem and you wanted to address it, your stockholder in your companies, and how do we handle that? And became just a really unbelievable experience of creating something new almost really as an entrepreneur in that respect.
Ankita D'Mello (13:10):
Super cool.
Holly Sraeel (13:12):
One of the motivations for having this panel discussion is because in almost all industry new opportunities, grooming opportunities are often fed to men. It's not the case with women. So in our panel preparation, sorry, we talked about Dorothy Aita and I talked about the fact that women have to develop their own reach opportunities, and so it was a motivating factor for why we're having this session. Let's talk a little bit about now when you made your first unconventional move or your first risky move, share with us, if you will, how it felt.
Ankita D'Mello (14:00):
Oh wow. So I mean, I'll talk about the same one. When I moved over here, it was so scary. I mean, I didn't know anyone to begin with. I didn't know much about the industry here, and I was going through the pains of even just moving countries, figuring out how to open a bank account. So some of the most basic things that you just have to do. And so there was a lot going on, and if I'm going to be honest, there's the imposter syndrome that just haunts you of, I have no idea why I'm here. I have no idea why I signed up for this. I'm terrible at my job. Everything is going to fall apart and this is going to be awful. And I think the thing that to your point about women and about the opportunities, I think that there's a part of you that really has to keep trying to convince yourself that it's going to be fine and that you're going to succeed no matter what, and that you've done this before, why should this be any different?
(15:09):
And at some point you do start believing that. And at some point I actually did get through it and I was able to say, oh, wow, okay. I did that. I mean, honestly. So I moved on the 9th of January, 2022, and it was on the 9th of January, 2025. That American banker actually named me to the list. So even that in itself, I remember looking at that and just thinking, wow, three years ago I was ready to pack my bags and run away, but I'm so glad that I stayed. But it really takes, I think perseverance and just I think confidence and believing in yourself that you can do it.
Holly Sraeel (15:58):
Well we're glad you stayed too.
Dorothy Conroy Rule (16:00):
I would echo scary, but many things in life are scary in terms of starting something new, leaving somewhere. I had been at Citi for 22 years in terms of moving on, but I think in terms of fear, like you were saying is that if you're afraid to get on an elevator, what do you do? You keep getting on elevators, right, exactly. You just keep doing it. And that's the way we all overcome things. There's so many things that we overcame just even starting out in the industry so many years ago where it wasn't a typical move for a female to be on the trading floor. I have 10 older brothers though. So just truth in lending on that one that I'm used to kind of male dominated rooms. So I had some level of comfort with that. But this aspect of just keep doing and who knows better than you, right?
Ankita D'Mello (16:52):
Exactly.
Dorothy Conroy Rule (16:53):
There's not anybody. I think a lot of us feel that there's somebody out there that's better. Some of the things you're saying, oh, maybe people didn't think I could do it, but who cares, right? You're going to put your all into something. You're going to learn, like I said, even didn't know what a hedge fund was. I'll figure it out. We'll all figure it out. And because we're hardworking and dedicated, we will figure out how to do that and advance in that way.
Holly Sraeel (17:24):
So two part question. When you're thinking about making a move that is a bit offbeat or perhaps linear or just unconventional, is there a process that you take yourself through in order to decide whether you're going to push through and go after that opportunity? And the second part of the question is, who do you turn to for advice?
Dorothy Conroy Rule (17:52):
I can start for it. For me. Look, we're all probably, we were chatting earlier, I think as women, right? We go through all the possibilities with respect to that. So at some point you just have to decide, I tend to be a pros and cons make list maker where what are the pros and cons of this? But at the end of the day, it just has to feel right. And you have to know that also what you're doing now, is it worth staying for? What's the path there? I think the first part is I'd say if it feels right and feels like it's going to be something new, you're going to learn something from it. All these pieces looking back get cobbled together. You don't know exactly where it's going to go. And like I said earlier, comfort with ambiguity is important. I don't really have formal mentors.
(18:46):
I don't know that it was such a thing, especially as a woman coming into the industry years ago. I have my brother actually who's in financial services, so sometimes he gives me good perspective as a man's view of all these things. And we are very close, have a lot of kitchen table conversations with respect to that. And I think I end up doing that with others too. Peers tend to be more who I bounce things off of. I haven't had someone that I've followed through in terms of a career where sometimes people have somebody that advances and you advance along with them. That's never been something that I really had.
Ankita D'Mello (19:28):
Yeah, I think I definitely agree with everything you've just said on the point about a move being linear, I think that that can be hard to sometimes stomach as a first impression when you're thinking about taking a step and you're like, how does this help me on paper? This looks like a really bad choice. And I think as humans, we all, you want progress. You want to feel like you're moving forward. I think that's just how we are created. So if you don't feel like that, you automatically don't want to make that choice.
(20:06):
But I think what's interesting when you take a step back, so if you actually zoom out for a second, a move that may look lateral immediately down the line might actually be the best thing that you did because it might actually exponentially boost your trajectory versus taking another move that looks like it's a forward move at your first next step. So I think you do have to take a step back and try to understand what the longer term picture actually might look like. And there's a bit of what's the potential? And that's also the calculated risk. Like, okay, fine, this might not make sense for the next six months, but there's a potential for this to change my life in the next two to three years. So you're taking bets on yourself in that way. So that's how I like to look at it in terms of who to speak to and who to reach out to.
(21:05):
I think that really, I loved the conversation around mentorship earlier and the different angles that everyone has around who their mentors are. My go-to is just talk to somebody that you really trust and talk to somebody that drops everything in the sense that is truly looking out for you and looking out for your best. So sometimes there'll be mentors who I'm talking to, but I know that there's suddenly an angle coming in of like, oh, but that doesn't work for my team, or that might not work for another team. And so there's all these different little ingredients that get peppered in, but if you have somebody who is truly just looking out for you, I think you sometimes get the best advice from those people. So that's what,
Holly Sraeel (21:55):
It's interesting because the question as I asked, it was not intended to talk about mentoring. There's a lot of conversation that's gone on about mentoring today and other days. Let me reframe it. So in my career, if I'm going to make a move that feels unconventional, although there's very few things in life that I've done that are conventional, but I go to a CEO to whom I've reported, and I ask him, game this, move out for me. Where do you see if I were working for you now? How do you see this move? And he games it out for me. So that's what I was asking when I was asking,
(22:40):
Who do you turn to? Because when you're going to make a move about a role that feels different, that feels unconventional, that feels risky, someone even sometimes say that it's, oh, that's suicide. If you go to somebody who is an excellent business leader and you ask them to game this move out for you, they will help you to see your way to the top. It's been invaluable for me, and I continue to do it all these years in my media career. So I don't know, do you have any response to that? If you're going to game it out with somebody?
Dorothy Conroy Rule (23:15):
Yeah, well, like I said, somewhat my brother, but I laugh because he always says, my money's on you, Dorothy, with respect to things. So I think you can game it out to a certain extent. And I think maybe in smaller companies versus larger companies, it makes a difference with respect to gaming it out because there's so much change, there's so many other parameters that exist, management changes and that changes the landscape completely. So for me, I feel like if I'm learning something new, like I said, looking back, maybe it wasn't having a straight line to the top or whatever, but I think in terms of what I do now, it's all those experiences that I have that I can bring in compliance or product management or whatever it is into the equation. I think that it helps you succeed in what you have. So it might not even be gaming it out in linear, I dunno.
Ankita D'Mello (24:13):
Yeah, I'd say something similar. I think mean my answer is still the same in that it's that pick somebody that you trust, but they've actually often been leaders in different parts of the organization. So I've found that quite interesting where I'll often go to the head of engineering or maybe head of banking,
Holly Sraeel (24:34):
Because they see things differently,
Ankita D'Mello (24:36):
They see things differently, and they give me a different take on what I've just said, and I will very often learn something new or get a different view that I'm like, oh, I didn't think about that. I'm going to go back and start again. So those are my people, I'd say.
Holly Sraeel (24:54):
Right. So let's talk a little bit about, now you mentioned Ankita earlier about a pivot. Let's talk a little bit about the pivots. You had two,
(25:07):
you want to talk a little bit about them?
Ankita D'Mello (25:09):
Yeah, of course. I mean, I think that the most fun one was moving out of consulting, moving into the beauty industry, which everybody thought I was crazy. I was up for a promotion and consulting and everyone was like, how are you quitting? And you're going to go be a product manager at this beauty box and you don't know anything about beauty? I was like, yeah, maybe I learned something. Anyway, but I went for it and honestly it was so much fun.
Holly Sraeel (25:39):
What was the role?
Ankita D'Mello (25:41):
So I was a product manager for a company, which you might have heard of. It's called Birchbox.
Holly Sraeel (25:46):
Oh sure, sure.
Ankita D'Mello (25:47):
Everyone knows Birchbox, the little beauty box. So I worked for them in London and they had just launched in the uk. So we were a team of 15 people. We had no idea what we were doing. Every day was different. So one day I was customer service. The next day I was actually in the factory putting the box together. The third day you were doing strategy. It was the most I've ever learned about how to actually build and run a business from scratch. And people always ask me, why did you do that and why did you then decide to come back into payments? And I think that again, in hindsight, they were strong gut-based decisions. But the reason I did it was because I felt that in management consulting I had built a really strong foundation, but I wanted to put something very different on my cv. I wanted to come back into the payments world with a different flavor and I knew that I had to stand out somehow. So yeah, it was wildly unconventional to go into beauty and come back, but the truth is that you can take any experience that you've been through and you can find value in it and bring that back and bring back new perspective. And that's what got me the job at wise, they really liked that I had come from such a different industry, but I could still take whatever I had learned and apply it into the payment space. So it was really fun. Yeah,
Dorothy Conroy Rule (27:26):
I agree. The aspect of building a business coming into MUFG, similarly, I had a payments background, like many of the folks here, but then moved into these different areas. I think I was employee number six I think coming into supply chain. So that aspect of wearing many hats and pulling together all the experience we had that Ankita talked about is really fun and challenging all at once. So from the aspect of pivot, it didn't seem like a conventional thing, but pulling together all of that I think has made me successful in this role because I can share with others that might've only had supply chain on their resume their whole time. I ran liquidity, so I knew the balance sheet, I knew the liability side of the balance sheet for many of you guys that might be in accounts and associated with payments and things. So this is the asset side of the balance sheet. But because I knew liabilities and the offset of assets, there's a lot of different things. Like I said, looking back that you realize these little twists and turns that you did of how it comes together as a business manager and that you can really help particularly in startups.
(28:40):
And even though I'm in a big company, it's still a startup when you're building out the business and we've gone from zero revenue to hundreds of millions in the nine years that I've been there. So it's pretty amazing.
Holly Sraeel (28:52):
So is the advice for people in the audience when they're considering a move to look at a move that will specifically allow them to acquire new skills?
Dorothy Conroy Rule (29:06):
Creative? What's a creative to your skill base is what I've tried to do and whether it's a new product is one thing, but skill-based is also really, really critical. And like I said, not being afraid to just make stuff up. Sometimes it's okay, there's not a lot of people that necessarily know something either and you're going to learn from them and then you're going to share with them and bring something different. I also think it's what kind of a team environment and a culture that you're getting into that's been for me, really, really important. I thrive in certain kinds of cultures I've realized.
(29:47):
And not very command and control from that perspective where that's also really important to me in terms of what's my everyday life and sometimes I've made change just for those reasons. So kind of accretive the skills and what kind of an environment do I want to put myself in so that I can succeed.
Ankita D'Mello (30:07):
Yeah, I definitely agree, especially on the environment thing. I think as you grow in your career, I think you really start to understand more about yourself and the spaces that you do well in. So I think it's important to set yourself up for success as well, as much as you possibly can. The one thing that I will say about pivoting as well though is to be open because you never know what you're going to learn or you never know what's going to end up being beneficial for you. So even if you don't have it all figured out, as long as maybe there's a couple of things that are pulling you towards that opportunity, maybe it's a cool problem to solve. Maybe you're really passionate about that particular industry or team or you really enjoy working with that set of people. As long as there's something in it for you, I feel like there's always going to be aspects of the job that play out that will benefit you down the line.
Holly Sraeel (31:08):
Do you think that women in considering a move, do you think it's more often that they are reacting to a situation that they're unhappy about? Or do they need to focus more proactively on making these moves to acquire more skills to work in say business lines and functional areas and so forth? How do you see that? Do you think most of the decisions are coming or the moves are coming as a reaction or a proactive move?
Ankita D'Mello (31:44):
That's a really good question.
Holly Sraeel (31:45):
I have thoughts.
Dorothy Conroy Rule (31:48):
I have thoughts too.
Holly Sraeel (31:49):
Go ahead.
Dorothy Conroy Rule (31:49):
And I think a lot of it is reactive to,
Ankita D'Mello (31:52):
Same.
Holly Sraeel (31:52):
I agree.
Dorothy Conroy Rule (31:53):
So even for myself in terms of times like this isn't the right cultural fit, and then you start to look or whatever, one of the things that I said is there were signs of varying things before it becomes a problem. Reading the tea leaves about where you are I think is really critical and being a little bit more introspective about that, of knowing the landscape of what's out there. But that's okay too in a way, right? Because even sometimes we all just need to push. I think a lot of us, particularly as women with our second shift as they call it, of having to take care of families and elderly and all these things that we have culturally and societally do. I think sometimes we just are surviving and keeping wor king to do that, but we don't really necessarily take care of ourselves in that and take that introspective view to say, am I thriving in this environment or am I surviving? And there were times I didn't even take phone calls sometimes from others because to change jobs was just too hard with everything going on in my life at the time. And then sometimes you need a kick in the tush to make that move.
Holly Sraeel (33:09):
It's a professional term tush.
Dorothy Conroy Rule (33:10):
Exactly.
Holly Sraeel (33:15):
Can you share with us a time in your life where you made a move, took a role, didn't work out, and what that felt like and how you navigated out of that, what you took away from it?
Ankita D'Mello (33:28):
Yeah, I have one.
Holly Sraeel (33:31):
If you just have one, you're lucky.
Ankita D'Mello (33:33):
Well, I have one that stands out. So it was at Wise actually. So it was all kind of internal versus it being a different job, but it was when I was in Singapore, I looked after East Asia as a region and the boss that I worked with at the time, we had just lost one of the product leads for another region, which was South Asia. And he sort of pitched this to me as, I think you should take this on as well. You'll be looking after two regions and that's going to set you up so well. And me being me and maybe others in my position were like, okay, that sounds like a great idea. But it meant that I looked after nine markets. So my job from looking after four became nine and everything basically completely doubled. And I couldn't even manage a single day because everything had stacked up. I now had nine compliance officers to speak to, and in hindsight, it was the worst move because I didn't have a team that was going to be able to sustain that workload. It was just me.
Holly Sraeel (35:01):
So what did you do to unwind that situation, or how did you get yourself to higher ground?
Ankita D'Mello (35:07):
Well, if I'm going to be honest, I first drowned a bit. So I think I struggled in that situation for three months. I think before I could really even understand that I was drowning. I think sometimes you're just in it. And then eventually when I realized that, hey, this is not good for me, this is not good for the business, I eventually had to have a conversation with my boss's boss pretty candidly because my boss actually didn't understand why I couldn't do the job. And so it became a very like, oh, but I think this is okay. And eventually when I spoke to my boss's boss, we actually ended up hiring a whole team. But it was really challenging because it didn't feel good, if I'm going to be honest, in the time it felt like I was not capable of owning such a big remit, and that can feel like failure when in effect actually it was, I should never have even signed up for that. So yeah, that was my experience.
Dorothy Conroy Rule (36:25):
From my perspective. I remember early on, and this is why I know cultural fit is really critical for me, there was a role that nobody wanted. So I figured, okay, I'll go in there and do it and be successful at it. And I think I cried in the bathroom every day. It's okay, we've all been there, but that's okay. I would go to a different floor to do it, so nobody saw me. And you just have to realize that it was just not right. And you figured at first you, I can do anything and I be successful, but you also have to know when to call it quits. So I ended up navigating and finding something else within the group. But again, reading the tea leaves, if you go back to that, nobody wanted the job for a reason, and a lot of it was the management and those kind of things, and I thought I could kind of overcome that, but sometimes you just have to know when to fold them, as Kenny Rogers would say.
Ankita D'Mello (37:35):
I will say though, I think as much as those experiences sound, I mean they were hard. They are hard and they're not fun to go through. I do think sometimes those experiences are what also teaches you so much about how to navigate your career because you're so much wiser and smarter about picking your next move. You've probably been burnt a little bit, and yeah, I think you just choose wisely next time.
Holly Sraeel (38:07):
So let's talk about some difficult things. I would love for you to give the audience a candid assessment on if a company is experiencing real or perceptual headwinds, is that a good time to step back and look for a potential new assignment? Just because you can see that the turbulence internally is going to go on for some time, which may cloud your ability to keep focused on your own career and move forward. So what do you think about that when there's internal turmoil and how that might inform your desire to move?
Dorothy Conroy Rule (38:52):
Yeah, I can take that. I think during times of crisis, sometimes it's good to stay to a certain extent, and then sometimes it's good to go. I mean, for me, I know at Citi I was there 22 years and there was a lot of turmo, both internal and external with the mortgage crisis.
(39:12):
And I ended up making a decision to leave. And from that perspective, it was a risk I left without a job in the middle of a mortgage crisis. And that was a lot of my skillset with respect to that. But I also knew that it was time to go that I looked at it as when I was going off to college where I knew there were possibilities out there for me and I knew there was someplace better. So decided to take that risk and know that I teasingly say I'm good, I'm smart. I'm nice that I had somewhat of a network out there of many people that I've helped over the years, that when I needed help, if I asked, they would help me. So I took it as an opportunity to say, okay, let's make this change now, even though there was huge risk at the time.
Holly Sraeel (40:08):
Yeah, I think the other side of that is when a company is experiencing turmoil and chaos, whether it's just a corporate issue around financial performance and pressure on divisions to step up their game or the financial crisis which hit many, many institutions, a lot of women often get tapped at that period to lead the troubled either company or division, which leads us into this discussion about a glass cliff. So during these times of periodic turmoil, you could make the case, it's a time to go, but how do you feel about taking on an assignment when it's clearly a troubled division, and what do you consider before you do it? The statistics on women and their survivability and roles like that is not great. So where do you stand on that?
Ankita D'Mello (41:07):
Yeah, I think for me personally, it's going to boil down to the actual situation. I don't know if there's a blanket statement that's like, yes, you should leave or no, definitely stay and figure it out. So again, I think you do need to be somewhat calculated in that particular opportunity or scenario that's at play. The one thing that I will say from my personal experience, having been in a few of those situations where something chaotic has happened or something that's quite troublesome has happened and you kind of have to come in and figure out what to do, I don't totally know why women are picked for those roles, but sometimes again, I'd like to think going back to the previous panels that we had, is that women are very good at collaboration and women are typically, I think quite good at maybe staying calm in a crisis or in a situation that's quite stressful.
(42:11):
And I have seen that play out in my time where if I've been put into that particular space, you do become that person who's trying to rally everyone together and sort of keep everyone calm and you figure it out. But I think the situation, it's really dependent on the situation. If there is some sort of light at the end of the tunnel that you can see that, hey, this is for a short period of time and you can figure this out, maybe that makes sense. But I think if there are other things at play, maybe it won't. The thing that I often think sometimes when it becomes down to if it's internal politics or things like that, the grass can always be greener on the other side and you might choose to go elsewhere, but that elsewhere might have the exact same issue anyway. So I think you do have to figure out if this is an industry-wide thing or if this is just this company, this moment type thing and take a call from there.
Dorothy Conroy Rule (43:22):
And I would agree it's situational. When I talked about earlier before with the derivatives crisis, that was a time where I sold myself into that job, not necessarily tapped, but with respect to that, that kind of worked out differently. So I think you do have to figure out and look, sometimes things work out and sometimes they don't, and that's okay too. It's been a lot. So you have to sort of take the risk and sort of figure it out as you go.
Ankita D'Mello (43:49):
I agree.
Holly Sraeel (43:50):
So I hate the question, what would you tell your 30-year-old self or 25-year-old self or whatever, because I don't think that women in business in any role, but particularly leadership roles should be asking about their 25-year-old self. What I want to ask you is looking at your career advancement and your leadership at this point in time, is there anything that you wish you had done differently and what are you thinking about for your future?
Dorothy Conroy Rule (44:26):
I think for me, the industry has changed so much. Sometimes it's nothing as powerful as an idea that has its time. I think my leadership style, I've been authentic always, but isn't always what was valued at that time. So from that perspective, I think we all just have to be true to ourselves. So I'm okay if I didn't become CEO or whatever because I think I have to also be true to myself. So I guess maybe not take myself so seriously along the way and maybe sort of the focus on those kind of things around fun. I mean, I had a lot of fun, even though it was hard work, developed a lot of great relationships with respect to that, but maybe didn't keep as much connections to people that I have. You sit next to people for 15 years and then you kind of don't see them again.
(45:24):
It's kind of weird when you think about work life stuff. So maybe in terms of some of those things, think about that differently going forward, I'm still going to be me and I'm okay with that again. And I think now, like I say, ideas that have their time. One of the other panels had talked about the collaborative work environment and things that many of us as women bring to the table is maybe a little bit more valued now. So maybe you start to come into your own with respect to that. I think the aspect of sometimes when you make something look easy, people think it is easy, and that was one of the other panelists talked about kind of self-promotion. You always think people are just going to notice you when you do a good job, and I don't think they do. And I think sometimes we make things look easy as women because we just do it. But that aspect of self-promotion I think is what I would change going forward.
Ankita D'Mello (46:26):
Yeah, that's a really good one. I think for me, if I had to look back, my old boss said this line and I really loved it where it was, I'm going to butcher it a little bit, but it was something along the lines of girls are taught to be perfect and boys are taught to be brave. And I think that it's so true when you actually look at how it plays out when you're an adult, because I think a lot of the time in a room, women, they're trying to be the balanced person in the room and men are being bold and brave. And so you get such a different mix of conversation in the room. So I think if I had to go back, I would just say be more bold. That doesn't mean be aggressive, it just means be bold and do things that maybe are risky and see how it plays out.
Holly Sraeel (47:31):
I'm waiting for the day where we don't have to worry about women being labeled aggressive. I don't have an issue with aggression, positive aggression, assertiveness, bold boldness, but we're clearly, it's still an issue because if you are bold and if you are brave, and if you are courageous, you get labeled often with negative things. So what will it take to change that?
Dorothy Conroy Rule (47:58):
Sometimes you just have to be stealth. I call it, like I said earlier, I'm the youngest of 13 kids with 10 older brothers, so I didn't have any brawn. I didn't have any position in family, so you had to be more stealth. There was a free bus for us kids where I grew up to go to the beach and we had one bathroom, so everyone would get off the bus and you wanted get to the bathroom first. So I was always the first at the door, the fastest, these kind of things. So I think it's just culturally there's things that, so that maybe was aggressive but in a different way. I was a little bit more stealth, but aggressive I guess. I ended up get to the bathroom and close it and lock it.
Ankita D'Mello (48:42):
I like that. But I also think the concept of that image of the strong, powerful man, so to speak, I think that image is also slowly changing, right? Today, knowledge is power, data is power, kindness is power. That whole narrative is changing.
Holly Sraeel (49:05):
Could you call Washington? Please?
Ankita D'Mello (49:07):
Okay, after this,
Holly Sraeel (49:07):
Do something about that.
Ankita D'Mello (49:10):
So yeah, I do hope that in time those things play out differently.
Holly Sraeel (49:15):
Okay, last question before we take questions from the audience. For everybody out there who either is here or will see this session on video, what's the best advice you can give the professionals who are risk adverse on how to go about advancing their careers? One thing, one key takeaway.
Ankita D'Mello (49:38):
Who are risk averse?
Holly Sraeel (49:40):
Risk averse.
Dorothy Conroy Rule (49:42):
I'd just say believe in yourself. There's so many things. We all kind of downplay all the skills that we've built over the years and the relationships that we've made. And I think if you truly believe, and I know it sounds trite or whatever, but it really isn't. There's a lot of professional capabilities that we all have. And like I said, just make things up sometimes and just get out there and do it right. What's the, no one's going to die. What's the worst that's going to happen with this? It doesn't work out and you take a new job, but staying stagnant is not the answer either, right? Because that just creates a lot of probably even resentment that you haven't taken those risks and regret. So I would say just believe in yourself and jump in the deep end. Yeah,
Holly Sraeel (50:37):
I always tell my team members and colleagues begin anywhere, just anywhere. Start, just do it. Don't wait. Anything final to add before we take conversation?
Ankita D'Mello (50:51):
Yeah, I think it's very tactical, but what I like to do is sometimes just take a pen and paper and write down the top three or top five times that you were the most proud of yourself or when you surprised yourself. And you'll often find that it's when you took a big risk and sometimes that gives you enough courage to know that you've already done it. So just do it again.
Holly Sraeel (51:20):
Okay. So we're going to take some questions from the audience. This is your chance if you're willing to ask these gals, if you're contemplating a move, you can mask the move that you're contemplating. If you're thinking about a pivot and you want their advice, you can go ahead and ask it or any other question on your mind, anything. Nobody has a question. Everybody is just busy taking on these new leadership challenges. Alright, so let me ask a question because this bugs me as a feminist. So the tenure of women in leadership roles is three percentage points behind that of male peers. So women often take on leadership roles in troubled situations. What will it take for women in greater numbers to start receiving leadership roles? What do you think has to happen? Because if more women receive leadership roles, I think more women will be compelled to pursue them.
Dorothy Conroy Rule (52:30):
I hope for the day when it's not like a man and a woman thing, right? Correct. I've sort of never, and maybe it's somewhat some of my upbringing or whatever and have to the sharp elbows at the kitchen table and be funnier than my brothers or whatever, but I didn't feel a lot of that. And maybe I'm naive in terms of some of the work stuff, but I don't think it needs to be that, right? You just want to hire the best person, male, female. So I think it takes men, I think, and maybe it's a generational thing, I don't know, but it takes folks viewing us as all equal of each other. And I think for me, even growing up, what were the expectations that women had in my age group? I'll put it, and they might not to be a senior in banking was probably not even on the radar. It was other careers and things like that. Where now I think there's a lot more discourse amongst, I see it with my own daughter and her kind of age group where there's more view of that sort of competitive spirit amongst each other. So I hope it's because we view each other as you want the best person for the job and that's it.
Ankita D'Mello (53:45):
Yeah. I'd say honestly, I think a big reason for that number as well is that women choose to have children. And it sometimes just comes down to they love their kids so much and they just want to spend all the time in the world with their kids. And that's completely fine. And I actually think that to your point, if that's what you want to do, you should do that. You don't have to do this job if you don't want to. I think where the issue lies is if you still want to do the job, but you can't, right? So I think that we're getting better at figuring out how to allow women to have families and also be the CEO at the same time, but it's still not quite there yet. The onus on women is still very much on the kid has to go to their friend's birthday party. Who's buying that friend the birthday present? It's most likely the mom not the dad.
(54:55):
So I think that there needs to be more shared responsibility between parents, which I do think is becoming much more of a thing. And I do think that workplaces do need to figure out how to have better policies in place for parents to have children.
Dorothy Conroy Rule (55:15):
Yeah, I mean one of the things that we have at our company is paternity leave. And I could think at other companies where men would never take it, even though it was there, they would never take it. But I see now maybe again a generational thing where at my company, all the men take it and it's all fine, and we all say, good for you. And there's more of a shared responsibility, and both careers matter. It's not like somebody's moving for one career or another. It's nice to see. That's why I said I think it takes all of us to say what the new norms are.
Ankita D'Mello (55:51):
I agree.
Holly Sraeel (55:51):
Well, here's two more women pursuing new leadership assignments and deciding to pivot. And we thank you for joining us on this session. Please join me in thanking Dorothy and Ankita for their insight.
Ankita D'Mello (56:06):
Thank you so much.
Dorothy Conroy Rule (56:06):
Thank you for having me.