Rachel Wilson: Early days when I came to Morgan Stanley, I had just spent 15 years of my life basically in the black box that is the National Security Agency and now I'm thrust into the private sector for the first time in my life. Knew nothing about financial services, nothing about banking. Every meeting was like being dropped in the middle of a foreign country and trying to figure out not just what is everyone talking about, but what is my role?
Stacie: That's Rachel Wilson. She's the head of wealth management, data security and infrastructure risk here at Morgan Stanley. She has established a powerful leadership presence that's absolutely critical to the firm. As she tells it though, it was not an accident, luck or even innate skill that got her there. She worked hard at discovering and developing her unique, authentic voice in the workplace and learning to use it with confidence.
She sharpened the skill first at the NSA, where she oversaw government hackers for years. Then had to build it again from the ground up when she brought her cybersecurity genius to the very different environment of Morgan Stanley. She had a strategic process to develop that voice and she's sharing it here.
I'm Stacie Hoffmeister, head of wealth management home office talent and diversity at Morgan Stanley. Voice is something that I think about constantly. How do we speak up in a way that's authentic to who we are and also adds value? How do we make ourselves heard in spaces that still may be male-dominated or just unwelcome? As one of the few female cybersecurity experts at her level, Rachel is the perfect person to answer these questions. I am so thrilled to have her here with us today on the first episode of Come In, Let's Talk.
All right so Rachel, thank you so much for joining me today.
Rachel Wilson: Well Stacie, thank you so much for having me. I have been really looking forward to this.
Stacie Hoffmeis: Let's talk about your backstory because it's pretty, pretty incredible.
Rachel Wilson: I've been at Morgan Stanley since April of 2017, but before that I spent 15 years at the National Security Agency, the NSA, and I had a few different jobs in my tenure there, Stacie. I spent a couple of years running the NSA's counter terrorism operations mission. Think of this as using technical means to get onto the devices used by terrorists and listen to their phone calls, read their emails, really try to thwart their terrorist planning.
Then I spent a couple of years in the UK helping the British get ready for the 2012 Summer Olympics. All kinds of cyber actors looking to cause problems in the context of the Olympics.
Then I spent my last five years at the NSA running the NSA's cyber exploitation operations mission, so this is really America's preeminent nation state level hacking group. So these are folks that are hacking into the network of our adversaries, stealing the secrets out of their networks, all with the goal of protecting the United States and our allies.
You can imagine, we've talked about this, that this was a strange environment to work in. These are folks that have gravitated toward the hacker community. It's definitely a very firm instantiation of the bro culture. Lots of military personnel, so folks that we had recruited, top technologists from all over the country combined with some real savants from our various military services, coming together to do something that for us was very inspiring because of course we were influencing national policy and help save lives, but for them this was really an opportunity to do something that would be illegal anywhere else. You can imagine I couldn't offer them tons of money but I could offer them the opportunity to do something really cool.
Not a lot of women in that environment, as you would expect. I could count the number of women on one hand when I got there in terms of the technical workforce, and sadly when I left I could still count the number of women on one hand. I consider that to be one of my greatest failures career wise. It was not through for want of trying, I mean, I did everything I could think of to try to bring more women into that environment, but it was a struggle.
And it was also a struggle, thinking about our topic here today, in the context of finding my voice. This was a workforce that was not necessarily open arms to new management coming in, having thoughts and feelings. My showing up and saying, "Hey, I'm here to help," they were skeptical, incredulous that I was going to have a lot of value to add. And I'll be honest, it took me the better part of a year to feel like I was giving more than I was getting in that job.
Stacie Hoffmeis: If you go back to those days in the NSA hacker program and being immersed in this bro culture, what are some of the ways that you made sure that you got heard?
Rachel Wilson: This was about getting myself up to speed, being prepared, and getting to a place where I felt like I had real value to add. I had to build my own confidence before I could develop that voice. And at the beginning that meant really getting my arms around what it was that I was managing. So establishing some trusted allies in the organization, people that I could go to with the questions as I uncovered them. Lots of preparedness. Going to meetings, taking notes, making a list of everything I didn't understand in that meeting. Those lists were voluminous in those early days. Actually giving myself a grade at the end of the meeting. What percentage of this meeting did I understand?
And I was getting Ds and Fs for the better part of the first six months, but all of that then became work to do. Long hours. Conversations with the experts that I had built relationships with. Doing my own research to try to understand better those concepts. As I better understood, that increased my confidence and made me into a place where I could project it with credibility.
Stacie Hoffmeis: It's clear when you describe that how being in an environment like the NSA would really force you to have to be strategic about how to be heard and how to get your voice heard, especially being a woman.
Rachel Wilson: Yes, and I think that is where the preparedness and the intentionality come into play. As you know, thinking about women in technology, we're at about 25% of the technology workforce but when you're thinking about that for cybersecurity, it's actually about half that. Only 12% of the workforce. Overlay that now with financial services, and I joke that the four of us have gotten to know each other really well, I'm not even kidding. It's a very small number of folks in this space, women doing cybersecurity in financial services today. But you're right, it's an opportunity to really hone that internal and up and out voice from an early age.
Stacie Hoffmeis: Let's talk a bit about your role today and your role here at Morgan Stanley. You have made your mark. You definitely have a voice and you are definitely heard and your importance to the firm cannot be underestimated. Can you talk a bit about why you moved to Morgan Stanley from your dream job at the NSA?
Rachel Wilson: Well Stacie, you're right that it was my dream job. I would very happily have been the queen of the hackers forever. It was fantastic and tremendously fulfilling, but that's not the way government works. Folks who have been in government know that you reach the end of your tenure and they want you to go on and do something else. And the something else that they were offering me were not terribly interesting to me. so I made the decision to try something totally new in coming to financial services and coming to Morgan Stanley, but for me this really, while it's been a transition in lots of ways, from a core values perspective it feels very close to home. Defending Morgan Stanley from all of those who would do us harm as a key piece of America's critical national infrastructure, it really is an opportunity to protect our country, Main Street and Wall Street, just in a different way and through a different lens.
Stacie Hoffmeis: Tell me a bit about your early days here at the firm and what were they like for you.
Rachel Wilson: Those early days, I'll be honest Stacie, they were rough. As I told you, it felt like language immersion. I had no idea what anyone was talking about. I had no idea what I was supposed to be doing. So it's one thing when you start in a job and you are someone's successor and maybe you have handoff and maybe someone tells you, "Here's your schedule. Here are your objectives. Here are your deliverables." But starting in a role as the first person to ever hold that role, the first head of cybersecurity for Morgan Stanley Wealth Management, there was no playbook. There was no blueprint.
And going to my boss and saying, "Okay boss, I'm here. What do you want me to do?" His answer, in all honesty, was, "Well Rachel, just keep us safe." Pretty ambiguous. Really little direction.
But the fact is, and you know this Stacie, the more senior we become the more we have an expectation, an expectation of us, that we are going to figure it out for ourselves. That we're not going to need a whole lot of guidance and direction. That we're going to be comfortable with ambiguity, that we're going to show up, we're going to cultivate a voice in that environment, we're going to be brave, and we'll figure it out. That's what I did.
Stacie Hoffmeis: When we say voice, what does that mean to you?
Rachel Wilson: For me Stacie, I think about it on a couple of different levels. There's the voice that we use with our peer group, with our teams, maybe that's the tone and tenor of the conversation that we have at our weekly team meetings. But then there's that other voice, which I really think of as your up and out voice. This is the conversation you're having with your boss, maybe with your second level leadership. It's the conversation you're having with Morgan Stanley's top leadership, with the board of directors, and it's the conversation you're having external to the firm. And that really is, it's a different tone, a different tenor, and it's quite different content, as you'd expect.
Stacie Hoffmeis: I'd love to hear more about how do you think about these voices? What are they and how do you develop them and at the same time still be authentically yourself?
Rachel Wilson: Absolutely, and that's a key piece of this. You think about the tone and tenor of the voice, the way you would speak to an employee who's come to you and is having a difficult personal situation. Obviously that voice needs to be warm, embracing, comforting, even maternal at times.
Whereas the voice that you want to have in a meeting where you're making a proposal, maybe even a proposal that's likely to be controversial, there, again, my approach is to talk fast and loud and with intent. Prevent that maybe inevitable interruption, but get to the point where I know that I've conveyed the information that I need to convey without being derailed or sidelined.
I think a lot of it, this is really just psychology 101. It's knowing going into the meeting who are the participants? What are their agendas? What are they afraid of and what do they desire and what does that mean relative to the topic that I'm going to be addressing?
Again, if I think they're likely to be afraid of or worried about something I'm going to raise, I want to address that with them upfront in advance. I want to make sure that that issue is going to be rectified and reconciled before we go into the meeting, as opposed to it derailing the meeting. Likewise, if I think any of the stakeholders have something that they want coming out of this meeting, how can I pre-coordinate that in advance so that I've got an ally at the table before the discussion even begins?
Stacie Hoffmeis: Another big headline that I've heard you say is about preparation and how important preparation is to developing your voice. Can, can you speak a bit about that?
Rachel Wilson: Well so as you know, I think this is critical, especially for women where it can be more difficult to have your voice heard. Being prepared I think goes incredibly far in making sure that our voices are heard. I tell people all the time that especially at Morgan Stanley, I am rarely the smartest person in the room but I am almost invariably the best prepared person in the room. I've taken those intentional steps to know what it is that I want to convey, to do the prep work to be ready for that meeting, and to make sure that my voice is heard.
Stacie Hoffmeis: I get preparation when it comes to that inner voice and knowing your business, knowing as much as you can about the who you're speaking to and letting that guide you. How does preparation come into play with your up and out voice?
Rachel Wilson: I think it's that same focus on intentionality. What is the message that we want to convey? How are we going to get that message across? What are the emotions that we want to evoke? What are the behaviors that we maybe want to change? Those sorts of things, coming in again with preparedness, with intentionality, I think that's the answer.
Rachel Wilson: But what I would say, Stacie, is being super prepared does not mean being super scripted. And in fact, I find that when I'm best prepared I don't need the script because I have total command of the issues I'm going to speak to and that can actually be the best and most natural way to convey information.
Stacie Hoffmeis: And for someone who values preparedness and at the same time you've changed roles and put yourself deliberately in situations where you are at the beginning of that S-curve of learning, as Whitney Johnson says, is that nerve-wracking? How do you prepare yourself for learning again?
Rachel Wilson: Well it never gets easy, right?
Rachel Wilson: You could imagine, Stacie, early days when I came to Morgan Stanley that I had just spent 15 years of my life basically in the black box that is the National Security Agency and now I'm thrust into the private sector for the first time in my life. Knew nothing about financial services, nothing about banking. Had never met a financial advisor until I met my own. Every meeting was like being dropped in the middle of a foreign country and trying to figure out not just what is everyone talking about, but what is my role? What is my value added in this place? Incredibly foreign, incredibly intimidating, but frankly, another opportunity to practice that exercise of learning new things and building a new network and expanding your knowledge base, building the expertise that's relevant to the new role.
Stacie Hoffmeis: I think that's incredible. I think that's really brave. Going back to getting heard and cultivating a voice, so let's say as one travels that curve of learning and possesses the expertise, does that still mean that they'll be heard? Is there anything more that we have to do?
Rachel Wilson: Well it's not enough to have the expertise. This is where I think the preparedness kicks in. So my challenge, for instance to my mentees, as they're looking to find their voice, is that when they're going to go into that next meeting with their boss, that they make a commitment, a promise to themselves, that they are not just going to speak in that meeting, but that they are going to very intentionally speak in the first 10 minutes of that meeting.
What I find happens to women all the time is they're thinking the thoughts but the men are so busy having the conversation that the clock runs out before they get a time to talk. They don't necessarily think that there's an opportunity for them to be heard. They hope that maybe someone will ask them for their perspective. That's not the way the world works, that's not how people get promoted they've got to be intentional about making sure their voice is heard and doing that in such a way that either is because they're very well prepared and they know the value that they're going to add, or it's actually through some pre-coordination.
I'm a big fan of this tactic as well, that if you want to make sure you're heard, it's maybe having a conversation with your boss in advance and saying, "Hey boss, these are the comments I think I want to make in this meeting. Let's make sure I've got an opportunity to say these things." Or maybe actually asking to speak to a couple of the slides. Actually getting yourself a fully endorsed and sanctioned speaking role in that meeting. Recognizing that you have value add.
And I think the last piece of it, Stacie, is knowing who's likely to derail your comments in a meeting. If you're coming into a meeting and maybe you're the presenter, it's have you thought through all of the stakeholders in the meeting? Do you understand their agenda, their motivation, and have you done the pre-coordination, the socialization, the diffusing of all of those potential issues in advance? More preparedness.
Stacie Hoffmeis: But I want to talk a bit about the double bind that we as women find ourselves in. So, lots of strides have been made in the financial industry especially in regards to women finding their place and their seat at the table and at the same time I definitely, in my role in diversity, still hear many stories about the double bind. That being that pressure that women are under to be assertive and to be heard, yet at the same time not to come across as too aggressive or too pushy. So needing to be assertive and at the same time needing to be warm. I'd love to hear your thoughts about do you see that? And how do you deal with it?
Rachel Wilson: Stacie, I see it all the time and it's exactly as you've described. Recognizing that there are societal expectations and unconscious bias that expects us as women to not just talk, but look and act in certain ways and those ways in a lot of cases are not commensurate with the same expectations they would have of a man and they're not commensurate with their expectations of what makes someone competent or a leader, and so it is that double bind that we face as women.
I've got a candidate, current ED that I'm working with right now, where she's going into meetings bull in a china shop, very aggressive, very pushy, and it is really turning the room against her and I worry about the long term consequences of that constantly aggressive strategy that she's taking. So in her case, I've asked her to back off a little bit. Be more respectful, warmer, more collaborative, different tone and tenor of conversation.
For other women though, many that I've worked with, they are so intent on being liked, on pleasing others, that they're missing some of that direct, some of that edge. Being a senior leader in financial services requires some degree of edginess and we have to be able to convey that in our voice.
Stacie Hoffmeis: That right amount of edge. That just right. Not too sharp, but definitely precise enough. How do you balance that demand for us as women to take up space and occasionally be uninterruptible with the knowledge that these behaviors can read differently on us than when men exhibit them?
Rachel Wilson: Absolutely. I think it's situational and it's all about risk calculus. So again, part of this preparing, and this isn't just for meetings, this is preparing for any engagement, it's deciding in advance what is worth fighting for? So what are your non-negotiables going into that conversation? Those are the things that you want to take the risk of breaking a little glass. Maybe using that edgier tone, that more aggressive style. The mistake though is to be using that across the board. We want to save that for the situations that really merit it.
Stacie Hoffmeis: So you went from just make us safe to someone who's a fixture in our culture at Morgan Stanley and a public figure. I saw you on CNN the other day in an ad. I'm like, "There's Rachel." You went from being pretty underground in your role at the NSA to now being on stage all the time. So you not just had to develop your voice as a leader within the firm, but you also needed to develop a voice and a presence that is presented externally to our clients, to our industry, and into the world. What's that journey been like for you?
Rachel Wilson: It has been an absolute uphill climb. Anyone who thinks that public speaking, having an authentic voice as a speaker, is something that you're born with, I totally disagree. It is a skill that great speakers work at, they cultivate, they prepare for it, they iterate, and that's exactly what I had to do. So you're right, 15 years at the NSA, couldn't talk to my husband about what I was doing at work, let alone talk to perfect strangers or be interviewed by the New York Times. It was a huge adjustment and it was not the expectation when I took this role that there would be a client-facing, a public-facing aspect to that. I don't think leadership and I certainly didn't recognize what an appetite there would be for content and engagement around cybersecurity and data security topics.
So certainly I had done a lot of presenting and I had done a lot of speaking internal to NSA, but it's a very different thing when you're facing off to clients, when you're facing off to the public. To your point, being that public face of cybersecurity.
Stacie Hoffmeis: I remember you telling me that this did not come naturally to you and you started to speak a bit about your journey and the early speeches that you gave and how you struggled in the beginning. Can you speak a bit about what those early days were like and what you were doing wrong and how you addressed it?
Rachel Wilson: Those early days, those early speeches?
Rachel Wilson: They were disastrous. You're exactly right. Cybersecurity on its face could be a very dry, very boring, not a compelling topic. I know that for a fact because I was all of those things in those early days. Coming in with pages of notes, sitting on a chair in front of the audience, providing granular detail about all of Morgan Stanley's cybersecurity controls and our data protection standards and our privacy policies, not recognizing that A, that was interesting to me but not interesting to anyone else, and B, that it was just incredibly distant. There was no connection being built from any of this.
So one of these early talks, Stacie, was in California where my parents live, and my dad actually came to the talk and he gave me feedback afterwards. He's he said, "Don't ever do that again. That has to change. It has to change 180 degrees." And so I spent the next six months figuring out how I was going to do this in a way that would resonate.
Stacie Hoffmeis: Tell us a bit about what are some of the most important changes that you made?
Rachel Wilson: It was all about telling stories. If you listen to great public speakers, all they're doing is telling one evocative, compelling story after the next that are all intended to drum up emotions or to build confidence. Last thing I would say, Stacie, is that humor helps. I was incredibly boring those first few rounds and trying to figure out what's funny about cyber security has led to some interesting conversations.
But it also it came down to, Stacie, also recognizing that while I have to establish credibility, I also have to be a human being. And so most of what I at least hope are funny in my public speaking events now, are actually stories about my kids. Things that they've done wrong. That kind of humanizing content really helps.
Stacie Hoffmeis: This is a podcast and folks can't see you or me. What I want to describe for the audience is that Rachel is not what you would expect to enter the room when you hear a cybersecurity expert is coming. Rachel is very stylish, very modern, Rachel always wears impeccable makeup.
Rachel Wilson: Well you're being very kind, Stacie, so I appreciate that. I think you're right though, that when people hear cybersecurity expert they're thinking a man, certainly. They're thinking a geek, which I'll tell you I think I am a geek even though I don't necessarily look like what people are expecting. But yes, it has been a challenge for me recognizing that that audience that I'm walking into, I am not what they are expecting to see.
Stacie Hoffmeis: Can you talk a bit more about how you interrupt those biases so that folks can kind of get past that and really hear your message?
Rachel Wilson: Well and I love the way you used the word interrupt because that's exactly what it is. And so I spend the first 10 to 15 minutes of an hour long presentation making it demonstrably undeniably clear that I am qualified to convey the information that I'm going to convey. So I spend a fair bit of time talking through my background, my bonifides, my education, my experience, my expertise in this space. Some of my peers, if they look like what the audience is expecting, they can skip that whole credibility phase. But I have to know going in that that bias is going to be there and I've got to thwart it right from the beginning.
Stacie Hoffmeis: Yeah, so I hear you saying to really establish your credibility intentionally and early so that we can interrupt that bias. I relate to you on that deeply. Again, you hear our voices, you don't see what we look like. I am a black woman and I absolutely have had those moments in life where I've had a connection with someone over the phone who hasn't met me in person and when I show up and they expect Stacie Hoffmeister to show up, they're not expecting me.
But I can relate to that feeling of, or that intention around establishing credibility and establishing it quickly. And as I've advanced in my career across the different companies I've worked in, it's something that I've had to be very, very conscious of.
And as a result of that, I say that I have adopted a style that at times can feel sharp. I'm conscious of being warm, but I also am conscious that there are times when I land sharply.
Rachel Wilson: We're supposed to be everyone's best friend and warm and maternal and emotive all the time, and that comes in direct contrast with that credibility where we want to demonstrate those behaviors that on a man are categorized and characterized in very positive ways and sometimes for women not so much. So I think it is walking that fine line, but I saw the same thing happen, Stacie, as I was honing my craft talking to clients around the country, is that I was overcompensating so much towards appearing credible that I was actually coming across as totally devoid of warmth, almost automaton like, and so the next phase really was how do I reintroduce?
Some of your earlier point around authenticity? How do I be my full self in front of an audience? Which is key. I've got to portray that credibility that I know I'm bringing, but that doesn't mean leaving the rest of myself at the door.
And so I started introducing more of that human connection. I think sometimes as women we shy away from humanizing ourselves because we are, to your point, so intent on being credible, but for me adding back in some of those personal stories about my husband, about my kids, cybersecurity mistakes that we've seen in our family, adding those meant that we were able to establish real relationships in these presentations. So between the firm, between our clients, talking to our clients on multiple wavelengths as experts but also as compassionate and empathetic peers.
Stacie Hoffmeis: Rachel, I could really listen to you forever. I also just want to say that as someone that has worked with you for a bit over the past year, you do strike well that balance between being 100% credible and 100% warm I don't think I just speak for myself in saying we are so glad that you made the move and we are just thrilled to have you as part of our firm, as part of our culture, So thank you, thank you for all that you bring.
Rachel Wilson: Thanks Stacie. I'll tell you, we all feel the same way about you.
Stacie Hoffmeis: Aww. Love. Virtual hug.
Rachel Wilson: Virtual hug. I'm ready for a real hug.
Stacie Hoffmeis: That was Rachel Wilson, head of wealth management data security and infrastructure risk here at Morgan Stanley. Thanks so much for joining us on this episode. Come back next time when we discuss stepping away from the job to find the balance and perspective it takes to return. My guest will be Morgan Stanley's head of field strategic services, Lisa Golia.
Come In, Let's Talk is produced by Sarah Hartong, strategic communications executive director at Morgan Stanley, along with the team at Freetime Media. Music is by John Palmer. I'm your host, Stacie Hoffmeister.
