S5:E13🎙️ LIVE with Anna J. Wheeler, USA (Veteran)

¡Hola!

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My name is Anna Wheeler. I'm the Vice President of Public Sector for Qualys. West brings value in the fact that we're new to public sector. We're the industry leader on the commercial side, but awareness and brand familiarity is lacking. So this was a great way for us to come out and get to know the public sector and let them get to know us. I recommend being a visitor at WEST because you get access to people that are very difficult to get access to otherwise. People come for additional information and they're great about walking around introducing themselves and really looking for various solutions. So having this caliber in one location is unprecedented. So to deter, compete, and win on a global scale, industry and the government have to be more closely aligned. The benefit to sitting down in an environment like WEST is not only do you have access to those leaders, but you also have access to other, sometimes competitors, integrators, and people where you can sit down and come up with global solutions or understand various needs across the landscape in a way that you probably couldn't have without so many different pieces of input. Well, the importance of WEST to the region is As the Navy and Marine Corps' largest show, you have the— it's a more cost-effective way for— to consolidate that leadership in one location. Industry is affected by conferences such as WEST because they get more hands-on, kind of direct feedback from the inline consumer, from the decision maker and the visionaries all the way down to the actual end user. I do find that we get much more open communication with people we don't typically interact with. As being new to public sector, we don't have a lot of the Rolodexes and a lot of the ability to walk into every office, but we've seen every level of leadership walking around the conference, and they've been approachable and open to those discussions.

All right, welcome to the, uh, final episode of the Leadership and Success podcast for today. Season 5, we are now at episode 13. I have a very special guest for you waiting in the green room. Before I bring her in, as you know, our custom is to start with moment of gratitude. So I've already done this 3 times today. So just a reminder that today I am really grateful for all of the illustrious guests that we have at Leadership Success podcast. I am really humbled for so many great people who come and share their wisdom, help us be better leader. And achieve a higher level of success, which our guest will do. So let me see if I can introduce her. I'm gonna try my best here. Today we're gonna be speaking with Anna J. Wheeler. She's a US Army veteran, former Black Hawk helicopter crew chief, and the cybersecurity and national security leader. She has led at the intersection of mission, technology, and people from combat aviation to boardroom strategy. Anna's journey is a masterclass in service-driven leadership, accountability under pressure, and building trust in complex environments. Please, ladies and gentlemen, help me welcome to the Leadership and Success Podcast, Anna J. Wheeler. Good afternoon, Anna. How are you doing today?

Good afternoon. I'm doing well. How are you, Bizy?

Really, really, I'm glad that you are here. Thank you so much for making the time. Maybe we can start What is one thing you are grateful for today?

You know, I've had so many amazing support structures in my life. I've had champions, I've had advocates, and I've had people who throw a picture of me with a tomahawk on LinkedIn and write an amazing write-up that I really need to hire as a hype man because that was fantastic. So you get these amazing elements of support that you don't always know are there. And that when you have somebody advocating for you, whether you're in the room or you have somebody cheering for you, even if you're not, it's a pretty amazing place to be. And I'm incredibly humbled and grateful for that.

Well, talking about people putting your pictures around, tell us a little bit about this picture. You went around the internet and made quite a stir. What was happening here? Maybe you can tell us a little bit about this Military Order of the Carabao.

Sure. So the Military Order of the Carabao is a 127-year-old, 128-year-old organization. Wow. And they're one of the last standing military orders. Um, the rest of them have kind of tapered out, and one of the ways they've done that is really to evolve in where they came from. So they were originally— you had to be, I believe, a fighter pilot who served in conflict in the Philippines, um, which you can imagine in today's day and age, they're kind of short on, uh, on their, their legacies there. So they started to open it up to— then you had to be an officer, then they opened it up to enlisted. So I got recruited into the herd. And as if you look behind me, there aren't a lot of females in that picture. So yes, one of the things they asked me to do— and there certainly were not enlisted, um, I was the kind of first one that they pulled in on my own. You could be a legacy through a parental affiliation, but, um, so I had to parade the beef, take it through the crowd with an actual fife and drum. So bagpiper, the works, and on stage, the Grand Mount Parabio picks it up, takes a bite, declares it fit for the herd. Wow. Fed and watered. And that was a year coming out of COVID We didn't have a lot of attendees. We weren't going to do really great on budget, so we didn't have a really amazing— it was kind of like the hotel rubber chicken thing. We're way past that now. We have a great menu. Last year was fantastic. Years, even better. But so I took the tomahawk back to my table and I set it down, and everybody looked at me and goes, you are not going to eat that in front of us. Wow. I just had to parade the beef. I am absolutely—

this in front of you.

Yes.

And, uh, the gentleman who took that photo made the comment, he said, then you can't use silverware. And I said, okay, good time. Like, you forgot enlisted are here now. I'm like, yes.

Wow, that's really wonderful.

That one to circulate, uh, several years later.

No, it's, it's really great for advertising and just bringing awareness. So you are going to be the master of ceremony for the 2026 annual, uh, WALLO next— actually next month, right?

I am.

Wow, that is pretty amazing. So is there something else about you that most people may not know? Like one picture of you that scared me a little bit, which I found, is this one.

Yes, so that was me paragliding in Turkey.

Um, wow, that's amazing.

I tend to, to be ready to go, right? Work hard, play hard. That's absolutely the military mantra. Hurry up and wait, and work hard, play hard. We do both really well.

Wow.

So it was a beautiful opportunity in Turkey to parasail off the cliffs, and, um, they took some amazing photos.

Wow, that is really amazing. So you've led in cockpits, classroom, and command center. What early life experiences most shaped how you lead today?

My father.

My father is my hero. He was born in 1929, lied about his age to get into World War II. He didn't actually see combat, but he was on his way over before the war ended. And then he was—

Korean Vietnam.

And by the time I came around, he'd retired from the military and he was a counselor and a college professor teaching personality and adjustment. And he taught me that you don't have to be where you're from and you get to shape and decide who you are. And every time you take a step forward or a step backwards, you're deciding where you are on that path. So that level of accountability and deliberate, deliberate motion is something that's always been very much in the forefront for me.

Wow, that is quite powerful because the truth is you are also one of the very first white female Black Hawk co-chiefs. What did that environment kind of teach you about earning trust quickly?

Um, adaptability for one. Um, and also there's things you can own and there's things you can't. You can own your behavior, you can own how you react. You can't always own how somebody else is going to react, and you can't always fix that. Um, you know, there were points since I was the only female in my unit for, for quite a while that I had some amazing, amazing soldiers I served with who stood by me and were, were there to, to lift me up. But there were plenty who it didn't matter. And again, this was quite a, quite a long time ago, so let's put that in context. But there were quite a few that, um, it didn't matter if I was good at my job or not, I was always going to be considered subpar. And if you can get up and self-motivate for mission and not worry about that aspect, then that is an amazing way to forge your step for your way forward. And also to remember that the right thing is always the right thing, whether it hurts or whether it doesn't, it's still right. Right is right. And show up, show up every day ready to go. Wow.

So being the only female in that environment, what else did that teach you?

It taught me to know who's on your side and who isn't. One of my favorite pieces of advice to give people I mentor or people in my team is if you wouldn't ask somebody for advice, be very careful in how much you internalize their criticism. Because if you ask somebody for advice, it's because you trust them. And you believe that they're looking out for your best interest. So if they give you advice or criticism, it's worth it because you know they're looking out for you. And if it's the other way where you have somebody who's just constantly on you or constantly beating you down and they're not somebody you trust, odds are they're doing it for a place of their own issues, not, not to make you better.

Wow, that's very insightful. Let's talk a little bit about your transition from the Army and now you've become one of the thought leaders in cybersecurity. I've met a lot of service members who kind of struggle, right, with their identity after leaving the military. So who did you become after you took the uniform off and how did you navigate that transition?

It was a difficult transition. I went from being the military member to being a military spouse. I had a young child. My mother's health was failing. I ended up moving back to Arizona, going to college. So, then, I was a non-traditional student. So, I have a history in life of never quite being the thing that fits. And really kind of pushing those envelopes. And again, that transition is a lot simpler when you can self— when you can look at to mission as motivation as opposed to needing the gratification or falling apart when things are hard. Um, I had— I, I did an interview one day and they kept telling me, oh, you're so resilient, you're so resilient, you're so resilient. In the moment, you can't be resilient. You can be tenacious, you can be positive, you can be, you know, you can, you can be a phoenix if you want to, whatever, but resilience comes later. You cannot be resilient in the moment. Um, so it really is that tenacity is something that, uh, that has really helped as I drove through. And it was similar, you know, um, I solve problems, I'm a systems thinker. So when they told me I had 36 months of GI Bill, because I was a Montgomery GI Bill person for anybody who wants to date me, um, so long time ago, they, uh, you know, I said, okay, I have 36 months Let's go do it. So I got my bachelor's in 2 and a half years. I took anywhere from 18 to 29 credits at a time.

Wow.

And I'm a board member, an advisory board member for the University of West Florida, and I always wonder why they let me talk to their students because I tell students, I'm like, just because this is how the structure is doesn't mean that's how it has to be. I absolutely went, did an end run around the system and went to a professor, said, I'd like to do an independent study.

Wow.

And he said, okay, tell me why. And I said, well, I think I've already got a handle on these aspects, what can I do? And we worked through it and he said, okay, there's a, an internship in Congressman Jim Colby's office.

If you can get—

wow—

and you can do a semester or I think it was 9 months, in Jim Colby's office. You're going to learn more about government than I could ever teach you.

Wow.

So do that, bring me a 100-page paper. And Anna, I don't care if it says Yellow Pages on it. If you survive the internship, you already know the stuff. I'm not going to read it. So then I went to another professor and I said, hey, I would like to do an independent study of your class How about I go get this internship and I write a 100-page paper? And so I did this for 6 professors.

Wow.

And that was one of my heaviest loads. And I did the internship. I was there every day. So it was definitely full-time work. And I was dealing with the Social Security offices, with the military offices, with Health and Human Services, with the different congressional pieces, who needs tours. Like, you touch small business, every branch of everything. And I wrote a journal and I submitted that to those professors and they were all like, this is great. It wasn't until after they'd given me the pass that they realized what I'd done.

But that's really amazing. I mean, we're talking about resilience. I, uh, named this episode from Black Hawk, uh, to boardroom leadership under pressure because really when I look at your life, you've really gone through the wringer, but you always come out victorious. It's quite amazing. So talking about pressure revealing leadership character, what was maybe a moment in your career that fundamentally changed how you view authority, accountability, or power?

So actually, I had somebody complaining about the middle management structure in a large organization. And a systems thinker, I took it apart for him and I broke it down. And I said, "Do you know why this level is so important?" And they said, "Why?" And I said, "It's very simple. They provide stability to the organization." Like, if you looked on my LinkedIn, it says I am not capable of thinking inside of a box. And that's true. I am outside of the box. I go do things where they're like, "That's never going to work." And then it does if I have the leadership that is allowing me to run with it. Because they can trust I'm never going to cross an ethical line. I'm never going to do anything that is going to blow back on an organization. And I'm going to take the heat for anything. I will not throw my team under the bus. I'll hold them accountable. But my job is to protect them and get things done. And so, when I explain that that middle management level is about about providing that stability. Because if everybody went and flew too close to the sun, we all burn.

Yes, yes.

But that stability layer is important. So by looking at all of it as a mechanism for the organization, you appreciate and you're able to really put words to why those elements are important, even when kind of the bureaucracy and things like that are frustrating.

Wow, that is quite insightful. Another thing you've spoken about openly is choosing to walk away from toxic environment. How should leaders recognize when staying will cost them much more than leaving?

Well, I mean, if you're not contributing to an organization for whatever reason, there's no reason to be there. Pretty simple. I was at a company and I was not being allowed to do my job. I was brought in to establish public sector as an emerging market, get the defense teams in place, all of the things. And I brought in highly technical people who knew the space and they were deemed not technical enough because they hadn't used a product, which didn't make any sense to me. And they went on to be CIOs, CTOs, and CISOs. So like they were executives who were coming because we were going to build something beautiful. And when I couldn't do my job because I had these handcuffs on, you know, I called the CEO and I said, you know, I think it's time for us to part ways. I'd like to negotiate a severance. And he laughed and he said, Anna, if you're resigning, you don't get to negotiate a severance. And I said, you know, actually I do, because the only reason I'm leaving is because I'm not allowed to do what you need me to do. So this is what's best for both of us. And when I told him, I said, look, I'm standing at the end of the pier with cement shoes and my hands tied. Like, I'm not just standing there till the pier falls off and I fall in. I'm not effective for the organization because this isn't working. And you're not effective for what I need. So we just, we need to make a smart decision for both of us.

Wow.

And be the grown-ups.

Man, that is incredible, the boldness. It's, uh, wow, it's, it's very refreshing. Let me just put it, uh, that way. So throughout your entire career, what's a leadership scar that you carry, and what did it teach you that success really never could?

Sometimes you— well, I shouldn't say sometimes, you always have to balance the machine versus people. And sometimes you can have the best people in the world and the machine is just not going to get there. Um, and usually it's because there's other people holding the machine or making sure the machine stays broken. But, um, I was recently in a company where the CEO is amazing, the technology was phenomenal, we were going to change everything, and And it was the investors and another founder who just would not let the company focus on the plan and get it done. And they had ulterior motives, which, you know, it happens. If you can look at why somebody's doing something and where they come from, you can usually figure out what they're trying to do. And at that point, it's, it's, it's time to where where the scar that I had— absolutely believed in both the— well, all— in all three and the CEO. And, um, yes, longer than I probably should have.

Hmm, wow, that is quite an experience. And I know in the military, usually, you know, we definitely believe in our mission, and most of the time the leaders we have are really ethical and moral and people we want to follow. So that must have been really hard for you.

It was.

Wow. What did that teach you?

Well, it taught me to pay attention to both.

Yes.

To understand which leaders are operating toward mission and which ones are operating for themselves. And as a general rule, You're going to have that. Everybody's got levers, right? Everybody's got a reason to be in the room. Everybody's got a family to feed. Everybody's got, you know, braces or college or a thing, Starbucks addiction, whatever the thing is. But understanding where they are in their journey, what they're focused on, and where they've been is a great way to really pay attention to some of that. And the old adage, when somebody shows you who they are, believe them.

Yeah, yeah. I learned that from Oprah. I think she learned it from her mentor, Maya Angelou. It's so true. Wow. Okay, let's switch and talk about cybersecurity and cyber risk. You're definitely one of the thought leaders in this area. Something I'm very passionate about, but you've challenged the term cybersecurity. I remember now most people write it as one word. I remember when it was written as cyber and then space security, two separate words. But anyway, you've reframed it as cyber risk mitigation. So why does language matter so much in leadership and strategy?

Well, particularly when it comes to cybersecurity, it's an unfair expectation. Right? If cybersecurity implies that there is a security to the environment, then people have an expectation of safety.

Yes.

But cybersecurity is not the point, um, and it's not real. Somebody will get through anything. It's not an if, it's a when, and it's a how, and it's how do you recover. So when you're having the dollars conversation or you're having the mission conversation, whether you're talking to the government or to industry, or to investors or to customers. It's not about cybersecurity because the board, that's not how they're tooled. They're tooled for return on investment. Return on investment is about risk mitigation. So you can come in and say, I need this shiny thing because it's going to be the greatest thing since sliced bread. And if they turn around and say, it's really expensive, what does it do for me? And you're like, it changes your risk profile by 0.2 2%? They're probably going to say, yeah, 30% of the budget, not worth 0.2%. Like, so have a different conversation. And if you can reframe it to cyber risk mitigation, yes, um, then you've level set and you've changed the dynamic of the conversation.

Wow, that is quite insightful. Another thing I see in cybersecurity, there are too many of us sometimes, we just think tactically, and it's about tools and things. So how would you help military officers or engineers start thinking more operationally or even strategically, right? Thinking in risk, trade-off, and mission impact instead of simply tools?

Well, I think one of the things to look at is strategy is used in multiple ways, right? It's kind of a catch-all for how do we put a tool in place? How do we respond to something? How do we get where we need to go long term? So, when I say I'm a strategist and somebody else says they're a strategist, I ask them at what point, what type of strategy are they focused on. And they said, "Oh, we're going to get this tool installed. We're going to do these things." Or, "I'm working on the response mechanisms." I'm like, "Great!" So, there is event-driven strategy. There's a response. There is a foundational, like, here's what we're doing in the short term to implement. There's an implementation strategy. And then there's kind of like the destination strategy, which, how do I get way over there? If whether I know where over there is or not. So one is very, where am I right now? And what do I need to do to stay standing? One is what is the journey? And one is what is the destination? And if you can look at those elements, it really helps you put a larger picture and understand where you fit into that picture.

Picture. Well, quite insightful. Now, another thing about cybersecurity, one thing I usually tell people when I make presentation is if you truly want a system that's 100% secure, basically you have to shut it down and bury it under the sea. It's secure, nobody is using it. As long as you turn it on, there is always risk, right? So you have to think about resilience. So what mistakes have you seen kind of leaders make when they promise security instead of resilience in your experience?

Yeah, See, I have something that's secure right here.

Right?

Nothing can get to it except liquid. So it's still not secure.

Right?

It's just a thing. No, I mean, as we're having these conversations with helping get ahead, again, take the promise of security out because that's not what you're doing.

Yes.

And you say, here's All of the risk. Here are the things that are important. Here's where we could see something. Here's where we couldn't. And here are our plans. That resiliency conversation is 100% tied to risk mitigation. We have risk mitigation. Great. Here's our risks. Oh, when those things go wrong, what will we do? Oh, resiliency. Those plans have to tie together. And they have to have buy-in by the leaders who own each of those elements.

Powerful. I believe this is Joel, he's asking you, when you take a leadership role in an established organization, how do you introduce new ideas without becoming a threat to the establishment? That's a very good question. So do you move quickly or do you take time to understand the culture?

Well, it's always worth understanding the culture, but the culture presents itself pretty quickly. The players don't. But the culture is usually pretty. But now, for new ideas and things, A, you have to understand what your authorities are and what your peers and your superiors and also your folks that are kind of doing the work, what each of their roles and authorities are. Because then you can start looking at what your action, how it impacts them. And that's where you can understand a threat matrix. Again, everything I do is systems. It's people are systems, systems are systems. But if you can turn around and say, oh, so-and-so is going to be retiring in the next 6 months. Okay. Are they pushing to get something accomplished before they retire? Or are they kind of retired in place and the person, and you've got 3 people jockeying under them for position. That's important to know. Those dynamics and those undercurrents are always interesting. And in the military, it's incredibly important because people are constantly moving around. You know, the joke is always, what do you do if you have a bad commander?

Yes, yes, because after what, 2 years or so, you're gonna get a new CEO, right?

And so, so you leverage and you really build the people who are going to be stepping up and who are If you don't have at least 3 people that you're grooming to take your job, you're not leading.

Yeah, yeah. I guess I was going to say, prior to 2025, when being a GS employee was a secure permanent position, yeah, you would just outlast your commanding officer for 2 or 3 years and they'd be out of there. Okay, uh, another insight. I believe that's Joel again. I like the discussion about risk management. A number of years ago, I work a project for the CNO, so Chief of Naval Operations, to measure our investment in different areas of naval aviation would impact readiness. Some areas required large investment but raised readiness only slightly. Other areas showed that a small investment had a disproportional impact. So we really need to think about leadership at scale, don't we? So let's talk about leading at scale, but without losing the human. So you've helped shape a multi-billion-dollar cyber portfolio. Congratulations, that's really a great achievement. But how do leaders maintain ethical clarity when operating at such a massive scale?

The simple part behind it is you empower people to tell you the truth.

Hmm.

If you are the leader that somebody walks in the room and thinks that they're going to either get something by you because you're not paying attention or they've got to handle you, or they don't, or they're afraid to tell you the hard things, then you're never going to get your arms around the organization.

Wow!

If you can turn around and say, "Okay, these are my mission-focused people. These people are 100% in, right reasons. What do they need?" And then you say, "Okay, these people over here, they've got something going on, right? They're either about to retire. They're looking for what's next. They're moving on." And at senior levels, you tend to get a lot of that. Particularly military retirement age, who's wanting to go on to the next thing. There's a trend over the last 10 years where a lot of senior leaders have been making sure that they don't, that they, you know, 3 years before they retire, they go say, how do I make sure I leave without OCIs? Right? All of those things at play come into how you look at these large organizations and the amazing parts of the infrastructure. But the thing you can't ignore, you can't get lost on the shiny object. You have to be sure that you understand the connective tissue between each of those elements. And the only way you can do that is to really bring in and embrace the people who either own those projects or maybe even a level down, you know, a PM who's really driving it and has all the frustration. On the defense side, you know, we have, uh, we have the, the new CIO coming in for the DOW. We have a lot of moving pieces, but this is one of the first times we've seen so many people who have no background in the DIB, and they're not coming in because they want a bigger, better job later. They're coming in to fix things. And they're doing it with the right purpose and they're doing it with the right interests and they don't care who's beholden to who. And it's a really interesting political climate right now for that reason. But we really have some strong leaders who, they left huge jobs in industry to come in and help and really try to get this right. Some of the things, you know, there's a lot of political questions going on and there's a lot of hot-button topics and we don't need to touch any of those. But you have leaders who come in who say, look, I am stepping down from roles to come do this because I want to get the budgets right. I want to make sure we're modernizing the things that need to be modernized and I want to make sure that the warfighter has what they need in a secure mission. Yes. That's so exciting.

Hmm. Yes. And also, by the way, I want to say on DOW, so that's Department of War. Myself, I'm still getting used to that. I've known it as DOD my entire career. But yeah, it's a lot of changes happening. So we really need to be flexible. And here, the truth must be safe. I couldn't agree more. Yeah, I believe that's, uh, Joel again. Thank you so much. And that is, uh, uh, so true. So the incoming Department of War, Department of Navy leadership, it's quite exciting the work they're doing. And I believe, uh, I don't know if this is the first time, but it's a one man— I'm connected with her on LinkedIn Her name will come back to me. She just got confirmed, the CIO.

The honorable Kirsten Lee.

Kirsten, yes, yes. She's really strong. I'm really happy she's there. And hopefully she's gonna be on the Leadership Success podcast sometimes this year. But yeah, it's really powerful to see how all of that comes together. So you've been a chair of a large women's network and we used to call DEI diversity, equity, and inclusion facilitator. But regardless of the label, what do leaders misunderstand most about inclusion? Because we know from the research that teams that are more inclusive and diverse outperform monolithic teams every single time. So how can they do it better tomorrow? That is the question. Leaders misunderstand inclusion.

Yeah, I don't know any leader that does not want a diverse team. Yeah, not one. I know people who want the best candidate and they don't want to feel like they can't have the best candidate because they're filling a slot. This is not a super popular thing I'm about to say, but veterans preference, which I have and I appreciate, is difficult for me because you, if you put a resume, if you put two resumes next to each other and they're solid, the veteran should absolutely be the tiebreaker, no problem. But we don't always see that. We see somebody who's not quite as qualified, who's, you know, if we have a point system, they're getting extra points, and then they come in and, and it's, it's difficult. So the same thing is happening over on the DEI side. People just want the best candidates. They don't want to feel like there's a quota. I have yet to see a leader that says, I don't want X in my organization. I have yet to hear a leader say, I only want X in my organization. That mentality, I feel like we've gotten away from. And then we're looking at, particularly in the cyber world, we have over 700,000 openings right now. And I think it's actually up to 2.2 million or something like that by the end of 2026. And if you've got 6 resumes and you don't have pictures, and, you know, some organizations are even stripping out names—

awesome—

then what, what should be— why should, why should that demographic conversation come into play if you have one strong, strong, strong resume, strong, strong, strong interviewer I think people are happy to see everyone have a voice. The ERGs are still going strong, the employee resource groups, which tend to have a focus to make sure that those voices are being heard. People just don't want to feel like they're being pigeonholed.

That's a good way of looking at it. And another thing you have said is facilitation is about walking beside people, but not leading them to the actual answers. I think that's quite—

That's the hardest certification I've ever taken in my life.

Yeah.

So how does that mindset kind of change leadership behavior in high-pressure environments?

It's listening for understanding. I know that as a leader, I am a, I am a very efficient communicator. I want to get to the point. I don't need a lot of fluff. I don't need— if, if I need background, that's great, but I don't need to know whose dog, you know, Walker did whatever. Like, I don't need any of that. But sometimes people need to take you on their journey. And so for me, the first time I took my facilitator test My tester actually stopped the test and said, Anna, there's no way you're going to pass. He goes, I don't get it because in training you were on it. You had everybody, like you had the class on it. Like you were doing the thing and like right now, like we get, you know the answer. You can't do that as a facilitator. And so he gave me, he had me sit with his co-founder for a couple of hours and then I took the test again. And at the end of the test, he holds up this big, you know, the 5x8 card and it's blank. And I said, "Oh God, did I fail again?" He said, "No, this is where I write where I took points off." He goes, "I've never seen anybody come through it clean." He goes, "You're a completely different person this conversation." And I said, "Yeah, because I realized it wasn't about fixing a problem. It was about helping somebody on a journey." And we forget that in the boardroom or in the executive levels. When somebody— we've got so many things coming in, we gotta move. We don't think about the fact that when somebody comes in and says, hey, this just happened, yes, or this needs to happen, let's figure out why. So as a facilitator, it's helped me bring that into my culture, um, is how I work as an executive, as a consultant. It's helped me do organizational assessments. Um, as a strategist and fixer. It's so many times you send somebody into— like, you'll watch, you'll watch, uh, people on contract send somebody into a struggling contract. They're looking to put a Band-Aid on a bullet hole. I don't care about the Band-Aid on the bullet hole. I want to know who has the gun, where they got it, and why they fired it. Wow. Somebody else can worry about the bullet hole.

Yes. Wow, that's, that's definitely a different way of thinking. And also throughout your career, you've usually been the one and only woman in the room, uh, and I know you do a lot with mentorship. So if a junior officer or even an engineer come to you and says, okay, I do want to lead, but I don't look like the leaders I see, how would you respond? What would you advise them?

Oh, so first off, cyber is amazing because we do have women leaders. I mean, you just mentioned the new DOW CIO. Like, she's a 3-time global CISO. She's powerful. She's brilliant.

I'm a big fan.

Um, we've got these spectacular people who— there are people who look like you now. Anybody. There's, there's people who are of Indian descent. There's people who are of African-American descent. There's women. There's people of different gender. Questions, they're out there and they're getting noticed for what they do, not what they are. And, you know, I was speaking to a woman leader probably 15 years ago. So, it was still a very glass ceiling conversation. And if you notice, there's not a lot of glass ceiling conversations anymore.

True.

But I was talking to her and she said, Anna, there's two things you need to understand. One, if we're going to have a DEI push and we have a limited workforce and we have DEI numbers that don't reflect the workforce available, we're going to be putting our leaders in a point to fail. So if you want a hard number of like this percentage is this or this is that, that's not building your capability, that's building a demographic. Demographic and then you have a talent pool that doesn't match that demographic, all you're doing is throwing out good candidates and searching for unicorns that aren't there.

Yes. Wow.

So, the other thing she told me that is a huge way of the way that I lead is everybody has a different capacity. She held up her fingers whether your capacity is this or your capacity is that. It's your capacity. And you have to be deliberate in how you spend your capacity. You know, she's like, as, as a mother, one of the things— she was, uh, she was a general officer and her husband was as well— and she said, I have to forgive myself for the days that I am 95% at work and 5% at home.

Yes.

But I have to make sure that I'm deliberate in realizing which days my capacity has to shift to where I'm I'm 35% at home or I'm 85% at home. But when I'm there, I have to be deliberate in how I'm expending that capacity.

Wow, that's powerful.

Yeah, if you look at your teams that way, it's the same thing. Everybody's got a different capacity. So expecting somebody to be able to do something outside of their capacity puts you both in a position for failure.

Hmm, that's really something. I guess it makes me think of how should leaders kind of think about energy, right, as a finite resource. Uh, that's, that's quite insightful. Wow, that's, that's, that's really, I think, a very insightful way to lead. I guess you really get there with, uh, experience. And how do you think, like, throughout your entire career, from the Army to, to what you are doing now in cyberspace, what, what do you think is one of the greatest lessons you've learned so far?

To build a network that can support you. Um, I grew up not always feeling that way, and that was something that I had to be aware of about myself. It's something that I had to really focus on, um, and be deliberate about. So now I have this amazing network who, I mean, calling them friends does not do them justice. And, you know, to get personal, a few years ago I had a health scare and I didn't tell anybody. And then we had Thanksgiving and I was still not moving around well, and I do a huge Thanksgiving for about 60 people. And, um, I was moving around like I was definitely hurt, and I had people genuinely angry with me because I never gave them the opportunity to show up.

Wow.

And that was something I took from them. And that's something that in my personal life I've, I've absolutely looked at. And as I've built this, this really amazing group of people who, who I know will show up, but I also know I owe it to them to allow them to, just in the same way I would show up for them.

That's powerful. Like one of my mentors says, right, your network is your net worth. That's powerful. So what do you think is the secret of your success? You've done very well in uniform, even though you were one of the few females in the community in cyberspace, like we talked, being a consultant, you've really led at the highest level. Why, why do you think you are so successful?

Authenticity. Um, as you saw with the tomahawk, you get what I don't hide who I am.

Yes.

Um, no, it's, it's— I will follow orders. I know how to be a good soldier, but I will let you know what I think about them first if that's the role. Um, so if you, you know, I was early on in my career, I was a subject matter expert, um, on GFEBs, the Army's Financial Accounting System. And largest SAP implementation in the world. I was the functional design lead, so I got all the problem children, right? I got foreign military sales because that doesn't always make a whole lot of financial flow workflow sense. I got the National Guard, and then I got the deployment company. And you know, you can't go get 3 quotes when you've got a unit walking out with $50 grand in cash in case they accidentally hurt something, right? Like, there's a lot of things where these don't fit. So instead of turning around and trying to throw the process out because it doesn't fit, you start thinking, or trying to tell somebody who can't do their job in the process, right? There were plenty of people who said, "Oh no, no, this is how it's been done." That's never an answer. But if you can turn around and give people the safety to come in and say, "Look, this is the problem we're having." I think these 3 things could help. And you've given them a safe space to solve a problem and to raise one. And you've grown them as an individual and as a professional. And so, you know, the earlier comment on truth and safety is very much— that's how anybody grows. If you're afraid to knock on someone's door, then that is a scary place to be. And that's when you're not going to knock on the door and you're not going to raise problem. And that's where we find holes in the system.

Powerful. So what are you learning right now? I know leaders are learners. What you're learning lately?

I am learning the balance on the consulting side to where I've had teams to— I have no problem rolling up my sleeves. But when you've had teams who are better at that than you are, I am not the best writer in the world.

Yes.

I know that about myself. People do it better, they do it faster. I will absolutely edit and help bring in the ideas and roll up my sleeves and do the reviews, but somebody's gonna write faster. And one of the interesting things we're seeing right now with AI is that that's picking up some of that. But somebody knowledgeable has to be willing to go through and shred it as well.

Yes.

And make sure that it's right. So doing kind of doing the whole end-to-end process is very different than what you do in a large organization with big teams and everything else. So that's been a little grounding, but enjoyable.

Yes.

I've been doing a lot of overseas stuff. So that's always fun too, because I love to Wow, that's really, really cool.

I mean, your life is really full of adventure, just as I can prove just by this picture. This is scaring me to death just to look at it. Wow. It's really awesome.

So jumping off the cliff was the fun part.

Wow.

That's just incredible. I don't think I will ever try that. Not for me. So let me ask you this. If you could choose 3 people to have dinner with, they could be alive, dead, or even mythical figure. Who would you choose and why?

Mm, 3 people to have dinner with. I would love to have dinner with Churchill.

Winston Churchill.

Um, absolutely. I think, um, because he refused to buckle to political pressures and he drove things because he knew they were right, and he empowered people who most people had like kind of, they were definitely their out-of-the-box thinkers, right? Um, he, he figured out how to let a hammer be a hammer and that not everything needs a hammer. So, um, he would be one. I would love, love to sit down and have, um, dinner with actually the gentleman over your shoulder.

Yes.

You know, Colin Powell would be such an easy one. And then I think for the last one, I think I'd love to hear the philosophies of Genghis Khan.

That's interesting historical character. Yeah, probably got some stories to say.

I mean, I just, I think I would love to understand the empire building and which parts mattered and which parts didn't.

And yeah, That's interesting.

I would love to see one of those figures look at how people have portrayed them and be like, eh, is it, is it not? I think that could be fun.

True. Yeah. I think it was on two days ago, I interviewed someone and they said, uh, Alexander the Great. It's another one of those empire building leaders who really changed the course of history. It's pretty amazing. Wow. Okay. So, uh, if you had to recommend a book, because we do read a lot here, which book would you recommend?

So one of my favorite books is actually called Range by David Epstein. Um, it resonates with me because it's why generalists flourish in a specialized world.

Wow.

And it really talks about how that, those, that diversified skill set can come in to solve a specific problem.

Wow, that is powerful. Range, I got it here. Uh, Why Generalists Triumph in a Specialized World. David Epstein. Wow, that is— thank you, thank you so much. And is there maybe a song or a book or even a movie that would be your life's theme or anthem?

Oh, you know, I think this is going to be really funny, and it's meant to be. This is not a serious one, but I think We Didn't Start the Fire would be a great one. That one resonates. I was in military boarding school when I was in high school, and the local school had blamed us for a fire that they had set.

Oh no.

And so the school's motto was, "We didn't set the fire." And what was interesting about it is they got— that class got blamed for so many things they didn't do. Wow. And I know they didn't do them because we did some of them.

Yes.

But they got blamed for everything. And I think that's where, as a leader, you don't have to necessarily— you have to stoke the fire.

Yes.

And you have to make sure it's a clean fire and you have to make sure it burns, but you don't necessarily have to start it. And if you do, you don't need napalm to do it.

Wow.

Thank you for sharing that. So we are getting toward the end, but let me ask you this. If you had one and only one day to live, what would you have liked your final contribution to be?

Um, I would love to be able to do a data dump of everything in my head and just hand it to somebody. Um, you know, I've— most of the lessons I've learned have been either the hard way or they have been in an abstract or abnormal way. And I think that they're very applicable, um, across the board. I have an amazing daughter who, you know, she's an Olympic hopeful. She lives up in Vermont. She's training. And when she was little, I had to tell her— I was like, I don't need you to know who you want to— what you want to be when you grow up. I, I need you to leave as many pathways open as possible. Um, they'll open and close themselves, things like that. I think we're at a point culturally and societally where we need to hear that, you know. We've got, we've got this pull on everybody needs to go to college, or now there's an undercurrent of vocational education's okay, and really it turns into find something you're passionate. So I would, I would love to take some of that and make those applicable and available.

Wow.

Which things that this podcast do. So thank you for the opportunity.

Absolutely. So privileged for you to be— actually, you made me think because you've also spoken about a future role maybe in diplomacy or maybe in ambassadorship, which I think would be really cool. But what leadership gaps do you see right now globally that prepared leaders must kind of step into?

Well, I think I think, A, if you've— anything in the US government, if you've ever looked at the Plum Book and you see how many vacancies there are, there is always, always a lot of openings. And so finding the right people and the right pathways to get through to those things, those are part of it. For me, I do believe that I would like to do something international at some point. I don't think I'm there. I don't think I'm ready for that yet. I think I'm still building and really enjoying, um, kind of enriching the space here. And but someday, someday that would be a, a thing. But I do think there was a really interesting, um, video I watched on how we're not going to have imperialism, like we're not going to have the giant, uh, national empires again, the US will probably be the last one, um, just because we're such an interconnected world anymore. You don't have the ability to, to sequester off with either— you know, you build around water and places that give you security and things, and then you put oceans around it, and that's kind of play the game Risk, right? We're getting away from that because the world is so connected and so easy, easy to traverse it.

At this point.

Um, so I think, I think global thought at some point is something that we're going to have to transition into.

That is, uh, quite insightful because in many ways I think history kind of repeats itself, but the change— the world has really changed at an exponential rate. Uh, I am really glad that I'm alive today, not 400 years ago, but just in the last 100 years it's really Amazing what technology has really done to bring us, all of us, close and really got rid of the distance. It's incredible. Wow. But so if you had like a magic wand or something and you could solve any problems at all, when you wake up tomorrow morning, what is the first problem you would like to solve?

Food security. You know, I mean, you just, if your basic needs aren't met, then, uh, then it's really hard to focus on anything else. It's really hard to make a right choice when you don't know where a meal's coming from. Um, that's really one of the things that I find very inspirational about the people who do come from, like, I, I did not come from comfortable circumstances. But there are certainly people who've had it significantly worse and you watch them rise. And what's exceptional about that is that they found their way, um, when most people would have been polarized and just, and just frozen by the fact that they didn't know where a meal was coming from. Um, so those people who, who step out or rise and are able to lead with integrity.

Yes.

I know quite a few CIOs and CISOs. None of us have an easy life.

Yes.

Um, but I think food security would change the world.

Yeah. And I'm really perplexed. Now, America, definitely the wealthiest nation in the world, just was it a couple of months ago, like more than 40 million of our fellow citizens rely on food stamps, and if they don't have it, they won't be able to eat. It's like including children. It just doesn't make any sense at all.

Wow.

Incredible.

Well, our food costs are through the roof as well. No, it's a difficult problem and it doesn't matter where in the world you're at, it exists. And that's— so if I could change anything in the world, I think that would have the biggest trickle-down effect or trickle-up effect. Yeah, because if you have food you probably— or if you have food security, you probably have security on your other basic needs.

True. Yeah, it's another thing. I— it's really a paradox. I live here in Silicon Valley and San Francisco. Now we have billionaires. Maybe— I think we've just got our first trillionaire, Elon Musk. But, uh, so many wealthy people and very smart people too, like the IQ is just off the chart. But we still have homeless people in the valley. It doesn't make any sense at all. How is that possible? In 2025 to have people, for whatever reason, are completely homeless in the wealthiest zip code in the world. It's really heartbreaking. Okay.

So, well, fortunately, I am not a politician, so that is not my area of expertise. But if we need to secure the EBT cards, we can have that conversation.

Definitely. So we are coming toward the end of the podcast. So how can we add value back to you?

I think it's really just reaching out and whether it is to somebody junior, somebody you know who's a colleague, another veteran, just be there for somebody and be that safe space.

Wow.

So I think those are the easiest things that are the call to action that anybody can do. And for those of you who are interested about that tomahawk steak, come to the Wallo.

We'll have a good time.

Wonderful. Well, thank you so much for your time, Anna. So let me ask you maybe what I believe is one of the most important questions I ask. If you could go back and give a piece of advice to your 17-year-old self standing at the edge of this incredible career you've had in the military, consulting, and cybersecurity, what would you say to 17-year-old Anna?

Oh gosh, 17-year-old Anna was angry. I think I would just tell myself to breathe.

Just breathe. Powerful.

You know, the world feels really hard sometimes. And just breathe.

Well, you've been such an inspiration and you are so resilient, really a role model for everybody to follow. It's really incredible. So to end, we're going to end in a couple of minutes. Let's do this lightning round. Rapid fire. Don't take too long to think. But what is one word that comes to mind that defines great leadership?

Honest.

Okay. Morning routine or practice that keeps you grounded?

I do— I have an electric toothbrush. I do squats while I brush my teeth because I'm a captive audience and I'm like, okay, I've got 3 minutes where I gotta do something.

Amazing. Okay. A book or a quote that changed your life?

Well-behaved women rarely make history. Wow.

Okay, who inspired you the most today?

Who inspired me the most today?

My daughter.

She, um, she's— I've never seen anybody so committed to the next 3 Olympics. Um, so she's a rower. She's up there just getting it.

What's the leadership habit you refuse to compromise on? Integrity. And what is the question every leader should ask themselves frequently?

Would I want to work for me?

Would I want to work for myself? Great question. So what did you want to do when you were a kid?

When I was a kid, I actually was failure to thrive and I wasn't supposed to live, so I didn't really see a lot of future, but I was very driven to go into the military.

Wow. And you did just that. Congratulations. Wow. That's—

I thought I'd be a lifer, but then I had my daughter and that changed. But thank you. And thank you for your services.

Yeah, I guess we, we had something similar in that because when I was a kid, I was sick all the time. And because I was able to survive, I wanted to become a military doctor because it was a military doctor who saved my life. Now I ended up joining the Navy and I'm not a doctor now, I'm a technologist. But that was what I was thinking. Wow. Thank you for sharing that. So what are 3 adjectives describing you as a child?

Tenacious, obnoxious, angry.

Okay. As an adult?

Still tenacious, gracious, and powerful.

All right, the very last question, and this is it, because I've already asked you, right? Is there a question I should have asked you that I didn't get to ask. Anything else you wanted to share before we end the show?

No, no. I think one of the really beautiful things about being a leader is you can be strong and kind.

Yes, strong and kind.

And I think we've kind of covered that.

Yes, that is so powerful. Really, there is no reason not to be unkind, is there?

Wow. You know, it's come through cycles, right? It used to be when we were having that glass ceiling conversation that kindness was weakness.

I am—

you'd asked earlier about why I am not nice. I am not nice in any way, shape, or form, but I am kind. Yes. And I do think those words are very different. So I think as we look at all of those elements, like, I think it's important to say, you know what, I can be strong and be firm. I can be a hard— I can be very hard-edged. And still be kind. And I think we've got some pretty amazing leaders that embody that. I'm very excited about that.

You've really given us a lot to think about. Thank you so much for being one of our master teachers today. The very last question, and this is it: What is one word that represents our shared experience on this podcast today? One word.

Leadership.

Thank you so much, and I'm so grateful. Everybody, Anna Willer. Thanks again, really appreciate that.

Thank you, thank you for having me.

Appreciate that. All right everybody, this is, uh, the last, uh, regular podcast for today. This was, uh, Season 5, Episode 13, if you can believe that. We are only on January 8th today, but, uh, really, really grateful to Anna Wheeler. So I want everybody to please follow her on, uh, LinkedIn, uh, like I have, uh, uh, shown, uh, before. Her LinkedIn address. Uh, wow, I've had quite a, quite a few people here. So here we go, Anna Wheeler-Leydos. So we are really grateful for that. So right after you, I guess in about 20 minutes, I will have my special edition podcast about the Book of Proverbs. Again, this is not a religious podcast, but it's about ancient wisdom mentoring from the Book of Proverbs. We're going to be focusing on ancient wisdom and leadership lessons from the Book of Proverbs. Today is January 8th, so we're going to read Proverbs chapter 8. We're going to do Proverbs chapter 9 tomorrow, and then at the end of the month, on the 31st, we will read all 31 chapters. It's something I started doing when I was about 12, 13 years old. Every year I read the Book of Proverbs in January, and then when I got married, I did that with my wife. So this is the first time I am taking this public. So I hope you can join and provide your insight as well. And then on Sunday, I will have the pleasure to speak to another cybersecurity leader and a female as well, Daya Ramesh, cybersecurity leader, founder, operator, and a mentor. We're gonna be talking about cybersecurity being existential. I mean, I'm really excited when I see more and more women getting into the field of cybersecurity because when I started this about, what, 15, 20 years ago, it was mostly male and mostly white, and it's really good to see the diversity in leadership in this special field. And then the following week, I believe on Wednesday, I will have the pleasure to speak to Lisa Fan. She's a mentoring architect. She wrote two bestselling books on mentorship, The Mentor's Guide and Bridging Differences for Better Mentoring. She also has a TEDx talk about mentorship, I think more than a Million people have watched that. And on the same day, I will be speaking to Commander Erika Dobbs. Like me, she joined the Navy as a seaman recruit, lowest rank in the military, and she retired as a commander, O-5, only 2 promotions away from being a flag officer. And she's now a tech CEO. So we're gonna be talking about seaman recruit to Navy commander turned CEO. You don't want to miss this. All right, that's all I have for today. And again, the books that, uh, And I recommend it to ranch— Why Generalists Triumph in a Specialized World by David Epstein. Uh, definitely I want to add that to your bookshelf. Okay, this is it for now. Thank you so much for watching. And for those of you who can, I see you in about, uh, what, uh, 30 minutes or so for, uh, Proverbs, uh, chapter 8. Again, ancient wisdom and leadership lesson from the book of Proverbs. All right, see you later. Bye.

Thank you for tuning in to the Leadership and Success Podcast with your host, Coach BZ. If today's episode added value to your leadership journey, be sure to subscribe, share, and join us again for more wisdom nuggets on how to lead better and achieve greater success. Remember, leadership is the most critical skill of our time. The world will always need leaders to inspire others, drive innovation, and execute meaningful strategy. So why not count yourself among the bold leaders shaping the 21st century? Until next time, stay inspired, stay committed, and keep leading with excellence.