Artificial Intelligence Expert Talks Social Intelligence Strategies
In this episode of Bold Encounters, Mark Cook presents his interview with Diana Kelly. Diana shares her professional journey, starting with being recruited by Microsoft while working at IBM. She was initially hired for her expertise in application security and later expanded her role to become the global Executive Security Advisor. Diana emphasizes the importance of focusing on the team you work with within a large organization to make a significant impact.
Diana speaks about her experience and career growth within Microsoft, acknowledging the scale of the company and the unique opportunities it offers. We were curious about her insights gained from navigating her companies environment, including interactions with colleagues and team. She told us about obstacles and challenges she has faced in their career, emphasizing the presence of opposition in life. We discussed Diana’s entry point into Microsoft and Diana gives examples of collaborating with the Consulting Group at IBM.
Diana believes that leadership starts with individuals themselves and then extends to their team objectives, mission, and vision for their firm’s ecosystem. Diana says she guards against any intention to dismiss or discourage anyone. Rather, she aims to present an encouraging, realistic perspective.
Diana believes that leadership starts with individuals themselves and then extends to their team objectives, mission, and vision for their firm’s ecosystem. Diana says she guards against any intention to dismiss or discourage anyone. Rather, she aims to present an encouraging, realistic perspective.
If you or another leader is finalizing plans for a Fall retreat or a 2024 kickoff, Mark Cook energizes audiences and groups. He gets leaders unstuck and thriving with their teams. Mark also creates "Proactive Referrals Programs" for Sales and Marketing meetings. Reach Mark at: Mark@WindfallPartners.com.
“Oftentimes,” Diana says. “People find themselves feeling stuck in their current circumstances, unsure of where they want to go or what they want to pursue. In such instances, it becomes imperative to reflect upon one's true desires without judgment.”
“It doesn't work like that; not at all,” Carolina Doldán, master communicator, said of typical c-suite messages. “If we have the values hanging in the wall, it's not going to do anything. We have a simple strategy that has a couple of steps. First, you have to make people part of that strategy…”
“It doesn't work like that; not at all,” Carolina Doldán, master communicator, said of typical c-suite messages. “If we have the values hanging in the wall, it's not going to do anything. We have a simple strategy that has a couple of steps. First, you have to make people part of that strategy…”
In my own career, I have experienced various roles and acquired expertise in different facets of security technology. One consistent factor that has fueled my journey is the exhilaration of acquiring new knowledge and then sharing it with others, ensuring responsible and ethical utilization.
For instance, during the early days of widespread Wi-Fi adoption, countless organizations struggled with its implementation. Recognizing this need, I immersed myself in understanding the intricacies of Wi-Fi technology. Consequently, I had the privilege of delivering numerous talks and conducting classes to aid businesses in effectively leveraging Wi-Fi while upholding security measures.
The common thread throughout this experience was the sheer delight I derived from the learning process itself, which fueled my energy and passion for helping others navigate the realm of technology Moreover, when you pursue a path driven by passion, your performance tends to excel naturally.
By immersing yourself in something you genuinely love, you are more likely to devote yourself wholeheartedly and achieve remarkable results.
In contrast, many individuals tend to settle for mediocrity or even opt for minimal effort when they lack enthusiasm for their work. Unfortunately, certain companies inadvertently foster this mindset. However, it is crucial to seek out a work environment and a role that truly ignites your energy and enthusiasm. This is perhaps the most significant factor in achieving success and fulfillment.
It is essential, to be honest with yourself. If your primary driving force is financial gain, structure your career around that objective. On the other hand, if your inner drive stems from a desire to help others, to make a positive impact in their lives, that is equally commendable. If you find yourself disliking what you do, it becomes exceedingly challenging to excel, and the likelihood of attaining success diminishes.
Acknowledge that while you may dislike your job, the allure of financial reward acts as your passion engine, propelling you forward. However, it remains imperative to identify and nurture that internal engine because, without it, your dedication and presence in your work will likely wane, hindering your chances of success.
“I'd like to emphasize the importance of patience,” Diana said. “Many individuals are aware of what they want to pursue, but the journey to reaching their goals can be arduous. It is essential to grant yourself the gift of patience and allow the necessary time for exploration and self-discovery…
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“Seek out tools and resources that assist you in unraveling your true passions. It can be immensely helpful.”
Remember, the pursuit of passion and the cultivation of patience go hand in hand. Embrace your genuine desires, explore diverse avenues, and invest in self-reflection. Through this journey, you will discover not only the path that ignites your enthusiasm but also the fulfillment and success that come with aligning your career with your true passions.
Indeed, patience is a virtue that holds great significance in various aspects of life. I often use the analogy of driving to an unfamiliar destination to illustrate its importance. The first time you navigate the route, it may seem as if the journey stretches on forever. Yet, as you become more familiar with the path and traverse it repeatedly, time appears to contract, and the journey feels shorter. Similarly, when we find ourselves waiting for something, time can adopt a peculiar quality, elongating in unexpected ways. Patience, therefore, plays a crucial role in maintaining perspective and persevering through moments that may seem interminable.
Reflecting on the past, we often come to realize the profound impact that patience can have on our lives. It is amazing how the once seemingly endless six months of job searching can now be seen as a fleeting moment in retrospect. This retrospection serves as a powerful reminder of the value of embracing patience and trusting that the desired outcome will manifest in due time.
The path to our goals is rarely straightforward, often filled with unexpected challenges. Patience becomes our greatest ally during these times, enabling us to navigate obstacles, stay resilient, and grow. Many accomplished individuals faced setbacks and uncertainty but persevered with unwavering patience until they achieved their dreams. Patience is an active force that allows us to appreciate the journey, embrace lessons, and foster personal growth.
Diana describes the process as a series of steps. The first step is negotiating how you can contribute best and seeking feedback to ensure that you align with the expectations and needs of the people you work with. By proving your value and becoming part of the core group, you can move on to the second step.
The second step involves recognizing larger missions or inspirations that require the collaboration of multiple teams to accomplish within a certain timeframe, usually one to three years. Diana suggests seizing the opportunity to support and contribute to these cross-functional initiatives, demonstrating your ability to work effectively within a larger set of teams as an individual team member. Through networking, idea sharing, and career growth, you can eventually find your way to higher organizational levels and other opportunities.
Regarding approaching a new relationship with a stranger, Diana doesn't focus on the logistics of communication channels but rather on her mindset. She acknowledges that at the beginning, there may be some uncertainty and unfamiliarity. However, she maintains an open and receptive mindset, being curious about the other person's perspective, ideas, and expertise. By approaching the relationship with genuine interest and a willingness to learn and collaborate, she aims to build a foundation of trust and mutual understanding when meeting someone new.
Diana focuses on understanding others’ needs and finding ways she can contribute to help fulfill those needs. She believes in approaching relationships with a mutually beneficial mindset. Sometimes the help she provides is direct, such as offering assistance with tasks or projects. Other times, it may involve offering advice or helping individuals reframe their perspectives.
Diana emphasizes the importance of connections and networking. She mentions instances where people reach out asking for help, such as finding a candidate for a job or a speaker for an engagement. Instead of dismissing such requests, she suggests considering how you can be of assistance. It's not just about being busy but rather thinking about what you can do to help them. This help can extend beyond direct assistance and include indirect or connective help, where you leverage your network and connections to provide valuable resources or introductions.
Diana also highlights the value of human connection in contrast to simply sharing articles or information. She emphasizes that knowing people and being able to connect individuals who can help each other is one of the most valuable contributions one can make.
Overall, Diana's advice revolves around understanding others' needs, finding ways to contribute and help, and leveraging connections and networking to provide meaningful assistance.
When interacting within people’s own team or with their immediate superiors, there can be consequences and potential impacts on one’s job outcome and success within the company. However, when someone like Diana Kelly from another team approaches your team and offers to be a sounding board or a source of support, there is a sense of safety and freedom in the conversation. It becomes a "freebie" where they can have open and honest discussions without fear of negative repercussions. This allows for more authentic and candid exchanges, fostering a trusting and constructive environment for collaboration.
Diana reflects on the importance of asking questions, particularly in the role as a mentor. people mention going through a Master Mentor program and learning the significance of asking questions as a way to create a safe space for open discussion. Merely asking a question can help remove mental blockages and allow people to see things in a new light. The power of questioning lies in its ability to open up new perspectives and facilitate deeper thinking.
The greats mention the concept of the "five whys" technique, which encourages asking "why" repeatedly to uncover underlying causes and understand the impacts. However, Mark and Diana express that getting to exactly five "whys" may not always be necessary or practical. Instead, the focus should be on going beyond surface-level responses to, at least, three levels deep. Call on curiosity to help you dig to a level of abstraction that prompts a much deeper understanding. That’s the goal. Break away from self-centered, conventional thinking and embrace out-of-the-box other orientation and ideas.
An individual who feels the importance of exploring the spirit of questioning rather than getting caught up in strict adherence to a specific number of "whys" usually has a better solution. The ultimate aim is to encourage critical thinking and broaden perspectives to foster innovative and creative solutions.
The acknowledgment that many individuals tend to focus solely on their tasks and what they can gain from others, without actively engaging in meaningful questioning or relationships is discussed. It is noted that some companies and roles may reinforce this inward, reactive mindset, where employees are expected to perform specific tasks without much room for questioning or exploration. However, it is emphasized that even in such situations, it is still beneficial to maintain a questioning mindset.
Diana shares their own experience of transitioning from a network administrator to a security professional. Diana shares a time when her network was attacked, which made the firm realize the importance of asking questions. Despite being overloaded with work and feeling rushed, the security breach served as a wake-up call, highlighting the gaps in their understanding of network security. This experience prompted the team to shift their perspectives and seek a deeper and broader understanding of the underlying principles, leading them to transition into the field of advanced cybersecurity.
The story underscores the value of questioning and the potential consequences of neglecting it, in favor of an “I know already” mindset, especially in high-pressure situations. This serves as a reminder that actively seeking knowledge and understanding can be crucial in overcoming challenges and seeking a deeper understanding of one’s field. Questioning is a valuable learning tool that can lead to personal and professional growth.
The conversation takes a broader turn, discussing the significance of being genuinely interested in other people and caring about their well-being. It is acknowledged that when one's focus shifts from being solely task-oriented to genuinely connecting with and caring for others, life becomes more fulfilling and success becomes more attainable. Even in the midst of busy or mundane tasks, taking the time to be curious about others and showing empathy can greatly improve relationships and overall satisfaction.
they're stressed out. And you have an opportunity to provide value, to share knowledge, and to make their lives a little bit better, a little bit easier.
When presenting, shift your focus from yourself to the audience. It takes the pressure off. You're there to serve them, to help them, and to share your expertise. And even if you don't have all the answers, it's okay. You can acknowledge that and offer to follow up or provide resources later. People appreciate authenticity and genuine efforts to assist them.
Carolina Doldán: https://www.wearechange.agency/about.html
Diana's LinkedIn Link:
Additionally, it's important to remember that everyone has their own unique knowledge and expertise. No one expects you to know everything, especially in a technical field where there are constantly evolving developments. Embracing the fact that you may not have all the answers and being open to learning from others actually demonstrates humility and a growth mindset.
So, in summary, acknowledging that some level of fear is normal, shifting the focus from yourself to the audience, and embracing the opportunity to provide value and help others can help alleviate the anxiety and make public speaking in a technical field a more rewarding experience. I can relate to that. There was a time in my career when things became challenging and it felt like I hit a roadblock. It happened during a period of economic downturn and uncertainty in the industry. Opportunities were scarce, and I started questioning my choices and wondering if I had made the right career decisions.
During that time, I received conflicting advice from different people. Some suggested that I should completely change my career path and explore new opportunities, while others advised me to stick with what I was doing and wait for the situation to improve. It was difficult to navigate through the uncertainty and make the right decision.
In those moments, it's essential to take a step back, evaluate your options, and reflect on your passion and long-term goals. It's important to gather information, seek guidance from trusted mentors or peers, and weigh the pros and cons of different paths. Ultimately, I realized that setbacks and challenges are a part of any journey, and it's how we respond to them that truly matters.
I decided to persevere and stay committed to my chosen path, while also exploring new opportunities that aligned with my skills and interests. It required patience, resilience, and continuous learning. Over time, the industry started to recover, new doors opened, and I was able to navigate through the difficult period and continue moving forward in my career.
The experience I had taught me valuable lessons about adaptability, staying true to my passion, and maintaining a growth mindset in the face of challenges. It is natural to encounter obstacles, but by demonstrating determination and a willingness to learn and grow, it becomes possible to overcome them and discover new avenues for success. Throughout this journey, I have often received conflicting advice, such as being told to focus more on technical skills or leadership qualities. It's important to remember that opinions and criticisms are inevitable, and there will always be someone ready to question your choices. Therefore, it is advisable to take such feedback with a grain of salt and carefully consider your own aspirations.
Diana and team strive to remain prepared for future opportunities, both physically and mentally. This involves taking care of her health, ensuring sufficient sleep, regular exercise, and a balanced diet. Although it may sound cliché, these practices contribute to overall well-being and readiness to seize future prospects.
Additionally, it is crucial to continue learning and honing skills in your chosen field, whether through reading, online courses, or consistent writing practice.
Lastly, maintaining an open network is invaluable for encountering new opportunities and job prospects. In times of adversity, it is essential to acknowledge the difficulty while avoiding self-criticism. Instead, focus on building resilience and preparing yourself for the future, as self-care—both physically and emotionally—is of utmost importance.
By prioritizing your well-being, you enhance your ability to move forward mentally and physically. During challenging moments, the role that other people play in Diana’s life is significant and impactful. Diana approaches it by seeking good support and listening to valuable advice.
Mentors can provide guidance and support by asking insightful questions and simply being present. Their presence alone can remind me that I am valued and worthy. It is common to become consumed by our own thoughts and concerns, but it is through the help of friends, mentors, and guides that I am able to regain perspective. Colleagues reminded Diana that her worth extends beyond the current circumstances and setbacks, such as market downturns or job failures. In the span of a 40-50 year career, most individuals will encounter one or two job-related challenges, but it is essential to remember that our contributions and identities are much more comprehensive. Friends, colleagues, and mentors have played a crucial role in helping Diana maintain this broader perspective. They remind Diana of her totality and encourage her to keep this in mind during difficult times.
If you're aiming to surpass the status quo and achieve extraordinary work, here are one to three specific pieces of advice that Diana would recommend:
Set audacious goals: Dare to dream big and set ambitious goals for yourself. Think beyond the conventional and envision what extraordinary achievements you want to accomplish. By setting audacious goals, you challenge yourself to think innovatively and strive for greatness.
Cultivate a growth mindset: Embrace a growth mindset that believes in the power of continuous learning, improvement, and resilience. See challenges as opportunities for growth rather than setbacks. Be open to acquiring new skills, seeking knowledge, and expanding your horizons. Embrace a mindset that embraces lifelong learning and embraces new experiences.
Build a strong network and seek mentors: Surround yourself with a supportive and inspiring network of individuals. Seek mentors who have achieved remarkable success in your field of interest and learn from their experiences. Their guidance, insights, and advice can provide valuable perspectives and propel you toward extraordinary work.
These pieces of advice emphasize the importance of pushing boundaries, adopting a growth mindset, and leveraging the power of connections and mentorship. Remember, achieving extraordinary work requires a combination of ambition, continuous self-improvement, and the support of others.
When individuals approach Diana expressing their interest in pursuing a career in cybersecurity, compliance, or related fields, she often emphasizes the importance of introspection.
“I urge them to delve deeper and understand the genuine motivations behind their aspirations,” Diana says. “It is essential to identify the driving force behind others desire and truly comprehend why they wish to embark on another particular path.”
“Frequently,” Diana continues. “I encounter individuals who are drawn to the field of cybersecurity solely due to the perceived financial rewards it offers.”
However, if monetary gain is the sole motivation for venturing into the domain, it is worth noting that there are other vocations that may prove to be more financially lucrative. Thus, it is crucial to evaluate whether cybersecurity aligns with their true ambitions and aspirations.
Diana is actively involved in the Cyber Future Foundation and their Cyber Future Dialogue in Davos, where they plan to have both in-person and virtual components to ensure global participation. When asked about the reengagement of people after a period of physical distancing, Diana expresses a positive sentiment, highlighting the joy of reconnecting with colleagues and the unique energy and genuine connections that occur in face-to-face meetings.
Diana believes that audiences in 2022 were more receptive and kinder, possibly due to the collective relief of being able to attend conferences again.
Mark Cook noted he co-authored a book on tasks and leadership, but later discovered the importance of “bold encounters”—the human side of effectiveness. And nothing great happens without other people. Nothing. Period. He talked of his continued experiences building relationships and engaging in conversations with new people, through interviews with CEOs.
Diana Kelly is an influential figure in the events industry who is passionate about public speaking to correct inaccuracies and share practical knowledge. She noticed discrepancies in information provided by other speakers, which motivated her to help others avoid similar challenges. Despite the recent dominance of virtual conferences, Diana firmly believes that the return of in-person or hybrid events in 2023 offers unmatched benefits. Her commitment to accuracy and practical wisdom has established her as a trusted authority, empowering professionals to navigate the industry with confidence.
Diana Kelly's experiences in the events industry, her motivations for public speaking, the evolving nature of conferences, and the significance of human connections in both professional and personal settings. The discussed passage highlights the importance of incorporating the human side into professional and personal tasks to achieve great outcomes. The analogy of a chocolate-covered shell and peanuts is used to describe the task itself, emphasizing that it doesn't have to be painful but can be enjoyable.
The reference to gamification and the game "Sims" illustrates how people can find pleasure in simulated activities that they may not engage in in the real world. The speaker reflects on the value of the human side, especially in the context of conferences and gatherings, where people now appreciate the opportunity to be together more than ever.
The conversation then shifts to the topic of the coexistence between a cat and a German Shepherd in the speaker's household. The cat is described as being in charge, capable of asserting dominance over the dogs, despite their size difference. The speaker expresses fascination with the minds of dogs and cats and mentions the emerging field of augmented interspecies communication, which explores how animals can communicate with humans using buttons.
Diana Kelly expresses her curiosity and fascination with understanding what goes on in her dog's mind. She humorously envisions a hypothetical scenario in the afterlife where she would request a brief explanation of her dog's thoughts. Diana describes the experience of interacting with dogs as a complex psychological puzzle, constantly trying to decipher their behavior.
Diana mentions the field of augmented interspecies communication (AIC) and recommends exploring it further. Diana shares an example from a veterinarian's work, where a cat's favorite button is "mad," indicating that cats may have their own unique ways of expressing emotions. She finds it intriguing how animals can quickly transition from being upset to being calm again, highlighting the complexity of their awareness and emotional states.
The conversation is joyful. The shared advice resonates and benefits others. Congratulations are extended for volunteer work, demonstrating patience and making a positive impact. The gratitude for the connection and anticipation of future interactions is expressed. The power of patience is emphasized, wishing continued success and inspiring others to embrace it.
(watch episode at: MarkSpencerCook.com/Podcast, co
Welcome! Hello, thanks so much for having me here, Mark. Tell me a little bit about your work therein the events world and being a board member and what you do.
Yeah, so the public speaking started because I was going to a lot of conferences very early in my career. I've been in this field for over 30 years now, so we're going back into the Dinosaur age of technology. But I would go to conferences and realize that some of the stuff that the speakers were saying wasn't entirely accurate or it wasn't the kind of information I, as a practitioner, really felt I needed. So I had this drive to get up because there were so many lessons I'd learned the hard way, and I wanted other people to not have to go through the hard way. So that's why I started submitting talks because I wanted to share knowledge with others. And decades later, I'm still doing it. As you probably know, a lot of them have been virtual, at least for 2020 and 2021. We started getting back in 2022, and I hope that we're going to be fully back in person in 2023 or at least hybrid-like.
One of the boards I'm on is Cyber Future Foundation, and we have the Cyber Future Dialogue every January in Davos, and I was just on a prep call for that. We're not only going to have some of the organization there in person with leaders, but to have an in-person dialogue, we're also doing a virtual portion so that we can bring the global community together, people that can't get to Davos next week. We still want to have that conversation with them. So for that, I like what's happening with that hybrid approach.
Yeah, digging a little bit into the human part of that, like what is your observation and getting reengaged with over the past couple of years with people regathering after a time that seemed so long ago, now that we didn't even want to be by each other? What is the progression of humans getting together again and the feeling about that in your experience? I don't know what you're feeling, but I think I've had some of the best hugs in the last few months of my entire life. People that I'd worked with, that we generally would see each other a few times a year at this conference or that conference, hadn't seen each other in a couple of years, and just this wonderful reconnected Ness to be together. Yes, we can share information virtually, and certainly if we can't be in person, virtual is better than nothing. But there is also just this genuine energy between human beings when they see each other. So that's the biggest thing I've felt, just this understanding of connection and community. And quite frankly, the audiences for speaking in 2022, I felt were a little kinder than audiences in 2019, and I think it's partly Because, instead of feeling like it's one more talk, it's one more conference, many of us were at the conference and feeling like we're back, finally. That says something about the best of us, doesn't it? Don't you think? Yeah, I hope so. I mean, I think that's a recent discovery in my practice, about five years. I mentioned it a lot, so I'll keep it short. But you know, I'm a co-author of a book that talks about tasks, and an Amazon bestseller that talks about tasks. Some of the individual leaders of one of my clients, actually two of my clients, were having a hard time getting them to do tasks, shockingly. And they actually paid me to rediscover, like, what is going on here and why is it so hard? And I said, well, that's just how it is. And they said, "We want you to see for us, you know, what's going on here." And as we dug into it, I redid some of my old interviews. I finished up visiting with about 1,000 CEOs over a couple of years. I found an obvious discovery, which is that the human side—you know, meeting a new person, approaching a conversation on a topic with someone you've never had a topic with—and the human side building the relationship a little deeper, even professionally and personally in an appropriate way, and the human side of paying attention to that part of the task, because nothing great happens alone, is really where the prediction of client outcomes and financial outcomes is. It's the, I call it, the chocolate-covered shell and the peanuts, the task. So, I think that's what you're describing, isn't it? Yeah, I love that, the chocolate-covered shell. Because yeah, you're saying that there's a thing we have to do, but it doesn't have to be painful. It can be actually a wonderful kind of thing. And especially if we're going to go through that chocolate shell to get there, right? Then you kind of get a little anxious for it. It's almost, it touches into gamification. If you think about the Sims, for example, people will spend hours, they'll spend their whole weekend getting their Sims to garden and clean up. And yet, they don't garden and clean up in the real world because it's fun in the Sims game. So yeah, how do we make it fun in our work? How do we gamify or at least engage that sort of part of us, that chocolate coating in our work? And what if a bunch of teenagers were down in my basement, which, you know, they're too old now, but if they were down in the basement doing some Sims, and the communication over their headphones was translated into the old-style computer talk, and all the grammar was cleaned up, and all they could hear was perfect robotic banter, it wouldn't be very interesting. I mean, a big part of that game is nowadays, especially, and as we head into the future where we're going to think we're together, all of a sudden, you know, it's really the human side. And it's just an interesting what I took from what you said is that before we took it for granted, we were the fish in the water. We couldn't see the water. And now that you're coming to these conferences and seeing and organizing people and being part of it yourself, you're seeing that people don't take it for granted. Maybe as much, at least not now. I'm sure we'll start to, but there's this really nice moment right now where everybody is just so grateful to have the opportunity to be together again. Yeah, well, before we dive into more business, let me ask you one of the other things that caught my attention. I got to know you a little bit briefly, practically a whole continent away, was you have that cat in the background, and yet on your LinkedIn, you have a big German Shepherd. Are those two getting along? I'm not a big dog fan, but I said yes to a dog after 27 years, and now he's my best friend because everyone grew up and left, except for my wife, who was very busy. So, you know, tell me about the cat and the German Shepherd, not dog but German Shepherd, how does that work out?
So, this is Katya, and she's about four and a half pounds. There's a slightly larger cat named Voilatomir, and he's somewhere right now, I'm not sure where. And then Nora is the dog behind me on LinkedIn, and her litter mate, who we also adopted, is Nick. Nick's about 70 pounds, Nora's about 60. Again, this is Katya, she's four and a half. How do they get along? She is in charge of this house, she makes the decisions. In fact, the reason that that's there is that she would kick the dogs out of their bed. So, we've got two big dog beds here, we've got them, dog beds and other parts. And if Katya decided she wanted that bed, she would just go, and the dogs have been trained that, look, you're 70 pounds, she's four and a half, you can't react. So, she just, with her paw, dogs get up and move. So, this was actually an attempt to give them a little bit of ability to be in their own beds, to lure her into a Katya-sized bed. That is funny, that's awesome. I think what's really going on there is once they decided they loved each other, they knew they weren't going to kill each other, and so it really comes down to who has the sharper, more sophisticated claw, and that cat does. Yeah, the dynamics are interesting, and I'm actually, I think if I hadn't gone into cyber, I might have gone into some sort of canine-feline ethology studies because I'm fascinated by how their minds work. Oh yeah, so I'm also fascinated by all the AI-C, the augmented interspecies communication work that's going on, and if you follow this, there are people on Instagram, there's a lot of scientists that are starting to study this, but essentially their dogs and cats are communicating with buttons, and there'll be a word, a sound on The button, and they start to communicate with people, so we're getting a bit of insight into how they think or appear to be, right? The research is ongoing, and it's fascinating because I'm pretty confident, looking at that, she knows, she absolutely knows she's in charge, and she kind of walks around the house like that. She knows that she gets to run the rules, which is amazing. Oh yeah, she's wired to be on a pecking order system. She's not like some mystery thing.
Well, I think it's interesting. I think if, hopefully in 40 years or 50 years when I pass to the other side and I wake up and I actually am still me, and my guide is there, I'm going to say, you know, all of this is really important, but I just need... just, just could I just have five minutes, could you just tell me what the heck is going on in my dog's head for a second? Because what in the world is going on? I think I know, and then I don't, and it's... if it really is, every time you go on a walk or interact with them, it's like this psychological Rubik's Cube. It's fascinating.
You might be interested in the AIC work because there is more. I mean, there's a lot of what we think. So, one of the cats, her person is a veterinarian at the Tampa Zoo, and so she's really used to interspecies communication shoots. So, I really enjoy her channel and her work, but her cat's favorite button is "mad." And if you have a cat, you kind of in the back of your head would think if they could learn "mad," that's probably going to be their fear. But she also gets over being mad very quickly, so she'll do "mad" a lot, but then she'll actually narrate "mad" all done. So, you might be... yeah, there's some really fascinating work, and again, there's some stuff that we... you into it if you're with them a lot, and then other things that it's fascinating to kind of get a little bit of a handle, like the "all done." For me, that was a really big eye-opener, that they're aware that they're upset, but they're also aware that it's passed. Interesting. Yeah, I don't know about that.
Okay, so there are a couple of things, and it's been... it's been a couple of weeks since we've talked. I've sent you some emails and things, but let me just... let me just warn you, and I'll ask you a first next-phase question, so I'm really interested in your climb and your ecosystem rise in Microsoft because not a lot of us get to work in, I don't know, I don't know how many people were there at the time, it's probably about 400,000, I would guess. It's certainly not the usual 2,000 employee company that most humans work for or less. So I want to hear a little bit, if you could give us your insights in wandering the halls and getting on the phones and Zooms and arise in a large company like that, beyond even a manager or something. That's one curiosity I have.
Another thing that maybe in the back of your head as we talk is there's probably a time where your career life has slowed down or even been stuck, or you faced a serious obstacle. Life shows opposition in all things, and so most people have that. And if you have not a life history, sort of a thing, but a moment or a single event where we could pick it apart, I'd love to hear about that. But let me ask you, first of all, where did you enter Microsoft back in the day, and then we'll talk about some of your more recent things?
So, I was recruited by Microsoft. I was recruited by... and I was at IBM at the time. And I had been recruited at IBM, so at IBM, the reason they recruited me was that the person who was the hiring manager, Caleb Barlow, saw something I was doing, speaking at the event that I had given on application security. At the time, application security was not as mainstream as it is now, and I was hired in to help with the application security strategy. But then, after I'd done that for a couple of years, they realized that I had a lot more than application security to bring to the table, so I became the global Executive security advisor. And instead of just advising around application security, I advised our largest customers around their entire Security program and also built the research security research publication process. So, you know, I think like when people think about big companies and moving up, two important things I would recommend for them. One is to really focus on the fact that you're working with a team of people. So even though it's a large organization, your team and what you're doing is probably pretty small when you get in. Work that you know to find out what your job is, to orient yourself, figure out where you are, what you can do for that team that you came into. And then once you've really established that you're doing a great job and you're providing a lot of impact with that team, the nice thing about a big company, whether it's IBM or Microsoft, is that once you started doing that, then you can start looking out across that large organization and see what bridges you can build.
So at IBM, for example, I started working with the Consulting Group, the Global Business Consulting Group on energy because they needed to have security knowledge in that team at the time. So that gave me an opportunity to go outside of the group I was in and start contributing to other groups. So look at how you can once you've created impact with your team, because it feels like, "Oh, it's so big," but really the team you're working with, then look for additional impact. Same at Microsoft. I got there and I needed to understand what I needed to do for my role within my organization, and then once I've established and understood that, I started to look out. And I actually, one of the last things I did before I left Microsoft was that I assisted Ann Borrison, who is the person who was leading the Digital Defense report for Microsoft. It was the first year that Microsoft was putting it out. She had been working on other reports at Microsoft. Someone told me, "I said, who's taking over?" It had been a security intelligence report. I said, "Who's taking it over?" Someone told me Ann Borrison. I said, "Ann, I just reached out to Harrison and I helped with the last iteration of this. I helped with it, the similar reported IBM. Can I work with you?" And she said yes, and we actually. Had so this is now three years ago, and a couple of weeks ago, I was on a call with her for another reason, and she brought that up to someone else, and she saw it as, "Oh, the way that she describes it, she's a lovely, lovely, brilliant person, but she's so kind." And she describes it as, she feels that she was so lucky that I reached out to her. But from my perspective, I was crossing an aisle that she was in a different organization. I hadn't met her before; she didn't know me. You know, Microsoft is a big company, so that's what I mean. When you're at a large company, do that with an open heart, see how you can help others once you know what you need to do for your work because any large company is made up of a lot of smaller groups and teams working together. Wow, that's great. I love that. In fact, one of the things that I've noticed is that if you have a leader that wants to know how to lead, you're going to put steps on a path forward, and it's going to be kind of right with an individual themselves first, and then an individual, and then it's going to be a team, and then it's going to be more to a mission level where there are multiple teams, and then it's going to be the ecosystem, including the client base, the target market, and it's going to increase in time.
You know, accomplish great things in five years, but today, what is one person going to do? But the second step of negotiating contributions with the team, you kind of describe that as the first step, and then the second step is once you've really negotiated how you can contribute best and solicited feedback so that you're really hitting the mark with the people that work with you, and you're proving you can be in that a spree to core group, so to speak, then you go past that and you realize that not a mission like an inspiration, which I'm talking about the ones that actually accomplish things, where the best leaders are. When there's something that we're trying to accomplish within two years, there are two, three things we're trying to accomplish, and those are always multi-team targets that we're trying to pursue in a couple of years, one to three years. And you're saying, "Okay, that's your chance, like help over there, cover and move," as Shaka would say. And you know, support them and show that you're bigger in a larger set of teams as an individual team member. And then you're meeting people, contributing, and they're feeding your ideas and career, and you're going to find your way up to the organizational level at some other opportunities. Exactly, is that about right? Yeah, yeah, yeah, that's interesting. I think most people, including me, didn't know that a few years ago, but um, that's very insightful, very insightful. What at the very beginning, when you haven't met him, I'm not looking for the logistics of phone calls, emails, messages, Teams, whatever, but what is your thinking as you're going into a brand new relationship that's not on your team? You know, when you're meeting a stranger, tell me about what's going on in your mind and how you're approaching that. I think about what they might need, and then if there's anything I can contribute to help with those needs. And if that's great, you look for the mutually beneficial approach. So when I'm meeting somebody, I want to understand what it is that they're looking for, what they need, and then how I can help. Sometimes you can directly help, but a lot of people don't realize that you can help in ways that aren't just direct help. You know, like in the case of the Digital Defense report, I could directly help. You know, I could listen to what the researchers said, help to write the analysis. But sometimes the way that you help is just, it could be advice. Sometimes people just need to step Back and reframe what they're looking at. Connections and networking are huge. We all forget, how many times have you gotten, "I'm looking for..."? I need to hire in this role. Can you do it? And it's like, "No, right?" Like, how many times do you know anybody that could do that? You know, could you do the speaking engagement? I'm busy. Don't just say, "I'm busy." Think about what, because that help is really... So, what is it that you can do to help them? And it's... It's not just that direct help. There's a lot of indirect and connective help that we can provide, too. Yeah, you know, it's not just emailing an article and saying, "Hey, I thought you'd like this," and then they're so busy, and they have to read another article because you sent it. You're saying you have a human connection, like, "I know people, too," and you don't know some of them, and they could be right to help you. It's really one of the most valuable things. That's really great advice.
The other thing that I heard in that... That's interesting, is that you know, there's another value that's probably hidden in that scenario that you just described, and that is that if I'm in a role, when I interact with my team, it actually affects my job outcome, my success at the company. If I go up to my manager or my matrix manager or something like that, or even a customer, it affects my job. There's consequence to the conversation. But when you have someone like... You have a Diana Kelly coming over from another team and just saying, "Hey, bounce it off me," no consequence. I'm not... It's just you and me, you know? It's kind of a freebie. It's like, let's talk, and nothing bad's going to happen. I'm going to be a little honest if it's between us, and we keep that as free decor, yes, yeah.
And that's, you know, so I do a lot of mentoring, and I also do a lot of practice on how to be a better mentor, and just in going through the Master Mentor program for EWF, and as I was watching these training videos, it's just again and again, ask questions, ask questions. And it was a great reminder that that's true. Sometimes just asking a question is that people being able to feel this is safe. I can talk about it. Isn't it just saying? Something that's this blockage out of our brain, we are able to see it in a new way. You didn't do anything but ask the question, but you opened up a new way of thinking for the person that you were interacting with, and we forget how powerful that can be. Yeah, really powerful. In fact, it gives me a little sting because you know, you always hear the five whys. You got to say why in a different way, what four, and what does that allow you to do? And I don't find that I'm able to get to five. I think it was the Coen brothers that said you got to get to three, three levels of abstraction deep. Like why, what, four, you know, three is plenty. Most people just go one. They just go, "Yes." Yeah, and I agree with you with the 5Y. Sometimes I've seen people try and really adhere to it, it becomes very much letter rather than spirit. The spirit is to not just have a reactive "why" cause, you know, like the spirit is really to think deeply about the whys and what the impacts. But yeah, I've seen people that just really... They get far too into that. It has to be exactly five. No, it has to be to the point where you've gotten a little bit down below just that reactive "why do we do this?" Because we always do it this way. It's the rule, you know, back when I was in the 90s and I was in a big four consulting, you know, the out-of-the-box thinking, right? That's what you want to get to, break out of that box and think a little bit more broadly. And sometimes, it only takes two questions. Yeah, true. But we're sitting here talking like that's the rule, like I said, like most people out there are really just thinking about, "What do I need to do? What's my task? And what can I get out of them?" And there's maybe no questions. Maybe no questions. Yeah, I mean, I do think... I think that there are a lot of people that get into reactive "I have to do this" mode. And let's also not forget that some companies, some rules are a little bit, you know, they're kind of the back old, old reference. But you know, Lucy from "I Love Lucy" on the conveyor belt with the chocolates, you know, that's your job. Just do that, and that's all you do. So, I think that for some people, certainly some of the rules, people earlier in career may be a little like that, where it's like you get, "This is your role. You must do it. You must do it in this way," so you don't have a lot of opportunity to ask questions. But even then, it never hurts to be thinking. I mean, the way that I went from a network admin and CIS admin to a security professional was that my network got attacked, and I realized I hadn't been asking the question, and I was... I was doing the work I'm going to say, I was doing the work of five people. I'll tell you why. It's not a brag, because when I left, they hired five people to replace, so I was, in fact, doing the work of five people. So I was constantly rushed and constantly pressured, and I really didn't feel I had any time to ask why. I just was in a very much "do" mode. But then the network got attacked, and I realized it was because I didn't understand. I knew how to build a great network, but I didn't understand how to secure it. Again, guys, this is early-mid 90s, you know? I wouldn't be bragging. No excuse now, but back then, it was still very, very emerging as a practice. And so I said, "Well, you know, I didn't ask the question, so let me start asking the questions." And I essentially started doing things like threat modeling, you know, like risk analysis of how can this go wrong, how could this be bad. And that, to me, opened up a whole vista of ways to be a much better network person, because if I'm putting out a network, one thing, putting out a secure, robust network is going to be much more beneficial to the company. So I think sometimes we think we don't always have the opportunity to ask the questions, but you always have the opportunity, in your mind at least, to question. And then you may or may not, depending on your current situation and current employer, be able to bring that into your role. Yeah, it's the best learning tool. Going back to Lucy on the conveyor belt line or whatever it was, you know, people have to do tasks, people do things. But whenever you're... What I've found in the past few years, whenever you're heading to another human being, you have to be interested in that. Oh yeah, when there's a break, when there's a moment, you have to be... Your radar has to be to the side while you're plucking the chicken. How are those people doing, rather than me, me, task, task, task, go, go, go? Life just gets so much better, and Success becomes so much more apparent and reachable if your radar is onto other people and you're curious about other people and you care about other people, even if you're plucking chickens, don't you think?
Yeah, I couldn't agree more. I get so many people who ask me how I, you know, am not scared when I do public speaking, especially in a very technical field. Because there's a, I don't know if you get this, but there's a term we use in security that's "stump the chump" because nobody can know everything in technology or security technology. And so it's not uncommon for a speaker to finish a presentation and have somebody come up with a question that's extraordinarily esoteric, very likely the speaker doesn't know. You're up on stage and you're like, "That's fair." And so a lot of people in my field are scared to get up on stage and have that happen to them, or they're just afraid they'll say the wrong thing.
They say, "How do you not get scared?" Two things. One is, of course, you get scared. Everybody gets scared. I still have moments right before I go up on stage doing a keynote. I still think, "You know, I don't want to mess this up." I think if you didn't have some level of fear, then you're not thinking about others enough. But the most important thing is, it's not about you. We think, "Oh, we're up on stage, the spotlight's on us." It is not about you. It's about the people in the audience. You are there for them. It's for their experience, their understanding. And remember that they've got their phones blown up cause they got 80 emails from the boss Saying, "You didn't do this." A dog is sick. A child needs to get to. A child just broke an arm at practice or something, right? They've got all this stuff in their life that's going on. When you're coming up there as the speaker, your job is really, it's not about you being so smart, it's about understanding that they have a very small amount of time. What can you do for them in that amount of time? And one thing is to make them, yes, teach, because most of the time as a speaker, you want the purpose is other people want to get something out of it that they can use somehow, but also for them to feel a little like better entertained at, you know, informed, engaged. That's all about that. So, I find that when people are really nervous about public speaking, if they can just understand it's not about you and being judged, it's about what you give to the audience, then that, I think, changes how a lot of people think about it. Yeah, you know, I do have a little tactic for that. In fact, I just used it the last couple of days. I always get stuffed anyway. You know what's interesting? It goes back to what you said earlier. Whenever you're in a large group and someone throws something out you don't know, I don't table it for after the meeting, I table it for the end of the meeting. I say, "I have a great solution for you, but I want to involve other people, and I want to leave this till the end of the meeting." And at the end of the meeting, I have about three different ways that I put a very speedy, a speed connects in play, where people at the end are going to interact fast and en masse. And one of the most casual ways to do it is if someone asks the esoteric middle or end, wherever it is, at the end, you say, "Now, Jimmy, stand up again. Make him stand up again. He owned it. He's going to have to stand up again. Jimmy, stand up again, everyone. We don't have time to really dig into this. We knew we wouldn't. I don't know, as I mentioned, exactly what to tell him. I gave him my best shot. What I'd like everyone to do, think of your best Answering what he said, your best insights, ideas, and opinions. And please approach Jimmy right after I close in 60 seconds. Thank you for having me, Bob. You know, you have—you don't have a thousand people go to him, but you have 20, and 20 people barrage me. But for Jimmy, just like you said, I don't need to be the one giving him the value if I don't have it. He gets 20 people coming to give him advice, and guess what he thinks about that speech after? He thinks, "Wow, that was really great," just because he got that experience of meeting new people and getting new advice. It had nothing to do with me, but I was the instigator of it because of my so-called network, these strangers in front of me, just like you said earlier about natural interaction with our own network. So anyway, the connective piece, it is true, and I will say outright, I'll say if I genuinely don't know, I have just nothing to, you know, if I know a little bit, I'll say, "This is what I know." But if I just don't know at all, I will say, "I don't know" and ask the audience, "So does anybody else out there know?" Because yes, if there's somebody in the audience that knows, it's an idea, let's bring this knowledge forward. It's about all of us being smarter, it's not about yeah, one after stage, yeah, okay, let's switch gears a little bit. Was there ever a time in your life or your work, um, where you slowed down or something got in your way? It was really difficult to move ahead, still, yes, yeah, there was a time. You know, after that, everything was just so great, guns in the nineties. If you were working in tech in the mid to late '90s, it was crazy. I literally went from one job where they tripled my salary, and then the job after that, they doubled. What? So, I mean, that's how crazy things were. Everybody, and then it all kind of slowed down. There was a big bust, and at the turn of the century, it was a lot harder in security than it had been because of that big technology bust. And I did, I started wondering, "Is this the right career? Where am I going to go? What am I going to do?" You start doubting yourself, "Did I make the wrong decisions?" I always get people give you weird 180 advice. And what I mean by that is somebody gives you the advice that's up here, and then somebody gives you the advice that's like the complete opposite that's down here. "You should be more technical." "You should be more leadership." And I think for me, like, look, that always happens, and somebody's always going to tell you you did the wrong thing. There's, I guarantee you, there's someone out in the world who's ready to tell you all your choices are bad. So yeah, like, take that with a grain of salt and think about what you want to do. And for me, I just try and stay on, be ready the next opportunity will occur. So be ready, try and keep yourself healthy. If you're not sleeping, figure out what you can do to start sleeping, keep exercising, keep eating. I know that sounds sort of like motherhood apple pie kind of stuff, but it's really keep yourself as healthy as you can in those downtimes because that means you'll be much more ready to run when the opportunity comes up. And then also keep yourself ready mentally, so whatever field that you've decided you want to focus on, you can read about it, you can take classes online with that. Make sure that you're still out there and keeping writing practice. And of course, keep your network open too because your network is where you're going to find those great opportunities and jobs. And if you just can stay with that and acknowledge and accept that it's hard when those kinds of downtimes happen, of course it is, but don't beat yourself up, make yourself stronger, and keep yourself ready because I think that's one of the most important things. We tend to have those moments, not take care of ourselves physically and emotionally, and we really need to. It's what we need the most. Yeah, and what role do you think taking care of yourself so you can move forward mentally and physically? Tell me in those moments the role that other people play for you and how you approached it. Good support and sounding worth listening to. That's what we were saying earlier about mentors. Ask good questions. Sometimes just being there and being able to say, "You're okay, you have worth, you have value." It's, we get so stuck in our own Heads up, but my friends have been the ones, mentors, and guides have been the ones that really helped me to remember that it's more than this moment in time and your contributions are broader than just the market having a downturn or if there's a job that has gone wrong, right? Most people have one or two jobs in their career over the 40-50 years of their career that went wrong, but you're more than that, you're the totality, and that's what, for me, friends have really, and colleagues and guides and mentors have really helped me to keep in mind.
Yeah, what do you think? It does get granular, and do not a role play, but give me a script when you're reaching out to someone and you're in a bad situation. The good situations are fairly common, and people are comfortable a little more, but when you're in a rut, what is the dialogue when you reach out to someone and you're leaving a voicemail or talking to them, and how are you asking for help?
So, if it's just a voicemail, I would say, "Look, I'd love some of your time, you know? I wouldn't go into too much detail, just, you know, I'd love some of your time, I'd love to bounce some things off of you." But when you speak with them, I'd be just, I think transparency is great. So, I would say, "Look, I have some things I really want to ask of you, but first, I'd like to know how things are going," and not in that "got to check the box, how are you? Oh, check, I sounded empathetic" way. But genuinely ask how this person is, you clearly respect and care about them because that's why you're connecting to them. So, respect and care about them enough to really want to hear how their world is. You can share about how you are too, but also, as you have that conversation, this kind of beautiful thing will happen, which is that you forget about this pit you've dug for yourself of "I feel like I can't get out of this rut and I'll never go anywhere," and you've reminded yourself that there's so much more to life. And here is this person that you respect and enjoy that's now telling you about their new grandchild or the New boat? They got something about, or that they had a family tragedy, and you're going to... Sometimes that is what you hear, but that really creates the closeness with them, so remind yourselves why you're friends and that that friendship is real, even if it's a work friendship. It's still a real friendship, and your level should be set up front that you were going to ask them. So, after you've had that connection, then say, "Okay, look. I know we don't have a lot of time, don't want to waste your time, but..." And now share with them and be, you know, try to be as precise about it. A lot of us have a lot of extraneous details that we bring in. Try and really streamline that. "I'm in a rut. This is why it's upsetting to me, and this is specifically what I'd like to do because I think it would help me get out of the rut. What do you think?" And then get their input because, remember, you're there to hear from that. So lay it out quickly for them what the problem is, then they'll probably start asking questions and being able to provide more help. And don't be afraid, and don't forget the friendly part at the beginning. It's not, again, it's not a check. It's really a very important human connection part for both of the people in the conversation. I love that, don't forget they're a person, don't forget they have needs, don't checkmark, don't checkbox it. Really care. I think that's people pick up on that. I love that, appreciate that. Okay, one more question before I get to the home stretch. Well, let me ask you. So, let's say they help you and maybe you get a job that's kind of status quo again, or you feel... Or you get a solution to something and so you're kind of in status quo land where most workers and people are. You've done a lot of great things in your career and you're involved with a lot of great things. If you were to give maybe one to three pieces of advice to surpassing that and to getting into the extraordinary work category, what is the most specific set of one to three things that you would recommend to a dear friend? The first thing, and I tell this every time somebody comes to me and says They want to go into cybersecurity or they want to go into compliance or far. Why? But not five of them, not seven of them. Just genuinely, what is it that you want to do and why do you want to do it? Because I often hear people want to go into cyber because they want to earn a ton of money. Which, if that's genuinely the only reason you're going into cyber, there are more lucrative careers. So maybe cyber isn't the right thing for you. And I don't mean that in a dismissive or negative way. It's just a genuine fact. So I think a lot of times people feel like they're stuck, but they are in their status quo. They don't know where else they want to go, but they don't know what else they want to do. So think about what you want to do, and don't judge yourself as you're thinking about that because what you want to do, you can feel it when you start thinking about what it is you genuinely want to do. It may be to make a lot of money. If you feel that, if that's what ignites you, go. That is a wonderful thing. If helping others ignites you, if helping others around a certain thing... Because no matter what it is, and in my career, the reason I've had a lot of different roles and I've been an expert in different parts of security technology is that one of the things that lights me up is learning something new and then being able to help others use it in a responsible and ethical way. So, you know, Wi-Fi, when it was first becoming a big deal, so many companies didn't know how to implement it. So I went deep in there, I gave many talks and classes on it, and the underlying factor was that it lit me up to learn about it. And that meant that my energy went there and my passion went there. And if you follow passion, if you're doing something you're passionate about, you're going to do it really well. And that's going to help you to excel. There were a whole lot of people quitting and just started doing the bare minimum, and some companies almost encouraged that. But find a place and find a role that really gets your energy. I think That's the biggest thing. If you don't love what you're doing, then you're not going to do it well, and you're probably not going to succeed. Some people fail, but you're probably not going to succeed. And it's okay to be honest. If really all you want, if the biggest thing for you is earning a lot of money, focus your career around that. Because then if you say, "I hate this job, but I love this money," then that's going to be your passion engine, like your passion engine. But find that engine because if you don't have that engine inside of you, you're not going to show up, you're not going to be present, and I don't think you're going to succeed. Yeah, that's great advice, thank you. I couldn't agree more. Actually, there's another one that goes with it, and that's patience. You know, a lot of us know what you want to do, but boy, hundreds and hundreds of hands have risen when I've said, "Who doesn't know what to do?" And there are a lot of people that just need to give yourself patience, and then you need to find tools to help you figure it out. In fact, I'll just record one on this episode based on your advice. It's a backdoor, so you won't have to hunt for it, but it's windfallpartners.com/12after, and that's the free version, so you can go get that. It's just a way to find different things that people are passionate about based on research. Just the patience, I love that. I use actually the example of when people go someplace for the first time, you know when you drive someplace, it seems like it's taking forever, and then when you're going there the 10th time, you're in, when we're waiting for something, time protracts in a very weird way. So yeah, patience is, it is, it's so... Sometimes you look back and that six months you were looking for the right job felt like forever, but in retrospect, that's so true, right? Yeah, that's so true. Well, I want to thank you for your graciousness. The first time we talked, you were lovely and wonderful to talk to, and I've loved talking to you today, and what great advice for me and for all the people that will listen to this. Really terrific advice about big companies, and congratulations on all your volunteer work and helping friends and their organizations. Congratulations on all you do. It's been great to get to know you. I look forward to interacting more. Thank you so much. It was great to talk to you today.