Ayesha Mahmood on Leading With Adaptability and Empathy
By: Caleb Brown
September 9, 2025 21 min read
Great leaders know one size does not fit all.
Ayesha Mahmood has built her career on adaptability, empathy, and a clear commitment to growth. As vice president of software engineering at Zscaler, she has led teams through rapid technology shifts while remaining focused on people.
Whether it’s building frameworks at Apple that are still in use more than a decade later to shaping engineering culture at scale, Ayesha shows that strong leadership depends on flexibility, transparency, and trust. Her philosophy is clear: Meet people where they are, create space for every voice, and prepare teams for what comes next.
In this episode of Keep Moving Forward, Ayesha shares lessons on situational leadership, building developer experience, and why adaptive user interfaces will define the future of cybersecurity.
Meeting People Where They Are
For Ayesha, situational leadership means adjusting her style to match what each person needs in the moment. Sometimes that’s inspiring someone with strong skills but low motivation. Other times, it’s coaching someone who has the drive but not the experience. Still other times, it requires providing clear direction for early-career employees or stepping back and delegating to highly capable, experienced team members.
This flexibility, and the ability to use four distinct styles, helps her connect with employees across skill levels, motivations, and even cultural contexts. She uses role modeling, anonymous surveys, and direct conversations to draw out perspectives and ensure every voice is heard.
Her core values of transparency, accountability, and having a growth mindset guide these interactions, creating a culture where trust and clarity drive performance.
Building Systems and Experiences That Last
Ayesha advocates for building frameworks to last, with an analytics system she created at Apple still in use today. “The ability to build things from scratch and be the builder, that is something that I really value,” she says.
That builder mindset carries into her leadership at Zscaler, where she focuses on platform engineering for its wide impact. Her process involves setting clear goals, weighing pros and cons, testing solutions, and including stakeholders in decisions. This disciplined yet inclusive approach ensures her teams create systems that scale and stand the test of time.
Preparing for an Adaptive Future
If she could change one thing in the industry, Ayesha would push for greater collaboration and shared innovation between companies, which would allow technology to advance faster. She also sees user experience becoming dynamic and context-aware. “UI will not stay the static UI,” she says, noting AI’s potential for making interfaces adaptive and responsive while transforming people’s interactions with technology.
In cybersecurity, particularly, she believes adaptive interfaces could surface vulnerabilities, suggest policy changes, and guide users toward faster, more effective decisions.
Ayesha offers a similarly forward-looking view of engineering culture. She encourages teams to see routine work such as documentation, testing, and code cleanup not as chores, but as investments with long-term payoffs.
“If it becomes natural, and you are passionate about it, and you’re doing it day to day, you start gaining velocity later on,” she explains. What feels incremental today can become the foundation for sustained progress.
Transcript
Ayesha Mahmood:
A couple of ways to humanize leadership is knowing that these are people, and they will make mistakes. I sometimes encourage my team to challenge me — obviously, respectfully, as I respectfully would challenge them to do certain things. Don't be afraid to speak your mind, because sometimes I get the best ideas and guidance from my team. I don't know it all. It's the team that makes it successful, all different types of ideas and opinions.
Caleb Brown:
Hey everyone, and welcome to Keep Moving Forward, the podcast from X-Team for tech professionals who are passionate about growth, leadership, and innovation. I'm your host, Caleb Brown, and in each episode, we dive into candid conversations with the tech industry's brightest minds, seasoned leaders, forward-thinking engineers, and visionary experts.
Today, we're joined by Ayesha Mahmood, vice president of software Engineering at Zscaler. Her journey spans from growing up in Pakistan to leading large-scale engineering teams in Silicon Valley. Along the way, she's changed cultural norms, built systems still in use more than a decade later, and developed a leadership philosophy rooted in adaptability, empathy, and relentless commitment to growth.
In our conversation, Ayesha shares how her father's encouragement shaped her drive for independence, the lessons she took from building at Apple, the role of situational leadership and meeting people where they are, and her approach to balancing developer experience with long-term technical strategy. She also offers a forward-thinking perspective on how AI will transform the user interface and why cybersecurity leaders must adapt now. If your leading technical teams are looking to navigate your own career towards high-impact work, this episode is full of clarity and insight. Let's get started.
Thank you so much for joining me today. Really happy about this. Maybe a way to kick things off would just be for you to tell us a little bit about that journey from growing up in Pakistan to becoming VP of software engineering in Silicon Valley. I'd love to hear a little bit about that journey.
Ayesha Mahmood:
Well, thank you so much, Caleb, for having me today. Yeah, it has been quite a journey. I was born in Lahore. It's a city close to the border, Wagah border, of India-Pakistan. I was, I think, in second grade when we moved to Islamabad, and then I lived the rest of my life there. My father was a professor of English literature, he's retired now, and my mother was a homemaker at that time. A few years later, my mother started working when my younger sister, the third one of our siblings, was a little older. Both of my parents were working parents.
Islamabad is a pretty kind of progressive city, but overall, it is still situated in Pakistan, and it's a very male-dominated culture, just like many other cultures. My father was very progressive. Most women at that time, or girls, would go for an arts degree and look forward to getting married and going off and getting financially supported by someone else, but my father had different plans for me. He always encouraged me to be independent. And I wanted to be a fashion designer and learn arts, and he said, "No, you're going to be an engineer." It's not one of those typical South Asian, oh, you're going to be a lawyer, doctor, or an engineer. It's more like, as a female, he wanted me to find a field that can give me more financial independence.
So yeah, I think at the time, I didn't like it, but now in hindsight, it was the best decision that he made for me, or pushed me for. I studied really hard, and did my bachelor's in Pakistan in computer science. Then I came to the U.S. in 2004 to get my higher studies, master’s, in computer science, majoring in animation and graphics.
Caleb Brown:
Cool.
Ayesha Mahmood:
I found that the front-end tech stack of SaaS, or web development, was really of interest to me. It was that artistic, designing kind of thing that I fell in love with. I guess I got the best of both worlds, where I get to do some creative stuff, but I'm still in coding and programming. Then I finished my degree in 2006, and I started working here in the U.S.. I had a plan to go back, but I met my husband, now, at the time, and he did not plan to go back. We stayed together for a few years, and then we got married, and now we have three beautiful kids and we live in the Bay Area. That's my journey.
Caleb Brown:
Love that. Love that. You mentioned your father encouraging you to challenge those stereotypes and things like that, and I wanted to dive into that a little bit more and just understand how that sort of early influence shaped your leadership style then moving forward throughout your career.
Ayesha Mahmood:
Yeah, I think one of the things that I really admire about my father is that he basically — when you're living in a society where there are too many boundaries, and I remember my friends couldn't go on a picnic together with me unless they have permission from their parents, and unless my dad goes and assures them that it's going to be safe and whatnot, and if he's driving us. There were a lot of these, and then they can't go out without their brothers. He was always challenging that and saying, "You are independent, you can go."
There's this really nice story where one day, we used to wait for our brother to come home because boys could go outside freely, and we were waiting for him to come back so he can bring something from the market. He used to charge us commission, by the way. My dad, we were just arguing with him, “Why is he charging us so much?” and things like that. My dad was like, "Why aren't you two going and getting it yourself?" "We can do that?" And he said, "Yeah." Now he was here last year, and we were talking about that incident, and I was telling him that how he empowered us that day.
Caleb Brown:
Mm-hmm.
Ayesha Mahmood:
We never looked back, and we just always then went out and did things. He told us that he actually followed us in hiding to make sure that we're safe and were not nervous or anything like that. Yeah, there's so many stories like that where he really challenged the status quo. I think that is something that's in me. Whenever I feel like, oh, people are constrained, they're building these constraints around themselves just because they see it happening. I challenge that, and I help people understand that's happening.
Caleb Brown:
Yeah. Yeah, that is a really good story. Thank you for sharing that. As I was looking through your career and everything in LinkedIn, you spent, I believe, over seven years at Apple. I think on our initial call, you described that as your life's best work. I wanted to dive into that a little bit more. What were some of the most valuable lessons that you took from that experience at Apple
Ayesha Mahmood:
I think it was truly the best work that I did of my life because I found at Apple, they have this saying that “your category one,” things that you're naturally good at, and they give you time to explore and find that. I'm really good at problem-solving, and I love coding for that very reason, because each thing, you're kind of problem-solving and then putting structure to chaos. That's one of my strengths. I think I really got to do that a lot at Apple and organically discover my skills.
One other thing that I loved was that everybody was super-smart, and these people are builders. These are engineers who are inventing the rope and not just the users. That's something that I feel like, in any other company, I didn't get to do much of that. I was mostly the user of the open source or the user of another person's work, but here I got to create my own work. In fact, the analytics framework that I created for Apple's external properties, dot-com, they're still using that today.
Caleb Brown:
That's awesome.
Ayesha Mahmood:
It's like a 15-year-old thing, it's a 13-year-old thing, and they still use it. So creating some framework — and it was an end-to-end system, basically from capturing user's behavior, to dumping it in Adobe Site Catalyst, and then generating reports off of that data to learn where should we invest more, and what should we change in the UI? All of that is still intact, with minimal changes that they have done to that framework. So, ability to build things from scratch and be the builder, that is something that I really value.
And I think there are so many other things that Steve Jobs had. He was a true innovator. I know he is unpopular among people who like a little bit of TLC, tender loving care.
Caleb Brown:
Yeah.
Ayesha Mahmood:
He was not that guy. I feel like he always challenged people, and those values that he had to challenge your own mind's constraints that you're building in there, that is still in Apple's DNA. Somehow they're able to maintain all of that in their DNA. And If you work there for so long, which people worked there for like 20, 25 years, right?
Caleb Brown:
Yup.
Ayesha Mahmood:
I also thought I was going to get the 10-year seal, but COVID hit, and COVID made people think differently about what they were doing. I feel like people, if they're working over that long of a period at Apple, that DNA gets embedded a little bit in your DNA, too.
Caleb Brown:
I think it was on the initial prep call that you had mentioned situational leadership, with four different styles for different scenarios. I was wondering if you could walk us through these styles and when each is most effective.
Ayesha Mahmood:
Yeah. Oh my god, that was a life-changing thing because every interview I would hear, "What's your leadership style?" I'd be like, "Well, it's pretty fluid when it comes to situations that require me to be different." I went through the situational leadership training, and I learned that people can be in four different styles of how much help they need, how much motivation they have. And in order to meet the needs of those four different styles, you need to show up as a different leader in four different styles.
If somebody is low in motivation, high in skill, now you need to show up as an inspirational leader. You don't necessarily have to coach them to uplevel or upskill, but you have to motivate them or help them find that passion in them, help them to discover that. In some cases, it's like an individual's skill is not there, and they're afraid of taking that risk or whatnot. In that situation, you have to bring a different style.
I know this training is focused on four different styles and four different needs, but if you expand that a little bit, you can understand when you're an empathetic leader, you can understand what a person is going through. They might have some personal situation, and they might be demotivated because of that. Allowing them that time to deal with that and then coming back could also inspire them or bring them back to that motivational level.
I think it's really one size doesn't fit all. Meet people where they need you, so bring that leadership style, but obviously, you have some core values. For me, it's transparency, it's accountability, and it's growth mindset. These are three things that I have strong bias toward, and so that's my core values. One has to meet those, and then we can work together.
I think one of the things that situational leadership taught me was that you cannot do it all, right? You can't always be operating at that best of your level, that you're meeting everybody's needs. You have to meet your own needs, too, when you're feeling down, when you're not feeling inspired. Another thing was being aware of your own needs and knowing when to pause and step away. And then take care of yourself and come back. Because as a leader, you need to show up. If you are not 100%, then you can't show up the way you want, right?
Caleb Brown:
Yeah.
Ayesha Mahmood:
A lot of these good things I took away from that training.
Caleb Brown:
Yeah, yeah, that's really interesting, and it truly makes me want to dive into that a little bit. That's really fascinating. You were talking about understanding yourself as a leader, and I want to know — I have a hunch I know — but I want to know your perspective on the “perfect leader” narrative that we sometimes see in places like LinkedIn, and how you think we should be humanizing leadership instead of something like that.
Ayesha Mahmood:
Yeah, I think this is something that I learned in therapy, that there's a pedestal where you put people based on what you think or your beliefs are. Like your parents, for example, or a leader that is your role model. But at the end of that day, they are going through a human journey, and that journey is rough. That journey has ups and downs. The journey is not as we see in Instagram or LinkedIn.
I think to me, it's important that we recognize that we are all learners, and we will make mistakes, but as long as we're learning from them, and we're not repeating them, it should be OK. I think the problem comes when we are not learning, and we're repeating the same things over and over, and then we're expecting different results.
Yeah, I think a couple of ways to humanize leadership is knowing that these are people and they will make mistakes. I sometimes encourage my team to challenge me — obviously, respectfully, as I respectfully would challenge them to do certain things. Don't be afraid to speak up your mind, because sometimes I get the best ideas and guidance from my team. I don't know it all. It's the team that makes it successful. All different types of ideas and opinions.
Sometimes I think leaders have to — like, for me, I'm a passionate engineer, passionate about user experience and some technology. Just understanding that that passion can come across as directive was also important for me. Ultimately, I think having healthy discussion and challenging each other is a good way to go about humanizing that experience.
Caleb Brown:
A hundred percent. That makes a lot of sense. Shifting gears, a touch on team culture and distributed teams, things like that, I wanted to talk with you about that a little bit today. You mentioned cultural differences in communications, particularly with teams in India. I wanted to know how you navigate these cultural nuances while maintaining, of course, that team cohesion.
Ayesha Mahmood:
I think it's pretty challenging in terms of, in certain cultures, hierarchy really matters. Speaking up is related to defiance or disobedience. Changing that mindset takes a while, and I think it takes people to see repeated actions from my side to really absorb that, “OK, yeah, it's OK to speak up, it's OK to share this.” It's repetitive role modeling, and then it also takes a while.
I also try to customize things based on differences. For example, I'd do a survey instead of asking in an all-hands, or I will anonymize the survey so people are more comfortable sharing open feedback. Various things to provide those avenues for folks to share their opinions. I would encourage the team, people think that they don't have a voice, they won't be heard, they're just a number, and there's 8,000 people, but I try to encourage my team to voice their opinions, and it all matters.
In fact, as a leader, I really pay attention to how people are feeling. What are they perceiving? Because it's really important how we feel and perceive things at work. It really differentiates the quality of work that we produce versus not. I pay attention to that. I encourage people to be open about it. I also start calling out people if I see they're not participating, I say, "Do you have a suggestion?" Some people feel like they're on the spot, so you just have to navigate that with that personalized kind of approach. Going back to “one size fits all doesn't work,” you have to personalize your interactions.
Caleb Brown:
You focused heavily on platform engineering to create consistency and efficiency. What approach do you take when standardizing tools and processes across these diverse engineering teams?
Ayesha Mahmood:
I think, Caleb, I've always been a platform engineer. I lean more toward platform because it has wider impact. Because it has wider impact, it's always important to make sure that you're doing enough pros and cons, comparing of options.
I always start with, “What are our goals?” For, let's say, if we're adopting a tool for a content management system. So what are the goals? Goals are: We have extensibility, and we can scale. We can have low maintenance, so maintainability. Set those goals, compare the latest and greatest options, do pros and cons, and cost is always a consideration, so do cost analysis. Based on these couple of goals, not just one goal or two goals, but a mix of goals, see where we can find the right balance. Once my team has done enough of that, we also try to do POCs to see, “OK, well, is it going to deliver on what we thought it's going to deliver?”
So, short list of tools, it's easier to do the POC because if you chose two or three out of the 20 you were looking at, now POC can be done quickly. Once we have done all this homework, I will start bringing in the stakeholders into meetings, presenting. I always go with one of my previous managers, Perna. She was really good at presenting such things, and I learned a lot under her. I would always do a little recommended option and then, “Why do we recommend it?”.
It also gives a sense to people that they were part of the decision. Right now, for example, I'm standardizing a tool for 24 different teams, or X number of teams. It's really hard to get everybody's buy-in. If we go with the homework, sometimes 90% of the people will say, "Yes, let's go with that. That makes sense." Then sometimes you'll have conflict, a difference of opinion. Ultimately, I say, "Folks, I understand, however, let's disagree and commit, because we have to go with a certain thing." A lot of the times, it's in the area where one team is using one thing, and they don't want to migrate away, so they're like, "Our tool is the best."
Caleb Brown:
Sure, yep.
Ayesha Mahmood:
But I think that inclusive approach, and then doing your homework, makes it very easy to get to a decision.
Caleb Brown:
Yeah, interesting. That makes sense. You had talked about having goals and, of course factoring in costs and things like that, but I was wondering how you measure success of developer experience initiatives within your organization, how you actually measure success of these things.
Ayesha Mahmood:
Yeah, I think we also set success metrics, which I didn't touch upon, but we try to say, OK, well — for example, we were just recently putting together a POC for headless library usage. We were building a proprietary design system, and we thought adopting a headless JavaScript library can add velocity to our development. When we were putting together that proposal, I had asked the team to put the success metrics. So, what was the level of effort before, and how much did we reduce? Then a couple of other things like, did it also enforce some best practices? What other benefits did it provide? Ultimately, we ended up saying, “OK, it reduces your effort, if you were spending two hours, it'll reduce it by 20 minutes.”
Caleb Brown:
Yep.
Ayesha Mahmood:
That's not a significant velocity gain, but then it will also enforce best practices or code style guide, so to speak, on how you should composite your components, how you should make them atomic, how you should compose them. This still is a significant benefit because then you're standardizing on the coding style, and this is not something that you can do with some linting or something. It's actually the way you compose the components. What should be the size, what should be utilities, et cetera, et cetera. It's kind of code organization, as well, that's influenced by that. That's still a pretty significant gain for a repository where you have 50 people working.
So yeah, those are the kind of things that we put in the success metrics and then some bonuses to say, OK, it still gave us some other benefit.
Caleb Brown:
Awesome. That's really helpful. How do you approach — this is I think within the same realm — I was wondering how you approach balancing immediate product delivery needs while investing in the longer term engineering efficiency, dealing with a tech debt and all of that. I am curious how you approach the challenge of engineers often wanting to work on the exciting features, the new stuff, while sort of avoiding what they perceive as boring work, testing, or documentation, just working on that legacy stuff. How do you balance that?
I mean, I've personally seen that a lot in my life, is the developers wanting to work on the new shiny stuff? And I understand as a developer, it's fun to work on the shiny stuff, but I'm curious how you balance that.
Ayesha Mahmood:
As an engineer, from the get-go, I had this opinion that 20% of your work is going to be boring. It's going to be documentation, it's going to be this legacy stuff, flat HTML files that you'll be touching. I encourage my team to plan how we can move away from the legacy stuff. Very often I hear, "Oh, this is going to take more time, and it's going to be this additional work." Frankly, when I worked at Apple, before I worked at Apple, accessibility was like an add-on. It was extra time that it would take me. When I worked at Apple, believe you me, I was writing code that was accessible in the lesser time than I was doing before because Apple's like “go, go, go.” I think a lot of it is the mindset. It's like, “Oh, I need to do this extra thing, it's going to take me more time.” But if it becomes natural and you are passionate about it and you're doing it day to day, you start gaining velocity later on, right?
Caleb Brown:
Yep.
Ayesha Mahmood:
It's kind of like that investment to make it your day-to-day. I write this function, I'm going to write a document that explains this function or code comments that explain this function, and then I'm going to write a test file with all the test cases, and then I'm going to make sure that I'm using semantic HTML. I'm going to make sure localization is there, dark theme, all of that good stuff, and I roll it out. And every day I do it, it becomes my way of life, and I gain velocity later on. That's something that I try to instill in the people that I manage or I lead. That's kind of one way of me doing that. Then, as a leader, it is also my job to make sure that my team has the mindspace and the focus to work on some of these tech debt cleanup or these projects dedicated, focused. It's kind of like a variety of things.
I kind of lost track of your original question, but I hope I answered it.
Caleb Brown:
No, you did. I mean, it was really just balancing developers often wanting to work on the new stuff versus maintaining legacy stuff and some of the stuff that's often pretty boring, like testing and documentation, but you absolutely covered that.
I was curious, I like to, when we're ending, when we're wrapping up, I like to look at future, really. I think it's truly probably my favorite part of this. I was wondering what skills you think will be crucial for the next generation of technical leaders — in the space in general, but also if you have anything specific about the cybersecurity world and leaders in that moving forward, I think people would be very interested to hear that.
Ayesha Mahmood:
I would love to answer this question because I've been thinking lately, my expertise is the user experience, the front-end. So UI, UX, the front-end tech stack. I've been thinking lately, there was this buzz, AI will take your jobs, and 20 years ago, AI was there, it didn't take anybody's jobs. In fact, it created more jobs with autonomous vehicles and Siri and all this AI that we've had. So I've been thinking about it, and I think that one thing that engineers in the front-end realm have to think a little differently, is that UI will not stay the static UI. We build pages, we build these apps, and they're pretty static. We have a navigation, we have a bunch of tables or whatnot. I think in the era of AI, UI will be very dynamic. It'll become adaptive.
And using AI ML, we could actually — and generative AI, co-pilots, and stuff like that — we could actually end up in a highly adaptive UI where you're trying to do something and there's some contextual help to tell you, "Hey, were you trying to this?" or even you can push up suggestions, "Hey, people with your role who are interested in browsing these things have looked at these other things." We already see some of this happening in multiple apps and websites, but I think it's going to happen more.
Cybersecurity is a little behind. I don't think any company out there today — CrowdStrike, Netskope, Palo Alto Networks — is doing any of this stuff, but I think cybersecurity is where it could be really, really useful because you're trying to protect your enterprise, and you want to get to value very quickly. This could become super-critical to have adaptive nature of the UI telling you, "Hey, this vulnerability was found, and you have a policy that kind of doesn't address that, do you want to change the policy?" Those kind of things can become super-helpful.
I actually wrote an article about it, so I think that's what people should look forward to. And think differently because it's needless to say, tech is always like this. Today, Oracle or Java. Tomorrow, you have to evolve, and a new language comes in, and it just takes over. People need to still keep evolving with the latest technology.
Caleb Brown:
Absolutely agree. Then we'll leave on this last question, which is, and I do love asking this one, if you could wave a magic wand that would change one thing about the tech industry and tech industry culture, what would that be and why?
Ayesha Mahmood:
Wow, that is a difficult one. I can't imagine myself having a magic wand. Everything in life, I had to work really hard.
Caleb Brown:
Yeah.
Ayesha Mahmood:
There was no magic wand.
Caleb Brown:
There's no magic wand.
Ayesha Mahmood:
One of the things that I would try to change is more collaboration. I think companies try to, and I don't know how this will happen, but it's kind of like a wish. Some companies are doing that where they'll join hands and they'll say, "OK, in the spirit of evolving this technology faster, let's join hands," but companies like Apple, they don't really open source much of their stuff, they just build for themselves. I think a world where we are more collaborative, we could advance technology far better and faster.
Caleb Brown:
Yeah.
Ayesha Mahmood:
I wish companies, large companies and small companies, and especially in the Bay Area, were more collaborative.
Caleb Brown:
Mm-hmm. Totally agree. If I get that magic wand, I'll send it your way so we can make that happen. Yeah, like I said, that was the last one. Thank you for sticking around. I do appreciate it. That was a great episode. Thank you so much for joining.
Ayesha Mahmood:
Thank you, Caleb. It was really wonderful.
Caleb Brown:
What a fascinating conversation with Ayesha about leading with adaptability and empathy in a fast-changing world of software engineering. One thing that really stood out to me was how intentional she is about meeting people where they are. That could mean tailoring her leadership style to an individual's needs, balancing developer experience with strategic priorities, or preparing her teams for the coming shifts in AI and cybersecurity. Her reflections on growing from early influences, building platforms that stand the test of time, and leading at scale with clarity and care are lessons any leader can learn from.
What resonated with me most was her forward-looking perspective on technology's impact and her reminder that leadership is as much about creating the right environment for people to thrive as it is about setting direction. Thank you, Ayesha, for sharing your journey and insights on what it takes to guide teams through transformation while staying grounded in values.
Caleb Brown:
Join us next time for more insightful conversations with tech leaders who inspire us to grow, lead, and innovate. Find us on Apple Podcasts, Spotify, or YouTube Music. Don't forget to share this episode if it resonated with you. Until next time.
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