Empathy Meets Accountability: Thomas Jeyaseelan's Blueprint for Successful Leadership
‍

Thomas Jeyaseelan, a graduate from the University of Berkeley, California with over 23 years, he's been in the technology industry in various capacities, software designer for over 13 years, and a managing for over 9 years. And currently, he's the Director of Engineering at Microsoft.

‍

Host:
Hi, Thomas. How you doing?

Thomas Jeyaseelan:
I'm doing good, thank you. It's very nice to be here.

Host:
This is Thomas Jeyaseelan. He's a graduate from the University of Berkeley, California. For over 23 years, he's been in the technology industry in various capacities—software designer for over 13 years and managing for over nine years. Currently, he's the director of engineering at Microsoft. So, nice to meet you.

Thomas Jeyaseelan:
Very nice to meet you here too. It's a privilege to be here.

Host:
Fantastic. Well, I'm gonna start off with some, I think, some soft, nice, easy questions. Since you've been at Microsoft for a reasonable amount of time, what’s your favorite thing about working at Microsoft?

Thomas Jeyaseelan:
The favorite thing I think about working with Microsoft is that it gives me a feeling of being in a small company, even though it sounds cliché. I like the fact that when I go to work, I work with a small group of people most of the time, and they have come to really mean a lot to me, more than just colleagues and co-workers. Even though Microsoft has over 100,000 people all over the world, it doesn't feel like that when I go to work. And that's something I look forward to when I go to work, when I go to the office. When I'm driving to work, I'm looking forward to seeing people, not just the projects that I have to work with.

Host:
So, is that something you went out of your way to curate for yourself, or is that sort of a cultural thing that happens throughout the organization?

Thomas Jeyaseelan:
It's a cultural change, I think. That's been emphasized more, especially over the last 10 years in the company. I've worked in this company for over 23 years, like you said. It's not to say that things were totally different when I first joined the company, but there's been a lot more emphasis on culture, working with people, how you make others feel when you interact with them. More than just, “Hey, have you shipped this? Have you checked in this code? Have you released on time?” Yeah, that stuff is still important, but just as important is how you work with people and the impact you have in creating the culture in the team.

Host:
Right, right. So, you know, you talked a little bit about the people. What is your favorite part when it comes to working with technology? What do you like the most about that?

Thomas Jeyaseelan:
Technology always keeps me on my toes. Just when I'm comfortable with something, lo and behold, news comes out that what I'm doing is maybe the second most interesting thing now because something cool has just come out. If you think everyone’s been paying attention, they'll probably think, well, the thing I've heard this year a lot is Chat GPT, artificial intelligence. And guess what? That wasn’t most of my career. Almost entirely my career has been about something that doesn’t seem that cool now, because artificial intelligence, deep learning, machine learning, supervised learning, that’s a big part of what’s interesting. But what is interesting also is AI isn't just about algorithms and creating these trees—decision trees, pruning. AI is much more than that. AI is engineering as much as it is about theoretical computer science. But that's just an example of what makes my job interesting, is you can spend a lot of time specializing in something only to realize you've got to keep your skill set constantly polished. You've got to be interested in learning and finding out. About things you don't know, I agree with that 100%, especially with what we're doing. You know, it's always interesting. We have people that, you know, they have different concerns at every junction, and every concern requires a different kind of solution, a different kind of technology, and that puts us on our toes, like almost, uh, at every engagement, every react, every interaction. And that's something some people find a little bit, uh, can they can find that to be a little bit tough. But, you know, it can also be sort of exciting if you're, you know, the kind of person that, uh, gets bored easily, you won't have to worry; you're in sort of in the right area, you know, that's for sure. 

Host:

And, uh, you know, working in technology so long, you probably have seen it affect people's lives in different ways over the years, so what's your perspective on that? And, you know, how does that—how does that affect you, and how have you seen that affect other people? You know, do you have any sort of, uh, a new perspective on that?

Thomas Jeyaseelan:
That's the thing about Microsoft, which I think is magical. You know, Microsoft is, I think, right now the second most valuable company by market cap in the world, at least in the US. So, you get to be in a very unique position in industry to easily make an impact on what might be like a whole continent's worth of people, and sometimes the whole world. I've been in a situation where I was walking down this terminal in Heathrow Airport, and I saw a kiosk, and I realized, that's my code, that's my team's code, that's running. So that's amazing in Microsoft, is that you get to really influence and make an impact on customers. That comes both ways. So if you don't do your job right, or you've got a problem or a bug that shifts, you are going to hear about it. And sometimes the customers will not pull any punches, just depending on what you work on. Recently, I worked on a project that impacted screen time for families to control how much time their kids can use PCs or devices, and that wasn't working properly, and all of a sudden, parents, you know, had difficulty for a short period of time, uh, you know, unlocking the devices for their kids. And so, that's an example of customer impact that goes both ways. If you do your job right, you, you know, you really feel proud of the work. If you don't do it, you know, it's on you; the responsibility is on you to make it right quickly. And so, we focus a lot on making sure we stay connected, we focus on quality, and we have to be vigilant at all times. [Music]

Host:
Fantastic. Um, so, you know, this also sort of settles into my next question, which is, you know, there's a lot of responsibility, and there's a lot of consequence with almost everything that you're doing. So, how do you manage how people feel about you? Like, how do you see yourself within this sort of landscape of the consequences of your actions, or the consequences of what you're doing?

Thomas Jeyaseelan:
It's, um, one thing is for sure, when it comes to public perception, we live in a world where people are less and less inhibited in telling you how they feel about what you're doing. And, you know, for better or worse, it's definitely blatant. So, how do you, uh, manage that in your own space? Reflecting on my experiences, I've realized that leadership accountability is crucial in moments of crisis or challenge. This is especially true in how my team observes my actions and how I respond. Early in my career, I focused a lot on appearing resilient and strong, but over time, I’ve come to see the value of showing empathy in leadership and allowing myself to be more authentic and vulnerable.

Leaders like Brene Brown emphasize vulnerability, and you see that echoed in examples of compassionate leadership throughout the industry. For me, showing my human side and acknowledging my own uncertainties is just as important. Sometimes, facing a difficult situation with customers or partners, it’s enough to tell my team, “Hey, you know what? That really sucks, and I’m not sure what to say.” Such transparency helps in building inclusive leadership by showing that everyone’s feelings are valid and that they’re part of a supportive team environment. My approach now is less about pretending to have all the answers and more about fostering collaborative leadership, where I encourage my team to contribute their ideas and perspectives in uncertain times. This approach builds trust and ultimately reinforces a culture of leadership accountability, as we all take ownership of the outcomes together.

‍

Thomas Jeyaseelan:
Uh and then on a personal level it's also important to realize not everything is your fault. Even if it is your fault you realize you're, you just have a misstep, you've got to take a step away and you've got to deal with it yourself. You've got to be honest about it that there are times when you might be burned out even as a leader you don't have to project a picture of perfection to your team. You don't have to your team to see you soldiering away and you know seeing them as seeing you know for them to see you as this uh person who is going to shoulder and single-handedly carry them through the hill. If you, again if you're honest with yourself you need to check out for a bit, have a little bit of space, reflect, spend time with your family and come back. That kind of authentic human behavior will really help cope with things that come up and I've been trying to do more of that than saying I have done over the last five years or before.

Host:
And I agree that I think you know, I think you know, I guess there has always been a lot of pressure to sort of not necessarily hide but you know delay, you know what's going on in general. I think most people have felt that way before but I think there's definitely a lot of value in just being very honest about what's going on and then allowing your team to sort of react to that uh in a way that I think it kind of almost improves efficiency because if they know what's going on, they know how to react to that. They know, they know that they should react to that and then that cycle is very fast and especially if it's a small team, you know, and if you're and you're definitely built a little bit of trust they can say okay, we know what's going on, we know you're doing your best, let's see how we can help you move forward as you know, as people who actually want to support you.

Thomas Jeyaseelan:
And I think that has a lot of value actually, it really does and some people think about it like being open is um sort of a kind of like a trick but it's more of a, I think of it more like as a way to be actually efficient because um other people feel faster than any, any PowerPoint you could ever make and it has a lot of value. You actually become more efficient exactly, like you said. It's amazing how many people are quietly modeling themselves after you when you are in a position of leadership or a position you can, you know, I, and I say you, I really mean myself here. I may not realize how many people are potentially even modeling themselves by copying me. So when there's a crisis, when there's a problem and I choose not to take a break, I choose not to take a vacation day, I just want to chill right through it, they might realize they have to do the same thing.

Host:
And so they don't feel comfortable disconnecting when it might be the right thing to do and now they're burning through the Midnight Oil, they're spending late nights and they don't become efficient, they don't become happy and at the end of the day, the work doesn't get done on time or if it does get done at a steep cost and so there's just a cascading effect of results that ultimately, you know, can really hurt the team.

Thomas Jeyaseelan:
Exactly and there's a lot of us, you know, about managing especially when you're talking about sort of taking rest and then doing work. There's a lot of, you know, the idea of managing Focus has become really really popular now but, um, it's only as believable as you know, your leadership allows you to do that. And I think, you know, if leadership is able to model that, like sort of philosophy, they're more likely to actually have it actually, you know, happen than any PSA or anything. It's, you know, people do what, you know, children do what their parents do, not what they say. Uh and I think, I think it's popular with children, but it's true in general, it's just...

Host:
I think that's a good insight and I think that's a good point. You know, um, so uh you've been working, uh, sorry I wanted to ask you just in general how do you feel about empathy uh in the workplace? So we talked a bit about, you know, people copying other people or people copying leaders and how that sort of, uh, how you lead people but I think if we're talking a little bit about empathy in general and then being able to perceive how people see each other—how does that permeate in a workplace, and then to what degree is that or isn't that sort of how you want to push people forward or push people back maybe?

Thomas Jeyaseelan:
Yeah, excellent question. Here too, I was thinking about this incident I read in such a book. So Satya wrote a book called Hit Refresh a few years ago, and he gave this great example of a mistake he made, and how that sort of brought about the subject of empathy. I think he had an interview with an interviewer, and the person decided to ask him, "Hey, Satya, imagine you see a baby on the road crying. What are you going to do?" And I’m paraphrasing this—you’ve got to read the book to get the literal account of this.
Yeah, you see a baby crying on the road, what are you going to do? And he said that he answered properly and correctly, "I'm gonna call 9-1-1." And the interviewer said, "Hey, Satya, that's a baby. Maybe you should just pick up the baby." And so that, you know, that really brought up this idea about empathy. And he gave that as an example of what empathy is, and how different it can change the way you respond. And that constantly comes up in my head—that empathy is not something you can exercise by training and trying to be empathetic. Empathy is about doing less, it’s about thinking less, and going back to what you are as a human being. And I’m not great at it, you know? As a person, I’m constantly learning how to stop being corporate, or how to, you know, step up and kind of cloak my answers with the right answers every day when I talk to my team members, and when they’re asking me for help.

Empathy is about not just answering the question, but about questioning why they asked that question. What is it behind them that led them to ask? And then maybe arriving at a different answer. So, for example, you know, a person is asking, “Hey, Thomas, I need two more weeks to finish this project.”

Where the shortcut is: can we finish it in the same time, but maybe getting help from another team? Or, you know, do we need me to talk to partners, or should we try to do it in one week?

But if empathy isn’t used, I will be going down this train of thought. But if I take a step back and say, "Why is this person asking for two weeks? What's going on? What's behind this question?" and go a little bit deeper, maybe the question comes up from the fact that they need some kind of way they need to deal with a co-worker on their team that’s having challenges, that they don’t necessarily feel as escalation, or there is a personal issue at play that they’re not able to articulate. They actually need time off to be away.

So the right answer might be that, you know, we need to let them take that time off and reassign this project. Whatever the answer is, empathy is about trying to get to the root of the issue and speaking human to human more than you normally do. And that’s just simply humanity that I think we, as leaders, constantly grapple with—how much humanity do we show? How much strength and leadership, and maybe ruthlessness or decisiveness, do we need to show? And what’s the right balance? How do we do that?

Host:
So, you know, what's interesting to me is like, in that moment, right? So you... you know, an unflattering view of leadership is a mix of cognitive load and stress, and a little bit of that is you're having all these things happen, and everybody's concerns sort of weighed on you as you're moving forward. How do you sort of—how do you take that all away and give your own mind space to allow that sort of feeling or that sort of perspective to come in?

Thomas Jeyaseelan:
Right? Because there are—for every question you get, there are 10 other questions that pop up that can—some might consider to be more important, but not in that moment. They're just more important overall and are pressing over the time of all the things that you're doing. But how do you get that? To not crowd out your mind and sort of like focus on this person and yeah sort of not react to it in the way that you kind of react to everything else that day. To some degree, it's very easy to have this knee-jerk reaction for every question that's asked. Maybe, especially as Leaders who work in the industry for 10, 20 years, you'll likely know a similar question that someone asked five years ago, so you can harness your experience and start firing away the right plan of action and just go down a certain road. But it turns out the more you spend time with people, the more I've spent time, the more I realized every situation is unique.

And that's a cliché, it's true. People, when you say that, it sounds cliché. What's more interesting though is that every situation requires me to ask more questions and have fewer answers. As I spend more time today compared to, say, 10 years ago as a more Junior leader, I realized I need to keep asking questions when someone asks me questions. If someone comes to me with a problem, I try to turn this around and help them steer the ship themselves instead of me taking over as Captain and saying, "Look, we gotta go down this road now." This is tricky because you could go down that new road that I just suggested and take you to an extreme and say, "Well, I'm just going to keep asking questions," and that might not necessarily be the right way. You know, if you just almost take you to an extreme, but what I'm saying is that we've got to move that needle from being the person providing all the answers to the person that's probably asking more questions.

 Balance that as Leaders with being accountable because as Leaders, we are also accountable for progress, for impact, for results. We've got to have results. So when someone comes to us with a challenge, at the end of the day, we need a plan. We need to move from the point where we're at to a better place, but to get to that better place, we have to co-captain the ship with the person who's coming to us with the problem and kind of guide them and say, "Here, you stay on, you press on, I'm here to help you steer the ship, but you're going to get through this problem with my help."

So, you know, we've been sort of dancing around the idea of assisting others, and I want to bring it down to something super concrete so people can latch on to that. And what I want to ask is, you know, when someone comes to me with a problem, what's the first thing you think? There is a training that I took a few years ago that really resonated with me, and I wanted to share that here. It's called The Coaching Habit, it's by Michael Bungay Stanier. I hope I didn’t butcher his name—Michael Stanier—and it’s easily found on search on the internet.

What I love about this training is how it turns the dynamics of a conversation around. Now, any conversation has, at least a type of conversation like this at work often, consists of two people where one person is bringing a problem to another person with the hopes that that person will give answers. That's usually how it sets up. And in a situation where someone is coming to me, what the coaching habit challenges me to do is to say, “Well, Thomas, I know you want—you are just bursting with advice. You've got 23 years of experience. I mean, you could just run Rampage here with the amount of spectacular advice you could give because you've got experience as a leader, experience writing code, experience building stuff, making impact, working in a big, powerful company like Microsoft, the tremendous worldwide impact. It's a household name. 

Host:

You've been working in a company like this, you've got advice that people would sit down and listen to you like a guru.

Thomas Jeyaseelan: 

Yes, but don’t stop. Don’t, and that’s what it tells you: take a pass, put the advice monster in your side. Really, he actually loves using this term, advice monster. Put it aside and start asking questions. And so this class, this training, talks about what key questions you can ask that will kind of elicit responses that will start the dynamics of the conversation and start steering it towards the person asking the question and saying, "I trust you. You came to me for help, but I’m trusting you. I know you can do this." A lot of cognitive research scientific studies that this is based upon that when someone comes to you for help, it isn't a binary thing. You don't have to help by answering the question directly face-to-face. You turn this around, ask key questions, and one of the key questions you ask is, "What's the greatest challenge here for you? What is it? Let's work on this together," and continue asking questions like that. You get surprising results like that, and that's really been the focus. I've really believed in this since I started pushing on this, even for my own one-on-ones and conversations.

Host:
Yes, and, um, I think, I guess in terms of when I'm engaging with people, you know, I don't think anyone has ever told me the problem that actually mattered—not because they didn't want to, but just because it just wasn't the problem. They've always had sort of what they presented as the issue. And the issue was, uh, maybe I would even say it's a month and maybe 23 questions away. Um, you know, sort of in a different sort of side of things, but a one-on-one context, it means something different. But in our context, it's always, "Let's, you know, you've told us what you want, let's really investigate. You know, let's—if we were to, like, sort of solve your problem very quickly, what would that look like?" And then in order to make that happen, it's a month of searching or even more. And, uh, it's always interesting to journey. It's always—it's never—I've never had an experience where it's exactly where I thought it was. It never—it's never there. So that's always been very interesting to watch.

Thomas Jeyaseelan:
Yeah, 23 questions away, yeah. How did you find the right questions and let those thoughts dance in their minds, get them thinking, get them realizing, "Oh, you know what? Oh, this is actually broken down into a slightly different thing that you have to kind of help me start doing anything about," and realizing that?

Host:
So, um, you know, and just, uh, you know, it does sound like your philosophy is, um, do not give advice, ask questions. That's what it really sounds like, and, and I think that's, you know, to put it succinctly, is sort of where you're pushing forward with. And I think that's very effective.

Thomas Jeyaseelan:
I wouldn't even go too strong if they do not give advice, as much as, uh, push back on the first urge that comes to you. It's going to be about giving advice. There might be advice that you really do have to give sometimes, but before getting there, had that dynamic between you and that person. Try to get them to think, try to get them to answer these questions, and yes, at some point, we all know when the time is right to give advice. What we want to do before that is to not turn it into a conversation that's dominated by myself giving that advice, just, uh, just that advice.

Host:
Sir, and I think, you know, within that context, you know, you're really giving, um, power to that person to, you know, figure out the space of their problem and see where your experience can interject and guide them in the right direction. But only when you've yourself have sort of given them that opportunity to present you as full of picture as possible.

Thomas Jeyaseelan:
Um, no, but, and, but, you know, sort of in that sort of space, because you're giving them, you know, quite a lot of, uh, I would say—I want to say power, but really opportunity. Um, you still have a situation where you still have to set expectations and limits and things of that nature. So, sort of with that sort of flipped dynamic that most people, I think most people are not familiar with Netflix's dynamic, and it can be kind of daunting, um, for leadership because there are expectations that need to be met. Um, how do you continue to build or maintain trust in the way that you're still comfortable with?

So, to add to the earlier part of what you just said about expectations, absolutely right, and that's what makes the job difficult as leaders is we are not just here as people who are giving advice to, say, a therapist or, you know, a psychologist might be the case, although that's a big part of the role. You want to be a person that has empathy in leadership. You talked about empathy earlier, being a person who listens, but you are also a leader. You're working in a company that has results to accomplish, work to do, and customers to work with, right? So we have to be accountable. As leaders, we ultimately need results. Results matter, especially if you're working in a company that trades in the stock market. Even if it doesn't, in many situations outside of the corporate world, results still matter. Results matter even if you're working as a priest in a church. You've got to be accountable to results, and that's what makes this coaching habit so interesting. It's rooted in you turning the dialogue back to the person and asking questions, but it's also about being accountable. One of the things you do in that structure, as he breaks it down, is not just asking questions but steering the person into action and leadership accountability. So one of the questions you travel through that dialogue is: "What are we going to do as the result of this conversation, and when are we going to do it?" Setting that framework ensures that not only did you have this productive exchange where you help that person understand the problem better, but they're also going to do certain things in a finite time window.

Yeah, and then sort of, you know, the obvious question from there is, if that continues to run on, what happens? How do you deal with that? Because there are people that, you know, they take advantage of that opportunity to no longer provide as much value as you'd hope. Some people are convincing at that, right? And it is a complex thing to just, you know, especially when you have large amounts of people that you're dealing with, to figure out if that's true or if that's not true. I think that's something I’d like to get your feedback on because that's challenging for almost everybody. It's the rules you play as a leader, where you are accountable for both the end result and the journey, the journey you take with that person, through compassionate leadership and collaborative leadership.

‍

Host:
Yeah, and sometimes in engineering, we talk about the "what" and the "how." We are responsible for both. We've got to be responsible for the "how," making sure the journey is calm and, for the most part, sensible and built on the right framework in the right team setting. So, in other words, you and your team, through the culture that you've created, are accomplishing your goals in a positive, flourishing environment that sustains good morale, well-being, and all of these things.

Thomas Jeyaseelan:
Yeah, and no matter what you do, there’s always going to be the possibility of actors or people in the team who may take advantage of it or may simply just not do well, no matter what you do, no matter what level. And that's not our fault, right? Those are the choices they make to work in the team, or it might be the result of a fit. For some of us, the team we've chosen to work in may not have the right project or environment that we like for a variety of reasons, and that's totally fine. But what it means is that there's a good possibility—or a small possibility—that no matter what type of team or environment you set up, there could be one or two people that just are not delivering results.

Host:
That's where you talk about the "what," the results, the outcomes, the impact you and your team are ultimately accountable for. And that's something that has to be seen as objectively as possible. We talk a lot about culture. In fact, I’m looking at it almost in reverse order, where we spend a lot of time creating a positive culture, but we must not forget that we are accountable for results. When it's time to evaluate results, we want to make sure that we understand whether or not this person or persons have delivered the impact they were expected to deliver in that time. And if they don't, that's something we have to be fair about. If we are not fair about that, we're not doing justice for the people that are delivering results.

Thomas Jeyaseelan:
Yeah, and people often come from the other angle where we talk about results too much and we don’t talk about the journey. You know, we're ruthless about making sure you deliver results, that you do things on time, but we don’t care how you do it. You can burn the midnight oil, and you can enslave yourselves and work weekends. I'm saying I'm looking at almost the opposite, where if that’s one type of problem, then it’s crucial to create a healthy atmosphere, fostering successful leadership accountability that focuses on sustainable practices. But you should also make sure when you create a healthy culture on your team and a flourishing place, that you hold your team accountable. Successful leadership accountability isn’t just about creating a supportive culture; it’s about balancing that support with clear expectations for performance and accountability. This balance creates a healthy relationship between you and your team, where they understand that they are still expected to do the job they’re paid to do, that they’re expected to deliver results. Your role as a manager is to coach, help them grow, and ultimately provide direction about how well they're doing through empathy in leadership. Compassionate leadership is vital because it ensures you connect with your team members on a human level, understanding their challenges while still holding them to high standards. When you approach leadership with inclusive leadership, you're ensuring that all voices and perspectives are heard, which helps create a more cohesive and motivated team. And finally, collaborative leadership encourages teamwork, where everyone feels they can contribute to solutions, making the journey to achieving results smoother and more unified.

Right, and I think you talked about culture and expectations, and I really appreciate that part of it. For us, it’s very team-based. So even discussions about how outcomes or results affect the team’s performance are crucial. Successful leadership encourages leaders to consider how each individual’s contribution influences the collective outcome, reinforcing a culture where results are a shared achievement. This focus ensures that outcomes are tied to the ultimate goals, and that every team member’s effort contributes to the overarching results.

‍

Host:
And I think, and then all, you know, sort of your, the way that we talk about empathy before in the first half of this, where we’re trying to make sure we are empathetic, uh, we are, but we are empathetic to their perspective as individuals. We are empathetic because we know that we, the team needs to take care of you, and we want to make sure that you also are able to contribute so you can take care of the team. And I think, you know, once, I think that's sort of how we sort of bring our culture together and if you are a person who has good intentions, I think that will always, there will always be a fit for you within that dynamic.

Thomas Jeyaseelan:
And if, you know, your intentions are not the most positive, then it's going to be difficult for you no matter where you are, but as long as those intentions are good and we can see that, then I think we can work with that regardless of your skill set. And, you know, if you don't have it, then you don't have it, and there's not much you can do from there. But we can definitely have a respectful conversation about that sort of, uh, that sort of thing and that perspective.

Host:
Right, and I think that's completely fair for all leaders. Uh, so, you know, in terms of sort of attacking the issue of the outcome with still being able to manage the individual and their personalities because they are people, and they are important, and they are part of the team, and they do matter. So, you know, I do agree with, uh, sort of how you're presenting that, and I think it has a lot of value, and it's really hard. It's genuinely difficult, and it is quite a nuanced thing. I mean, I've worked with so many people in my career, so many names come to mind of people who are simply just not doing great in the team that they were at. They came to me, we've had this conversation, performance wasn't meeting expectations, and these are nice people with just people you would want to be friends with. You take, you'd invite them home to dinner, they were just not doing that. And so, it's on us to be able to have the right conversation about impact, delivering results, not delivering results, and then potentially steer them to a place where they could do well, not your team it turns out. But why don't you help them to be at the place where they can be successful, and in many cases they've turned it around by changing the place they work or changing something else about the situation they were in. Turned the story around the next year into a great outcome, great results.

Thomas Jeyaseelan:
Right, and I think, you know, one of the things that's always interesting to me is, you know, with my experience working with people and I think your, I think, Apple experience working with people is, um, you know, they wanna, I most people I would hope want to do well, and I'm not sure it's always true, but in my experience I think most people want to do well, and, um, there are different things in their way. I'd love to ask you, what do you see are the obstacles, not that other people put in front, but they put in front of themselves that you're able to see and guide them through or around or across or help them sort of, you know, break that blockade?

Thomas Jeyaseelan:
My career has been most almost entirely in engineering, software engineering and I've been a leader mostly with engineers in my team although not always there have been other disciplines or skills that have been part of my team. Many of the people that come to me with problems had engineering challenges in front of them that we both discuss and realize, you know, there could be a gap in what's expected for this role and what they're bringing to the table at the moment. But most conversations lead to me realizing the problem is not the skills that are put on the table, the technical skills. It's not even about the people around them that's posing the challenge, but it's about something within themselves that has turned around and posed the problem. It's about the person in the mirror.
This is, I'm not saying this as a report out of the people that have talked to me. I myself, when I kind of count the number of problems I see or things that bother me from a day-to-day basis, it often turns into that man in the mirror I see. And so when we hear this, when I have a one-on-one where someone is coming to me with a problem and we are trying to break this down, for example, the coaching habit is a great idea, but what I've seen through these conversations, reflection or self-reflection that needs to happen that hasn't happened with this person, this person realizes, you know, if this is not about this partner missing a deadline and constantly requiring me to follow up with them, this is about this person that is just setting me off, or this is about me being frustrated that my voice is not heard in a meeting where someone keeps interrupting me. That leads me to be frustrated, that leads me to feeling like no one cares about what I think. So many, many cases come down to a challenge that a person needs help with to change the way they look at something.

I've noticed that it really helps to open a notepad, and for those of you in Windows, you know, notepad is still my favorite application because it opens up faster than any app. But what I like about it is it's a scratchpad, right? It's literally a sheet of paper online. I've noticed that this really helps me, and I've spoken to some of the people that I've had conversations with or who have even mentored me, they like to open a document and they just write down what's going on in their head. As you think about this, as you feel frustrated, write down what's going on, what is it that's tugging at you, what's pulling at you. And the conversation often steers into what is it that's eating at them, what is it that's really trickling them or provoking them, and what—and ultimately about how can I realize I may not be able to change the people in front of me, but I can change how I respond or how I can let it get to me or not get to me. This brings us to the importance of empathy in leadership, understanding that we can only control our reactions, not others' behaviors. And in those moments, compassionate leadership plays a crucial role in helping guide the individual to look at things from a new perspective, showing kindness while maintaining boundaries. When leaders adopt inclusive leadership, they ensure that everyone’s voice is heard, which can help prevent those frustrating moments from escalating. In situations like these, collaborative leadership can turn these individual challenges into team opportunities, where everyone works together to improve communication and find solutions.

‍

So we had a—you know, I'd like to share a little bit of a story. We had, you know, as a consulting firm, we deal with a lot of people and we do, and within the technology space of course, and we've had an experience with—or I've had an experience with an engineer that's very, very talented—but had a, you know, English wasn't his first language and he tried to be as productive as he could, but there is a limitation. And I always think people who aren't, you know, producing in a language they're not familiar with, they're exceptional sometimes by default. And, you know, his whole—and he wasn't with us, he was with our client, and I think in order to, you know, when we go in, we try and make people productive, and, you know, by example and by assistance, and one thing we were able to sort of help with or unblock was just the way that information was presented to him could have been done in a way where he could understand it, but he didn't necessarily need to know the language. So they were presenting it as essays, and then if—and you know, something as simple as putting it in some sort of graph or some sort of table would have gotten him exactly what he needed. And I think it would have—and it did get me exactly what he needed, sort of without that translation issue, where there's just less of a certain kind of information that he's not familiar with for him to focus on, and the one that he can't understand. He could focus on and it's these sort of small tweaks when you're giving when you give people the opportunity to express themselves that you know they can present themselves and really help your team. And how does it help this person? He just helped him because he, you know, something as simple as a 200-word paragraph or just a page worth of requirements, sort of the logic in between that, if that can just be presented as a table, he understands immediately. Because the table is a non-language-based way of communicating. So because it's just a table, he understands: turn this on, turn this off, this is what we want and vice versa. You can even kind of see it where the x's and o's would be, and he says, "Okay, this is what I need in terms of if and else's, and because of that, that's how I need to make this application." And this is what business wants from me, and I can understand this pretty clearly. And this is sort of non-... Of course, on the business side, it's not specific enough; it doesn't really mean anything because what is being turned on and off? But on his side, he already kind of has that context. So all he needs to do is know exactly where those things are, go find them, and go switch them on or off. And I think that's all you need to do within that constraint. And I think that helped him a lot, and this gave him time and confidence that he can do what he needed to do. So that was something that, uh, it was interesting to see, and I also encourage other people to learn how to communicate with him as well. Because he had the confidence to do this, he did it, and people say, "Okay, he can do things, let's make that effort to help him out in that way. Let's make that effort to present it in this way." And I think that just that level of success, that bridge he crossed, I think that, um, that kind of heals that peace and continues to move forward because that builds trust. You see that someone can do something, and it's always nice to see.

It could be so easy to misunderstand all the things you're seeing from this person and really think, "Wow, this person is not understanding what I'm saying. Maybe I should find somebody who is better, somebody who is smarter or quicker." However, successful leadership often means recognizing that these misunderstandings are not necessarily performance issues but opportunities for growth and adaptation. This is becoming more common in our industry, where inclusivity and diversity are central. In many cases, successful leadership requires patience, cultural awareness, and a commitment to creating an environment where every team member feels valued.

Our industry is relatively young, remote, and open, inviting people from all over the world, which increases our chances of encountering diverse perspectives. Leaders who are tuned into these dynamics, understand the importance of empathy in leadership, and know how to work through cultural and language differences often find greater success. This adaptability and open-mindedness are key components of successful leadership accountability, allowing leaders to look beyond surface-level misunderstandings and truly understand what is happening within their teams. By embracing inclusive leadership, these leaders create environments where all team members feel heard and valued, ultimately improving collaboration. In turn, compassionate leadership fosters a deeper connection with individuals, where leaders can truly support their teams through challenges. This creates a space for collaborative leadership, where everyone works together toward common goals, leveraging their diverse perspectives to generate innovative solutions.

‍

Host:
One question I was dodging this whole time, which I think is really important, is, you know, with leadership kind of scale and sort of a lot of these things are interpersonal interactions, and one thing that's always interesting to me is, you know, you have a small core team that you're working with, but somehow, whatever you're doing, you have to perceive the outcomes not only in that team but throughout the organization that you are responsible for. And how do you sort of do that? How do you know what is and isn't working with a feedback loop? Some feedback loops are really about graphs and charts and outcomes and things of that nature, but culture is a little bit of a softer one. It may or may not represent in whatever representation that you have for how organizations are being successful, and it may not be the right way to assess it. So how is that, that sort of softer skill of saying, "Okay, my co-work, this workplace is like this, I am perceiving it as it is not as it is presented to me," and sort of the small nuances of human interaction that could either be misunderstood or isn't present because you're not in that space? How do you deal with that?

Thomas Jeyaseelan:
Thanks for bringing this up. This is something that I deal with every day at work. I don't know if I have all the answers because it was one of the most difficult challenges for me, and even today, when I talked to my manager and ask for help from her and from others, it's, "How do I get better at that? How do I get better at being more effective at scale and listening and really getting your pulse for whether or not what I'm doing is connecting with the team, or my team hasn't gone in a totally...?"

Um, as I've gone through this journey, I will tell you first and foremost I have not perfected it or I'm not in a position to write a book about this. I have noticed through mistakes that I've done what works and what doesn't. Um, and I made a lot of this and that. Number one, I have to be open to feedback, and being open to feedback is not about saying, "If you have any feedback, send me an email." That's not what being open to feedback is about. That's a very cliched way of just, um, you know, just taking a small step but not going through with that. Ultimately, and I think you mentioned this earlier in the interviews about building trust, we've got to build trust, and trust has to happen at a deep foundational level. However, trust is difficult to do if you have a large team that you're managing. It's difficult for you to reach out and create a deep connection with every single person, so that's not the goal. The goal is not to be best friends with every single person on the team, but the goal is to create a foundation of trust by looking at the leaders that I've seen that are reporting to me or that work closely with me and make them as almost agents for change. It's important to have values that matter a lot to you as a leader and make sure that everyone on the team understands that, understands what's important to you, and that starts with the people closest to you: your staff, managers, or the leaders that are working for you in your team in different capacities. Communicating that is key. Connecting with people at different levels has also been important. If you cannot, if you have a large stream of hundreds of people and it's not reasonable to meet with every single person often, meeting with them in different ways, whether it's at a, you know, you know, at the coffee machine or whether it's at an All Hands event or at the smaller scale team events where you meet individual teams at a certain cadence. Mixing this up, finding different ways for you to have collisions, is key to successful leadership. I like to work collisions, and I think it was Dr. Anita Gray who mentioned that having lots of collision opportunities with people increases the chance for quick but powerful connections. These connections, when done often, are essential for successful leadership because they allow leaders to reinforce important values consistently.

Finding ways to connect, even if you’re a high-level leader who might feel removed from day-to-day interactions, can keep people engaged and authentic. By contrast, if you spend too much time in isolation—like in a "Wizard of Oz"-type world where you’re just sending out edits and feedback from behind the curtain—it limits your impact. You need genuine interactions to build long-term trust and authenticity.

I’ve found that creating opportunities to intersect and meet people in different ways, while being clear about your values, is crucial. This approach not only scales your influence but also helps plant the seeds for building the team you envision. By prioritizing these types of connections, you can foster the commitment and alignment that define successful leadership and bring others along on the journey.

‍

Host:
Well, Thomas, thank you so much for joining us. Thank you for, uh, advising. I think all the listeners and I also learned a lot from all the things you sort of told me and, uh, you know, thank you for joining us. Where can people find you? How do they reach out to you?

Thomas Jeyaseelan:
First of all, thanks so much for having me. I really appreciate this time and it really made it a lot about it. I hope it is...

Host:
Alright, okay, well thank you so much. Thanks a lot. Have a good rest of the day.

‍