Essential questions & leadership principles to navigate change, fear & uncertainty w/ Rukmini Reddy #214

We're doing a special in-episode feature on the future of AI-powered incident management with our friends and sponsor X-Map. People as a primary integration layer is really fragile. With multiple people and all of that coordination, you become slower to find the root cause. The slower you find the root cause, you then don't know what action you need to take to resolve it. Getting to that fast is the goal.

Later in the episode, Mike Bennett, who leads the engineering team at X Matters, shares why human-driven coordination creates outage risk and how AI-powered orchestration can dramatically accelerate your path from event to resolution.

There's never going to be a right or wrong answer, right? Because organizations are dynamic. It changes. Today you may have a role in this team. Tomorrow you may need to move to a different team. So I encourage managers who are leading this conversation, even the humans I'm coaching in that moment to say, don't make false promises.

Because you actually can control what you can control. So, my coaching moment is always like: focus on the outcomes you can control today. This is not an outward look. And I'm here as your coach and someone who's invested in you and your manager or your executive to listen, to be a listening year, just practicing active listening and see how I can support and nudge you. But this is for you to own your own, like what you can control. What are the controllable controllables?

Hello and welcome to the Engineering Leadership Podcast brought to you by ELC, the engineering leadership community. I'm Jerry Lee, founder of ELC. And I'm Patrick Gallagher, and we're your host. Our show shares the most critical perspectives, habits, and examples of great software engineering leaders to help evolve leadership in the tech industry.

In this episode, we are joined by Rook Mini Reddy, SVP of Engineering at PagerDuty, who shares with us the invaluable leadership lessons on navigating transition, uncertainty, and fear. And in our conversation, we cover actionable strategies like the five essential questions to help you lead your team through change. We talk about hugging the elephant to overcome fear. We also talk about approaching org change from first principles.

Shifting your team from informed pessimism to curious optimism when it comes to AI adoption and building high trust peer support. If you're looking to strengthen your leadership and build more resilient engineering teams, this is the conversation for you. It is packed with essential insights to help you navigate the toughest challenges that you'll face with confidence.

Let me introduce you to Rookmini. Rookmini Ready is SVP of engineering at PagerDuty, responsible for managing product and platform delivery, infrastructure, and data science. Before this, she was SVP of engineering for platform at Slack, where she guided the vision, strategy, and execution of a comprehensive rearchitecture, transforming the messaging software into an automation platform that empowered users to streamline their work.

With over a decade of experience in senior executive roles at various enterprise companies, Rookmini has a proven track record of driving engineering and product strategy during periods of hypergrowth and product transformation across SaaS, B2B, and B2C businesses.

Enjoy our conversation with Rookmini Red. Rook Minnie, just want to say welcome. Thanks so much for joining us on the show today. How are you doing? What's going on in your world? Uh I am doing great. It is spring, so I'm ready for it. So that's what's going on in my world. Excited to be here and excited to be here. This is a really interesting reflective moment when it comes to thinking about leadership. One of the ideas that you and I were talking about was how leadership has evolved.

from 2021 to now being 2025. And so I was I guess I was wondering if we'd start there from from this like reflective philosophical place. How have you seen the role of engineering leadership evolve? From twenty twenty one, a year post the start of COVID, there's a lot of change and disruption going on, but it's a markedly different kind of change versus now 2025. So what are you observing, what are you reflecting on in this big shift from twenty twenty one to

You know, that's such an interesting question because I use Google Photos for like just like what happened and I actually got this reminder on my phone today five years ago. I was actually standing in line at Seife. checking out before the Bay Area shut down. So I was just like What it's at five years ago today, and I took a picture saying, I might want to remember this moment. So it was just an interesting picture of my shopping cart, but I was just like I was.

uh you know, in advance of our conversation today, I just chuckled a little bit, saying, Wow, it seems so surreal that five years have passed, but also like it doesn't feel like a lot of time. Oh my gosh, yes. I remember going to Costco and getting two giant packs of toilet paper. Like it was the big toilet paper rush of twenty twenty. So I I I totally know that moment.

Yeah. So I think like, you know, if we fast forwarded like where leadership was in twenty twenty one, I was just thinking about the themes that resonated with me and when I was reflecting about our conversation and I think this like So much about like this combination of crisis management.

I think that's the word I would use. Less resilience because just like the challenges of the whole world going digital a year in, the scaling, reliability, then shifts to like technology and being at the forefront of everything even my then first graders were doing, right? Uh worrying about keeping the lights on and becoming like a little bit of a little bit of a little bit

so operational. Like if I look back, I think it was very important to be super operational and look at everything from a first principles mindset. At the same time, like technology organizations were like growing. extremely rapidly. So you had to keep the lights on, you had to keep the business on. Business was meeting new scale at a daily on a daily basis. You had to hire faster than everybody else. And we were all kind of competing for the same digital workers.

That resonates, right? What do you think? Like crisis management and resilience was where we were, if I were to put them thematically. I I think it captures so many different themes'cause I I remember so many of our early conversations, especially twenty twenty, twenty twenty one, were sort of one, how do you make that shift when the massive massive onboarding where tech's at the forefront where all of a sudden now everything is much more

async communications happening online versus an in-person meetings. How do you do this whole shift? And then it was also like all of these challenges around scaling and hiring. I remember we did a conference that was specifically focused on hiring.

all day and it was about the full hiring stack. And it's like we haven't done anything since then. But it was like in that particular moment, like the competition was so high that everybody was looking to figure out where was the edge where they could compete in terms of of hiring great talent. So yeah, all those principles like I I just I I see them reflected in so many of the different conversations we hosted right around that that era.

And you know, I think you asked like what has changed today. And I feel like one thing that I actually stayed the same thematically is resilience. And I think it just resonates in a different context. I feel like What's today is like we're all leading in like highly adaptable and agile environments. And adding onto it, there's like a rapid once in a generation because I have been around to see other technological advancements and shifts and I think this quite not

to the scale of what we've seen with AI, where there's an advancement into AI into all employee workflows, irrespective of whether you're a tech worker or not. I think that's been incredibly different. But I think it's the resilience theme kind of stays unique and the same. So we're talking about resilience as a high-level theme. Are there other skills or mindset shifts that you see emerging as more essential for leaders?

Today, for them to be successful? Like, are there other elements that are surfacing that mark the the shift between you know a few years back to now that leaders really should be focused? So I read an article a couple of weeks ago that said that the let's see if we can guess this number one priority for engineering leaders in twenty twenty five. But last time we said hiring in twenty twenty one, but you know what I came across Really I chuckled. It was financial acumen. Really?

It's like it's just like so interesting because it couldn't be more different than everything we've learned as tech leaders for the last fifteen 20 years, like financial acumen being it's always important, but being the most important was where it was like really interesting. And I thought like engineering leadership always evolves, but I think right now it's about meeting the business where they need you to be as a leader.

Talk to us a little bit more about that that concept. Because like when you're talking about like financial acumen and like comparing that to hiring is like being the big focus now, like I I also am seeing that reflected in a lot of the conversations that have come up in the last year where There's all this conversation about communicating engineering to the business and being able to control headcount and cost.

and to drive to efficiency. These are all sort of saying like you need to understand the cost of running your technology organization and how to make it either more predictable, more efficient, or more clearly connected to revenue or profitability or some of these other business metrics. So like I see the financial acumen. But when you say like you need to meet the business where they need you to be.

Diving a little bit more into to what that means to you and where that came from. Yeah. So it's interesting. So at the core of how I laid is like, like alignment with my core values. Like I did core value exercises years ago. And when I choose an environment to work in, alignment of the mission and vision of the business to my core values is really important.

Like that's like table stakes, right? Now I think the questions I ask on top of it and I ground myself in these questions is like, what does it mean to become the leader your business needs? Is like one, will what I'm doing drive a meaningful impact? to the customers? That's the first question. Will my team's output or like how engineering partners with the rest of the organization make a meaningful impact to our customers? Does our team position us to win in the market?

And as a team, holistically, right? Are we fostering a culture of excellence, accountability, and shared success? Those would be like my three, like, you know, that's the table stakes I ground are my team in now, which I think has resonated really well with folks.

So this is interesting because I've been I've been ref trying to reflect because there's been a c a few different projects I've been starting to engage in and one of the blocks that I had was this connection to personal mission where like I I couldn't make that leap yet and I was really struggling with it because it was like, you know, on paper I was like, oh this

project that I'm working on is super interesting and it sort of checks rationally or, you know, academically that I should like it, but I couldn't figure out the connection.

When when you're sort of using these as a as a tool, what what does it look like to sort of go through this and all and create this alignment? And then how do you use this in alignment within what the business needs? Like is this answer this first and then find the alignment with the business? Or how does it intersect with that?

I think first understand where the business is trying to go, where their strategy is, where they're heading on a long term horizon, like I think three years out, eighteen months out, twenty-four months out, and then what's our mission, what's our vision, what's our Company strategy. And then you work your way backwards to like, how can we partner with the business to be able to realize our potential?

That definitely makes sense. I as soon as you shared that I was like Like I I feel like a sense of peace. I'd love to get into the conversation a little bit more about what it means to become the leader your business needs because you know, you and I were reflecting on what were the leadership challenges of 2021. When those challenges shift. How do you as a leader make that that shift?

Especially I know one idea you and I were talking about was we have certain natural strengths or or certain characteristics that we really value and that are our core strength. But then when the environment shifts or the challenges shift, we have to change too. Tell us me a little bit more about like the dynamic of becoming the the leader that your business needs. I love um

How to change things when change is hard. Uh that uh you know, the Heath Brothers framework. I've used it for years. And I think uh there's so much about like, are you familiar with the elephant and the rider in the path? I'm not. No, but I love Dan and Shepeath. Their their book, The Power of Moments, like changed my life.

No, this also was like a life-changing book for me personally, because it talks about when you have to change things when things are hard. The elephant represents the emotional core of how you make your decisions and how you move on an idea or change.

your leadership philosophy and the writer is the logical, rational, analytical side of your brain. Like it's your brain. And if you think about it as an engineer, I like to believe most days I'm very logical and very analytical. And the goal is for this elephant and rider to go on a path together. That's your strategy or that's where you need to head. And if they're in disagreement

Who would you put your money on? Oh, I hundred percent put the money on the elephant. The elephant wins every day, absolutely. So I learned something unique at like my past job at Slack where we talk about hugging our elephants and I always wondered what that meant. And what I learned over the years was hugging your elephants means hugging your emotions.

So, you know, you actually processing them on like asking hard questions of yourself, saying, What are you afraid of if you have to go through with this change? What do you need to be successful?

How can you lead your people through change when you don't understand what's going on? Or like what do you need to make sure you have all the information and access to visibility and transparency so you can make informed decisions? If you're able to process these questions and answer that and Hug your elephant. You can actually lead your teams better. And I think that's what's been a shift for me, like whether it was in 2028 or 2021, which required a completely different.

theme of hugging elephants to now, it's different, but it's more like, what does our business need? Where do we need to go? What do our customers need? Again, it's not about the business. It's always about the customers, right? Like making sure your customers are the core of everything you do. Because if you bring value to them, you will find value in your business. And just like making customer success your North Star and your guiding principle.

helps you work backwards from like talking about all the human stuff. Like what what's gonna happen if I do this or I don't do this? Can I trust myself to do this? Am I making the right decision? But in most leadership positions, Decisions are murky and hard. You will never have if you're waiting for all the information to fall in place, you'll be waiting a very long time.

We're taking a quick break for a special feature on the future of AI powered incident management with our friends and sponsor XMAC. Mike Bennett, who leads the engineering team at X Matters, shares why human-driven coordination creates outage risk and how AI-powered orchestration can dramatically accelerate your path from event to resolution.

We're the ones that are correlating the alerts across the platforms. We're the ones that have to remember that a similar issue happened six months ago and this is what we did about it. We're the ones that have to figure out this is a symptom in service A. but it has a dependency in service B that we need to know what that dependency is and how that could impact this thing. We decide on who is going to be page based on some informal knowledge.

It's it's not scalable. I mean it that all of that works in a in a very small scale environment, but as as systems grow, as teams grow, people as a primary integration layer is really fragile. So the outage risk is with with multiple people and all of that coordination, it you become slower to find the root cause. The slower you find the root cause, you then don't know what action you need to take.

N not knowing immediately what the problem is, so you don't know what the route for that mitigation is. with all of the information that is out there, getting to that fast is the key goal and is the key problem when you've when you're relying on people to do it. When a signal comes into X Matters, the first thing that you can do is based off of that signal, you can then make a call out to the right people.

for our incident process internally, a signal comes in that says we've got a system problem, the first thing it does it pages out an incident commander and an ops person because those are the two people that are most likely to be on uh you know required in any call. From there, the incident commander can then use automations that are set up in the incident because it it automatically creates an incident for us.

It's linked to the ticket that generated the incident. And from there we can determine, okay, well I've seen I've seen this before because my incident suggestions is saying this looks similar to this incident you had last week. We've got built-in automations that can do stuff. So within an instant you might have an automation that says automatically restart pods or automatically rollback services. Like I mentioned before, we can also do that as part of a response.

to the signal that comes out to say, okay, this has happened, do a rollback and I can just Touch my phone and go back to bed without even getting out of bed. all of the automation, the flexibility of the tool and all the the things that you can build in along with the data that you've got with the service catalogue, with your on call, with your who's on duties and get you to get the right people

at the right time on the call if you need to get to a point where you're in a conference. X Matters automates the entire incident lifecycle, taking you from initial event to final resolution. To see how their purpose-built AI slashes your resolution times and gives your team the context to stop disruptions before they start, head to xmatters.com. That's x-m-a-t-t-e-r-s.com.

So I'm trying to get a sense of like my goals, I'm trying to understand what is hugging the elephant look like twenty twenty one versus twenty twenty five, like.

Twenty twenty one, I start to think of, you know, some of the different town halls that people were were having to start to process the fear and the emotions behind all of the uncertainty around COVID and the work from home and the new challenges that parents would face and the new challenges of communicating with your team and the new challenges of like the financial constraints of changing buyer behavior and customer behavior as a result of all these different dynamics.

So is there anything that comes to your mind about like what it looked like for you hugging the elephant in twenty twenty one and what it looks like now in twenty twenty five? Yeah, I think hugging the elephant in twenty twenty one, you hit it. It was the same themes, right? Like, well, how can I make sure my team feels connected and engaged? Uh like for example, from twenty twenty to twenty twenty one, I didn't meet any of my Slack team for the first twelve months. Isn't that wild?

I literally do not see a human being in person. So I just told everyone I'm six feet tall, which I'm not. I'm actually only five feet something, but I was like, if I can be anything, I'm gonna be a very, very tall person right now. So when they saw me a year later they were like, Ruke meanie, I was like, Well, I had a good time, it was a good run. I realized some of my lifelong dreams. It's stuff like that. Like if you look back like it's um Almost like you I was so buttered about it.

people keeping people connected to our mission when they were so far removed from each other, like they were operating on social films or just were navigating completely new ways to work. I used to always wonder how do I align my org? How does information get lost? In the virtual hallways, like when there's like an employee sitting at the computer, maybe it's an engineer. Do they understand the why behind their work? Like that used to be my greatest worry in hugging my other.

Now we shift that a little bit and we think about 2025. I think there's like a really interesting time as makers, as creators. Like I think of all things, right? Engineers are one aspect of it. I'm sure if you're in design or product. Also, you have all these feelings about it. There's a rapid shift in which AI is becoming a part of all our employee workflows.

And this is a once in a generation shift and it's happening so rapidly with every new model, with every new platform. There is a almost, I want to say, an exponential shift from the previous version. So I think this is a very unique moment in that in previous platforms when they came by, the time to update the version of the platform where you could catch up was a little longer than it is now. I feel like you're constantly building on an evolving platform.

I think that's what's top of mind for everybody. It does it resonate with you, Pat. I I think it does. As you're sharing that, like I'm thinking of some of the big operational shifts of AI products. in which I am feel like I'm playing catch up every day to figure out, you know, first How do I integrate a chatbot leveraging LLMs? And then it's like, okay, now how am I building an agentic system where tasks are being done on behalf of

of me. And then it's like, but how do I even incorporate that in my workflows, let alone build that product?

And each one of those requires like a a different shift in understanding of the technology and how it all applies. And then you have then the enduring challenges of of security and privacy and and all these other other big areas of focus. And I'm like, wow, you know, I if I take a week off, I come back and I'm like, I don't even know how to operate the interfaces of things anymore because I'm like, How does this all work?

So I I do s I do see that that speed and then I especially see the existential question of Am I being left behind and is my job relevant? And I I think that's like a really hard thing for people to reflect on in a lot of different roles where this is powering a lot of teams, but then like the speed in which it it takes off. And you're like, Well, how do I how do I wrestle with this? Yeah. I think that's

the most human part of this all, right? Like it's a Maslow's hierarchy of needs at the end of the day. Humans ask ourselves, like, you know, the same, I feel like same five questions, no matter what the changes, whether it was the change of 2021 or it's a change of twenty twenty five, the core of what we go through as humans and as we hug our elephants, like what does this change mean for me? Me the human, is my job safe? Can I see myself in this role in future?

Can I trust them as in the royal them? Like you know, the system of like maybe the platforms and LLMs and what's coming up? What's planning? What do I not know? So kind of like suspicion and fear of the unknown. And if I don't change, will I still be?

I love these questions. Can you break these down a little bit more for us? Like when do you use these questions? How do you how do you leverage these as a as a tool for I've used it in like most change management exercises I've done, whether it's like, you know, a regular reorg or like introduction of a new technology or like in past times when we had to

Be merged or acquired. Like it just depends on a large transformation change happening in any business and any context of a business. First, As a leader hugging my own elephants, asking myself these same questions. Because if I don't have my elephants, I can't show up for my people. It just doesn't work. You can't, you can't fake it as a leader, right? So it's like making sure you can actually ask the same questions. What does this change mean for me?

What is my job safe? And once I go through that and I like write down, I like to journal a lot. So I write down like what my process and I feel like, okay, maybe some things are good. Maybe I need clarity. Maybe I need to go ask someone something. But most of the time like Like I'm clear on my process. And then the way I like to engage with everybody on my team is go through the same structured, like five questions with them when I inform them of a change.

Whatever that change might be. Maybe it's like, hey, let's adopt more AI, for example. Right. Like it's good to just be like, let's zoom on and think about what does that mean. Ask yourself these questions. Go away, reflect. And if you feel like sharing, I'm happy to be here and like listen and partner. But I need you to like process these because I think when left unprocessed, this makes

change really hard to land because you think of change as like, oh, the entire organization is going to change or not. The entire business is going to get changed or not. The question we should ask ourselves is that human going to change or not? I think it's a really powerful distinction. So you mentioned the like maybe we're introducing more AI into product or workflow. Are there notable examples from your experience as a leader where you've walked through this framework with

Yeah. Because I can immediately see like an org change, like how this applies there. But like are there other contexts of like change or transition that this really helps guide folks through and and brings them into the conversation? I'll share you a little bit of story of how this framework came to be. I would love that. Yeah.

I once had a really interesting work set up where there was like a interesting boat scenario play out without giving out too much details. I had just had my twin boys and they were five days old. Yeah, and I remember my then manager calling me and saying, Okay, I need you to know this because you're going to see it on the wire.

So I had to make a call today on how you need to find out this information and walk me through like the entire process of what was happening. And you know what was a new mom question I asked them? What does this mean for my health insurance? Yeah. Because I had five-day-old premium twins. Like I did not care about everything. And then I had this realization I was already in an executive position at that point that. Oh my God, what I thought would matter on that day?

what I needed was something completely different and very basic and very human. So just gave me this like lead with empathy. Put yourself in other people's shoes on when they're experiencing change for the first time. And just like, I really appreciated that phone call. It was like one of the most meaningful phone calls for my career and also like how much my manager cared about me to have that really hard conversation.

I'm sure he was in two minds. Do I call, do I not call? Is it I'm so glad he calls, right? So um I've used this like a lot in like mostly re-org, change management, mergers, acquisitions have also been like when, oh, I don't know what this new culture is gonna be like. And you're like, well, let's let's analyze. What does this change mean for you? Is your job going to be safe and there as a result of this action?

And then obviously like you know, I think of like org debt as tech debt. It's something most organizations re-org wherever I've been for the last 20 years, like every year or so. So whenever you're changing something like a person's manager, it's good to have. So, all the way from like a company strategy change to a technological change to like a team change or a manager change, the framework kind of applies across. All dimensions.

And I kind of wanted to go into like if if a question is answered yes or no, like what maybe what are the next steps that happen? So like, you know, I think what does this mean for me? I think is like the big empathetic moment of like are you actually taking the time to understand how does this impact them and what does it mean for them and why are you telling them? But then so like the question, is my job safe?

can be kind of like a yes or no or maybe a conditional or will my role exist in the future? Like what are what are some of the considerations like when you're reflecting maybe on on those parts of well, we'll do the second the second half after. But like maybe on those parts, like what are some of the considerations that you're thinking through there in that moment to help create like a powerful conversation around transition?

So this is how I think about roles and jobs and this is like my my my coach hat now, not your executive hat, I'll always tell people, never promise people something that you cannot guarantee. And jobs and roles have always shifted since the beginning of time. So I would encourage like self-introspection and coaching and support that they need.

to be able to navigate the answer to that question because there's never going to be a right or wrong answer, right? Because organizations are dynamic. It changes. Today you may have a role in this team. Tomorrow you may need to move to a different team. So

I encourage managers who are leading this conversation, even the humans I'm coaching in that moment to say, Don't make false promises because you actually can control what you can control. So my coaching moment is always like Focus on the outcomes you can control today. This is not an outward looking exercise. This is more an inner reflection.

And I'm here as your coach and someone who's invested in you and your manager or your executive to listen, to be a listening year, just practicing active listening and see how it can support and nudge you. But this is for you to own your own, like what you can control. What are the controllable controllers? And things that you can control. So I would say question two and three are just very hypothetical to kind of acknowledge that you can actually control something.

And it's better to let go. And then when you get into the the the bottom two, so like can I trust them or like can I trust the system? And then if I don't change, will I be okay? Like what are some of the dynamics there that you're you're working through and considering? Yeah, can I trust them and this is where like I can give clear

Overviews of like where the business is heading, why this change is important, and you know what are the plans, right? This is where like if you have like clear vision and mission and alignment, you can craft talking points and actually walk people through, like, let me now tell you why we are doing this.

And what is it going to unlock for our customers? Again, start exactly where we started, right? What does this mean for my customers? Am I adding value? Customer success has to be your North Star. Then how do what does this mean for the business? Will this help us win? And then what does this mean for us?

And if I don't change, will I still be okay? Hmm. This is a little harder and spicier, right? Like because it depends on the individual's context. But I always nudge again. Like I like to take examples of like my first camera was a Kodak. As a 10 year old, I remember getting Kodak and it being the most important day of my life. And the company ceased to exist.

So I just think about like in a span of twenty, thirty years, a beloved everyone's first camera and we don't hear about it. I spent many, many endless summers in Blockbuster, did you? Absolutely. Hollywood video, Blockbuster, all of the stores. All of the things. And I try to root people in like, you know, you need to change with the times. Things that you once thought were like almost ubiquitous to your daily life, but no are no longer here.

Because they refuse to change with the time. So it's not that organizations change around people don't. So you're a person and your responsibility is to help this business succeed as an employee here. Now you may take a different process. The second question you can ask is, I need help. I don't understand. Can you support me? That's like, yes, absolutely. What can we do to make sure you feel confident going into this?

That's great. And now I I have to connect it back to our earlier conversation about hugging the elephant. So how does how does hugging the elephant sort of get woven into this conversation? Because it it sounds like, you know, this is a good framework to help guide teams through transitions. Hugging the elephant to me almost seems like the first thing to think about is like what's sort of the unspoken fear maybe to address. Is that a fair assumption?

Yes, that is a fair assumption. Almost to a point where in some teams earlier I used to have a hugging elephants channel where we would have like a private space as a leadership team to hug our elephants every week.

That was a very 2021 thing to do, Patrick, where there would be like a shared channel where once a week we could hug all our elephants because it felt like every week there were new elephants coming our way and we would have like a safe space creative where the team could be like, This is what I'm bothered about and these are my fears and

It was almost like a peer-based like group, very high trust, high performance, right? Because the demands were so high, the businesses were growing at such a rapid pace. But in the end of the day, you need to ground yourself in hugging elephants and sometimes having a peer group with the high trust. I think you think of it as a intense empowerment, but also intense accountability, yeah. So the context of the group was was sharing fears and worries and then being able to find support.

Sometimes emotional support, but also sometimes tactical support. Like what what was kind of the support look like? Like, yeah, that's exactly like you nailed it. It was like we used to start with let's hug our elephants this week. What are we all most worried about? And then we would start with like and then everyone would step in and say, I can partner with you on it, or the conversation is to be friends. I'm hugging my elephants. I don't need any solution.

I just want to vent. You're like, okay, it's a venting session, it's fine. But having that space to do that is is really amazing. For somebody listening to this, if they were going to try to introduce this To maybe their peers within their company, or maybe they're gr bringing in or creating peers in sort of their network. What advice would you have for somebody creating this space for the first time? Because I think exactly.

For everything you share, this is so powerful to have the space to be able to talk about the fear or the worry, to have support like that, but also to have both just the space to share and also the space to find solutions at some point. But I think the non solution element is also oftentimes like more helpful. So uh what advice would you have for somebody maybe doing this for the first time?

I would say like first and foremost it needs to be a group of people you know pretty well. I think this will be really hard to pull off at strangers. Uh it's really important to understand how people operate. If you have an operating manual or something that helps like establishing like norms for the group.

This group is a place where you can go ask for help, tactically, a place to just win, but having those norms defined would be really helpful because you need to be able to have familiarity to grow trust to be able to have these kinds of conversations. And I've often found this in executive quorums pretty well, like because most people are like, I can finally talk to somebody who gets exactly where I've been.

We ha we host a a number of different peer groups and the the norms element is is super important for that and having a shared sense of context. So like you said, like the more senior you become, the less amount of people understand that experience or the the types of problems that you're dealing with. And so having other folks external to that is super important. I have an analogy for that. I say it's a C leadership is a C and the amount of stuff that gets

to you is like exponentially more. So I have a lot of empathy for all my managers. I'm just like, I don't even want to know what your day is like, but I want you to know I appreciate you and I see you for the amount of context you hold. Absolutely.

So our conversation has evolved really in a really interesting way. So we sort of started with hugging the elephant, which is part introspection, part how you're supporting uh somebody on your team one-on-one. And then from there, we also talked about the five essential questions that you ask yourself as you're going through transitions with your team. So we kind of have this like self, individual, and team element we've looked at so far. Uh and I know the the other side of this.

That is interesting in times of transition is rethinking what your team or your organization needs from first principle. And thinking about some of those transitions. So I'd love to get a sense of like, what do you mean by that? And then what what does that start to look like? And what does that mean in today's environment?

I think we talked about like the I and me. So I have like this framework that I've used, like that has evolved from many well known frameworks. So I'm most mostly a pattern matcher and it's interesting the patterns have stayed the same no matter the environment's changing. So one of my other favorite models is the Elizabeth Kubler-Ross model, right? When you're leading your organization through any change.

the amount of time your organization spends in the dip is the most harmful. So you need to really think about what your team needs at various stages of the change as you start to roll out the change. So if you zoom out and you think about how do you get an organization from point A to point B, the first step is just the clarity and empathy, which we talked about at length here, like being clear with people, being empathetic, but then you make the shift.

For them to get out of their dip. It's where uh informed pessimism. That's what I call that stage. Informed pessimism. Where at first you're like, you're knowing it, you have no idea what's happening, and bam, the change happens, and then you're in this informed pessimism. And how do you get to be like curious optimists? I think that's the shift I like to call out. And it comes down to two things that I have noticed capabilities, and then finally motivation.

When people are ready, like capabilities, this is how we can do it together. This is how the organization itself is enabling you to be successful. These are the five steps to get from point A to point B. And then motivation. Hearing about the vision again, starting with what are we doing for our customers? Why is this important for our customers?

then what does it mean for our business? Then how do we participate in it and have a play in it as a team, a good teammate, right? So if you break it down, then the organization tends to like move.

through the different phases, if that's helpful. If you're visualizing it, I'm like I'm I'm totally tracking. Like as soon as you mentioned the dip, I was like, yes, we're on the curve. I'm I'm right there with you. Yeah, it's on the dip. So informed pessimism, you need to spend least amount of time. So I think But the themes of what people feel and what you need change.

So I have like this like seven-step framework that I've evolved over the years. And one is like we talked about this in length, hugging elephants, checking your own feelings, right? The second thing is communication is key. This is before the dip, right? Gaining buy-in, making it personal, and then bam, the dip happens. And then you have to be very clear with next steps, be transparent and then celebrate product.

And throughout it is like this undertone of building capabilities and enablement and support systems to make sure people can get from the first stage to the stage of just exploration and innovation and growth.

Do you have an example maybe to walk us through the dip moment? So maybe the clarity and empathy, the shift. And then the informed pessimism dip and then now folks are shifted to curious opposite. And I think there's probably a big moment that that is probably universal to anybody in the world of engineering right now. And that this is probably all of the different details of AI adoption, how it goes in the engineering workflow, product integration, uh, how it's just sort of everywhere.

Bring us into to how you're thinking about that, like f going from informed pessimism to curious o optimism, using this as our anchor for change and transition. I love that. I think like we could both agree the industry is in the depression. But we see it, we see the power, we know as technologists, it's what a great time to be alive and also what a scary time to be alive because of the rapid advancements.

And this is where like I think if you go back to the framework, we have to all hug our elephants and ask ourselves the same five questions, right? What does this change mean for me? Is my job safe? Can I see myself in this role? Can I trust them as in them AI frameworks and what's happening? And if I don't change, will I still be okay? And I think this is the crux of most of my conversations these days. Like fellow engineering leaders, fellow executives.

This seems to be the trend. Is that resonating with you, Patrick? Is this what you're hearing as well? As soon as you started it saying those questions, they're probably the first place that That's it's like top of mind for everyone. And I think this is how I like to coach my team or my other fellow leaders and I was like, look, again, go back to like controlling your own destiny. These are principles we've talked about and focusing on the controllables, which means

You need to first give yourself permission to be able to go learn and you need to become familiar with what's new. If you go back, you can place these boxes on the different stages of the change curve. Have a beginner's mindset. First hug your own elephants, write them down, process them, control your destiny, and then for starting to lean in, embrace youth, build familiarity.

And then you need to realize this promise of AI agents or A I don't know whatever is gonna be new next to become a highly productive and engaged employee. Again, if you're in service of your customers and that's what you wanna do, you need to be more productive in service of your customers. It's both personal, but it's also like you can move the business forward if you engage.

I love Jensen Hong's quote, like where he said like, Don't be worried, you'll be replaced by AI, but you're definitely gonna be replaced by a person using AI. And I thought that was a pretty like interesting code. And if you'd reflect on it, it's just like your fear, don't let your fear get in the way of your learning. Well I I'm just thinking of

How people are doing things powered with AI versus not. And probably less so in terms of the actual software engineering component and the coding component, because I think people have different opinions there. And that's not necessarily the example I'm talking about. But like some of these other use cases where like you have zero skill and it takes you to like 80% good at

I'm I'm talking to a few folks that are, you know, trying to start their own business, their first time being entrepreneurs and like they're using these as like co pilots to help pressure test ideas. And so the element of like research or structuring

customer research or structuring research around the market is helping them get there within a day versus something that could have taken a month or so beforehand. And it doesn't replace like in-person like interviews or things like that, but like the ability to build these skills or start to gain like at least like an 80% good enough framework. for how to even think about a problem is so wild. And I can't even put my head around the implications of what that means.

Either for builders but like for humans in general, where like all of a sudden if you can increase somebody's capability from zero to like pretty good. Yeah. Like even if it's just eighty percent good enough. Like what does that mean? And and that quote I think is is such a powerful thing to consider is like how fast do those people move compared to other people

We were having like a lunch and learn about some cool use cases we tried this last week and one of my amazing teammates, Ever Aldo, you know, he quoted, he said something like, Oh, the gap between what I didn't know and know is rapidly diminishing. And I was like, oh my God, I love that. That's really insightful and brilliant because you can now maybe have your startup without a technical co-founder for the first time because you could possibly like give a structure to

prompt to cursor and cursor can do the code for you, right? Like so it's kind of like interesting. I'm noticing a lot of like net new ideas come out, but it's a scary time. There's a lot of people in the dip right now where you need to get them to a place of experimentation. and looking forward and realizing our promise with a beginner's mindset.

When it comes to hugging the elephant, like what are some of the common fears that you find folks sharing around this? And then are you finding anything helpful to help navigate overcoming or building resilience to some of those fears or finding strength in that transition and making that

Yeah, I think, you know, one of the things is just like software engineering. Like is this good enough? Can we trust it? Is it gonna be secure? Is it gonna be performant? Is it gonna be reliable? Like all the same concerns. It's also like

Like, what about my job again, the human side of it? And I've thought about like this framework that I've recently spent a lot of time on on like the four E's of adoption of AI. And the way I like to think about this is evangelism, right? Like celebrating the innovators.

Sharing examples like you just shared, like that's that's a pretty cool example of market research. Like examples of those who are using it in fun, creative, cool ways. Then there's experimentation, enablement, and I think finally enforcement. Walk us through a little bit about what role do you see each of those phases playing? The first phase has to be evangelism, right? Because people are scared. Then you want to bring them to a place of curiosity and openness and learning.

So I would always start with the evangelism. Like find out who your top AI users are in the organization. Ask them a few questions, be curious, and then encourage them to share and evangelize what's worked for them. For example, like I recently did this really fun use case where I downloaded my because I was onboarding, I downloaded my entire like Google calendar.

ICS file into like a LLM and had the LLM analyze exactly where I was spending my time. Wow. Amazing, isn't it? I I imagine you probably had some really interesting insights that come from that. That like patterns that you probably couldn't have pulled out otherwise.

A hundred percent. And then it's also like, you know, as someone who's onboarding your priorities shift and I could actually see how they shifted from month one to month two to month three. So that was also like a good affirmation on like, okay, I'm actually spending my time on the right things, but really interesting insights and It was just something I just played with and was curious and I learned and then I've been sharing that with my team saying, look, I did this use case, isn't this?

cool and fun and people are like, that's pretty cool. Let me go try the same thing on my my calendar. But you know, that's a very small example. But I think there's different ways where you can evangelize like just how this is working for you, whether it's like internal AI showcases, like leadership advocacy. And then you move into experimentation, right? Like whether it's like having the time to prototype.

something net new and novel without a fear of failure and being able to learn from those iterations and trying something again. Uh having hackathons or like AI days or AI sprints like Carving time for experimentation and prototyping the path are going to be really important as well. Because then this just builds like resilience and curiosity at the same time. It takes the curiosity from the first phase and then just like, oh, it's okay to fail. It's probably not gonna work perfectly.

But there's no failures, there's only learnings, right? So you've learned something from this last iteration. What can you go do differently next time? And then just kind of encouraging that culturally. And then finally, I think we've talked about this. Like this is as old as time itself, enablement, enablement, enablement. provide people skills.

hands-on labs, access to the latest and greatest knowledge bases, documentation know-how, a peer who can partner to teach you something new. I think there's endless ways. We've done training a lot as technologists. Now they think there's a way to rethink training, maybe very meta wise, use AI to do your training, like another use case. But there's so many ways you can actually enable people. Do you have a a favorite enablement or skill giving format?

So you you mentioned like knowledge bases, documentation, peer learning. Like is there one that that you particularly lean on or like is there a mixture of a few different ones that you prefer? Learning is such a Personal activity. Every one of us learns so differently. I cannot learn with a long document. My team knows as well about me and they laugh about it. I'm like, please, I'm such a visual learner. Do not send me a long doc. I just can't write long doc.

I like to. That's why I think various mediums of learning is super important. My reading has accelerated because of the advent of large language models and just like using AI to summarize like books I wanted to read for years. Suddenly I'm like, wow, I could actually read an entire concept and then if I like it, I go back and I read the details.

But my time to learn has uh increased rapidly. I enjoy watching like videos, like fun videos that other people are using. So demos. Demos are my favorite way to learn. So the bar to entry, like to come to share something cool with me is very, very low. I'm a huge fan of a two minutes or less demo thrown in a public channel. I love that. We were doing a conversation on measuring engineering productivity and Farhan Thouar joined us.

from Shopify and his perspective is the best way to measure productivity is demos. And I was like, that's great. I love that. It's spicy and it's counterintuitive. I agreed. So we've got evangelism. And so these are are different ways to sort of Showcase what's possible to sort of spark inspiration by the folks on the team sharing or you yourself as a leader sharing.

We've got experimentation, so this is a little bit more of a formal structure to prototype without fear of failure. And so you mentioned things like AI days or hackathons. Um, and then enablement is like more of a skill delivery perspective. And then from an enforcement side of things, like can you share a little bit of context about the role that that plays within within this curve? It's fascinating. Like, you know, many, many decades ago I did a

uh master's thesis on why people do or do not adopt technology. And it was a multi agent system. It's probably not nearly as complex as today's multi agent systems, but I just thought the paddles were uncanny and I again had a good laugh about

full circle moment in a way, like that the fact that this is so current and it's kind of something that stayed in the back for twenty years. But one thing I learned about user adoption of any technology, even back in the day using agents, was that there's one, the you.

as in you and your elephants and how you show up and the person and where they are from a innovation perspective. Are you innovator on the bell curve? Are you like the average of everybody or are you like the laggard who needs to move? And then you finally have the second variable, which is mandate common ordinance.

socially like research showed back in the day, even twenty years ago, that no matter where you stand on your own like attitude at beh uh from a behavior intention to adopt a technology. what really moved you over the edge was actually like an organizational mandate or an industry mandate or something that says, Okay, you need to use AI now, otherwise you're going to become irrelevant. So it's kind of like an external forcing function to get you over the hump of the bell curve of adoption.

And I think that's really important. I think it's an important takeaway for all leaders. Like, you know, we can evangelize, experiment, enable all day, but in the end of the day, I think you need to make it measurable. You need to have a KPI, you need to make it a part of people's goals and and then encourage them through.

This is it's it's really interesting to see this sort of as a as a transformation curve because uh the uh the evangelism you sort of have is like the early adopters that are kind of then like showcasing, like testing the limits of it. The experimentation side is sort of like

crossing the chasm, you get a little bit more wider adoption. Then the enablement is then when you sort of get the mass adoption moment. Uh then the enforcement side is like, you know, the laggards, like you know, think about all all the change the changes

Is then it's like it's more structured, it's more uh a core part of the process or structure of the organization. So now it's like, well, we gotta use it. And I think of like for those people, it's like the people using AOL dial up and that only just got discontinued a few years ago. It's like, you know, they're like, Well, I guess I'll m I'll make the change now because that's the option. Or like Skype.

that I used still used to use till recently to call people that I couldn't reach in other countries. That is now officially getting discontinued. I'm like, okay, I rode that bandwagon for like a good ten, fifteen years.

So Rukmini, we we've talked about hugging the elephant. We've we've walked through five questions. To help navigate transition with your team. We've gotten through the areas of of AI adoption, evangelism, experimentation, enablement, and enforcement. When you're thinking about the demands that engineering leaders face today, now in 2025. Are there any other thoughts?

or advice on how leaders can navigate the moment now. Or maybe there's one behavior shift or something that you think somebody could implement today that'll help them be more equipped to endure as a leader in today's moment. That's such a great question. I think the one behavior shift again that we've talked about this plenty already for the last 40 minutes or so, it's really important is grounding yourself in the why of your customers.

If this one shift everybody could make today is like grounding yourself in why is this important for my customers, what value am I bringing them today? That changes your entire perspective. That's a powerful centering question to close our conversation with. But we're not done yet. We have some rapid fire questions. So if you're ready, we can jump in. Okay, let's do this. All right, all right. The first question. What are you reading or listening to right now?

I will I've just reread Good Strategy, Bad Strategy by Rumelt recently because I was just working on something new. It's still so relevant. What I love about this framework is like it grounds you in actions versus other strategy frameworks that seem to be too theoretical. Like that's the aspect that I really enjoy about this because it just says, okay, what is the diagnosis or current challenge? Like

enforces like keeping it succinct and clear because you know we all like to say that everything was somebody else's fault, right? So it's like good to ground you in like just like a very what is the current state diagnosis and challenge that you see? What are some themes? And then what are the coherent actions you will take? So I feel like it's more just not just words, but it's words and actions combined and I I really appreciate that framework.

And it helps give you the space and time to think eighteen months out or I typically like to do eighteen month strategies because three years is a long time. Like you you and I have spoken about four years has been a very, very long time. I love that. Okay. Next question. What's a trend you're seeing or following that's been interesting or hasn't hit the mainstream yet? I'm not much of a trend follower.

I don't. I spend most of my time looking at dog videos on Instagram. And I'm not gonna apologize for it. That is literally how I unwind every day. I don't do any other social media. Social media strictly for dog videos. We'll we'll dog content only. You know, people are talking about what's gonna be the next social network. I think you've just, you know, declared an opportunity for an exclusive social network based on dog video.

I would I would subscribe and I would also pay good money for it. There's never enough good dog content in the world. I love it. I love it. Final question, Rukmini, is there a quote or mantra you live by or a quote that's resonating with you right now?

It always resonates with me. Love, love, love Brene Brown. Clarity is kindness. It resonates with me. It always has. And I will continue to use it. What a powerful way to capture the most important elements of the questions you were sharing with us earlier.

Clarity is kindness. I love it. Rook Mini, thank you so much for joining us for the conversation today and to help empower people with some frameworks that can help them navigate transition, have important conversations, you know, hug the elephant in their own teams and navigate a lot of the change of the moment. We really appreciate it. Thank you so much for having me, Patrick. I appreciate being here.

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