From Self-Taught Developer to CTO and Inspiring Leader with Danielle Leong

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Join us as Danielle Leong shares her inspiring journey from marketing to becoming Twilio's first female engineer and on to senior leadership roles at companies such as Github and FireHydrant. Danielle opens up about her experiences managing former peers, building self awareness and confidence, communicating transparently and holding people accountable.

Danielle also shares some of her management templates and playbooks that she has open-sourced to the world in the form of a GitHub repository.

Tune in to gain a wealth of insights on effective leadership, communication strategies, and continuous learning from one of the industry's most dynamic leaders.

You can find Danielle's open-source management playbooks here: https://github.com/dmleong

Full Transcript

Keith Cowing: 0:00

In today's episode we talk to Danielle Leong, who is Chief Technology Officer at FireHydrant and previously of GitHub and Twilio. She is an incredible leader and I learned a lot from talking to her. I think you will too. Let's dive in. Danielle, Welcome to Executives Unplugged. Thanks for joining us.

Danielle Leong: 0:19

Yeah, thanks for having me.

Keith Cowing: 0:21

Super excited to have you here. We've talked a little bit about your leadership style. You're extremely thoughtful about the way you approach leadership and managing your teams and your relationships. Your self-awareness as well. I'd love if you could start with your journey, walk us through that moment when you first got promoted from being an individual contributor to having direct reports, and a little bit about what you learned about yourself as a leader as you went through that process.

Danielle Leong: 0:44

Yeah, so I have a little bit of a non-traditional background. I am actually originally a self-taught developer. I originally came from marketing. I was a copywriter my first job out of college and so I originally had no designs to join tech at first. As I moved on throughout my career I realized marketing really wasn't the best fit for me personally, and I remember I saw somebody using a terminal for the very first time and I thought that was the most magical thing that I've ever seen in my entire life. But you can just type something and the file opens, and you can type something and the file gets deleted. It was just really cool and a very defining moment for me.

Danielle Leong: 1:18

I studied really hard three months every day in a coffee shop for eight hours a day just teaching myself how to code, and then from there I went on to be Twilio's first female engineer. I was very early on over at Twilio I think I was like employee number 50s or something there and then from there I joined GitHub afterwards as an engineer there on what is now known as the trust and safety team Before it was community and safety. So we built a lot of content, moderation tools, a lot of tools to help people have more productive and healthier conversations in the open source world, and my manager on that team actually left after my first year and a half or so, and so I inherited the team and really started my journey in management and leadership in that way, by taking over the team that I was originally on, which was a very exciting moment to one day be peers with people and then the next day they're reporting to you. So that is always somewhat of a tricky relationship to navigate, but that's that's where I started.

Keith Cowing: 2:18

Amazing. I bet we have a lot of listeners that can relate to that. One day you come in, you're a team member. The next day you come in, the team reports to you and you're responsible for the whole team. And some people may be ready for that, some people may not be, some people may have thought they should have gotten that role. Walk me through a little bit how you built those relationships with your new direct reports during those first months.

Danielle Leong: 2:39

Yeah, it helped that we actually had an offsite. That was planned pretty soon after my previous manager had departed, so that was a nice little cut over to okay. We are now officially in a new team situation. We are officially moving into new roles, but I really had one-on-one conversations with everybody and I said, hey, you know we don't have a manager. Right now I'm talking to our skip level director and she's saying like she wants to put me into this role. Do you have any issues with this? Is there anything that we need to talk about? How do you want to work together? How do you want to hand off projects? How do you want to communicate any sort of feedback back and forth? So, just being very upfront about this, it was very helpful that I had a very close relationship with my previous manager. She had been training me this whole time to be her replacement, so it wasn't really a surprise to anybody and everybody was very much on board with like, yep, we already know. We're all clear on this one.

Danielle Leong: 3:40

Nobody else had any sort of desire to be a manager either. I think I was one of the few people on that team that really, really wanted to give it a shot, and I'm a big believer in. If people don't want to be managers, you know you shouldn't push them to do it, because they have other people's livelihoods in their hands. But this was something that I was really interested in. I had seen my previous manager, helen, be an incredible manager and she really inspired me to take up this new role in my life, because I saw somebody doing it really really well and I wanted to emulate that. I wanted to take that responsibility and make it my own, and I'm truly grateful that I learned from some of the best in that situation.

Keith Cowing: 4:21

What'd you learn about yourself as a leader going through that transformation? That?

Danielle Leong: 4:24

situation. What'd you learn about yourself as a leader going through that transformation? I think one of the big things that I really learned was it's very difficult to quantify what you do on a daily basis, going from an engineer to a manager. An engineer has tickets that they get to work on every day. You get to merge pull requests, you get to participate in stand-up and you have pretty clear, defined projects that you're working on. In any one given day. You merge your PR, it's done. You get a little dopamine hit and you know that you contributed meaningfully hopefully meaningfully to the code base that particular day.

Danielle Leong: 5:01

When you become a manager, that becomes a lot more difficult. Your job becomes unblocking other people, and the definition of unblocking can change based off of what you're doing. So it could be you are, you know, asking a hard question about, like, where a project is and why is it going so slowly. It could be that you are talking to somebody in a different team that you have a dependency on, but their priorities are not the same as yours. It could be that you are having a tough performance conversation with somebody and that may be moving the team forward, but it may feel like you're not moving that individual's career forward, but really any sort of feedback will always move somebody forward anyways.

Danielle Leong: 5:42

But it becomes very difficult to sort of quantify success, and so I find a lot of new managers in particular will often burn themselves out because they're still trying to get that same level of dopamine hits on a daily basis by doing the same things that they were doing before. So what you need to do when you are changing roles is you need to realize you may have gone from a senior engineer, now you are a junior manager, and so reframing this, as it is a completely different role with completely different expectations, with completely different definitions of success, that will help mitigate a lot of the burnout that I definitely felt when I moved up in that role and every single subsequent role that I definitely felt. When I moved up in that role and every single subsequent role that I've gotten to after that, I've definitely had that same moment where I've burnt myself out early on because I was still trying to do the same thing. That was still my previous definition of success. It just needs to be redefined each and every time.

Keith Cowing: 6:41

And when you work with managers now and you're coaching managers and they're going through this change, how do you coach them or set expectations for how you're going to manage and hold them accountable and measure success in a role that they haven't done before? How do you coach them through that and help them define what success looks like in this new position?

Danielle Leong: 7:00

So if they are in the same organization that I'm in or the same company, it's a lot easier if you have very defined career ladders so you can say, ok, you've gone from a senior manager to a staff level manager. What are the expectations at this level? You might be expected to run larger projects that are much longer and less defined. You need to coordinate across many other different stakeholders that have significantly higher titles than you. There may be a significant chunk of ARR that is attached to your particular project, and so I like to ask people what is the most important thing that you are working on that cannot be done by anybody else? Because I find a lot of the times when you are moving in, when you're changing roles or you're moving up in your career, it can feel like your to-do list never ends.

Danielle Leong: 7:54

We're all victims of procrastination, and so it becomes easy to do the things that you're familiar with, because you might not want to try the new thing that you might fail at. You might not want to try the thing that is a little scary because you've never done it before, and so when you move up in your career, oftentimes there are tasks that only you can do. There's nobody else who can possibly do it. Those are the most important things. Do it, those are the most important things. If there's anything else, most likely it can be delegated.

Danielle Leong: 8:27

Or you just need to be honest with yourself and say that that's actually not going to get done because it's not actually that important. And so a big lesson when you are moving in your career and you're changing roles is to be very honest with yourself. What is the most important thing that I need to do today and what am I doing tomorrow? Because if it's just little tasks that you know keep piling up, either you need to be honest with yourself and just say, like this is not important, or give it to somebody else. You know, give somebody else a chance to try something new and stretch in a different way and delegate, because you only have so much time in a day. Your time is your most precious commodity. So what are you doing to make sure that you're using that time effectively?

Keith Cowing: 9:12

You mentioned delegation a couple of times. It's a particular practice that's a huge part of your success as a leader, Also something you don't practice until you're in that leadership role and you have people you can delegate to. How do you think about what to delegate what to do yourself, or what to delegate and supervise where you give it to somebody else but you provide support?

Danielle Leong: 9:26

It goes back to that whole prioritization thing. If your time is the most important thing that you have, then you have to focus on the most important things. Sometimes that does mean pulling extra hours later at night when it's quiet. I will sometimes do that. But if I have a clear idea of where all of my direct reports are in their career progression, I will have a very clear idea of what they want to work on. And so if we are having regular career conversations which you definitely should be on at least a quarterly basis then you should know what they are good at and what they are looking to improve upon. And so if your task list includes something that could be a good match, then that is something that I highly encourage helping somebody out to learn that skill.

Danielle Leong: 10:16

My primary objective as a leader is always to provide opportunities for people. I always want to help people be the best engineer or the best manager that they possibly can be, either in this company or the next company. Tech is a pretty small world, so I assume I'll find most people again eventually, and so it's in everybody's best benefit that I help somebody grow to the next level in their career. Rising tide lifts all boats, and so if I help somebody get better, then that's a win for everybody. So I'm always on the lookout for anything that I can do to help somebody grow in the next portion of their career.

Keith Cowing: 10:53

Let's talk about self-awareness a little bit. That's. A huge part of leadership is first understanding yourself and then understanding your relationships with the people around you. You have what I'm going to call an incredible playbook on GitHub about you and yourself as a leader and how people on your team can relate to you. Walk me through what that is and the story of how it started.

Danielle Leong: 11:11

Yeah. So I have a manager repo that I keep up to date on my own personal GitHub profile. It has a lot of playbooks that I've run before as a lot of templates that I might have for meetings or for one-on-ones. In particular, it talks a lot about my guiding philosophies as a leader, and I started writing that because I was originally a copywriter first off in my career. So I think that the power of writing is vastly underutilized in career advancement. So the better you are as a communicator, the better you are as a writer, the more helpful it is for you in your career. These days you've got AI as well. That can help you start, but if you were able to edit and write effectively, that's going to be so helpful for you in your career.

Danielle Leong: 11:58

But I had started writing a lot of these templates because other folks within GitHub had asked me how I was doing things, how I was approaching stuff. In a lot of manager peer conversations people will be like, well, how did you approach this? I'm like, oh yeah, I have a template for that over here. Let me just share that with you, and I had shared it so many times. Internally. I said you know what I want to put this in one particular space where I can share it openly, and I figured GitHub was such a fan of open source software. This, basically, is what I do on a daily basis, so I want to help other managers out there be more successful, and if this is a good starting off point for people to gain inspiration from, then that's super helpful, and I also use it as a hiring tool.

Danielle Leong: 12:45

So I believe that hiring is a two-way street. I think that if you are joining an organization, it's great to see what the leadership style is of the person that you are going to be reporting to, because then you have a clearer understanding of what things are going to be like in that organization and you can decide if that is something that works for you or not, and so I really like to have clear, transparent communication. Sometimes my style doesn't work for people, but if they read that, they'll have a clear understanding of if it does or if it doesn't, and then they can make the right decision for them, which is also probably going to be the right decision for the organization as well, because this is how things are going to be and the guiding philosophies of the organizations that I run. So I think it's a two-way street. It's very helpful for people when they are applying to see if it works for them or not, and I think it vastly helps in a lot of the hiring decisions that we've made.

Keith Cowing: 13:38

It reminds me. I coach a number of CEOs and I frequently work with them on crafting monthly board updates to send to the board about what's happening in the business and what are the goals and what's the progress and what's happening next. And there's obviously the communication and keeping people updated. But then there's writing it down. Itself can be incredibly illuminating about what the real priorities are and just how to structure that email. In and of itself, as a practice that, even if you didn't send it to anybody, can be extremely valuable of writing it down. And so when you sat down and wrote some of these templates, give me an example of something that you clarified in your thinking.

Danielle Leong: 14:11

I'm sure even if it was so, for instance, I generally don't really care what type of technology we use, as long as we are solving the customer problem. And so how we get there is less important to me than making sure that we are solving the right problem. That is a guiding philosophy that I have that I discovered the more that I started working in startups, for instance, the more that I went up in my career, the more that I realized customer problems are the heart of why we have a business. It's the reason why companies are founded, it's the reason why we all have jobs. It is the reason why people want to buy your software, and so if you are not solving the right customer problem, then why are we building the things that we're building? So a great example of this is so I work at FireHydrant right now. We just released Microsoft Teams as an integration.

Danielle Leong: 15:25

One of the incredible engineers on the team was leading the project and had said okay, there are two main ways that you can interact with a Microsoft Teams integration. What he ended up doing was he investigated and said they actually have something called tabs at the website hosted within the Microsoft Teams application. Within that website, we can do anything that we are used to doing. And he's like is this okay? And I was like what is the most important thing that we're trying to do here? We are trying to build an application for our customers to declare an incident, and so if the best way to do this is to do it through tabs, because it will give us the most amount of flexibility, it will be the best user interaction for our users and it will get them to resolve their incident faster.

Danielle Leong: 16:15

That's the thing that I actually care about. How we do it, that part doesn't really matter to me. It sounds like you've landed on the better option. So I am fully in favor of doing this, because my guiding philosophy is solve the customer problem. So that's like a little bit of how the values that I put in my manager repo have played out in real life and helping my engineers feel a lot more confident that they are going in the right direction as they are making their own decisions about how to integrate with something in their daily lives.

Keith Cowing: 16:49

Relationships are really important to you. You've talked about how you really invest in understanding the human and not just the work. Talk to me a little bit about how you develop relationships one-on-one with your different reports and how that plays into how you lead and how you set direction and how you make sure that the team is ultimately successful on the business side.

Danielle Leong: 17:07

I think it's very important to make sure that we're paying attention to people as people. As you become more of a leader and as you look at budgets and spreadsheets, it can be tempting to disassociate from, like, the numbers on a spreadsheet versus the people, but people are the reason that we are here. They are the people that build the product. They're the people that have those personal relationships with customers. Customers are also people too. People are the most important things in a company. When I manage a team, one of the first conversations that I'll have with people is I'll go through the template that I have. It's called First 101s. I have different ones for individual contributors. I have different ones for managers. I have different ones for very senior individuals as well. Sometimes those can be a little bit different because each one of those people will have very different previous bad relationships with previous managers. That is always going to be the case, and so for me coming in, particularly as a new leader in a new organization or a new team, it's on me to build that trust with that person, and so I want to learn about what are their hobbies? What's their communication style? What are the different types of projects that they want to work on? What are their career aspirations? Do they know where they are in their career or do they need help defining it? Do they have a clear understanding of what's next for them in their career and what they actually need to do in order to be successful? When was the last time that they had a feedback conversation with a manager where they understood where they were in their career and what they needed to work on? Are they only working on the things that they like to work on, like technical problems, and are they ignoring some of the softer sides, like communication and interpersonal styles, that actually get you pretty far in your career, beyond just the technical applications?

Danielle Leong: 18:56

And people ebb and flow. Sometimes they have good days, sometimes they have bad days. You need to be able to adjust to how your team is doing on a given basis. If somebody has family issues that they really need to focus on, I wouldn't assign that particular individual some really tough tasks. I wouldn't assign that particular individual some really tough tasks. I would probably assign them something that is pretty easy, straightforward, easy dopamine hits, tiny tickets for them to work on because they're going through a lot, and these are the types of things that people will always remember that when I was going through a tough time, my manager was really supportive. They talked me through it, they adjusted the things that I needed to do and we had conversations about it. So I think that it's really important to show that human side of you in a working relationship.

Keith Cowing: 19:44

I'd love to hear a little bit about how you would coach leaders to think about what is an ideal relationship between you and a direct report. It's complex. There's a lot going on, so how do you think about what makes an ideal relationship between a manager and a direct report?

Danielle Leong: 19:58

I think that it is very important to have that distinction, that this is a working relationship. It does mean that I cannot be as close with certain people that report to me as much as I would like to, and so we could be going out to drinks after work, but I'm always being held responsible to any sort of legal ramifications that naturally comes with that. Power imbalance does not exist Because, no matter what, my direct report always will view me as their boss, no matter what, and so it is my responsibility to make sure that I am honoring that relationship as much as possible. So I always think about when I'm speaking to somebody. I'm always aware that it can come off as their manager first, as opposed to me as an individual. If I want to connect with somebody very quickly on a topic, I don't just send them a Slack notification that's hey, can you talk? Or I will never put something on their calendar that says quick sync with zero context whatsoever, because in those moments I am always the manager first. I am never the individual. Me, no matter how I see myself, they're always going to see that power imbalance first. I will always say in parentheses you're not in trouble, do you have a quick moment to talk right now, or this is good news Do you have a moment to talk right now? Or this is good news Do you have a moment to talk right now? So I'll always preface it in that way, because I may want us to be close friends, but the reality is I will always have that power imbalance. I will always be somebody who is in charge of their livelihood, and that's something that I take very, very seriously.

Danielle Leong: 21:51

Now I do learn a lot about people. I know all about their kids. I know all about their pets. I know who's going to what school. I know what people's music preferences are. I know what people are doing on the weekend. I always try to get to know people as much as they want me to know them, because that's the other thing. They may want to have that boundary as well, and I have to respect that. I can't force my way into becoming best friends with somebody with that power differential there, and so I do care very, very deeply about everybody that has ever reported to me or is in a peer relationship with me, or if I've mentored them or coached them. Like. I think about these people all the time. I really do, but at the end of the day, that power imbalance is always there and it is my responsibility to make sure that they know I will never cross certain lines because of that relationship there relationships with others.

Keith Cowing: 22:53

Now let's talk about delivering complex projects. Put us in the room in a moment where you had some stressful thing to deliver or get done. Your team was reacting to it. You had to set the tone, manage the team, lead in a direction. Walk us through that.

Danielle Leong: 23:04

There's a great example of actually a project that I delivered fairly recently. At FireHydrant we have a product called Signals. It is a pager duty competitor, so you connect your observability tools like Datadog, you can create monitors off of those and you can receive alerts if something is going wrong to the team that needs to be paged in hydrants. The product was in beta, but we were looking to go GA general availability in two months, and when I joined, I was like, okay, where are we at with this project? And they're like okay, things are going. And I was like what do you mean? Things are going. And they're like well, still going. But we got a lot of stuff going on and I was like we have a launch in two months. Do we know what we're launching? And people were like yes, stuff, I guess. And I was like no, no, no, no, no, no. Okay, all right, like, this is not good enough. We have to work on making sure that we are delivering products. And they're like well, we've never, ever, delivered a product on time before. What do you mean? You've never done this on time. No, that's okay, all right. You know what?

Danielle Leong: 24:08

This is a new era. We're doing things a little bit differently now. So what we're going to do is we're going to have a Gantt chart and we're going to have regular standoffs and check and see. All right, this is the feature burndown list that we're going to have. This is what we are delivering for beta. These are the beta customers that we're going to be working with. These are the gain days that we're going to do in order to test reliability of the system. This is what we are going to do every single day until we launch in two weeks. What is our go-to-market plan? Do we know what that is? No, we don't know what that is Great.

Danielle Leong: 24:40

We're going to go start setting up syncs with our go-to-market team and make sure that everybody knows exactly what is going to happen. And so I think there was initially a little bit of resistance there, because it was something that was very new and it wasn't something that people had ever done before and it was uncomfortable. I did have to hold some people accountable. You said that you've been working on this particular thing for eight weeks. What's going on here? I'm like well, we're still working on it. And like what part are you still working on? What can you tell me? What are the outstanding tasks? Can you tell me what you need help with? Do you need to talk to anybody? Do you need additional documentation? Do you need support? Is this project too big for you? Tell me what's going on.

Danielle Leong: 25:21

And they're like oh no, this should be done by Friday. I'm like okay, monday, I check in. How are we doing on this? Any issues? No issues. Check in on Wednesday Any issues? Are we still on track for Friday launch? No issues, friday comes along. Are we done? Are we good? Oh no, I still have outstanding questions. I had to chew this person out in front of other people. I was like we have been talking about this all week. We agreed upon the delivery date on Friday, and if you still had questions, why did you not ask them before this moment? And so it was a lot of holding people accountable in uncomfortable situations, because we needed to launch a product that our customers and our investors were relying on, and so it was a lot of new muscles, a lot of new pathways that we had to build in order to build the most effective engineering organization that we possibly could have.

Keith Cowing: 26:16

So in this situation you jumped in, you grabbed the reins, you led the team forward. There's a lot of confidence that I hear in that story of you understanding at least how you needed to frame the problem so that the team could work on the pieces of that. There's this constant dichotomy in leadership of you need to be humble and open to feedback. Otherwise, if you're overconfident, you might just go down the wrong road. And you have to have transparency and trust with your team, which means they can tell you when they see things or see information that goes against previous decisions. But you also have to have conviction and confidence, because if you don't have that then you can't rally the team. So how do you balance having that conviction and the confidence to rally the team with the humility to being open to feedback, knowing that you're not always going to be right?

Danielle Leong: 27:02

Yeah, I think that's an interesting balance that needs to happen really on a daily basis, if not an hourly basis, with everything. I have had the privilege of working with some of the best engineers in the world. I worked at Twilio, I worked at GitHub. I've worked with some truly incredible people who have managed to build some amazing things, and so I have a good frame of reference for building software at scale and building something that is made to last, and I've also been on a rocket ship from something that started from very early on and IPO'd. So I've seen a lot of different mistakes that have happened many times, and I've been in charge of some very mission critical pieces of software. You know I used to run GitHub's identity and access management, so if you've ever logged into GitHub and used any of the resources that are there, that's something that I have helped build. And so constant availability, reliability, being able to fail over, being able to scale properly these are the pillars of what makes a good engineering organization, and so I have a lot of experience in seeing that firsthand, helping build out what is a high-performing engineering organization. The nuance then becomes where is the difference with the new organization? So, in coming in at Fire Hydrant, one of the things that I was very careful about was learning about what the organization was currently doing. What is the organization good at? What are areas of improvement there? Do we know why things are the way that they are and what is the team's appetite for change and in what way are they interested in changing? And then what needs to happen in order to actually enact that change?

Danielle Leong: 29:05

Engineers want to be excellent. I find in general, most engineers want to build something that is important, that has meaning, that provides value to the people that are using it. You have to hook into that motivation and say this is how we're going to get there. We have to be very reliable. We have to make sure that we are solving the right problems. We have to make sure that we are delivering on time and we're not just sitting here spinning our wheels and debating to death something that, in the grand scheme of things, doesn't really matter. That is where you can have conviction of I know what good looks like, and then the humility to know when you want to implement things and what is the right order of operations, and then to be able to gather that feedback and say like was this the right decision for this particular organization at this particular given time. That's where the trade-offs come in and when you're thinking about these types of things.

Keith Cowing: 30:06

When I listen to you, I hear you asking a lot of questions. When you frame problems, either just inside, you're asking them over yourself, or maybe you're asking them out loud in front of your team. I believe one of the most important leadership skills is asking the right questions and then therefore teaching your team how to ask the right questions. Especially in an AI-driven world where the value of performing tasks is going to continue to go down, the value of judgment and leadership is going to continue to go up. A big part of that is asking the right questions. It's also something you don't necessarily learn in school. You learn how to answer questions, not necessarily how to ask the right ones. How do you train your team to ask the right questions?

Danielle Leong: 30:42

This is actually something that I am currently working on with one of my engineering managers. So something that I recognized as we were launching the signals product was, with some of these heavier infrastructure questions or reliability issues. I was the one who is leading a lot of the questions I would ask. Engineering has a concept of five whys. Why is this service down? We had a connection issue. Why did we have a connection issue? So you keep going down the line until you find the root cause analysis. With the signals product, I found that I was asking a lot of those questions and I caught up with my engineering manager afterwards and I was like hey, what's going on here? Do you have a clear understanding of what the problem is that we're trying to solve? And she was like, honestly, not really. Infrastructure is not something that I'm very familiar with, so that was an area that I wanted to push her to learn more about.

Danielle Leong: 31:37

I have a very similar path in my career. I originally came from front-end engineering. I came from marketing, then I did front-end engineering, then I did full-stack engineering, platform engineering, something I'm very comfortable in right now, but it took a lot of work, and so when I find that somebody may not have questions. The thing that I ask is do you have a firm grip on what problem is? And so if you don't know what the problem is, or you don't know what good looks like, or you just don't know enough about a problem space to ask questions about, that's usually a sign of maybe we need to work on more technical understanding in this particular area. Or if somebody is only asking questions about tasks as opposed to one-on-one discussions about learning about people, I might ask the question what is typically your relationship like with the people that you work with? Have you had a bad experience, maybe with another manager where you don't feel like it's useful to have that personal relationship? Why is that? Do you prefer it that way? Do your people prefer it that way? What is your understanding of the situation with people? And so it's a lot of asking questions about where do people feel like they are strong in, where do people feel like they might have some weaknesses in and need some areas of improvement?

Danielle Leong: 33:00

But you have to have a well-rounded sort of education in the entirety of the stack. You have to have a clear understanding of emotional intelligence and how people talk to one another, the different relationships that people may have within a team or cross-functionally with another team and, honestly, you need to have a lot of business understanding to know what's the most important thing for the business. Where is the economy going? What is our industry doing right now? Who are our competitors and what is the thing that they are very good at versus what we are very good at? How can we use this to our competitive advantage?

Danielle Leong: 33:38

It's uncomfortable to learn new skills. It was uncomfortable for me to learn how to read a P&L, but I had to do it because I knew that that was going to help me become a better executive. But that's not something that anybody has ever taught me in the course of engineering, but it's something that I picked up because I knew that if I knew how to do this, that would help unlock a lot of conversations at the executive level or at the board level, to have a clear understanding of where we're going in the business and then help me understand where do I need to direct my people so that we can have the best possible outcome for the business.

Keith Cowing: 34:14

If you had one piece of advice for a team leader who wants to improve their game, what would you share?

Danielle Leong: 34:20

Talk to somebody that doesn't do what your role is. I think that having conversations with people in different parts of the company, really understanding where their values and where their motivations are, is something that is incredibly valuable. Who are currently on the job market right now? Or if I talk to managers who are really sort of looking to level up, the first thing that I will tell them is start listening to the Economist podcast. Read about business, read about where we are going as the economy. Get off of Twitter. This is, I think, particularly in the Twitter-driven engineering leadership bubble. It can be very easy for us to get caught up in what's the latest tech drum, but what is actually going to further your career? It's understanding what is important to a business standpoint. It's understanding what a board member or an investor might be interested in.

Danielle Leong: 35:22

When I was an early manager, a lot of the decisions that were made on an executive level didn't really make a lot of sense to me. I'd be like oh, that's so stupid, like why would somebody make that sort of decision? That sounds so dumb. Don't they know what's going on here? And maybe the answer is no. They may not know what's going on. Have you tried telling them? Are you giving the feedback to your executive team so that they have a clear understanding of what's going on on the ground level? Possibly not.

Danielle Leong: 35:52

And then, on the flip side, do you know the different things that somebody at a leadership level might be trying to balance right now?

Danielle Leong: 36:00

And so if you have an understanding of what are the motivations from an executive level, from a leadership level, from business level, you can then ask better questions when you do have that one-on-one time with somebody in leadership.

Danielle Leong: 36:16

And so I always really love it when some of my engineers will ask me where is the business going? What's the most important thing that you're thinking about right now? What's the most important thing that you're thinking about right now? What is the biggest hurdle that we're trying to do? Who are our competitors right now? What is our competitive strategy as we are starting to tackle this market? That stuff leads to some really interesting conversations and can help give some color and meaning to what somebody might be doing on a daily basis. While manager books are super important in learning how to manage a team and how to manage team dynamics and build culture, that is super important I would definitely recommend people also pay attention to the business side of the house so that you can have more color to why people in your leadership team may be making the decisions that they are making.

Keith Cowing: 37:05

Danielle, thank you so much for sharing all these stories and how you think about leadership. You're an incredibly thoughtful leader. Engineers are lucky to work for you. Leaders are lucky to learn from you. So thank you for joining the podcast sharing your stories. Where can people find you online?

Danielle Leong: 37:19

LinkedIn is probably the best way for people to find me right now. I still have a Twitter account as well, but I'm not on there as often, so LinkedIn will probably be the best place. I've got a bright yellow photo. You can't miss me.

Keith Cowing: 37:32

Awesome. Well, thank you for joining us on Executives Unplugged.

Danielle Leong: 37:36

Thank you very much for having me.