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Episode 7: Role models, restructuring and living in the future with Danielle Leong

    Guest Biography

    Danielle is a seasoned engineering leader who is passionate about creating healthy, inclusive, productive engineering teams and helping them do their best work. She has a wealth of experience ranging from building teams at pre-seed startups to Director of Identity at GitHub to being an early engineer at Twilio. Danielle is also the creator and founder of Feerless, an app that provided crowd-sourced, preemptive notifications for Netflix users with PTSD. In her spare time, she runs a photography studio that specialises in colourful, fun, and inclusive headshots. 

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    Links and Mentions

    Transcript

    Patrick Kua: Welcome to the Managing Managers podcast. I’m your host, Patrick Kua, founder of the Tech Lead Academy and curator of the newsletter for leaders in tech, Level Up. In this podcast, I’m chatting with senior engineering managers, directors, VPs of engineering and others who have walked the path of managing other managers, where we will uncover some great stories and lessons learnt. Let’s get started.

    Patrick Kua: Hi everyone. Welcome to the managing managers podcast. Today we have Danielle Leong. Danielle is an engineering leader passionate about creating healthy inclusive productive engineering teams and helping them to do their best work. She’s currently the VP of engineering at Maca, helping SAAS companies optimize their pricing structures with data. Previously she was the Director of Engineering for Identity and Access Management at GitHub and was an early engineer at Twilio. Danielle is also the creator and founder of Feerless, an app that provided crowdsourced, preemptive notifications for Netflix users with PTSD. In her spare time, she runs a photography studio that specializes in colourful, fun and inclusive headshots. Welcome to the podcast Danielle.

    Danielle Leong: Thanks for having me.

    Patrick Kua: It’s really wonderful to hear about your background. I was reading about you and we haven’t had that much overlap professionally. But I’d love to hear about your background in your leadership journey. So how did you get into the management track and what motivated you to move in that direction?

    Danielle Leong: Yeah, so one of my, the first team that I was on at GitHub, I had an amazing engineering manager. Her name was Helen. She really inspired me to see what a manager could be. She was incredible in terms of helping people along their journey, asking the right questions, leading people into learning about what the problem was and then leading them how to solve that problem. Rather than just being a top-down manager. This is like, okay, you need to do this, you need to do this. But she really brought you along on that journey and really helped me grow as an individual. So when she left GitHub, there was an opening there and because I was so inspired by her leadership style I was like, “Okay. That is actually who I want to be when I grow up.” We still remain to be very good friends to this day. I actually officiated her wedding earlier this year.

    Patrick Kua: My goodness.

    Danielle Leong: She remains a very very important part of my life. So she really kicked this off. In terms of what the craft of management and leadership could be.

    Patrick Kua: Yeah, that’s such an amazing experience and a) I know how hard it is to get good managers and also to get that style of management. I think it’s a really great example of having that role model. It sounds like it definitely had that big impact on you and created also the opportunity when she left. What was your transition like as you started to move into management? So you obviously had a good role model at that time. What other support did you have as you moved into that role?

    Danielle Leong: Yeah. So I had a lot of support. I was very lucky. I had an incredible group and network of people within Github that really helped me. Lynn was one of those people. Jim was another one. Anais is another one. These were all people that were invested in my journey. I had made personal connections with them. I had talked to them. Oftentimes they were my skip level managers and so when I stepped into this role, they were invested in my growth. So anytime I had a question like I don’t understand how to do this, or like I’m overwhelmed, I’m drowning, what the heck am I supposed to be doing? They would actually take time out of their busy days and really invest time in me to talk me through all of these different questions. Particularly being a woman of colour in a leadership position, you can have different sorts of issues that might pop up that maybe others don’t. So really having that female network, that female leadership, particularly female leadership of colour, that was incredibly important for me to not only help me grow as an individual and help me grow as a leader but to also help me feel less alone. Like we’re in this together. They were invested in my journey. They really wanted to help me succeed and you can’t replicate that. I do feel incredibly fortunate to have such an incredible support group around me, who really spent that time to help coach me to that next level.

    Patrick Kua: Yeah, that really sounds like a very unique environment. I’ve talked to lots of leaders and particularly as they step into their engineering management role for the first time a lot of people are left there to then work out how to do things by themselves. It sounds like you had such an amazing support network within your own organisation, through those skip one to ones and people with lots of different representation and probably different perspectives and experiences as well. I can imagine how that really helped ease you into that role and give you that support. Even it’s really difficult given that as you said leadership roles can be very lonely.

    Danielle Leong: They definitely can. Because you used to have a peer group of engineers that you could commiserate with. You could talk about the different problems that you’re going with but as you step up in leadership, that pool of people gets smaller and smaller. You have privileged information. You have decisions that either you know have been made or you have made yourself that have further repercussions down the line. They need to be planned out. That communication needs to be very thoughtfully put together to reduce fear, uncertainty and doubt. So that pool of people that you can confide in tends to get a little bit smaller the higher up you go. And so yes, it definitely is a privileged position but also it can be a lonely one and so without the right support network of folks that are at the same level, who understand the problems that you’ve gone through and can lean an ear or a shoulder and support on what they might do or even just to vent with somebody who understands those types of problems. That is incredibly vital.

    Patrick Kua: Absolutely. Everyone needs that place to let off steam and it’s not appropriate to talk about that with some of your people in your organisation and you definitely need that support network.

    Danielle Leong: Right.

    Patrick Kua: So we’ve heard a little bit about your journey into starting management. What’s the journey from there to when you started to become a manager of managers?

    Danielle Leong: Yeah. So I had been with this original team at GitHub for I think close to four and a half years. And at that point I was really looking to start growing. I had wanted to branch out from trust and safety. I had wanted to try something a little bit different for my own personal growth. I loved the team but my own personal growth felt a little bit stalled at that point. So Lynn, who I mentioned earlier, she said that she had a position from one of the managers on her team was going out on parental leave. Did I want to try leading the identity and access management team at GitHgub? So I said absolutely. Let me give this a shot. I’ve never done it before. That’s never stopped me before though. I love learning. I love trying something new. So I thought you know, let’s do it. Let’s do it. Let’s give this a shot. So I switched on over to identity and access management. Completely different field. It’s a highly technical field. It’s a platform team. It needs to have high reliability. It needs to have high security. It was just a completely different set of problems because we also had enterprise customers as well. In taking a look at the team I realised that they were doing too many things. There were 24 work streams for 10 people and I said the math doesn’t really add up here.

    Patrick Kua: That is a lot.

    Danielle Leong: As I started, that’s not how math really worked. You can’t have one person split across two and a half projects. What I did was I then took a look at the identity data model which was all of the different things that this one team was supposed to be in charge of. Then I started asking around and I said okay well who else touches these different projects and so in looking at that you actually became 3 different teams. Because I said it’s very clear that this one team is actually doing three different teams’ responsibilities. If you group them in this specific way then it starts to make sense. When you have an overlap of three different teams. who are technically owning one specific model, that’s why it takes a whole month to solve a support problem because it’s being kicked in between three different teams. If we split that out then it becomes very clear, ok, this very clear ownership here. Now that means that we can go faster with that clear ownership and then we have the ability to work on different projects and still be able to deliver to our enterprise customers. So that is how the identity and identity access management team became the identity organisation.

    Patrick Kua: Wow.

    Danielle Leong: And so then that split into 3 different teams and then I started managing managers from that point on.

    Patrick Kua: Wow.

    Danielle Leong: So it just happened to solve a problem I started managing managers.

    Patrick Kua: Yeah I mean it’s a very natural thing particularly with restructures, where suddenly there are more teams or a different point and it sounds like it was large enough that you wouldn’t be able to get involved in every team. You’d just overload yourself. So it definitely makes sense from that point. When you started to find people who would maybe lead or manage those teams were they more people internally or did you end up having to hire or was it a mix of people for those three groups?

    Danielle Leong: It ended up being internal. With the GitHub acquisition from Microsoft there were several teams that actually came over. The authentication and the external identities team. Being those 2 different teams. They had actually come over. Luckily they were also incredible engineers. They were incredible groups already. So it just happened that they came over together as a unit. So I was able to start managing whole groups of teams that already had an incredible workflow already. They already had relationships with one another. So it is a little bit different in the sense that I got lucky in that way. But certainly hiring managers is a whole different skill. We can go into that in another podcast. But building it from scratch I’ve built the internal team at Maca completely from scratch that definitely takes a long time. You’ve got to figure out what requirements you’re looking for. What does that role look like? That’s a completely different ballgame but in this particular case, I got lucky and I was able to have managers that were already experienced in their craft as well as with their team.

    Patrick Kua: That sounds like it’s a great place to be because when you’re dealing with particularly 3 groups of people and each group is chaotic, it could take up a lot more of your time and it sounds like you had a nice transition into managing managers where the team sounded like they were already in a high-performing state. They had good processes as you said and a good manager. What was it like when you were working with those managers for the first time? So I understand that probably the ones that came over from Microsoft you probably hadn’t worked with before. What was that like as you were thinking about building your management team?

    Danielle Leong: That was interesting. I would say that that was definitely the thing that required the most amount of communication. Because we are now merging 3 different cultures into one organisation. How do you take the best of each different previous history and each different previous culture and blend them into what will become a new organisation? So that ended up being a lot of back and forth. There was definitely some pieces of friction as well where we had disagreements about what is the culture that we are trying to build here? If I were to do it again I would have those explicit conversations up front. I would say, What do we value?What does each person, each manager here value? How do they like to get their work done? How do they like to run their engineering teams? What are the values that they have for their engineering teams? What is important to you? Is it building incredible software well? Is it building software fast? Is it getting promotions? What are the things that you value as an engineering leader and what is the best that we can take from each one of these and what can I as a leader say that is like, okay, this is what I want my organisation to be.

    Danielle Leong: Thank you for providing this context. But that’s not how we are going to be doing these things going forward because of these reasons and this is where I want to see this organisation go in the future. That is something that ended up being a lot of different conversations. If I were to do it again, I would have even more of those. Be very explicit. Have those offsites. Really start to think about what is the culture that we are trying to build here? Because it’s not just how are the engineers doing work. It is also what is the culture of each one of these different teams. What are the levels of autonomy within those different teams versus what do we collectively need to work towards as an organisation together? How do we present that united front as a leadership team? Then what are the things that are you’re free to do this within your own organisation because you are a leader as well? How do you want to run your own teams versus how do we want to be together as an organisation.?

    Patrick Kua: I think given that teams themselves have their own differences, it’s that extra factor of different company cultures and that merger acquisition (M&A) that adds more complexity to the scenario that you’re dealing with that probably a lot of other directors or people wouldn’t normally need to deal with. Most companies don’t go through an M&A every day. It sounds like a really interesting challenge. One of the interesting things I heard you also say was that finding that autonomy and that balance between what is it at a team level, what’s maybe at maybe at organisation level. Fast forward through the cultural differences, at what point did you then decide as a group, what would be more permissible at the team level and versus the things that you would expect say every team to do? What are maybe some examples of where you bounded those different types of autonomy?

    Danielle Leong: I think it was very much like, okay what are the things that I care about as an engineering leader at the end of the day? I care that people are working together. So if one person on one team needs some help we should. They are our teammate. We are all in this together. We are all moving towards the same direction. So if somebody needs help, we help them. We celebrate each and everybody’s wins. It’s an us. We are the organisation. It is not that team is celebrating something. It is we as an identity organisation are celebrating together because when somebody wins, we all win. That was definitely, those were the things that I really cared about. Which is we want to be in this together. We are a team together. We are an organisation together and so we help each other out and we also celebrate what other people are doing. Ultimately, we do need to get stuff done as well and so how do we get stuff done is very much up to the teams themselves. Each team has their own processes. Is it a very strict agile format where you have to do sprints and you have to do points? Yeah that’s an implementation detail that doesn’t really matter so much to me.

    Danielle Leong: What does matter to me is how do we agree on what is done? How do we agree on what the schedule is like? How do we agree on breaking things up into iterations and showcasing that value at a regular basis? Those are the things that are important to me. Another thing is how do we do calibrations at the performance level?

    Patrick Kua: That one’s always tricky.

    Danielle Leong: Always tricky. Always tricky. But if you back into how well are your engineers doing? That then becomes, okay, how do we know how well your engineers are doing on a regular basis? What sort of check-ins are you doing with your engineers? Are you having 1 on 1s with people? Are you having regular career conversations? When I have skip level, 1 on 1s with people I should be able to ask them, hey. Do you know where you are in your career? They should be able to answer yes. How that happens, how you have those career conversations, how you have your check-ins with people. Again, that’s an implementation detail. But the end result is your people should be challenged. They should have a clear idea of what the organisation’s priorities are as well as the company priorities and how those two relate. They should have a clear idea of how that work that they’re doing on a daily basis relates to each one of those rolling up priorities. They should know where they’re at in their career. So how that happens is an implementation detail that is up to the individual manager. But as a unit together we need to hit those milestones together and we need to agree on this is what quality looks like. How you get there is totally up to you.

    Patrick Kua: Great. So if I understand it right, then there’s the clarity of probably the outcomes that you’re expecting as a director around things like the definition of done or the quality and then how teams would like to do that, they can choose different processes. Similarly, when it comes to the planning processes that you probably want to see the concrete valuable milestones or something valuable. Not horizontal slicing. More vertical slicing or something that’s more releasable. But then how teams want to go and manage that is really up to them. Is that an example of how you would describe those differences?

    Danielle Leong: Yep, yep. Definitely.

    Patrick Kua: Great. Excellent. One of the interesting things I also heard you say and I love the focus on culture, the focus on we. Because I definitely have seen this with entering managers which is like, “It’s my team”. It’s all about the team. One of the things I heard you say was we need to celebrate as a whole group. So how do you encourage that? The philosophy makes sense to me. But what are some concrete ways that you encourage that behaviour within your group?

    Danielle Leong: There’s a couple of different ways that I like to do this. You have your typical all hands. I used to have them once a month. We would have the celebrations upfront. It would be from every different team. Maybe it’s a promotion. Maybe it’s something in somebody’s personal life. Birth of a child, for instance. That was always celebrated. A completion of a project. Onboarding of new customers. Those are things that we celebrated together as an organisation. The other way that I like to do that is through cross-pollination. So when you have a larger organisation you, have more opportunity for different career opportunities. You’re not just limited to one specific team. In order to create a little bit more of a cohesive culture, you can take folks from who want to grow in specific ways and say hey there’s an opportunity on this team over here. Why don’t you join them for this project? Then you can help with that communication. It becomes more of a us culture swap. Bring the best practices from one team to another and then there’s a little bit more connective tissue there.

    Danielle Leong: A really great example of this was with the authentication team. They had a really great pair programming culture. They had brought that over from Microsoft. They pair programmed all the time. They were really comfortable with doing that. Then the authorisation team had a really great documentation culture. They were very good about project planning. They were very great at writing out the tickets and thinking through the problems before they started but not so great at pair programming. So I actually swapped members on two of those different teams. Like okay we’ve got 2 people over here, they’re going over here. I’ve got 2 people over here, they’re going over there. It’s going to be for one project, approximately a month, maybe a month and a half. Enough for them to complete something together. But they still had their regular team meetings as well. With that, the pair programming culture started shifting on the authorisation team. The documentation culture started shifting on the authentication team. Then they felt more comfortable like tossing questions on over. They’re like hey, how do you do this? I saw you working with this stack over here when I was over here. I think we’re trying to do something over here. Can we have a quick sync up and talk this through because I’d seen this over here and I don’t quite fully remember how that works and so that connective tissue really started growing together. Then because they had that personal connection, they knew what was happening on the other team and they were able to celebrate because they had that context of what happens over here. What happens over here? Oh right? We’re actually working on similar things. We are together as a team. Oh that’s great. I’m going to celebrate that as well.

    Patrick Kua: Yeah, really great examples of that personal connection, Of getting people to spend time in other teams so they’re not completely siloed off. And also an interesting thing, which I find fascinating, is that you also notice the interesting differences between the teams. So one team having that strong pair programming culture. The other one, documentation. How did you, for instance, get to know about that given that normally people who are not the direct managers are further away from teams? How did you start to notice that yourself?

    Danielle Leong: I definitely wanted to invest a lot of time in my skip levels. I had originally been the direct manager of the IAM team which then became the authorisation team. So I already had a strong connection there, but I didn’t have as strong a connection with the rest of the organisation. So I made sure to have those skip level conversations with those folks on a regular basis. So I made sure that I met with each person at least half an hour every month or so. Then I would ask those sorts of questions. I would hop into weekly syncs. Sometimes. You don’t want to be in there all the time and that pressure.

    Patrick Kua: Ooo. The director’s here.

    Danielle Leong: Oh no, we have to be on our best behaviour! That’s not super helpful for anybody really. That’s unnecessary stress. But I would occasionally pop into slack channels and ask questions. Be like hey, what’s going on here? I would ask questions about how things are going? I actually still have like regular 1 on 1s with some of the folks from the identity organisation. Because I got to know them very well. I got to know them as people. I got to know them where they were at in their career. Where do they want to go? So I have a list of questions that I typically ask my direct reports. I ask these similar questions with my direct managers. I also ask these questions of my skip levels as well. These are all templates that I keep in my manager repo. It’s on GitHub. It’s freely accessible to everybody. I always update it on a regular basis. But having that personal connection really makes sure that you have a finger on a pulse of what’s going on. I also had some staff engineers that reported directly to me and so I would have one-on-ones with them on a weekly basis as well and say hey, what are you worried about? What’s going on? How do you feel about this? How are people reacting to this news over here? If I said this is what I’m trying to say, what is it actually resonating or how is it actually getting translated to the individual contributors? So really making sure that I invest in the people that report to me. Because at the end of the day software is made by people.

    Patrick Kua: Absolutely.

    Danielle Leong: You have to invest in each one of those folks. As your organisation gets larger, it’s a little bit harder to have all of those one on ones. So maybe you have them a little bit less frequently. But it’s still important to not lose track that you are managing people. Those people need attention. Those people have their own wants and desires and needs and it’s important to know, even as a checkpoint for yourself as a leader, how am I doing? If I am saying one thing, what is coming out the other end? Because that’s a really good checkpoint to say, okay I’m trying to do this, what is your understanding? What do you think that we should be doing as an organisation? What are you worried about as an engineer within this company, within this organisation? What are you concerned about and what needs more clarity from you? So really having those regular conversations across the entire organisation really helps with that alignment there.

    Patrick Kua: I can see really the value in developing those personal relationships. Particularly in your role where you have more authority or perceived authority and that can often create a distance for some people and by investing in those relationships, that hopefully then gets people to open up beyond the shallow first couple of points because people are worried about what you might do with that. I can see the value of you getting that transparency of information and being able to get more context about your organisation. One interesting thing with the team and the people swapping from team to team is probably dealing with managers. So sometimes managers get very defensive. It’s their team. Why are you moving people around? Did you have any of that when you were navigating that swap or how did you overcome that defensive behaviour?

    Danielle Leong: Yeah, yeah. Definitely did have a little bit of that. But I think that at the end of the day, that comes from a place of anxiety. So it’s important to dig into, okay, what is causing this anxiety? What are your base values as an engineering leader? What are you concerned about that would threaten this idea of us working together? Is it deadlines? Is it the amount of time it would take for this one person to get up to speed? Because the deadlines are probably set by me. So if you’re concerned about that, work with me and we can create that buffer zone. Because if ultimately this is something that we are trying to do as an organisation, then we can always add in that buffer time so that the understanding, of okay we have this buffer time this is where that person is going to take time to ramp up. That means it affects the project in this way. That means that we need to add this amount of time at the end to really start to figure out that. If it’s a timing thing? Great. That’s definitely within our control is it a career thing? This is my organisation. This is my team. This is my area of responsibility. Get out. Then that’s something completely different. So then you have to start really investing in that relationship and say like okay, where are the lines of autonomy? What is your responsibility to your team? What is your responsibility to the organisation? What are your motivations as an individual with your career? Is working together part of what you are being graded on as an engineering leader I would argue, yes. Because you can be very productive in a very narrow area. But when you work together with other people, a rising tide lifts all boats. So if nobody wants to work with you within the larger engineering organisation, is that truly being successful as an engineering leader? Or are you being successful at the expense of others? In which case I would say no. That’s actually not fulfilling your responsibilities as an engineering leader. Because it’s a fairly narrow-minded way of thinking about things. So I would have that conversation about what is causing this reaction? That protectiveness. What is really causing that? Let’s address the real problem there and let’s also take a look at how are our responsibilities as managers really being graded upon? So if those two are mismatched then we need to have that clear conversation that this might be a reaction but it’s not actually going to get you very far at the grand scheme of things.

    Patrick Kua: Great. Yeah, the triangulation of the source of whatever that is, requires listening, probing, really open questions and then adapting your style to whatever you discover as part of that probe. I think that’s a really great approach to that. One of the things that I was hearing you say was around thinking about those responsibilities and one of your responsibilities is often assessing how good is a manager doing. Do you have a framework in your head about what is a good engineering manager?

    Danielle Leong: Yes. So this is actually part of the templates that I do have in my repo. I like to be very clear about what my expectations are for engineering leaders. As I mentioned before, is your team happily challenged? Are they working towards career growth and are reproducing themes that we are producing things on a deliverable timeline that is providing value for the company as well as the rest of the engineering organisations? Those are the benchmarks that are important. But there’s also the things like as I mentioned before, are you having those career conversations? Do your people know where they are in the grand scheme of things? Because if you’re only keeping an eye on this is my team, nothing else matters, you’re missing the entirety of not only the engineering organisation, not only the company but this individual needs to have opportunities in their career. Are you truly doing them a service by keeping folks isolated and only focused on a team or should that you be looking at like their career growth as a whole and then looking for opportunities to help them grow and get challenged in different ways which may be helping out folks on another team?

    Patrick Kua: Great.

    Danielle Leong: Really helping people take a look at the larger picture. How do we produce things within our own organisation but also how are we part of a larger group that is running together in the same direction?

    Patrick Kua: Excellent, Very well articulated. We’ll also make sure that the link to your repo appears in the show notes. It sounds like there’s lots of great resources for people out there.

    Danielle Leong: Yeah, definitely.

    Patrick Kua: Let’s talk about your journey stepping into managing managers. Looking back at this. What were maybe some surprises for you?

    Danielle Leong: Surprises. I think that one of the biggest surprises was, and this is a very naive assumption, which is how I manage people is completely different from how other people manage people. As a line manager I had a very specific way of doing things. Again, documented in this repo is how I actually do these things. So it was a big surprise to me, as you step back with that layer of abstraction, you have to relearn how everybody does it on their different team and the more teams you have, the more you need to learn about how each one of those different teams actually operates. What are the strengths of how that person manages as well as what are the gaps? Maybe you’ve done in the past or maybe even how another team does on another side. You really need to take that time to say like, oh, I take for granted that I do XYZ tasks on a daily basis. Or this is how I fostered the careers of the people that report to me when I’m a line manager. Does that happen with everybody on this team? Really coming at it from like an open mindset of like, okay, here is what I envision management to look like. How do you do it? I want to learn a little bit more about how this is. Okay. Great. Now I have a clearer picture of your style of management. The strengths of how, what something is done and maybe some areas of improvement. Here’s how we can improve those different areas. So blindly assuming that everybody does things the same way. Terrible idea. Terrible idea. I do not recommend that. So really keeping an eye on how things are done. What are the strengths? What are the areas that we could improve? And then the other thing that really surprised me was thinking ahead, further than I had done before. One of the things that I like to think about as you move up in your career. It’s actually all about time travel.

    Patrick Kua: I love it.

    Danielle Leong: Nivia Henry and I actually have a great conversation about this. She actually did a LeadDev talk on this based off a Twitter conversation that we had. So when you are a junior engineer you are in charge of the tasks that are in front of you that you are doing right now. As you become a mid-level engineer you are in charge of the tasks for the next couple of hours. Senior engineer, maybe you’re thinking ahead, maybe two weeks or so and you’re helping others in the present really understand what the tasks are going to be. As a manager you’re thinking about similar timelines which is what are the tasks for the next two weeks, and how do I convey them to the people who are living in the present that report to me? As you start to manage managers. you’re thinking three months to six months out in advance. As a VP right now, I think maybe six months to a year sometimes out in advance. How do you break down those things into action items? Into a plan? Then how do those plans then break down into tasks that relate to what somebody is doing right now? So some of the frustrations that you can come up with as you become to manage managers is you’re living in the future. You’re thinking ahead, three to six months.

    Danielle Leong: And people in the present might be asking questions about what’s happening right now. Because they live right now. So it’s your responsibility to time travel backwards and say, okay, I live in the present right now. The folks that I’m talking to live in the present right now. They need to know where we’re going. And so how do you package that information in a way that brings people along with you on that journey and say like, okay, we’re going in that direction. This is the plan for the next couple of months. Here’s how what you’re doing right now actually affects how we’re doing in the future. And then you have that alignment and you have those regular checkpoints and say like okay this is where you are. This is where we’re going. And that skill I find is really really hard when you first become a manager of managers. Because you live so much in two different points in time and it’s hard to reconcile those two different things until you get used to it.

    Patrick Kua: Yeah I love it. I’m picturing here, maybe because I grew up with Doctor Who, but here of like the time travel Tardis, and making sure that you do keep in those different time perspectives is really key. I also do recognise how people have really struggled really trying to look up or look further into the future, given that their habits are probably in that 2 week time frame that you were talking about if you’re a more engineering manager. Great, great lessons and great surprises. Maybe a couple of closing questions. What are maybe some books or a book that you think have been really helpful for you in a Director or a VP engineering role.

    Danielle Leong: Let’s see. The one that I read recently is called Leading with Heart. So that is a really great book because it’s all about how, it’s kind of funny because it actually starts with, you as a leader have caused all of the problems that you are complaining about. I’m like, hmmm.

    Patrick Kua: Ouch.

    Danielle Leong: That is a strong stance to start with. But it talks a lot about how what we do as leaders has repercussions. They might seem very small to you. You may not even like realise that this is happening but with that, oh god, I gonna I’m going to have to say it, with that power comes responsibility. So with this power structure, you might say something to an individual contributor and they will say they will see that as a directive and then go do something.

    Patrick Kua: Yeah.

    Danielle Leong: Then that changes what’s going on and that this disrupts a schedule. I’m like, oh my god, this is the thing that is now the most important thing because so-and-so said that it was, when it might have been an off-hand comment. Being very cognizant of the responsibility that you have to your actions and what you say is incredibly important and so this book talks a lot about how do you lead with empathy? How do you make sure that you are reducing the churn that’s happening within your organisation? But also taking care of yourself and so are you exercising? Are you eating well? Are you sleeping well? What are the things that you need to do to be your best self in order to be the best leader that you possibly can be? I don’t know if you’ve ever been in a meeting where somebody in leadership was hangry?

    Patrick Kua: Oh yes!

    Danielle Leong: Or exhausted? That has downstream effects. That may have undesirable consequences. So how do you take a look at your own habits? Take a look at your style of communication? The things that you are saying that you value versus what you’re actually valuing and then how are people reacting to it? So I thought it was a really interesting book from a more meta perspective and it’s not if you start this plan, these things are going to happen, which I find a lot of management or leadership books tend to be. Five tricks to like start your team being more productive but really taking a more introspective look at what are the actions that you as a leader may be doing and unintentionally causing these downstream effects? So I thought that was a really really interesting book.

    Patrick Kua: It sounds like a fascinating book.

    Danielle Leong: It’s great. It’s definitely a different way of looking at leadership. And you have to be prepared to take a look at yourself and how you might be affecting the problems that you are actually already dealing with? So I thought that that was a really interesting book. The second book that I’m reading is Principles, so that is very much like what do you value as a leader. And then again, how does that have those downstream effects within your own organisation.

    Patrick Kua: Great. That’s a chunky book. I remember the Ray Dalio one.

    Danielle Leong: Yes, yes, it’s very good. It’s very good. I just started on that one.

    Patrick Kua: Excellent. Excellent, So maybe one last question or maybe one last question. One is, if you were to give any advice to a first time person stepping into a managing manager’s role, what would that be?

    Danielle Leong: Oh man. Just listen for a little bit. You might have a lot of ideas in terms of how things should be run. But anytime you step into a position where you are managing other people and then managing other people who are managing other people, take a look and see how are the individual teams doing? As well as how your managers are doing? So one of the things that I wish I had done earlier, was not only investing in how the teams are doing, but don’t ignore how your managers are doing. Don’t ignore how their careers are going. Don’t ignore how they think about how they’re doing their jobs. How they’re doing their jobs. Making sure that you are also investing in the managers themselves really helps with cohesion. Really helps with binding that culture together. And really helps with understanding why, because you have that layer of abstraction, how things are happening all the way further down the chain. So don’t forget your managers. Don’t forget they are people who have careers. Who have aspirations of their own. Who have their own motivations, and have their own way of doing things. Don’t forget to invest in those folks as well.

    Patrick Kua: Fantastic bit of advice. My final question for you is where can people find out more about you or reach out to you?

    Danielle Leong: So I am on Twitter at tsunamino. Just Google my name. Danielle Leong. I’m also on Linkedin as well. I’ve got a bright yellow photo. You cannot miss it. So I am on those two platforms. Twitter less these days. But I am also available on Linkedin as well.

    Patrick Kua: Fantastic! and we’ll make sure all those links are in the show notes once again. Thank you so much Danielle for the wonderful conversation and insights into your experience. I’ve learned a lot throughout this. I’m definitely going to be adding the book that you recommended onto my reading list as well. I’m about to go on holidays. So I’ll make sure that I read this on my break. Sounds fantastic. But it sounds also like I need to prepare to read this book. I’ve really enjoyed the conversation, so thank you very much for being on the podcast.

    Danielle Leong: Yeah. Thank you so much for having me.

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