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Home » News » Episode 13: Digging your well, the Staff Engineering Manager and managing burnout with Anjuan Simmons

Episode 13: Digging your well, the Staff Engineering Manager and managing burnout with Anjuan Simmons

    Guest Biography

    Anjuan Simmons has led software development teams for over two decades, and he excels at shipping features that customers love while also managing healthy teams. Anjuan’s goal is to help everyone he meets become the best possible version of who they are meant to be.

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    Transcript

    Patrick Kua: Hi everyone. Welcome back to the Managing Managers podcast. I’m really excited to have Anjuan Simmons with us today. Anjuan Simmons has led software development teams for over two decades and he excels at shipping features that customers love while also managing healthy teams. Anjuan’s goal is to help everyone he meets become the best possible version of who they are meant to be. I think that’s a really wonderful goal for all types of managers and leaders and I’m excited to have him here. So welcome Anjuan to the podcast.

    Anjuan Simmons: Thank you Pat. I am so happy to be here with you.

    Patrick Kua: Now you’ve got such a great amount of experience. Particularly managing and leading other teams. I’d loved to hear how you got into leadership in your own career. So when did you start going down that leadership track?

    Anjuan Simmons: You know it’s really funny because in many ways I did not have much of a choice. So I started my career at Accenture. Anderson Consulting at the time and the consulting model was very much you come in as an analyst. I was a fresh college grad from UT (University of Texas) Austin and I had no experience. So they bring you in. They make you credible. They put you in front of clients and you’re supposed to solve their problems. You eventually get promoted. The idea is that as you go from analyst to consultant, is that you will eventually become a manager. That model is very much up or out, meaning that if you did not hit the promotion points, you were pretty much asked to leave. So this is, again I’m old, this is the late 1990s. That model fortunately has decreased in its usage but in many ways, part of my job, as a consultant at Accenture, was to make those promotion marks. That means that I eventually had to take on leading teams and becoming a manager and managing individual contributors and helping them be successful the way that I was successful as an IC.

    Patrick Kua: Wow. Did you have a lot of support when you were being pushed into that management track or was it a pretty much you have to do this by yourself and if you don’t then you’re out?

    Anjuan Simmons: It was a mix. I think that if you were able to have mentors at Accenture, if you were able to have peers, you also were being promoted then you could construct some sort of playbook. Of course we had really good documentation. To date that time we used Lotus Notes back then for data.

    Patrick Kua: Oh yeah. I remember Lotus Notes.

    Anjuan Simmons: So you could read documentation about like here are the things that are expected of an analyst, of a consultant, of a manager. When you get promoted to manager you went to what was called “new manager school,” where you learned about the art of career management and the art of managing large projects. I would say I had support. But it was very much, you had to figure it out. So I think that I was very lucky to be able to give in the opportunity to lead teams that were composed of people who I enjoyed working with. I also had really good managers as well, who served as really good role models for my development into a leader.

    Patrick Kua: Yeah that’s such an important aspect of having great role models. That support network of mentors or people who are also going through that transition. It also sounds like you got to do some training, which not a lot of managers sometimes do when they’re in their first. It sounds like you had a generally pretty good experience even though there was lots of learning at that time as well. So let’s fast forward a little bit and then how long was it until you were starting to manage other managers or at what point were you leading other leaders?

    Anjuan Simmons: So going to managing other managers, that happened at Accenture as well. The way that Accenture works is that you’re put on large projects. So I was put on a large project. Once I was there for about three or four years where we were working with a large telecom company and that was the time where we were going with the offshore model. So I had a local team in the United States that I was managing. ICs. But I had a manager in India where we had a team of engineers and one of our indian development centres or IDCs. And so I was managing managers in India who had huge teams of engineers while I had a smaller team in what’s called the onshore team. So that was the onshore-offshore time if you were working in technology in the mid, let’s say the early 00s. 2003, 2004, 2005. This was a very common model that I think has kind of gone in and out of vogue. But that was my first time where I was not directly managing the software engineers who were doing the work. I had to work through a layer of managers to be able to do that.

    Patrick Kua: Wow. Can you remember what some of your surprises were when you started managing through other managers?

    Anjuan Simmons: I think that some of the surprises that I encountered when I started managing other managers were really around two things. One is, you’re not close to the work anymore. When you are the manager of a team, you are very close to the work. You can see the work almost every day. You’re talking to the people who do the work almost every day. So you have a very tactile exposure to that team. When you go one degree of separation up, you no longer have that. I think that that’s a big adjustment to be able to, I think, that the biggest adjustment is being responsible for the work without the day-to-day interaction of what the work is doing. That was a big adjustment.

    Anjuan Simmons: I think the other big adjustment was the importance of frameworks. Because when you are a manager you know how performance management works. You know how work may work. How you structure the work and what you do with the work. But when you’re managing managers you really have to be responsible for understanding what’s working with these processes? Are we really having robust career management tools? Do people know what’s expected of them? Then you’re responsible for making sure that those processes and frameworks are working and if they’re not working you have to often manage up to explain why it’s not working. Get the capital you need from the upper parts of the company to make a change and then explain that change to your manager. So I think that those are the two things that were really surprising that I really struggled early on making those things effective and efficient.

    Patrick Kua: Yeah. That’s an amazing insight. I can definitely empathise and relate to the distance thing that you’re talking about. Of being further away from people doing the work and then also knowing about the frameworks or the processes and making sure that those things are also working and are aligned. I find it’s fascinating as well, you’re right, I think at that time, with that nearshore or offshore model. I guess one of the other interesting things that you probably encountered was also managing people from different cultures. Was that also something that was very new and different given that they were probably in a different time zone and just very different culturally?

    Anjuan Simmons: Absolutely. It’s funny because the first, I would say, month or so of that project, I had no way of meeting the people who were doing the work. We all got on these very late night calls using a telephone system. This was way before Zoom. Way before Microsoft Teams. Way before we had easy ways to do video. So we spent a lot of time communicating over phone calls. You can do a little bit with that. You can make progress. You can understand what the team is doing. What the work is doing. But it’s really hard to understand what’s going on. There were, I think, differences in how we thought about the work. We being the near shore team and how the team over in Bangalore thought about the work. So you really had to understand those changes in how people think about work. There were all these holidays in India that I didn’t know about. It’s like, oh, the team’s going to be gone for a week in the middle of this month where I thought we were going to get a lot done because there are these state holidays that they have, that we don’t have. So even understanding holidays and how they differ between holidays in the states and holidays in different countries. Those things you have to navigate. Because you have to respect those holidays but you also have to plan for them too. But I really was served well by the fact that after that first month or so the company actually flew the engineers over to Houston, where I was leading the local team, and we got to meet face to face. I got to know, not just names in a spreadsheet, but faces and how they operated. Because even though they all came from that part of India and that culture, you also realise that these people are different. They have different personalities. How they receive feedback. How they need guidance. So that was invaluable for my success and so I absolutely had to navigate the different cultural aspects of that team. But I was able to do that really effectively when they came to the same place where I was, and we could work together for a few weeks. We could do planning before they went back to Bangalore to do the rest of the project.

    Patrick Kua: Yeah I can imagine what that was like when you get to meet those people for the first time in person. Also, as you said, the tools and technology weren’t really there around video conferencing. I think I can remember the brand of the phone, with that sort of star phone, that you typically have in conference rooms. I can imagine that’s probably where you huddled with all your managers quite often. But so different today when you can do everything with video conferencing and Miro or other boards, where you can interact at the same time. It’s much much richer but I can imagine it would have been such a different experience back then. What would you say as a manager of individual contributors, as you built up some of that management skill, what helped you as you transition to managing other managers?

    Anjuan Simmons: I think that there are a few skills that really translate well when you’re making the leap between managing ICs and managing managers. One is people management. My people management style is very much high trust. Meaning that I assume that you’re doing what I’ve asked you to do unless you prove otherwise. I assume that you have good intentions unless you prove otherwise. That high trust, leading the trust, aspect of what I brought to my role into my team as a manager, translated very well to managing managers. With my managers, hey, same thing, I trust you. Not only that but I really do care about you. I think it’s easy to say that as maybe a throw away line. But I very much invest in the people that I managed. In my mind if you manage the people, and if you take care of the people, then there’s really no problem that you cannot solve. If you don’t manage the people well, then all those problems become even harder to solve. So I believe that people management very much translates well going from managing ICs to managing managers.

    Anjuan Simmons: I also think that one thing that helped me is that I do love building software. I love writing code. I love delivering features to users that they really enjoy because at the end of the day if you’re doing it the right way we build software to solve problems and ideally, you’re getting a really good view of what people are using now and the ways that that’s not working for them. Then when you create a solution you can create an even better way of solving those problems in a way that hopefully is less painful than the current state. I just love doing that. I love seeing feedback from customers and how the teams that I’m leading are solving their very real problems. So those really translate well. So whether you’re directly managing the people doing the work or managing the manager doing the work, all that. You get echoes of all that even when you become someone who’s managing managers. I also think that one of the things that translates well, at least for me, is I’ve always been curious about institutions and how they work. Even when you’re a manager, you have to be aware of them. But when you manage managers you really have direct contact with the rhythm of the business. You have very direct contact with often the leaders of the business. My early curiosity about well why do we do these things? Or why does performance management happen in these ways? Why do we do an annual review at the end of the year? Why do we do mid-year reviews? Why don’t we do this and that? I think that if you have that curiosity as an IC or as a manager then that might be a bellwether that hey you may have a really strong capability to manage managers because at the end of the day I’m responsible for the environment that my teams operate in and helping the managers focus and explain that environment to the ICs. That’s all processes. That’s all the mechanics of the work. Not just the building software/shipping code. So I think that those are the things that really translate well for me when I manage managers.

    Patrick Kua: I really love that focus on the people. As you say, knowing those people and being able to manage them well as individual contributors and managers. Managers are also people. Then a lot of those skills I can see translate really well. And you know that curiosity, as well, I think that’s a really interesting aspect to managing. Of really understanding the rest of the company, the rest of the context in which you’re operating. Given that you might be operating in a really large context or a smaller context if it’s a smaller startup. But that curiosity given that other departments run their teams differently and you might need to abide by certain policies that you don’t really understand but being able to have that context and share that. I can see that being really really valuable. One thing I heard you say was around thinking about you’re responsible for managers and I think one of those difficulties sometimes with managing managers is you’re not necessarily there on the day-to-day with the team. So what are some of your ways of knowing if a manager is doing well?

    Anjuan Simmons: I have one main tool and it’s not a surprise but it’s 1-1s. Having weekly 1-1s with your managers and making sure that you understand what’s going on with them with their teams. But also what’s going on literally with them. How are you doing this week? How are you dealing with this news that came out from the company a few days ago? I think that having healthy 1-1s, I think we both know Lara Hogan, who has done a lot of work on 1-1s. I highly recommend if you just Google her name and say 1-1, you get a wealth of information about how to do them well. Another tool, very much similar to what I just mentioned, is skip 1-1s. Having what are called skip levels. While you cannot have skip levels as often as your 1-1s, I do think having a regular cadence where you are talking to the people who report to your manager. That’s extremely extremely important because by having those skip levels you’re one, or ideally showing that you care about them. You’re a busy person. You’re taking time out of your busy schedule to give the one truly non-renewable resource. That’s time. To just understand them and to understand what’s going on. You’re also getting an insight into how they operate and what the items that are in their span of control are doing. You get a sense of understanding how the work that they’re pushing forward is doing.

    Anjuan Simmons: So I think that those are very simple tools that can go a long way for you updating your mental model of where the work is going and also understanding the times where you do need to, I would say, intrude into their work. Because, as I said before, I’m very much a high trust person, but there are times where you do have to directly go into the work and make changes. I think that ideally, that’s happening in those 1-1s with the managers. You’re helping them understand what you expect. You’re helping them understand where your expectations aren’t being met and also what they can do to fix that. But the skip level 1-1s are giving you the opportunity to go beyond maybe some of the blind spots. We all have blind spots. Even the most experienced managers have blind spots. But you’re getting opportunity to do that in a way that you can bring back to the manager. This is tricky because you want to do it in a way where you don’t betray the trust of either person. Either the manager or the person that they are managing. But you can ideally do it in a way that’s sympathetic but also helps to solve the problem. I think that those are, 1-1 or skip level 1-1s are very lightweight tools that can go a long way to getting over that degree of separation that you are from the actual work.

    Patrick Kua: Yeah, it’s a great tool both for your managers and then also for getting direct information from people in that team. You’re right, which is being careful about how people perceive those 1-1s. It’s not undermining managers, but really about getting a different perspective. One thing that can often happen with skip 1-1s, is, ooo, here comes a senior manager who wants to talk to me. I’m not sure what this is about. Do you have any advice for how to counter that power imbalance or that perception or power imbalance?

    Anjuan Simmons: You raise a great point. There is a huge power imbalance in a skip level 1-1. You’re a level, you’re two levels above the person that you’re talking to. This person knows that you have a lot of power over them and that you can use that power in a variety of ways. Some ways that they may like. Some ways that they may not like. What I try to do is the first couple are just getting to know you. Hi. How are you? I’m Anjuan. This is my role. How are you doing? Oh where do you live? Oh what hobbies do you have? So just asking those questions and making those first couple get to know you 1-1s really go a long way towards the later ones where you are probably uncovering a problem and you’re understanding what you need to do to solve the problem. Often the skip level is afraid that oh am I getting my manager in trouble? Or sometimes they like getting the manager in trouble, just to be honest.

    Patrick Kua: Troublemakers.

    Anjuan Simmons: But if you, and I go back to the old adage, dig your well before you’re thirsty. You should establish those relationships early with your skip levels.

    That I’m a human too. I’m coming to you human to human to just have a shared experience. So that if you build those early relationships well then you can draw on those early relationship building activities and outcomes when things get hard. So I think that that’s really important to make sure that you’re utilising those skip levels in a way that is effective down the road.

    Patrick Kua: Yeah, you know that’s the first time I’ve ever heard that saying around dig your well before you’re thirsty and I love it. It’s a great example here of, yeah, making sure you build those foundations before you need to tap into that and completely makes sense in this context. One of the interesting things I guess with managers and understanding performance is that there’s often that perhaps perspective or differences. So there’s maybe what you expect and also there’s personal preferences about how you expect things to get done. And often managers may have a different style from you. How do you differentiate between somebody’s performance and this maybe style of management and how do you reconcile that?

    Anjuan Simmons: I think it’s important to understand that there are multiple ways to be successful. I have a very built in style that’s very much based on, again, going on 25 years, though maybe more than 25 years, of doing this for a living. And I very much know how it works. But I also know how it doesn’t work. So I think that when you’re managing someone who has a style that differs from yours, assuming that they can get the same positive outcomes, then I think you have to be okay with it. I think that it’s important to understand as a manager that your management style does not work for everyone. So your manager having a different style that may actually be a feature not a bug. Because you may be able to solve problems and there was someone in a way that they enjoy but there might be someone that you take the same approach in managing, where they may revolt to be honest. Because you may be more laissez faire. Kind of hands off. I’m keeping things at arm’s seat (length) because I trust you. There are some people who are like, no, I actually want some direction here, because honestly, I’m scared of making the calls here and I don’t want to be responsible. So I need you to give more hands-on, what some people might call micromanaging.

    Anjuan Simmons: I think that it’s important to understand that if you’re managing someone whose style differs from yours, assuming that they’re getting the outcomes, assuming that they’re meeting the needs of the organisation, the needs of the team and that they’re meeting the wide-scaled expectations that you set, I think you have to be okay with that. You actually may be able to use that to your advantage because if you are managing multiple managers, and you understand their style then there are times where let’s say manager A is having challenges, where manager’s B style will be effective, you can either help manager A understand the aspects of manager B style, that they should bring the bear to the problem. Or if you’ve really done the work, you can even have manager B sometimes kind of step in and help to co-manage that person. So I would say that you can’t be married to your style. You sometimes have to kill your darlings, to use a writing phrase. That there are times where you have to be willing to lay down the things that are familiar to you. That you’ve even seen work well in the past and understand that you have to lay them down because they’re just not fit for purpose for the problem at hand or for the person at hand. I think that having that humility is key and that actually unlocks more tools at your disposal to solve problems that you may struggle in your home and data style.

    Patrick Kua: Yeah I think it’s also a reflection probably of your experience, of A) being able to recognise different leadership styles and preferences and B) also understand the best placement or where it makes sense in different contexts. I also like that approach that you talk about of really connecting managers who may be able to complement each other given that each manager is often going to have their strengths or weaknesses or skill area gaps and being able to support each other as a management team. I think that’s fantastic.

    Anjuan Simmons: Yeah, thank you.

    Patrick Kua: I’d love to move on to your current role. So I find it fascinating because I understand that you currently are a Staff Engineering Manager and that’s a very unusual title. So I think staff engineering, in general, is also a confusing title for a lot of our industry. Will Larson’s book (The Staff Engineer) has gone to help clarify some of this and we have a few more books like The Staff Engineer’s Path but tell us what is a Staff Engineering Manager?

    Anjuan Simmons: Staff Engineering Manager. It’s a funny title isn’t it. At GitHub, a Staff Engineering Manager is actually the same level as a director. There’s no promotion from Staff Engineering Manager to director. A director at Github, and I really have to say this is all within GitHub, because I’ve seen these things play out at different companies. So I’m going to tell you how things work at Github because that’s where I’m at right now. It’s the context that I know the best right now. Your mileage may vary at your organisation or company. So take that with a grain of salt. But directors directly manage managers. It’s very much what we were talking about earlier. A director is a manager of managers. At GitHub a Staff Engineering Manager could manage managers but very much manages ICs, so that’s the major difference between the two titles. And let me pause here and say that I’ve been very lucky in my career to be able to move between managing managers to managing ICs. To be honest I really like both. I like managing managers for reasons that we talked about but also like managing ICs, for a reason that we talked about too, which is being close to the work.

    Anjuan Simmons: I’m going to pause here and give a star trek analogy. If you’re a star trek fan and you watch star trek generations, that’s the movie where Captain Picard and Captain Kirk meet. There’s a scene that’s fairly well known where Kurt gives Picard some advice and that is advice is, “Don’t let them promote you.” Don’t let them take you to the enterprise and out of the captain chair because the captain’s chair on an enterprise is where you can make a difference. I can honestly say that when I’ve managed ICs, the difference that I can make directly in their lives is way more than what I’ve been able to do when I was a manager of managers. So I would say that they both had different aspects that I enjoy. I’m currently managing ICs. But if you can, in your career, have the opportunity to go back and forth and see how they operate and which one really is your jam, I really do advise that. But getting back to to Github and what a Staff Engineering Manager does again very much, we manage ICs but I think that what distinguishes a Staff Engineering Manager from even a senior EM (Engineering Manager) is really, as a Staff Engineering Manager, you are expected to find problems that maybe people don’t know about. And to devise solutions. An Engineering Manager’s remit is within the domain of the team and the problem area that they’re working in. And the part of the codebase.

    Anjuan Simmons: As a staff EM you’re doing that too, but you’re also figuring out what are some of the problems that the team or the department has, that people aren’t doing anything about yet. To give a couple examples where I’ve done this at previous companies. I worked at a company where I realised that the interview questions were great but they were all private. Again this is not unusual. Most engineering companies, most software companies, don’t publicise their interview questions for a variety of reasons. But I got feedback from inside the company and also some people have been through the process, that if we publicise these questions, put them in a public repo on GitHub, then there are benefits. For example, some of the benefits are that some of the people that come work for our company don’t speak English as a native language. So if you are a non-native English speaker and you show up to an interview, you have someone who is a native speaker of English, you had a bit of a disadvantage. I shouldn’t say that. You may be at a bit of a disadvantage because you’re translating in real time while the interviewer asks you your question in English you are translating in your mind. Maybe it’s your native language. You’re thinking about a good answer. You translate that back to English and then you’re saying it to the interviewer. I think often there are things that may be lost in that translation. There may be things that you wish you would have said after you say your answer.

    Anjuan Simmons: So I got really good feedback from people who were engineers at the company who did not speak English as their native language. How that can be very difficult. So that was one thing that I wanted to solve. The other problem is that even if you speak the same language as the interviewer you may be someone who simply needs more processing time. Not everyone is great at off the cuff responses. Some people are amazing. They give off the cuff responses that are crisp. That are detailed. That are great. There are some people who may be similarly skilled but they just need more time. By publicising the interview questions I was able to solve a problem that I identified, both within the company and outside. I got great feedback from that. So that’s the kind of thing that I’m not chipping code. I’m not doing things for ICs. But I’m helping people’s experience and even interviewing at the company be better.

    Anjuan Simmons:

    One quick other example that I did is that I worked very closely with recruiting at a previous company. For a variety of reasons there were some concerns about when we hired someone, especially a senior leader, there were questions about why did that person get the job over someone else. So I partnered with the head of recruiting and we came up with something called a hiring summary. It was simply, for any position, especially if it was a leadership role. I’m talking a manager, director, VP, we publicise all the people that applied to that job. All the people who made it to the first round of interviews. To the second round. On and on. To who got the final offer and who accepted it and why we hired this person. What did we love about the person who actually got the job? By doing that we just told the story of how this person got a place, which in many ways removed a lot of the noise we had about why this person was hired over that one.

    Anjuan Simmons: I will say that the part of the benefit of the hiring summary was that there were times. No one said this really out loud but if a person of colour, or a woman was hired, then there were sometimes concerns about well why did they get the job? Is this a diversity hire? But the hiring summary told them the story. No, we had 3000 people apply for the job. Then 30 people made it to the final stage or close to the final stage. This is why they were hired and so it was also an act of inclusion. But again, that’s all stuff that an engineering manager, especially an early one may not do, but those are the types of things that a Staff Engineering Manager will do. Is solving problems not just in the domain of engineering but what, as a company, needs to be done and how can we find those problems and solve them in ways that are effective.

    Patrick Kua: Yeah they’re really great examples. I would often think of these in my terms, in terms of working on the system. Which is, I guess, the organisation or the processes in how things run. You’re working to improve that system. And I can see the really great example of being more inclusive. Of helping people go through that interview process in an easier way, given that people will have different backgrounds and different comfort levels with english or a specific language. Then also then the transparency of, yeah, why did we end up with the person for this particular role? So really great examples. So maybe going back to your Staff Engineering Manager role at GitHub, I’m just picturing Anjuan and his team floating around, do you have a set scope or responsibility? Or what is the scope at the moment that you’re working with?

    Anjuan Simmons: Absolutely. So I’m in a part of GitHub called developer outreach. This is the part of GitHub that I was responsible for. It’s on the tin. We reach out to developers to make them super fans of GitHub and also to make sure that we’re creating solutions that help them become more effective at using the tools that we provide. I am specifically the Staff Engineering manager for GitHub sponsors. So I don’t know if people know about this. But GitHub sponsors is a program where you can make contributions to the open source dependencies that you rely on for your software. Often these open source projects are the unsung heroes of your work. Like your code literally will not run or would take a lot longer to write if these tools or these projects didn’t exist. So it’s a way for you to give back to the developers that work on these projects. Often, like at nighttime. Outside of their regular job. What we do is that we surface the dependencies that your projects rely on and then you can make contributions. Either one time. Or recurring. Or you can make contributions either one time or recurring to those projects. I’m hopefully not floating in space. I’m at least on solid ground.

    Anjuan Simmons: So as the Staff Engineering Manager for GitHub sponsors, I’m responsible for my team delivering features for GitHub sponsors but I’m also responsible for partnering with the other teams within developer outreach. So that’s the developer relations. Or a DevRel team. I work very closely with them because they are literally talking to developers every day. That’s a great way for me to get feedback about sponsors. But also giving me a way to talk to the people who use sponsors every day. So I also manage the team that I’m responsible for but I very much manage horizontally to the other teams within developer outreach.

    Patrick Kua: Great. Yeah, the sponsor function is such an important thing. I think we were sponsoring some things when I was CTO. Because you’re right, a lot of these open source projects are mostly voluntary. A lot of people don’t do much unless they can sustain that. It’s a lot more sustainable if they’re sponsored. So it’s a great contribution to our industry and I think it’s a fantastic platform feature for Github. Exciting area. It’s interesting also to hear how you’re talking about managing horizontally, because how many people are we talking about? How big is the developer relations or DevRel group?

    Anjuan Simmons: Yeah, yeah. So DevRel is inside the developer outreach. We are… That’s a great question. Let me go to… This is something I can probably answer in real time in Slack. I can go to the developer outreach channel and give you at least the number of people. Over two hundred people. So not a small, tiny department. But that’s DevRel sponsors, OSPOL, maintainers, we do work with for maintainers. It’s a lot of different groups within that. I mean we have a docs team. So not a small department.

    Patrick Kua: What does your time look like then? My impression is that GitHub is quite large. Connected in with the whole Microsoft thing, even larger. So you know how do you spend your time with your team versus other teams? Like what does an average, maybe, two weeks look like for you timewise?

    Anjuan Simmons: That’s a great question. To give you a little bit more context I gave you like the rough size of developer outreach at GitHub. I don’t know if we could publicly say how much. We have hundreds of engineers. So GitHub Engineering is way bigger than the developer outreach. But where I spend my time, honestly, in a lot of meetings. That’s not a surprise. The further up you go up the management chain, usually the more meetings that you’re in. I actually think that that’s a good thing because, to me, like the worst place for an engineer to be is in a meeting. The meeting is of low value. I often joke that meetings are where value goes to die because often they’re overstaffed. There’s way more people in the meeting than really need to be there. Often if an engineer’s in a meeting, maybe there’s maybe 5 minutes of content that’s really relevant to what they need to do and then the rest of the meetings often wasted time. So I can go on about that. But I really believe that as a manager my schedule gets filled up with meanings so that my engineers don’t have to be in all those meetings. Because a really important part, in my experience, when I was a software engineer working day to day writing code, you really want to be able to get into the zone. This, what’s called a, flow state where things are happening and things that you may have even struggled to work on for days start coming into place.

    Anjuan Simmons: So giving engineers what I call think time, to be able to get into that flow state, is really important. So I really try to keep my engineers out of meetings. Therefore that means that I’m in the meetings. So typically the higher you go, the more meetings that you’re in. But I have a weekly sync with my engineers, where we just at the beginning of the week we have one in about an hour from now, where we get together. It’s a very quick meeting. Hey, how are we doing? What are our goals? Very quick status meaning. Then I let them go do work. I meet with my product manager on a regular basis. We have a product designer. I very much am involved in compliance work because GitHub sponsors, we transact money. There’s lots of legal and regulatory things that I need to be aware of. I often meet with the compliance team. With the privacy team. We have an attorney who I meet with. It’s a lot of away from the engineering work because the engineering cannot work if it’s not compliant. The engineering cannot work if we don’t protect people’s private data. The engineering cannot work if we’re not doing it in a secure way. I didn’t mention security where we have security reviews. So a lot of my week is spent in meetings where the primary outcome is I’m building context for my team so that I can give them clarity on what’s really important.

    Anjuan Simmons: Often in those meetings I’m learning a lot of things. I’m learning a lot of facts. Most of those facts are not directly applicable to the work that the teams or the managers are doing who I’m leading. I like to be aware of them. But I’m also responsible for unburdening my teams from having to know all that context. Ideally they trust me to be able to let them know what they need to know. So a lot of that meeting time is getting that context and then figuring out, well, what do I need to give to the team that’s meaningful out of all of this content that I’ve just gathered. I’ll say that the other thing though that I do want to say because I think that often when you go from being an individual contributor writing software to even being an EM or Staff EM or director or VP is that it is vitally important to give yourself think time. That think time that I mentioned that engineers really thrive on. Managers need that too. So I block off my schedule. I just call it focus time or call it think time where I need to absorb 3 or 4 days of just massive amounts of information. That I need to figure out and distil down to what’s really important to what I need to do. To what my fellow managers need to do. To what the IC needs to do. So I would say that if you are thinking of becoming a manager or manager of managers, don’t give up your think time. Schedule it in. Block it off. You may say in your calendar invite, hey, ask me before you schedule over this. But you really need to have think time because there’s just there’s too much in real time things happening for your brain to fully process it. You need at least a couple of hours every week to just think.

    Patrick Kua: Yeah. I think that’s really highlighting your experience. I think it’s a great bit of advice for everyone of having that clear focus time because I’ve seen so many of those managers go from meeting to meeting assuming that they’ll somehow find the magical answer by sometime. But it never really happens because they’re in the next meeting and switching to a different context. I think that synthesis time or that focus time going through what you said of what is really important is such a key skill to develop and also something to protect in your calendar. So great to hear. One of the topics I’d love to talk to you about is I know that you’re very passionate about talking about burnout. So what do you do as a manager of managers or what can you do as a manager of managers to help manage burnout in your organisation?

    Anjuan Simmons: I think that one of the things that you can do to help manage burnout is just to talk about it. To be able to say in those hopefully weekly 1-1s you’re having with your managers that burnout is something that you know happens in software development. That is a very common thing. I think that just saying that out loud is really important. I think that there are certain things that are important for leaders to say out loud. For example, I care about burnout. I care about creating an environment where people are less susceptible to burnout and by saying those things that communicates that you care. Some of the other things that I think people should say out loud are I care about inclusion. I care about having a respectful environment that’s psychologically safe, that people can do their best work and all those things. So burnout’s one of those things of many things that I think you have to say out loud. I think that if you’re a manager who’s listening to this podcast, right now, hi, how are you? You need to say out loud, you care about burnout. That you know it happens. That you’re very much invested in helping protect the people that you’re responsible for, for going through burnout. So that’s one thing. Just to say it out loud.

    Anjuan Simmons: One of the things that I think is important is that you should tell your manager or your manager of managers, or that, look, you’re probably very capable. You wouldn’t have the job if you couldn’t do massively difficult things and be successful, but you are not qualified to diagnose burnout. You’re not a healthcare professional. You don’t have the training. It’s really important that you never go to someone and say, hey, I think you’re burned out. Or you are burnt out. Because that’s something that could have very difficult unintended consequences. So what you can do however instead of diagnosing burnout is to understand the components of burnout. So the 3 primary components of burnout are emotional exhaustion and that’s where you just don’t have anything left to give. You’re not physically tired usually but you just feel mentally exhausted and so some of the symptoms of that are increase in sick days. People taking time off their work. People who just came back from a two week vacation, saying, oh I’m sick today. Or other signs that people are taking time off from work. That people are exhausted.

    Anjuan Simmons: There is also the second component which is depersonalisation. You no longer see people with people. You see people as obstacles. Some of the hints of this is where you hear someone saying, hey, this person is blocking. Or I don’t like this person because of what they’re doing and it’s really important to know and distinguish between the person and their behaviour and that you can still treat the person with dignity and respect, even when you don’t like the behaviour that they’re doing. So when you are burned out, when you depersonalise, you have a hard time doing that. You attack the person and everything about them. But then there’s also the third component which is the loss of satisfaction. Meaning the things that used to bring you joy, don’t bring joy anymore. Most engineers celebrate getting that PR merged. Or getting that feature to production. But even those things don’t satisfy and you can even see this often in slack or whatever tool you use for talking to your teams. The things that you used to celebrate and you would get you know 20 hearts, no one even responds to it anymore. So those are the 3 components of burnout. So I think talking to your managers about, hey, here are the components of burnout. Here are a few examples that you can look for. Having those conversations are I think are really really important. But in addition to that.

    Anjuan Simmons: In addition to just talking about burnout and the signs, you can do a few things. You can, as a manager or a manager of managers, maybe you’re a director or maybe you’re a VP, you can advocate upward. One of the most important things that you can do as a manager or manager manager or as you go up to org is to understand that you can often negotiate more time. Because honestly we put timelines on projects because you have to. We all need to have something we’re marching towards. Most of those timelines however are negotiable. They’re all set because maybe someone gave you an estimate or maybe there’s something else. But they are rarely immovable. Often you can adjust them. One of the things that you can do when you realise, whatever you are in the manager hierarchy, hey the team is running hot right now. People are getting sick. People are stressed. I heard about a fight between two people over slack a couple days ago. Let me just take some of the time pressure off. Because one of the most important tools that you have as a manager or a leader is the schedule. Then giving people space in the schedule to let things cool down. Or they give people time to catch their breath and then go forward. One of the things that you can do is to use the tool of time in order to help mitigate burnout.

    Anjuan Simmons: We talked about those skip levels. The skip level 1-1s. Hey, you gotta let people know that you care you have to be a human to them. You got to talk to them about their partners, or maybe your partner. Maybe your pets. Or your goals. You may find out that you know a lot of the people that you work with, hey, they’re playing through Baldur’s Gate 3 just like you are and then you could talk about playing role playing games or maybe there’s a sport or some other shared experience. By doing that, you’re building those relationships. Again, you’re digging your well before you’re thirsty and relationships lubricate stress. If you have the relationships in place you can help your team manage even layoffs. Or sometimes there are people who may lose their life who you know who are close to the team and managing that. So you got to do those things because those really help to mitigate the effects of stress what helps people avoid burnout.

    Patrick Kua: Yeah that’s some really very practical advice and things that I’m sure many managers and listeners to this podcast will benefit from. So thank you for sharing that Anjuan. I have two quick questions for you before we wrap up. One which would be for a first person who’s about to step into their first time managing managers role. What one bit of advice would you provide them?

    Anjuan Simmons: I would say one bit of advice that I would provide them is, as you step into this role, you’re getting farther away from the work, which we’ve talked about but you’re also getting closer to the business. You’re getting closer to the leadership team. A key part of what you should be able to do is 1) begin to dig deeply to understand that leadership team. I think people call this managing up but whether it’s the director, VP, CIO, CTO, CEO. Whatever. But you should really very much lean into getting to know them again. They’re people too. They have lofty titles. They have lots of power but they’re also people. So getting to know them as people. That’s important because a lot of what you need to do as you go up the ladder is to abstract away the noise of the business. Because there’s always things happening within companies that often scare people who are ICs or even line managers, that you need to help them process and to hopefully put to the side. Again I mentioned layoffs. A lot of people who are listening to this went through layoffs earlier this year. You either heard about friends who were laid off. Maybe you were laid off. The industry really went through a tough time where companies were contracting and then getting rid of a lot of people.

    Anjuan Simmons: So that was something, that was I think, again, it’s not noise in the sense that it doesn’t matter. But it’s often noise in that if you weren’t laid off, you’re still often burdened by the fact that people were laid off. You have, maybe, survivor’s remorse. So you have to abstract away all that noise and the only way that you can do that is to lean very much into the people at the top of the company. You have to very much lean into the business of the company. You have to lean into the processes of the company. Because the only way that you can abstract something away is to understand it. And really lean to that part of the job because that’s something that you don’t get a lot of experience doing when you’re an IC, or even a manager. By understanding the upper hierarchies of the business you were empowered to abstract it away. To unburden the people doing the work from things that really don’t matter to getting things done and then helping to be more effective. So I think that’s the one piece of advice that I would say that’s something that I came too late in my career that, thankfully, I’ve become I think fairly good at. But that’s something that you should do as early as you can when stepping into this role.

    Patrick Kua: That’s a fantastic bit of advice and I wish I had learned that earlier in my career as well. So we could all learn something. My final question for you is where can people find out more about you or reach out to you if they’d like to get in contact?

    Anjuan Simmons: Ask someone with a fairly unique name I’m easy to find. I’m @anjuan at most places. That’s a-n-j-u-a-n. Whether that’s Twitter or I guess we’re calling it X now. Or you can find me on Instagram. You can find me on Threads. Pretty much @anjuan. If you look for me, you’ll find me. I will be happy to say hello, how’s it going?

    Patrick Kua: Fantastic! Thank you and we’ll make sure that all the links to all Anjuan’s socials are in the show notes as well so it makes it easier to find as well. Thank you very much for spending the last hour with me. I’ve really enjoyed our conversation, Anjuan. So many great insights and I wish I could delve more into your long career. Unfortunately we’ve run out of time today. But I really really want to thank you for sharing your experiences and your stories.

    Anjuan Simmons: Thank you Pat. Spending time with you is always a pleasure and I always learn a lot by spending time with you. So thank you.

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