You Won't Guess How Many Promotions It Took To Principal Level Eng Manager

lifelong friends at Microsoft I'm a principal level engineering manager but the number of times that I've been promoted in my career might actually surprise you in this video I'm going to walk through my career Journey starting from my internships in University to my first job outside of University and then all the way to Microsoft and I wanted to share this journey with you because I see a lot of people online sharing their Journey about how they were able to start in their professional career and make it to some level at senior or Beyond very quickly and while I think it's great for those individuals and it's awesome that they can share their experiences with you I wanted to offer you a different perspective into how this can look before I jump into my story I just wanted to give you a quick reminder to subscribe to My Weekly Newsletter I'll put a link in the comments below so you can check that out but every week I try to share an exclusive article Early Access to videos and a bit of a recap of software engineering and net topics it's totally free so there's no strings attached all right so my professional journey in software engineering starts way back in un University at the University of water where I attended for computer engineering we had to go through this Co-op program and this is a really awesome experience because for me at least we had to go through a school semester which was four months and then immediately right into work and this went back in fourth for 5 years straight and to be totally honest I wasn't really into school I took Computer Engineering because I was into software but wanted to get exposure to hardware and it really just wasn't for me but the internships were awesome this is my first experience working in a professional environment with other software Engineers it was the real deal if I think back to that point in my life my work ethic wasn't quite the same as it is today so how I approached doing my internships looked a lot different than how I approach work one thing that I am thankful for is that because I had a total of six internships based on how the school and internship went back and forth for 5 years I took advantage of going to different locations and getting a different feel for at least some of them I wanted to make sure that I could have a good experience and go back to some companies but towards the end I wanted to venture out and try a different things my first two internships which each were four months long were at a company that was a small Consulting software company and I got to focus on what was needleless injectors for farm animals and this is super cool because it was embedded software development as well as some exposure to some desktop python coding on the side as someone that was writing console applications and wind form applications at the time I thought it was so cool to have something Hands-On that was embedded and do some programming that way I had a great mentor at this Co-op job but honestly when I reflect I feel like I didn't try to extract more information and insights from him than I could have because he's totally an awesome guy still runs this company to this day and not only is he super smart but he's super kind as well so I do kind of regret not really leaning into that and just trying to leverage him as a mentor while I could have but after two internships with him I ended up going to another opportunity for yet another two semesters which was really focus on operating room software and this sounds pretty intense and it's pretty interesting but it's not like I was uh necessarily working on devices that would be like cutting people open or anything like that but it was for cameras and really high defin uh cameras and video feeds to be able to have people that were operating really expensive devices have visuals and have control over what was going on in the operating room so this is a huge Twist on what I was doing before because in the previous role I had someone mentoring me and guiding me through things but in this role I essentially had free reign I worked closely with someone who was giving me specifications for what to build but I was the only developer I got to go create all of this operating room software completely on my own and it was really interesting to have complete architectural Direction on something that was essentially Green Field and while I stayed at this internship two semesters as well something that's important to call out is that when we're talking about promotions and progression I mean these were internships I wasn't getting promoted or anything like that at this point in time so this is really just about getting as much different experience as I could and the theme so far speaking about experience is that I was sticking to really small companies I wanted to make sure that the work I was doing was going to be impactful and then I wasn't going to feel like I was stuck in a cube somewhere just kind of coding away at things or doing something that was going to have very low impact things started to shift a little bit when I went for my fifth and sixth internship however I still stuck at small companies they were just in one case a little bit bigger and in the other case a little bit further away from home so the fifth internship I had was at a bigger company it wasn't a startup but it also wasn't big Tech they made software that allowed Banks to configure bank machine screens and how you could interact with that as a user this is a bit of a hybrid between the first two roles that I had in my different internships because I had mentorship guidance but because it was an architecture team that worked on prototypes I also had some of that free reign as well it was really cool because the people that were mentoring me would give me these challenges to work on like we don't have this anywhere else in our software but we want users to be able to do X and then I got to go under their guidance prototype some of these things and it was awesome because I could go explore different Technologies and pull things in and then demo to them and get their feedback and iterate on it with them again a really awesome internship accumulating experience having a different perspective on things but again not really looking at promotions was my pay going up sure slightly but in this case it was really like going from one internship to the next and the pay kind of like maybe keeping up with inflation or something like that or maybe being slightly higher just because I'm at a higher level in University but overall not really achieving anything groundbreaking but at the time it didn't really matter right I was getting some assistance paying for my schooling because of it and I was getting really awesome exposure so I was pretty content with that now the last place that I'm going to talk about before I get into my professional career after University was a company that was like I said further from home so I'm from around Toronto Ontario and this was all the way out in San Jose so this was my opportunity to finally go to the US to try out something that was in like Silicon Valley and something exciting I had a lot of other peers from school that were doing this kind of thing so I was like I'm going to try this out it's going to be super cool and it was it was really awesome to be able to live away from home have this whole new environment around me and work at a little startup and this startup made software that would work with iPads and documents and they had this really cool solution where you had end to-end encryption including immediately before the document was rendered on screen now another thing that made this internship different for me other than just being further away from home and being in the United States was that I had to use a whole new different language that I was totally uncomfortable with not only that as a c developer at the time guess how many different operating systems I'm used to using one windows and because this was for iPads that meant that I was using Objective C and using a Mac two things I had never touched before and that's probably surprising to a lot of you but I just don't use Apple products so this was a really interesting experience for me um it was uncomfortable because the code I was using and the tools I was using but what was really awesome was that the people in leadership positions at this company are all brilliant Engineers from Nvidia so they truly understood how to run their business but at the same time everyone up to the CEO that I was working with were incredibly intelligent and had this awesome engineering mindset so any question you might possibly have about the code or how to approach things like you could speak to them about anything and you'd have these really detailed like well explained answers so again I got some of this mentorship um sort of experience that I had in my first internship but from totally different sets of people on completely different things and that essentially wraps up my internships before my professional career started after that and again just to recap because I wanted to talk to you about promotions and compensation's part of that but the compensation was higher at this last place that's probably largely due to the fact that one this is my last internship that I have in University so I'm sort of at the highest level as a student but also because it was in the United States and I think that's a huge differentiating Factor compared to what I was seeing did that matter to me though not at all like at that point in time it was still like I want these different experiences the fact that it paid higher just meant that I could cover a little bit more in terms of rent and catching up on student loans but whatever I'm still a student I'm still learning and one of the things that that first internship taught me my mentor in particular at the time was saying leverage all of your internships to learn things he had also graduated from the University of waterl so he had gone through this experience and as much as I enjoyed working with him at his company he did suggest go try different things and I took that to heart and that was something that I tried to leverage as I went through all of this but that's just the Preamble because now we're going to talk about my professional career up until this point I'm still an individual contributor a software engineer and as I embark on my journey in my first real job out of school that's what I'm going to be doing I am a software engineer so fresh out of school I ended up taking a job at a company in the city of waterl which is where I went to school that was started by a former police officer and to me this is a really interesting and intriguing opportunity because it was a startup it was very small and early it was founded by a police officer who happened to have a technical background so that was kind of cool they made digital forensic software which was totally w wild to me like that sounds really fancy it sounds really exciting I know nothing about it and the last part was that they were profitable but without any investment and when I thought about startups that I had worked at they were already underway they were funded in some capacity or they were like I said underway and had paying customers and that kind of thing so it never felt like a risk but what I had heard from other people going to startups was that you got to be careful because you might start there and because it's a startup it's pretty likely to fail but hearing that this company was already profitable without Investments and they were able to just continue on and start to scale I thought that was a really awesome opportunity when I thought about the size of the team and sort of where the product and stuff was at to me it just seemed like I was back at one of the other places i' had been working starting on a newer project it just felt like there was a lot of opportunity to learn and to grow so sure I tried haggling my salary a little bit but I'm pretty terrible at this kind of thing so so it seemed like a good opportunity pay seemed decent heck yeah I'm ready to go and I'm ready to start putting myself into the work I'm doing or was I because early on when I was going through those internships like I said my work ethic was a lot different I was excited to be able to start this job full-time because that was exciting but my work ethic going into this wasn't so great for my internships I basically just put in my 9 to5 when I could it was like work was interesting but I don't want to be here so I'm going to get out and as much as I was trying to take opportunities to learn at work I really treated that work time as like this is my window and anything outside of that not going to touch but this was a bit of a different Beast because when I started and I probably had a bit of that same mentality carrying over I realized how fun and exciting this was I realized that the people I was working with were building something really awesome it felt super rewarding to be able to contribute to it and this is the most cliche thing ever but it felt like with a small group of us it was a bit like a family we would stay late and fix bugs and then we would go out on Fridays and Saturdays together and hang out and I know that this isn't like the normal thing that you would do at companies and I'm not saying to go look for this but this just seemed to happen naturally it was really fun to be able to work together and I can remember times really early on I wrote about this recently but one of the worst bugs I ever had to fix had to do with licensing and I can remember going into the office it was like 2: in the morning working with one of the other guys actually the first engineer that they hired and we were trying to figure out this licensing bug super late but it didn't feel like work like I was happy to be there working on it with him and I know that sounds odd it's not like I was getting I wasn't getting overtime pay or something like that it was just something that I felt encouraged and motivated to do and that's what we did and that mentality carried on and it wasn't long it was probably I think within like 6 months or so that they had realized that as I was trying to hire more people like there's only a few people that are probably like able to kind of coach or talk to some of the other engineers and it's not because they have years and years of experience it's just because they're able to communicate with them and seem to be able to guide them I was one of those people so this is one of the first opportunities that seems kind of like a formal promotion but they really just said hey you're kind of leading these teams right now could we just more officially organize you guys to have some different scope and we said sure like we're already doing that makes sense let's keep going so 6 months into my first job no promotion but my scope changed I was effectively leading a team and I was effectively not realizing at the time becoming a formal manager so on the surface at this point in time I was thinking cool I'm responsible for these different product areas on the engineering side and I'm going to be helping people navigate the code and tell them how to build things but I didn't really realize that I have direct reports and what does that mean when you have direct reports I don't know let's just keep pushing through the code and if they have questions and stuff we'll talk about it in one-on ones but it didn't take long kind of following that pattern where I realized that's not going to scale I have a bunch of people reporting to me now I think it was as high as eight or so near the beginning and I realized I have to dedicate time towards helping these people out and in fact that's when I initially created Dev leader Dev leader started as my blog where I started to talk about the different things I was doing as someone that had gone from an individual contributor to a software engineering manager I had no idea what I was doing so I wanted to make sure that things I was learning I could share with other people and it was a struggle because I was used to being an individual contributor I was used to kicking off some of the initial code bases and working through them so for me to be able to do what I thought my job was which was produce code I was going back and forth like a pendulum coding for a while really hardcore and then kind of backing off not coding anything to try and catch up investing time with the team But as time continued on we had more growth in our products not only in the scope of what these products were doing but in terms of the different products we were supporting and during this time frame yes every year thankfully my salary is able to go up because of I mean we have things like inflation that we're keeping up with but also because of how I'm performing my salary is going up too so that's great news but promotions well it's a startup I'm one of the first people at this startup on the engineering side and we don't even have levels not to mention I'm now managing people and there aren't many managers or directors or anything else so how does that work for any type of leveling even as a manager well didn't exist but did I care not really I kept working and I kept investing myself into this company because they were compensating me very fairly and I felt like the work I was doing was really exciting so a couple of years into it iend end up moving to manage a different team that I'm kicking off and we're focused on doing mobile Acquisitions in digital forensics if that sounds cool it's because it is it was super awesome to be able to recover data from phones and it was iPhones Android phones and we had this big competitor that had a monopoly over the whole market and guess what we were just a small team and we started to catch up to all of their feature parody rapidly it was so exciting to be able to go build this software and then start to catch up and have results truly feeling like the underdog like taking like huge strides and catching up honestly like one of the most rewarding things I've ever done in my career but in addition to that so we have this team going that I'm managing for digital forensics on mobile phones I'm now leading prototyping for some other things that we might want to try out so as you can see my responsibilities at this company are growing right so I'm managing a team but also kicking off these different initiatives to be able to do different types of digital forensics now partway into this we're already over 100 people 200 people and the scope and scale of the company in terms of hierarchy starting to evolve so they realize we need to start introducing different tiers and roles and levels to the engineering side as well as the management side so I remember getting a conversation about the new title I was receiving and it was technical manager awesome super cool so did my responsibilities change no did my pay change no but this was almost maybe kind of like a promotion except not it was just a title change so up until this point I'm several years into my professional career and I have still not had a single promotion however I am a manager and my pay has gone up and I feel well compensated not only that I'm doing things that I love all of these things really resonate for me but if you think about it on the surface I haven't been getting promoted and I haven't been chasing promotions either so so far so good but maybe not compared to someone else that was was jumping company to company and getting higher and higher levels along the way but I wasn't really caring about that I was really doing stuff that I enjoyed if we fast forward a little bit more in my last few years at this company I was now managing two teams at this point because my hands had been in so many different things and I'm managing two teams I honestly didn't even have a lot of time to program I still enjoy doing it but at my desk at my computer at work not coding too much if I was coding it might be after hours to help out it cuz I really enjoyed doing it but the reality was in terms of time investment it just didn't happen at work that's because I was either working directly with my teams or I was spending time working with some of the other teams that had spun up from the different projects that I helped kick off it was also at this point where I was spending a lot of times with other teams that were not from projects I kicked off but because I had knowledge about the history of how these things evolved by this point it was about 8 years into working at this company so when we talk about things like Legacy code on this channel refactoring how we test stuff like I had written code that had lived long enough to be the Legacy code so I had to help guide people through that I was guiding them through like working with the new product managers even though I'm an engineering manager about some of the different decisions we made in the past and how we could maybe approach going forward re-exploring some of those things but by this point my role and responsibilities had evolved so much since when I started there as a software engineer building products that were already established into someone that was helping spearhead new products lead engineering teams and offer assistance to all the product managers on all these other areas so now I'm 8 years into my professional career still no promotions but when I reflect on the experience I don't think that I could have learned any more in that time frame literally every day was a new learning opportunity so many different challenges you name it in terms of prioritizing things addressing Tech debt how do we get features out the door how do we fix critical bugs how do we everything it was so amazing to be able to work through all these things and it felt like a whirlwind the entire time and again no promotions but I worked with some of the best people that I ever have and a lot of them are lifelong friends and truthfully none of those experience I would train for anything this leads me to my most recent career path which was going to Microsoft and for me this was the biggest transition in my entire career this was a point where I was taking an engineering manager role that was directly and specifically managing teams of Engineers and that meant that I didn't even have responsibility for writing code anymore even if I wanted to at work there's not really a lot that I could obviously get my hands into so it was really interesting to go from something that was like you're an engineering manager and you code to even if you want to code like it's going to be a little bit awkward for you to get your hands into it it was a huge life transition for me too because it meant moving with my girlfriend at the time now my wife down to Seattle all the way across the continent to start work at Microsoft I was used to working with teams that I had built all of the code that they were working with I had expert knowledge in all of the domain areas of the software because I was there at the beginning when it was being built and now I was coming into a territory where I need knew nothing about it and it's worth mentioning I was building desktop based software before for digital forensics and now at Microsoft I manage two different deployment teams that help deploy all of the M365 Services globally in the entire world and I was hired into Microsoft as a principal level software engineering manager and I'm telling you that not to gloat or boast about it because I've just told you I've never been promoted in my career so far I have 8 years of experience leading up to this point professionally and have have never been promoted so how did I get a principal level software engineering job I had all of these different experiences that I accumulated along the way when I went to interview at Microsoft I was able to demonstrate those abilities I was able to talk to different principal level and partner level individuals they could understand those and despite not having any type of fancy title because we really didn't have titles and levels at the place I was working at they were kind of just rolling out I was still able to demonstrate that I met the criteria to be successful at the job and even though I didn't have experience deploying to Data Centers across the world I was hired because they wanted someone with the different perspective I was able to lean on my experiences and the fact that I have a unique completely different perspective than a lot of the people that are currently working in that space now things have changed a little bit for me over the past few years after coming to Microsoft because the work ethic that I employed at the previous job I can't get away with that anymore it's not really sustainable I put in many many many long hours often working 7 days a week 6 days a week and I don't know sometimes like 12 to 14 hour days it's just not realistic anymore I do have a wife and I think it's important that I'm spending time with her I think it's important that I have some of my own time but I have a really good work life balance at Microsoft and even though I'm working with teams in different time zones so I work with individuals that are paired up with us in China so we have completely opposite work schedules and we still make time to meet and that might mean some early mornings or late nights to be able to collaborate I'm still extremely passionate about the different projects we have and making sure that we can drive those to success but honestly this has been so eye opening for me because I really want to invest my time in my teams I'm less interested in how good the code looks I'm less interested in the best architecture and the reason I'm less interested in that is because I know if I work with my teams and help Empower them they can do that they can do a much better job than I ever could if I help them excel in their career and make sure that they're engaged in the work they're doing and so now it's been about 3 years at Microsoft I still have never been promoted in my entire professional career and that's okay I think part of being at Big Tech is looking at promotions and following that path and that's become top of mine for me I am interested in being able to grow and kind of continue on in my career that way but honestly I think as long as I'm receiving challenges that are very interesting I have an awesome team to work with and I feel fairly compensated that's enough so my takeaway message to you watching this is that all of our career paths are going to look different I feel like personally even though I never received like what I would call an official promotion I still feel like I've been able to move my compensation to match what I feel like I'm valued at I've been able to prioritize learning not only from like the technical perspective but just really like business and how a software company Works in general I've been fortunate to have projects and things like that that I'm extreme extremely motivated and passionate about and I've worked with amazing people all of these things are absolutely awesome for other individuals they may not prioritize a path like that that's okay some people will be focusing on how they get right to the next level as fast as possible and I think it's important that you're prioritizing a path that helps you benefit yourself in your career I just don't like when it's done at the expense of actually being good and experienced at what you're doing so for example if you hyperfocus on just getting to the next level regardless of what company you're at and doing it as rapidly as you can I suspect you reach a point where you're feeling like your imposter syndrome is not really just impostor syndrome it's potentially that you don't have the skills to actually keep up in your role and I'm not saying that happens to everyone it's just a warning so that if you're trying to approach like this uh shorter path to get different promotions and things like that that you're just keeping tabs on your capabilities you don't want to arrive at a level where you feel like you can't actually deliver at that so just ensure that along the way you are building up all those experiences and for those of you that follow a path similar to me if you're not focused on chasing down your promotions and things like that it's not that it can't happen it's not that you can't excel in your career and get to where you want to be it just might look different but something common in both of these paths is that you are responsible for driving the progress in your career waiting for someone to give you opportunities I don't think is a good strategy so in the One path you are chasing down promotions and trying to get to the next level but hyperfocusing on that the path I took I wasn't chasing promotions but I was chasing more responsibility I was continuously trying to demonstrate look I can do this and I can do it well I was very fortunate to be at places that rewarded me for that so they would give me that opportunity they trusted me and then I could deliver on it if you're not in an environment where that can happen you will probably feel very frustrated because you will be trying to do that not have the opportunity and then if you're not chasing for the promotions you're just going to feel like you're stuck so all of that to say we all have different paths and I highly encourage you to think about what things that you value in your career so thanks so much for watching this and letting me share my experience with you