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Making the Decision to Be an Individual Contributor or a People Leader



Michael Winslow explains the factors he considered when choosing between being an individual contributor and a leader, including his personal strengths and interests, and organizational opportunities.


Michael Winslow has played key roles at companies like Aramark, Ortho-McNeil, Oracle and Xfinity Mobile. He is a seasoned international public speaker who enjoys using his platform to uplift engineers and create powerfully diverse teams in technology. Michael is currently a DevOps advocate, Agile enthusiast, and transformational people-leader at Amazon Music.

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Winslow: My name is Michael Winslow. I am the Director of Music Client Experiences at Amazon Music. I can't wait to talk to you about my journey of being an individual contributor, a people leader, and all the stops in between. I'm going to give you a brief backstory about myself. I think it's really important to set up my story of being an individual contributor. All these Marvel movies have everybody thinking the moment that they hear the word backstory, that somebody's going to talk about how your hero learned how to fly, or learned how to breathe underwater, or their body is half cyborg. It just so happens that all those things are true about me. This is me doing scuba diving, skydiving, and then having some fun at Halloween dressed up as Bumblebee. Although this is meant to be a joke, it's also meant to give you some context that I'm a very curious person. I like to explore. I like to do wild things. That helped me so many times in my career, just staying curious.

Another thing that I loved since I was a child, it started when I was about 10, was programming. For those of you who are new in the industry, or even people who've been in the industry for 10 to 15 years, you might not know what it was like to be a computer programmer at 10 years old, in the '80s. This is an idea of what it was like. My friend Jimmy and I would go to the local shopping mall, we would go into an electronic boutique store. In there, there will be PC Magazine. If you bought the latest version of PC Magazine, and open up to the compute it on your own section, they would write GW-BASIC code, print it on the pages of the magazine. Then you were supposed to buy the magazine, take it home, and then reprint all of the text into GW-BASIC. The interesting thing about it, and this taught us a lot of patience, was that you didn't know the outcome of the program until you were done. You could only imagine that as you type this code in, and this will be pages and pages of code, that there will be misprints. When you finally ran it at the end, you then would have to debug any fat fingered text that you put in there. This is how I established my early love for programming. It was just me and my friend typing in his Tandy 1000, and just staying up all night long doing this. We really had a joy and love for it. Now, once we got into the text in there, a little bit later, I really started getting into the graphics. If you want to know how graphics were done back in the '80s, it was on graph paper. You would trace your favorite cartoon character. As you would take it over to the graph paper, you would then have to plot the coordinates. If you look just above the Jurassic Park sign there on the graph paper that's behind, you can see a bunch of numbers that I had put out on there. That's what you had to do in order to plot each individual point in order to deal with graphics. Needless to say, I was obsessed with programming enough to have the patience to be able to plot points out for graphics. Like I said, this was where I established my joy for it in middle school.

The College Years Happened

When I got to high school, though, I wanted to change my image a little bit. I got a little bit more into sports, and put down the computers for a while. Then, when I got to college, the good thing about that is, it was like riding a bike. I went to school at Rowan University in New Jersey. I majored in computer science. It was a no-brainer, I never had to worry about what my major was going to be. The college years happened. I did some internships. I further established my foothold as an individual contributor of technology by the time I graduated in 1998. One of my more recent mentors quoted this to me, at one point, "The first part of your career is all about gaining expertise. The next part is all about gaining perspective."

From then (1998) Till Now - Individual Contributor

When I talk about how I graduated college in 1998, I want to talk about how I spent a large chunk of my early career, building my technical expertise. At the time, my language of choice was Visual Basic, I believe it was 5 at the time. Later, I got into Visual Basic 6. Then as Microsoft turned the corner in the early 2000s, and finally started adopting object oriented programming, I picked up .NET and C#. That was a big part of my early career. Things like being a people leader, or being a leader of any kind, weren't really on my mind at all. It was just about heads down programming, and producing great products through code.

Individual Contributor and People Leader (2008)

Then, after about a decade into my career, I was then working at Oracle. It was a time when I started to figure out, there's probably the next level of my career that's coming up. I want to talk to you a little bit about how around this time, I was taking a journey of being a 50/50 individual contributor and people leader. I want to talk to you about how that came to be. It all starts with the idea that somebody at Oracle decided that we were going to adopt Agile. Up until then, the idea of iterative software development was not a completely new topic. As a matter of fact, if you wanted to be certified in Microsoft, you had to pass the Microsoft Solutions Framework. In that, they had an iterative development model, very much like what you see in modern day sprints, and Agile. Agile and the Agile manifesto made it a lot more prescriptive. Things like sprints should be two weeks by default. You should have daily standups. You should have sprint grooming, sprint demos, sprint retros, sprint planning, sprint estimations, they were very prescriptive about all the parts of Agile. The interesting thing at Oracle at the time was, we were not going to invest in Scrum masters. We were going to take all of our lead developers, of which I was one, and say you are going to run the sprints. What came to be around this time was my mind started to think a little bit more than just my own contributions to code. It was also, how do we organize these individual contributors together in sprints, in pods, in teams, and produce good software as a team? Technically, I was still an individual contributor at the time, but being a Scrum master changed my perspective enough so that I was starting to get a taste of team development.

Around this time, my boss, the same leader who brought Agile to the company, was ready to take a two-week vacation in Asia, and he needed somebody to cover for him. I said yes to it without thinking that I was going to do anything that had to replace his job. I was just going to keep the ship afloat while he was gone. While I watched him do what he did, going around from person to person that he was the boss of, seeing how they're doing on a day-to-day basis, I emulated that for the two weeks that he was gone. I distinctly remember one of those engineers, her name was Krupa, we worked as peers for the longest time, when I was checking up on her playing my duty as the proxy boss, while my boss was gone, she just turned and said, "Mike, you're really good at this. You should think about management." Those words stuck with me because I thought that maybe this was something that would be good for me. One thing that I can say is when my boss came back, I asked him if I could have more management responsibilities, and that started my journey into being a manager. I'll tell you this, Krupa and her thoughts about me being a manager at that time was absolutely wrong. I was not ready to be a manager yet.

This brings me to one of my first tips for the audience here. Understand that being personable does not automatically make you management material. Why do I say that? To this day, I see a pattern at a lot of companies, where an engineer or an individual contributor is good at their job, they get to a certain level, they start showing signs of things like being a good mentor to other engineers, or just having a deep knowledge of the product that they code for. All of a sudden, leaders will think, they would make good managers. I'm not saying that they wouldn't, myself included, eventually I did shape up to be a good manager. What is it about somebody just doing a great job as a leader, as an individual contributor that makes you think that they do the things that aren't required for management? Remember, in management, you have to discipline underperforming employees. You have to work with budgets, and finance, boring spreadsheets, doing talent reviews, year after year. There's so many times when you observe an individual contributor, that you can have no idea of whether they'd be good at those management tasks. Before you jump the gun, and think that just showing leadership potential from an individual contributor seat, you might not want to lose them as a leader, as an individual contributor, you might want to keep them there. Instead, you take them and put them in a management role, where they may or may not be good for the team. Needless to say, I still took that leap, and I became a manager, but I still was coding at the time.

People Leader (2015)

I want to fast forward to 2015. I'm no longer at Oracle, and now I'm at Comcast. Basically, I'm ready to take the next step. I've been a manager for quite a few years. Now I'm looking to step it up a little bit and work with larger teams. In 2015, I began working on a secret project at Comcast called Modesto. At the time, we weren't allowed to tell any of our colleagues that we worked with previously, what we were doing on this project called Modesto, because it was a brand-new secret initiative. I can speak about it now, because it's public knowledge. Modesto would eventually become Xfinity Mobile. We launched Xfinity Mobile in 2017. I started two years before the launch, while we built it from the ground up. At the time, I was still very heavy into code. In fact, I wrote thousands of lines of code for the Modesto/Xfinity Mobile back office. I was having trouble at the time, trusting a lot of my engineers enough to do as good a job on the code that I did. This is where I really think that I had another growth opportunity. Because when I finally found out that I was ready to really take the leap and become a full-time manager was really around the time when I hired an engineer that was so much more talented an engineer than I was. This person, from a code standpoint, and an architecture standpoint, could run circles around me. That was not a bad thing. It actually allowed me to take my hand off the steering wheel, and feel confident that I had a leader sitting in an individual contributor seat, taking care of that piece that I used to take care of, and I can do more things as a manager to help my teams grow, and to help my individuals do better in their careers.

After the launch, and maybe a few years after Xfinity Mobile was in production, a new part came into my life that let me know that I was ready to grow and take things to even another level from a people leader standpoint. That's when our HR department sponsored an insights evaluation for the entire team. If you haven't taken the insights evaluation before, let me just walk through what this readout of mine is telling us. This section over here is my less conscious evaluation. This basically means that when I'm by myself, the red bar there is my dominant trait. Red means that I like to get things done. I don't disagree with this. This is exactly how I am when I'm by myself. If you look at the other colors, the yellow means that I'm personable. How personable am I? How well do I talk to others? The green is for how much do you care about people? How deeply do you care about their feelings and their family and their pet? Then the blue has to do with how organized of a person are you. As you can see, when I'm by myself, I really index on red and getting things done. It gets interesting on this conscious persona. This is when you are around others, and the face that you put on when you're not by yourself. As you can see, I'm still very high in the red. Look at that yellow shoot up. That yellow, as far as the personable aspect really starts to flourish when I'm around others, and so does the blue. This didn't come as a complete surprise, because what it means is, in a team environment, I understand that if we really want to get things done, and really support that red aspect of me, I can't do it all alone. I need to coordinate with others. I need to inspire others. Through that I can actually grow as a team and get that need that I have to produce. That shift right there, and through meetings that I would have with colleagues and bosses, led me to really wanting to take on bigger responsibilities. I wanted to take that step next, to not just be the manager of a small to medium-sized team, I wanted to be a leader of an organization. These three points that came out of the insights evaluation, support me wanting to go down that path. Michael is motivated by tests which predominantly involve the group, a relentless drive to competency and effectiveness, and special task teams to interact with. That means I always want to take on new challenges, and I want to go into it with a team.

Organizational Leader (2019)

After getting that evaluation, that's when I really started seeking around Comcast for opportunities to be an organizational leader. I wanted to be a leader of leaders. My next big jump at Comcast was to be the head of visual experiences for the Xfinity Stream platform. That's basically the companion application at the time for your cable. Where a lot of people watch cable through cable boxes, and through television, my teams were largely involved with the mobile experience, Android, iOS, Roku, and then the Flex box. This was my new challenge, and a challenge it was. Some parts of this I just wasn't ready for. I'll go through my challenges that I had here. As I got into such a large team, you could only imagine how much you have to be that blue part of the insights exam. You have to be organized. That hasn't always been my strong suite. I went into it ready to go. I had four direct reports. Being a strong people manager, people leader, I knew that one of the main things that I was going to do was give them the attention they need. Here you can see a spread across the four days, everybody got a one-on-one every single week for my four direct reports. Those 4 direct reports had 17 total people that reported to them. Once a month, I would schedule a skip level meeting with my 17 skip levels. Not too much overload. Of course, I need my own one-on-one time with my boss. Once a week, I would get my one-on-one time with my boss. Once a month, I'd get my skip level time with my grand boss or my boss's boss. Twice a month, we would have product reviews. We had to go to them, it was such an important piece of what we did. Because the product moves the product forward, the other very important piece when you're dealing with an application that has millions of users, is the reliability meeting. That was every single Friday, with the highest members of the organization in there. It's just something you can't miss very often. As you can see, the calendar is filling up here. I can't forget about keeping relationships with my peers, and the teams that work adjacent to us, that my teammates need to be able to communicate with. I have to keep that alive. Four meetings throughout the month would be just with those management peers of mine. Then, finally, just random stuff would fill in the blanks for everything else.

This was the biggest culture shock when I started dealing with leading very large organizations. Because just before that, even though I was comfortable taking my hand off the steering wheel in Xfinity Mobile, to allow another stronger engineer in there, I still would dabble in code every now and then. I actually thought there would be a chance that I can still dabble in code in my new job. For anybody who's attempted to do this kind of thing, or anybody who knows what it's like to really focus and debug code, you would start to see that, all of a sudden, just while I'm in a zone, I would say, "Let me just cancel this one meeting this one time, they won't mind. I meet with them every week. Let me just skip this meeting right here. That's not important. Where's the agenda for this meeting?" I really started doing a disservice to the people that reported to me. Some of my peers would sometimes need to meet with me, and I wouldn't do it. I realized very quickly that this was not something I'd be able to do anymore in this position. Here's a quote. I realized after I put this up there, this can be taken two ways. I want to make sure that I put across the message in a way that you really get a good takeaway from this and not a bad takeaway. The quote from Lau Tsu is, "A leader is best when people barely know they exist, when the work is done, the aim fulfilled, others will say: we did it ourselves." The way I want you to perceive that and the way that I take it when I put this up here is, your job at this level is not to do the work, it is to enable the work. The people, your individual contributors should be the ones doing the work and they should feel the pride in that, even if you're the one that set up the whole thing. Basically, I thought the way that this could be taken in the wrong way is, you're just an invisible leader that's never around and everybody has to fend for themselves. That's not what I mean here. This really is about giving credit to the team. Not even necessarily giving credit, just not looking to always get the credit yourself. They earn the credit.

Here's the good news. If you do come from a background where you are a coder, and you move into management or organizational leadership, what I've found is, I don't have to completely throw away all that great knowledge that I've accumulated over the years, just because it's the coder's job to do the coding. It is the coder's job, in my opinion, to keep coding the tasks that are related to the software that you actually put out as a company. You should not be side by side coding in the code base, in this case, I shouldn't be in the code base for Xfinity Stream and putting stuff out there that gets tested, and debugging, and things of that nature. It doesn't mean that I completely have to give away all my coding expertise. Because as a manager, why not take advantage to actually use your coding expertise to make your life easier as a manager. A tip that I've given to a lot of people that they don't know about is, in every Microsoft product, Word, Excel, PowerPoint, whatever, there is this hidden gem. If you go into Tools, Options, and then Customize the Ribbon, there's this by default, unchecked box at the bottom called the developer box. If you activate that, it opens up a world of, I don't want to minimize it to Macros. Basically, it opens up the entire code behind those things. If your job is to create spreadsheets, and your job is to create Word documents, this could be a powerful way to really make your job a little bit easier.

Why don't you think about things like automating aspects of your weekly status reports, or your monthly status reports, or even your quarterly status reports? Complex data comparisons. I remember specifically, and this is another thing, and maybe some of you can relate to this, there are times when you have to do things as a manager or a leader, like manage and compare budgets. Find out differences between what finance thinks you should be spending, and your actual spend, and marry those things together and find out what the delta is. Most of your individual contributors are not allowed to view this data. You have that ability to view this data because of your position as an organizational leader. You can't have other people come in and say, why don't I get the help of a programmer to help automate these tasks? Because they're not allowed to see that information. You can go in and use your background as a coder to do things like comparisons, text manipulation, what have you, to make your job easier in that world. Then the other thing that I picked up around this time, was bot creation. In our case, I would create a Slack bot that would answer a lot of my questions for me really quickly. I'd put a lot of brains and string manipulation into the bot to help me search Wiki pages, search GitHub. Search other parts of the Slack channels. This allowed me to get to my information faster. You don't have to throw away everything, if you can actually manage your time well.

Individual Contributor (2021)

This is where it really gets interesting. In 2021, I had an opportunity in front of me to become an individual contributor again. After 2 years of leading a team of over 100 people, I explored the idea of being an individual contributor. Some people would ask, is it because you didn't like leading a large organization? That wasn't the case at all. Let me walk through my decision-making process in 2021, to go back to being an individual contributor. After George Floyd happened, and that tragedy, as many large companies did, there was a huge focus on diversity. I had been a mentor for many years, and I saw this as an opportunity to really uplift the BENgineers at Comcast. The BENgineers was a group of Black Engineers. We were really starting to make a name for ourselves. There were about 150 people in the group, and they were looking for some direction. Through our meetings, we realized one thing that was an area that we could really improve at the company, was an increased number of Black Engineers at really high levels. We just didn't have that to look up to. As a matter of fact, you may know, in early 2021 who the one black Distinguished Engineer at Comcast was. It was our very own Leslie Chapman. I still remember when I met her in 2015, how in awe I was. The tattoos on her arms. She was just such a true engineer that I was in awe for. Not to mention, I think Comcast did put out a commercial about her, and then I saw her in the flesh. That being said, other than Leslie, there was not a lot of role models at the Distinguished Engineer level, where our young BENgineers can look up and say, that's the track for me. This ties into what I was talking about earlier, whereas it would be a common pattern to get to about an Eng 4, or Eng 5 level, at best sometimes, and say, I think you'd be good in management. Since those Eng 4s and Eng 5s didn't see themselves at higher levels, then it did make sense for them as well to start going on to that paved path over into management. I really wanted to try to change that a little bit, and be a part, I wanted to be the change that I wanted to see. At this time, I'm leading 100 people plus at Xfinity Stream. I had engineers of all kinds, not just black engineers, but there were some that were in striking distance of becoming Distinguished Engineer. As my role as a leader, I wanted to go in and say, what is the criteria? How can I help my people become distinguished engineers?

As I was going over it with some of our top engineers, I said, one criteria is thought leadership. You have to be able to have influence over a large organization. While I knew that we had that with several of our engineers of all kinds in my group, I also said, that's something that I display as well. Business impact, the work that I've done at Xfinity Stream as well as X Mobile, has certainly had that going for me. Mentorship was a no-brainer. Everyone at Comcast knew that I was addicted to mentoring. Every year, I'd have at least seven, eight mentees under my belt. Memberships and awards, I've got them externally and internally. I definitely had some that I could show. Then external peer reviewed work. I'd already started speaking publicly at conferences. I had been published several times, for white papers and for technical papers. All of a sudden, I realized, while I still had a few folks in my organization that qualified for this, I also thought to myself, I can't believe how closely I qualify for this. There was an opportunity for me myself to contribute to more diversity at the higher technical rank, if I so chose. On top of that, because it wasn't solely about that, around this time, there was an idea that I wanted to spread in the organization that I wasn't having a lot of luck spreading as a people leader. I wanted to change how we work a little bit. I realized I could do this as a distinguished engineer much easier than I could by influencing over an organization. After I thought long and hard about it, myself and a few others applied to become distinguished engineers, and in 2021 class, to help and to join Leslie, we actually got three more black distinguished engineers brought in at Comcast. Here you can see, myself, Todd, Leslie, and Trevor speaking the next year at BENgineers Conference on how we got here, a distinguished engineer's panel. It's definitely a source of pride. People ask me all the time, what was your reason from going for such a large organizational leadership state into individual contributor? This was it.

Director of Music Client Experiences (Now)

That brings us to today, because as I told you at the beginning, I am the Director of Music Client Experiences. It's another very large organization. How did I end up at Amazon Music? In order to tell that story, I have to go back and fill in some of the missing pieces that I didn't tell you earlier in my story. This goes back to that 10-year span from 1998 to 2008, when I was a heads down, computer geek programmer. One thing that I didn't mention earlier, is that during this time, not only was I working my day job, but at night, I was a DJ at bars and nightclubs. The interesting part about this is, I had a great time doing it. It was a huge part of my life. At one point, I was the house DJ at a place where I worked three nights a week, while still working five days a week during my day job. Fast forward to around 2018, I am far past my days of DJing, and I started doing talks. In those talks, when I would talk about my days of being a DJ, I say, it wasn't like I could come to work and say, I DJ at night. Because when you say that you're a DJ, it's not the same as saying I play the guitar or I play classical piano. When you say that you're a DJ, all of a sudden, people want to give you high fives instead of handshakes. Then they yelled out in the hallway, "Boo Boo, wakey-wakey." I also forgot to mention that my name was DJ Boo Boo, so that didn't make things easier either. This was one of the slides that I would use in that talk, it always got a laugh, my other desk is a turntable.

Here is actually the first time I got on stage and spoke about that time when I was a DJ. I'd probably spoken at about three or four large conferences, before one day, when coming off stage, somebody walked up to me and said, "Very inspiring. I love what you said up there. That idea of having to keep your nighttime being a DJ separate from your daytime being an engineer was awesome. I have one question for you." They had one question for me. "Why do you still keep it separate? If you love music, and you love technology, you can still be a highly paid professional these days in that industry." I don't know why it hit me like a ton of bricks right then and why it never came to me earlier. I said, "I never thought about that." Now, when I started getting recruiters calling, I had a criteria. I said, "I'm very happy at Comcast. I'm not interested in leaving, but I will entertain the talk if you talk about one of two things, sports technology, or music technology." Before long I got the call from Amazon Music, and I had a shot to interview for the job that I have right now, Director of Music Customer Experience at Amazon Music. It was a grueling process, but it was so rewarding. Everyone out there right now, just go and look up the 14 leadership principles at Amazon, no matter whether you plan to ever interview at Amazon, or work at Amazon or not, you will learn so much about yourself as a professional if you think about how you rank in those 14 leadership principles. I said leadership, not management, so that means if you're an individual contributor, take a look at those 14, if you're a manager, take a look at those 14 because they benefit everyone.


Number one, management is not the same as leadership. Going back to early on in my career when it was thought that, you're pretty good at working with your peers, then you must be good at management. Dive into it a little bit deeper. Look into it a little bit deeper. Go and look at the mundane aspects of management, and find out if you still think that you're organized enough to do it. If you're ready to do those things on a yearly and annual basis, over again. Number two, it's ok to stay technical, but differently. The other thing I see is people swing too far to the opposite side, which is, you spend the early part of your career becoming a technical expert. Then you go into management and you decide that you're just not allowed to be technical anymore. It couldn't be further from the truth. It's one of the things that makes you valuable. You should be able to turn that dial up and down to help you as you need it. Three, and this can really help you guided along the way, this is the passion part of the job. Every company is a tech company, so if your job is tech, try to find your passion in tech. I'm not going to make it seem like it's the easiest thing in the world, even when that person came to me when I stepped off stage, and gave me the idea of mixing music with tech. It didn't happen overnight. It took a while before I actually found the opportunity to come to Amazon Music. That would be my third takeaway from it. If you can find the thing that you're passionate about, along with the technology, do your best to pursue it, because then you're going to do whatever it takes to upskill your stuff in that environment.


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Recorded at:

Mar 05, 2024