Host Intro (Gene Kim)

Gene introduces Michael Winslow, who has spoken at DevOps Enterprise Summit six times as a technology leader at Comcast, ranked number 26 on the Fortune 500, with over 8,000 software developers. Across those years, Michael has been a director of engineering, then a senior director, and now a distinguished engineer. Gene notes that Michael previously told stories about being asked to lead the SRE initiative for a critical Xfinity back-office service, critical because it enabled revenue-generating services such as activation for direct-to-consumer and storefronts.

Gene explains that the conference has a strong preference for experience reports: real stories about solving problems with evidence that someone appreciated the work. He also likes talks about advice speakers would give their earlier-career selves, citing Luke Reardon from Target, Paul Gaffney, Courtney Kissler, and others. Because of a specific decision Michael made a couple weeks earlier, Gene asked him to talk about why he chose to switch from a management role to an individual contributor role, and what it would take to get him to switch back.

Michael Winslow

Michael opens by greeting the DevOps Enterprise Summit audience and asking them to make noise. He thanks DJ Kelly and DJ Marguerite, then explains his flashy entrance: while researching the Chelsea Theater, he learned Bruno Mars was the resident act there for two years after the theater opened in 2013. Michael is a huge Bruno Mars fan, so he wanted to come out flashy, but says this is not how he will do the whole talk.

He then resets: he is not Bruno Mars. He is Michael Winslow, a distinguished engineer at Comcast in Philadelphia. He also lists executive director because that is the equivalent management role. Gene had mentioned that he has spoken here six or seven times before; in most of those talks, Michael talked about the team. This time Gene asked him to tell his own story, which makes him uncomfortable because he prefers to talk about the team, but as a leader he is comfortable being uncomfortable.

01Backstory: curiosity and sharing

Michael gives a quick backstory. He jokes that when people hear backstory, thanks to Marvel, Disney, and Jason Cox, they expect a superhero who can breathe underwater, fly, or replace body parts with cyborg parts. He jokes that those things are true about him, then says in seriousness that he was raised by wolves. He shows a 1975 photo with his father, who raced huskies, and says he is not afraid of dogs and thinks huskies are beautiful. The photo includes his big brother Sean and dogs named Bobo and Oslo.

Fast-forwarding to 1985, when he was about 10 and in middle school, Michael says he did not have many friends. He had one friend, and that friend had what Michael thinks was the only computer in the neighborhood. They bought magazines from Electronic Boutique that had GW-BASIC code in them, and they typed it in. They got into graphics, using graph paper to trace shapes and write coordinates. He jokes that although a slide says 1985, it is clearly 1993 because the Jurassic Park symbol is visible.

A few years later, Michael wanted to be cool, so he went to a barbershop and asked them to put the year in the side of his head as he entered high school. He did not want to be the computer geek anymore. Later he started a rap group called Suburban Underground. A few years after that, he wrote his own DJ software, which many people know him for, and shows an early ugly website for DJ Boo Boo.

The point of those stories is that he was curious. He had many things he wanted to tackle. Even at a young age, it was about problem solving and learning new things. He adds that if you are curious and want to get into leadership, taking in information is only one part; the other is sharing information freely.

Michael quotes his late uncle, who was his mentor for many years and for whom he worked in Amsterdam: a true professional should be able to speak intelligently for five minutes about any subject. Those words changed how Michael viewed interactions. When someone told him something he did not think mattered to him, including an intern-era example of a person who did medieval recreation on weekends, painted themselves blue, and made arrows, Michael remembered his uncle's words and asked to hear more. A decade later he had a grandboss who did the same thing, and sharing that story helped his career.

02Speaking, rejection, and a natural brand

Michael says he is on stage because he wants to share. He wanted to get on this same stage in 2018, but his first submission, about automated release notes, was rejected. He jokes that if an email does not say congratulations in the subject, you did not get in. He felt dejected and thought he would not fly to Vegas, but his friend Chuck Mounts, who had attended before, told him to give it a shot because he would love it and it was what they talked about all the time. Michael came anyway.

Some people may remember the talk he gave that year, "There Are No Side Projects," where he talked about the DJ software he wrote and how it helped him professionally. That talk became the beginning of his real coming-out party, not just at DevOps Enterprise Summit but back at Comcast and everywhere. He wanted to share knowledge all the time.

This leads to building a natural brand. Michael says everybody tells you to build a brand, and then you wonder what tools you can use to do it. The more natural it feels, the easier it will be; you may not even know you are doing it. At Comcast, DevOps became the brand for Michael and Chuck Mounts. When people said DevOps, they pointed to one of them.

At first Michael did not even know what DevOps was when he started talking with Chuck and others. What he knew was that he loved helping people succeed, especially engineers, and he loved automation. When he talked to people who did not know DevOps or talk much about automation, he bored them. One woman, Cindy, after being bored by him, said she needed to connect him with Chuck because he was speaking Chuck's language. That is how Michael met Chuck, and they became the face of DevOps at Comcast.

03Project Modesto and opinionated leadership

Around the same time they were becoming synonymous with DevOps, a super-secret project was happening inside Comcast. It was secret even within the company. The project was called Project Modesto. Modesto was a small locked room on the 36th floor that no one could enter. One day someone took Michael to that room and said they had heard he knew DevOps and needed him to be part of it. That project became the beginning of Xfinity Mobile in 2015.

They could not say what it was at first because of partnerships they were building, but Michael emphasizes Gene's point: there were no job postings for the thing they needed. His brand got him that job. He could not have found it or applied for it.

Once he was there, another leadership lesson emerged: you cannot be afraid to have opinions. Michael quotes Steve Jobs: if you want to make everyone happy, scoop ice cream for a living.

He tells a story about a disagreement with his leader at Xfinity Mobile. Before a new leader arrived, Michael had led the mobile back-office team, and they created what he calls the most beautiful monolith you would ever see. He says he loved the monolith: it had domain-driven design and a perfect Spring MVC implementation. Seven months before launch, the new boss came in and said they were arbitrarily moving to microservices. Michael said no; the boss said yes, and the boss had the bigger voice.

Michael disagreed vehemently but committed once he knew they had to do it. He lists his reasons for opposing the move: they did not have a big team size, which is one reason to move to microservices; they did not need to limit blast radius because they could load-balance the monolith; they could not take advantage of autoscaling because they were not in the public cloud; moving so late would be an operations nightmare; versioning would become a big problem because every microservice has its own version; and they had a tight seven-month timeline.

He lost the battle, but they still made a great application because they disagreed and then committed. Because he did not quit, throw things down, or disengage, one of his best-received talks here, "What Tech Leaders Need to Know About Microservices," came from the fight: he had fought so hard that he learned everything about microservices in order to do it. At that time, in 2018, he was a director.

04The power of community

Michael then talks about the real power of the DevOps Enterprise Summit community and says he might get emotional because the community has done so much for him. After speaking here and meeting Gene, Jeff, and many others, he went back to Comcast with Chuck and shouted from the rooftops that they needed internal DevOps conferences. The community helped them learn how to throw internal conferences.

Gene Kim and Jeff came to Comcast facilities and helped make things happen, even mentoring the person running Lean Coffee. Michael also mentions Nathan Harvey, saying he cannot talk on stage without mentioning Nathan and telling him he loves him.

Michael says community does not stop at the walls of the Chelsea Theater. He is a huge part of an organization at Comcast called the Black Engineers, or bengineers. When he learned the skills of public speaking and throwing conferences, the same community helped Comcast's Black engineers do the same thing. They started bengineers conf in 2020. In 2022, it became Comcast's largest external conference; they hold it every February and planned to do it virtually again in 2023.

He shows some of the bengineers and points out Jay Josephine on the right, who is now his employee for the dojo, through connections made in this community. He asks people to look up the bengineers and says he is proud of the group.

To recap the power of community: it does not stop within these walls. Do not just attend events. Be active and try to solve real problems while you are there. Share stories and ideas freely, not trade secrets, but freely.

05From team leader to organizational leader

Michael turns to what Gene asked for and says he will move quickly. The question is how he went from senior manager/director to executive director and then individual contributor again.

He shows his Insights evaluation and says he cannot believe how truthful it was. One part represents personality when alone. His very high red bar means he likes to get stuff done, concentrate, and not let anything get in the way. Another part represents how personality changes around others, when putting on a show. There, the yellow bar, which represents sense of inclusion, goes up.

Michael says his personality knew that to get things done by yourself, you do not need as much inclusion. But the moment you start trying to get things done as a team, you need to tie into inclusion and get it as high as possible.

The evaluation said his top motivators were tasks that predominantly involved the group, a relentless drive to competency and effectiveness, and special task teams to interact with. Those motivators made him suitable to be a large organizational leader, and he was willing to take that on.

He skips quickly past a graphic showing how fast his calendar filled when he became an organizational leader. He was not prepared for that transition from individual contributor to leader. Once his calendar was full, he still tried to take quick tickets and handle them. His one-on-ones with direct reports started falling by the wayside. He was failing his team because he was deciding to pick up code.

The reason, he says, is that when you code, your focus narrows: nothing around you makes sense except the one little dot you are staring at. If you want to keep coding while you are a large organizational leader, he advises doing it inside Microsoft Word by enabling the developer ribbon and automating status reports, data comparisons, or maybe making yourself a bot. Do not go into production code with your team; it is not that helpful.

06Returning to individual contributor

Michael shouts out Leslie Chapman, who has spoken at the conference many times and whom he calls Comcast's matriarch. She was the first female distinguished engineer and the first Black distinguished engineer at Comcast. Michael asks the room to applaud her. Leslie inspired him to get out of the management game again and return to being an individual contributor.

He thanks the audience and gives a quick shout-out to his team, Abhishek and Jay, who came with him. This is the first time he has brought a team to the conference, and they enjoyed it.

Looking ahead, Michael says the road is uncertain. His time at Comcast has been wonderful, but he is not sure exactly how much longer it will be. He wants to explore his love of music and technology as a next step. He hopes that the next time he is on stage here, the audience may hear about an opportunity he has taken to blend technology and music.

Q&A / Bonus Time

Gene indicates there are four or five minutes left and asks whether Michael wants to make a point. Michael says yes and calls it bonus time. He says one thing Gene always wants, and he did not get a chance to discuss, is what he needs from the audience.

Michael says he would love to hear from anyone who came to the conference with 10 or more people from their company. He wants to know how that journey went, either to come or to convince people at the company to do so. Comcast and DevOps Enterprise Summit have had a great partnership, but for some reason Comcast has not gotten over the hump to bring 50 people like American Airlines did or 25 people like Discover did. Next year Comcast wants to come in force, and Michael would love to hear stories about how others made that happen.

He thanks everyone again.