The Life of an Introverted Technical Leader

Hello, this is the Powerful Introvert Podcast and I’m your host, Greg Weinger. If you like this content and you want to help spread my message that we’re all better off by making space for the quiet voices in the room, search for Powerful Introvert on Substab and subscribe, or go directly to Powerful Introvert, one word dot substac dot com. All my content is free. In this first interview, I speak with Jeff Cowan. We met 14 years ago at a local tech company where I was abruptly introduced to his team as their new manager. The team was cut out of the process and the news of my hiring and Jeff’s words was not universally well received. This was my first stint as an engineering manager and Jeff was really kind to me and helped me navigate some pretty choppy waters. Jeff is an introvert and he’s a very well respected technical leader. We discuss his journey as a technical leader, the importance of self-awareness for introverts and how we can take care of ourselves in high stimulus environments, how the workplaces changed over the years. We lament the demise of the private office and speculate if we’re all just giddy pigs in some architects, grand social experiment. I had a fantastic time talking to Jeff, I’m so appreciative of his being my first guest. So without further ado, let’s get started. Hello, this is the Powerful Introvert podcast. This is one of the problems with introvert. It’s really hard to say that word. Introvert. Yeah, it is. Yeah. Yeah. All right, so we’re going to try that again. All right. Hello, this is the Powerful Introvert podcast. I am Greg Wanger and I’m here with Jeff Cowan. Thank you for joining me. Thank you for having me, Greg. Yeah, just a brief introduction. Jeff and I have been friends. I think about 14 years now. We met at a software company where you’re an engineer and I was brought in as your manager and I’ve been trying to put myself in your place. So I have an English degree, English literature. This was the first time I was an engineering manager. I had written Java code for 10 years, but I was basically put on a team with everyone was like a really good engineer. Do you have an engineering degree? I do have a master’s in computer science. Yeah, so you really know your share. And so I walk in. I think I walk in, yeah. No, you do. When day I walk in or you walk in and they say meet your new boss. And you didn’t get a chance to interview me. And as I understand it, one of the guys on the team was a influential kind of technical leader. I was so pleased with this news that he quit on the spot. That’s right. Yeah, we had a lost or previous manager kind of suddenly and the decision was to bring in new management. The CTO at the time had just undertaken a search himself. And we typically would try to interview anyone that was coming in for leadership within the engineering just to make sure that there was a good general team fit. But that process had been bypassed in this case, hiring you. And so yeah, that was that was not universally well received. As you and I both know it worked out pretty well actually in the end. Yeah, yeah, we work things out. It was funny because I was a little bit kind of thrown into that situation by that CTO. But the fact that we’re sitting here 14 years later, great bonds are formed and you know, in the little bit of chaos. It was kind of a unique and interesting work situation overall, especially in terms of my career. But like you said, I think there were a lot of really smart technical people that the company had hired. It had somewhat of a storied past. There were acquisitions and mergers. There were layoffs. So it was kind of a unique time where things were growing, things were changing. And it was just sort of a fun place to be even though it was a bit chaotic at the time. Yeah, there are really great people there like creative talented coders and you know, some strong personalities and interesting dynamics there. As we got to know one another, I realized what a deep expert you were in that code base. It was a little bit older code had become a Byzantine thing where like you really knew all the ins and outs of it. And you were really kind trying to explain it to me up to the point where my eyes would glaze over and you kind of was like, okay, you’re like, okay, he’s a fallen into that role and the number of jobs of I will never feel comfortable myself as an engineer until I understand things to a certain extent. You frequently come into projects where there’s a lot of existing code and a lot of history and you have to spend a lot of time getting up to speed on it. So I always tried to pride myself on helping people who were coming in after me like transfer a little bit of that knowledge. Yeah, well, it was definitely appreciated. There’s one other event I was thinking I was trying to remember were you around for the flood? I left one week before the flood. Yeah, the flood. This is one of the more humorous events from that time where in order to save money, the parent corporation that put their data center in a flood plane, like a 100 year flood plane, I don’t know if it was the Mississippi or the Missouri River, but yeah, it was one of those 100 year floods and then we had to work for three weeks straight on. We have three shifts working around the clock to evacuate that data center and was done successfully, but that was an interesting little side event there. Yeah, definitely. Don’t build your data center in a flood plane. Cautionary tail folks. Cautionary tail, don’t do it. You know, incidentally, I think we also looked at the map and the data center was at a piece of land that was off the end of the airports runway and close to the fuel storage tank. So, you know, I hope this never happens, but you know, if there were any kind of a mishap, it could have been like even worse, I think, all all around. But the round was cheap. You saved a lot of money on that. I’m wondering, do you consider yourself a technical leader? I guess I do by virtue of my experience. Yeah. You know, I’m someone that’s accumulated a lot of knowledge in certain software systems, particularly in Java, data systems and databases, backend data processing, big data, stuff like that. So, I do consider myself something of a leader in that area. I would say, yes. I wholeheartedly agree. I mean, you demonstrated that all the time where I saw you, your debex routine and people really would come to you and value you for that. I sometimes wonder if this happens in other fields where it’s certainly a thing in technology where people who do not have a formal title are absolutely leaders. They may be more influential than the people who have the title as a manager. I’ve definitely seen that in my career. I think there’s a lot of forms of leadership and it’s not always necessarily recognized by someone’s job title. Kind of segueing into the whole topic of introversion. As I’m reading it, there’s a bell curve where you kind of have extreme introverts at the one end and extreme extroverts at the other. And there’s actually up to 50% of the population are on the more introverted side. And then you go up from there. So, I’m curious. And this is one of those questions. I’ll be asking everybody on the podcast. Where do you see yourself on that curve? It’s an interesting question. I would say that when I was younger, I was on the very introverted side of things. It is something that you can sort of learn to adapt to and get better over time. So, I think I’m much better these days at being able to greet people. I don’t know, have a conversation with people. I don’t know. Those were the situations that I really struggled with when I was younger. Yeah, it’s something that can be worked out. I would say I’m a little closer to the middle of the spectrum now, but I still have my periods where I’m kind of like, well, I’ve had enough social interaction. Yesterday, I’m going to kind of stick a little bit more to my own activities today kind of thing. Yeah, I think a lot of us who are introverts kind of a similar experience. Maybe you start out that way. You learn ways to be social and adapt in situations. And then I talk about this a bit, but the classic definition of introversion is not really shyness. It’s where do you get your energy? And so you touched on that where, okay, I kind of got my fill of people and all this stuff. So I need to recharge. And that’s where we get our energy. I’m going to ask you this question. On behalf of us introverts, can you help to explain to extroverts why we hate people? Is there terrible? Exactly. Yeah. No, no. I think it is a misunderstanding that sometimes introverts are either overly moody or that they might have a disdain for people or whatever. And a lot of times it’s just that, again, your energy is being focused internally and you’re not as able to engage energetically with the outside world. I’ve been paying more attention to this lately. I’m starting to more consciously manage my time. So if I’m out and I’m stuck in it because I’m because of my job, sometimes I’m stuck in a and all day meeting or something is like getting out and you know, it’s really like, okay, I really need to manage my energy that way and that’s been helpful. I think that to a certain extent, if you just try to be more self-aware, this is something that I think was also part of getting better at engaging with people I didn’t know was being self-aware of my own internal state and sort of managing through that. I think a lot of it comes down to internal awareness, which is something the introvert generally is pretty good at is like living within their thoughts. Yeah, I think you’re right. I think a lot of introverts are pretty in touch with what’s going on or more in touch. Certainly when you’re on your own and then the louder or more chaotic the environment, the feeling of overwhelm can build and so it might cause you to lose touch with that. Yeah, I think that’s true, you know, and I think we live in a very high stimulus world now when people still work in offices if that is even the thing anymore. Yeah, a lot of times the offices are trying to move desks and tables together and take barriers down, which means there’s a lot more noise in your environment. We have all kinds of electronic devices now that are constantly, you know, vying for our attention. If you are struggling with interversion, it’s made worse by having too many external inputs that are kind of shortening your attention span as well. Agreed. And starting to read, find things in the literature, case studies, where management is intentionally trying to create spaces for introverts and setups in the office like places where people plan up downtime. Other areas are for common interaction that kind of things. Some promising things are happening there. I think the work space is going through a big transformation. People spend so much time at work that one size fits all approach, doesn’t really work for how busy people are these days and how many different lifestyles people are leaving. I don’t think that that’s as acceptable anymore. You know, you want to give people options and make people feel welcome at work. Agreed. What kind of setup do you find ideal? I was lucky enough at a couple of jobs to have my own office. In an office building yet, like an actual office where you can close the door. And it’s pretty incredible. I have to admit, it’s really nice, but most companies are not willing to really do something like that these days. I’ve always liked smaller teams. And so smaller spaces, the idea of having like four to six people that kind of sit in the cluster, but then there’s a little bit of something that surrounds that group. Having 25 people in an area just creates too much cross to our cross jadder. Back to your office. I had that once in my career and I agree it was amazing. I almost felt like my office became the fourth therapies. Office, people would come in and talk to me. So it was maybe not the best for productivity, but yeah, I mean, when you had to focus, so that was fantastic. For the focus time, it was really great. And then it was actually nice because if one or two people wanted to have a quick meeting, but you didn’t have to find a meeting room and at other places that worked, there was sometimes even a challenge finding a meeting room. It’s like, well, let’s go just find a quiet space to talk about this. Every room is blocked. Every room is blocked. And so you end up having to have a conversation in the middle of everybody else. I always felt bad because I hate when people do that near me. So yeah, I didn’t want to do that to them, but sometimes you have no choice. And the opposite extreme is the completely open floor plan and probably like 30 plus people filling the same area with sound. Sometimes people were playing music. I was like, talk about like, the worst kind of situation for an introvert to be affecting. And all the headphones go on. Like last time I worked in a space like that, everybody would come in and immediately put headphones on. So the theory from the architecture and the space planning perspective was if you get people together in an open space, they can cross collaborate really easily. But what I found was that everybody was coming in and immediately putting headphones on kind of debunked that theory right away in my mind. But yeah, and then you got the headphones with a light on there where you can flip it on. It’s like, oh, don’t do not disturb right now. This like totally undermining all the space planners. Exactly. What their bad theory. There’s been a lot of theory behind that. And I think I know a lot of architects and they’re all pretty things smart, amazing people. But architecture is a field that has had a history of people who for whatever reason feel like they understand human dynamics maybe better than other disciplines. And they kind of impose these ideas. It’s sort of like as a sociological experiment through the architecture by creating this space. You kind of create the dynamics. So I don’t I’m not saying all architects are like that that most are not. But I think within the history of architecture there are these big minds that have come with big ideas. And they they don’t always pan out. But you and I are the are the gamey things. Exactly. Where the guinea pigs really unwitting. Yeah, pretty much. I had a couple more questions about introversion. You kind of touched on it. But what are your feelings about that aspect of your personality these days? Well, I think I acknowledge and accept that that’s the way I am. Like you said, it’s a lot about where you get your energy, you get energy from groups of people or more from being alone. I don’t know, I very much like those aspects of my introversion that I have. It’s it allows me to sit and to think more and have my peace. And also I kind of like that aspect of it. I do recognize where it may be a limitation. And again, like I mentioned previously, there’s things that I’ve worked on over the years in the office. Can I get up and give a presentation in front of a group of my peers, for example, or or managers or whatever. You just kind of learn to adapt and cope and get more comfortable with those things. So, you know, over the years, I think it’s something that I’ve worked on. I’m kind of at a happy medium. I don’t know. I don’t feel like I have a lot of work to do on it. Unless, unless someone comes knocking on the door tomorrow and telling me I’m doing it all wrong. Oh, you’re definitely not doing it all wrong. You know, from the outside, it seems like you’ve been very successful in your career in your life. And we all have these different aspects. And one of my motivating factors in doing this work is I don’t think you should have to change anything. I think the world should adapt more to introverted personalities. That’s a huge part of the population. And I think we can get more out of everybody that way. Like you said, I think that the workplace has adapted more people are working from home. I think that’s a model that suits introverts pretty well is having more control over your space at the end of the day. If the if the work is getting done, satisfactorily, I think allowing people different models for that is a good thing. Good point. I think COVID was one of the biggest boons for introverts. You know, I was having a great time. I hear about, you know, extroverts are like, oh, they were really miserable and depressed. And I was like, I’m good. Home office is working out great. Yeah, I was working with God. And you know, my current job, we have a office downtown. I go like a couple days a week or, you know, there’s people come into town. I’ll be in there three or four days. And I was like, well, how did I ever do that? You know, yeah. Yeah. Do you see the pendulum swinging back the other way in terms of like getting more people back into the office or finding a different balance again? Because I feel like that with the pendulum very quickly swung one way. And I feel like companies are wanting it to move the other. But I don’t I don’t have a good read on that. I think that’s so interesting. So the most famous example right now is is Amazon there as a January first, they’re requiring five days of it in the office. Personally, I think it’s a mistake. You can see right away, Microsoft and Google pounced on them and said, like, we’ll take your, we’ll take call your great engineers. Amazon, but Amazon’s always that’s part and parcel with that culture. It’s very opinionated and not the most human friendly culture that’s out there. But Amazon does not have a great reputation for a, you know, baby and its employees. It’s, you show up to work there. You’re expected to work a lot. And then when you’ve had enough, you know, you’re free to leave. Exactly. Don’t let the door hit you on the, on the butt on the way out. That’s right. For me personally, two to three days a week would be fine. In office, I can’t see a reason in my industry why you would need to be there five days. Yeah, you know if your people are getting their work done from home, right? Because the projects are getting done. My company is also very distributed. And I think a lot of companies are very distributed these days. So it kind of doesn’t make sense when so much of your team is spread across the country already or across the world. My kids are just this year started college and but so many of our employees have young kids at home and creates a much more sane atmosphere for them. Just to have that flexibility to be able to take someone here and there and adapt work to their lifestyle and a much better way. Work from home has helped companies rethink where they’re located, you know, where they’re hiring employees, where they’re drawing talent from. So if in some ways it’s probably made companies stronger and more resilient, they can hire talent from a wider pool. Don’t have to worry about necessarily providing a full office experience for them. Maybe in the end, it’s kind of a win for employers and employees. Yeah. That’s that’s a really good point about the talent pool. Maybe if you’re Amazon, you’re like the talented people will come to our cities or our offices anyway. But for smaller companies like ours, who would have found the Portland market kind of limiting to it’s been really nice to be able to hire outside of the area? Yeah, that my previous employer, I think, really benefited a lot from from being able to hire across the country and even across the world. You know, finding different pools of talent in different places that’s, you know, maybe had been overlooked before I was not available because those people weren’t in the two or three tech centers that they had set up. So yeah, it’s interesting. So Greg, I have a question for you about interversion because you worked a lot in software and with software engineers and you have your own sense about how introverted people are within that domain. But I know also you’re managing at a higher level now and you have different work experiences and maybe working more with higher managers that are higher up on the chain. So what’s your, do you get a sense that the level of introversion is equally distributed across professions and levels or do you find that there are, you know, that varies. What have your experiences been? Yeah, thanks for that. So it absolutely varies across different fields. So in the last five years, I’ve spent a lot more time with marketing people and sales people and sales teams and with our executive team here. And yeah, there’s still way more in, you know, into that extraversion field. And so I find it’s very relative. And so when I’m in my departments with engineers and even product people, I find that I’m on the extroverted side of us, but I’m on the introverted side when I go to these other areas. So I find myself really comfortable speaking up in all these day-to-day operational situations. And then it’s literally hard to break into the conversation. There’s just so much faces being filled up by everybody’s personalities. So I actually think before I speak still. And so and you know, that’s like a limitation. It’s just how it is there. I’ve had the chance to mentor several product people who are wanting to make more of an impact on their job or have more influence, but managers of them as well. And for the most part, it’s actually extroverts are in the minority in our discipline. It’s been great to see that. And I think having gone through that myself, I have a lot of sympathy, but also I do some practical advice for them as they go through that. Yeah, yeah. I think that matches my experience as well. There’s just certain fields where you never would have gotten into it or made it in the first place if you hadn’t been able to really get out and engage with people. That’s an important skill when people that have that. That’s their leveraging it to their best ability, which is great. Although I have learned through my research that there is training and a whole bunch of people who train sales for introverts. And they are examples of people who are multi-time leading salesperson who happens to be an introvert. And what happens is they leverage their listening skills and their empathy and that side of it. And they don’t come on with that big classic sales personality, but they’ve found a way to be incredibly effective at their job by leveraging some of their strengths. So it’s kind of interesting. It’s not a one-size-fits-all even in those fields. Yeah, I do think it probably gets back to what I was saying about you can train yourself out of some of your introversion. You can also probably learn to leverage it correctly. And then on the flip side of that flip side of every extroverted salesperson is a customer that may or may not want that experience of a hard sell. And they might be looking for a salesperson that’s a moreable listener and you know, leverages their empathy to understand their particular problems. I think there’s a place for all types in that area. Yeah, yeah, I agree. I’m going to try to talk to some of those folks on the podcast here. At some point. Excellent. Yeah, you definitely should. That would be very interesting, I think. So getting put down on my question list, what would you tell your CEO or senior leaders what they ought to do to make things better for or more balanced for introverts? That’s that is a good question. I would say introverts oftentimes, as you pointed out, want to think carefully about what they say before they say it. So I think being patient and training the organization or or letting people know that like case, sometimes you’re not going to get a lot of engagement from an introvert on the first pass around. It doesn’t mean they don’t hear you. It doesn’t mean that they don’t care about what you’re saying, but they’re probably thinking very carefully about their response because they it’s going to take them a lot of energy, you know, personal energy to kind of convey that. So I think educating organizations about communication styles would be a great starting point. I think that would be probably one of my top items, but I think also, you know, creating flexible workspaces that would allow people’s ability to work alone for part of the day or have a little more quiet time or a little more isolation can also be beneficial to bring the noise level down and sort of tighten the context around someone’s work. Is your sense that senior leaders generally do or do not get that? I think it’s improved over the years. I think the last set of leaders that I worked with were very patient. You know, if they asked a question, it seemed like they were more willing to wait for you know, a careful precise answer. So I think that there’s an understanding that that’s going to take a little more time for someone who’s introverted to maybe convey their ideas around something like that. I would say the state of leadership is probably improved in that area. The more training a company does around communication and working styles and working practices, the better it gets for everyone. So I would say that I’ve been pretty impressed with the leaders that I worked with at my last position. They all seemed like they were very thoughtful individuals. So I would say things are looking up. So I hope full-known. I liked when you turn the tables and asked me a question, do you have any other questions you have for me? I guess, yeah. So you said you’ve been doing some research around interversion. Have you been focusing on things like books, papers, where are you drawing some of your background information? Aside from personal experience, I mean we all have personal experiences and you’re a very perceptive guy. So I know that you probably have been absorbing a lot of information from your environment, but I’m wondering what external resources you’ve been using? Yeah, it’s really starting with books. I’d like to get to the point where I feel like I’ve gained what I can from the literature and I’m starting to go to primary sources or look at new studies as they’re coming out. It kind of started with this book called Quiet by Susan Kane. She had a famous TED Talk. It’s actually been I think over 10 years now since all that work came out, but that’s where, and I came across this recently and I think it’s like, where the hell has all this been? Where have I been? Because so many of these things just made so much more sense to me and I think I could have come to a more of a place of self acceptance with more familiarity with some of these concepts or some of this knowledge. There’s a good handful of leadership books. There’s some more psychology books. A lot of them are from psychologists, but you’re starting to see some books from people in the field like that because I was like, I should write a book about it and then I started researching. I was like, oh, there’s a lot of books about this. Where I plan to go on with this is is not just that, but to try to do some primary research myself, just talk to a lot of people, interview people. I would love to have a number of these authors on the podcast. I’d like to have just leaders, people who are dealing with some of these issues that we just discussed on the leadership level and people who are introverted themselves. There’s nothing like representation seeing people who are up and doing that. This is something that impacts everyone’s and I’m sure a lot of people have thought about it. So it’s great. So it’s a cure on a great trick. Appreciate that and I really appreciate your time, Jeff. This was great. A V2Dude to help an old friend out on a Sunday afternoon before you’re are you going to I don’t know what your plans are. Are you going on a bike ride or anything? Want to visit some friends this evening for just a casual hangout a couple hours in the dinner. But otherwise today’s one of my usually set Sunday aside to take care of errands and chores around the house a little cleaning and laundry and that and shopping. So that’s on the agenda next. Excellent. And hopefully it makes your introverted side very happy to take care of all those things. Yeah, it does when you do take care of your environment, you feel good afterwards. I’m so glad I did that. It’s like a weight lifted. There you go. Another tip. All right. Thanks, Jeff. Thanks for joining. Thank you so much, Greg. Thanks for having me. If you like this content and want to help spread my message that we’re all better off by making space for the quiet voices in the room, search for powerful introvert on substack and subscribe. Or go directly to powerful introvert one word dot substack dot com. All my content is free. It’s tax time, y’all. If you want to file free, this next one’s for you. Love that jam. Up next, commercial. For more information, visit www.ter botax.com.com. 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