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Transitioning to Management with Confidence

Episode 5

This week, we’re talking about the programmer to manager to leader transition. What makes this transition hard? Is it possible to become a manager if you’re lacking good role models? How do you really become the leader you want to be proud of? Tune in to find answers to these questions and more.



Show Notes

  • Why is the programmer to manager to leader transition hard? For starters, you’re no longer “just” coding, so it feels like you’re leaving something you love. It’s also difficult to envision the transition, especially if you haven’t had good role models.
  • Marcus: “We learn to be a leader, a manager, by being led and being managed.” 
  • Marcus: “…it is very hard to ask yourself, ‘Have I fallen into the habits of doing this in a way that is never what I wanted to be?’ Instead, become the leader you want to be proud of. 
  • Marcus: “…join those of us who want to revolutionize what engineering management and leadership looks like, who believe that leadership is what happens when people of all ranks get together, problem solve, and empower each other.”
  • Help your boss establish a growth mindset by changing your language. Insist on talking about growth and learning and change. Ask, “Where did you learn that?”



Announcer: Welcome to the Programming Leadership Podcast, where we help great coders become skilled leaders and build happy, high-performing software teams.


Marcus: All right. Welcome to the Programming Leadership Podcast, where we help great coders learn to become great leaders. I’m your host, Marcus Blankenship. Now, if you’re like me, the idea of becoming a leader is not something that’s really comfortable for you. It probably reminds you of hair gel and matching socks, and those shiny shoes, or maybe suits and BMWs and arrogant, old white men, okay? There’s a lot of misconceptions about what leaders are, because we have been in a society and we have grown up seeing a certain kind of person who is called the leader, the manager, and frankly, as an engineer, and I’ve said this before, I didn’t want to lead anything, because I absolutely didn’t want to be one of those people. What that meant was, when I did get the opportunity to lead people, it was really challenging for me to wrap my brain about what that meant.


Marcus: I want to talk today about the programmer, to manager, to leader transition, okay? Because for me, this transition was incredibly hard, and I want to help it be easier for you, all right? I want you to have an easier time than I did and I want you to not make the same mistakes. So if you are struggling, if you feel high-centered on the programmer to leader transition, if it seems like it’s overwhelming, this episode is for you.


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Marcus: First, one of my favorite things, and I don’t why, but one of my favorite things to talk about is, “Why is it hard?” So let me ask you, why is it hard? What has been hard for you? If you’re like a lot of people, the things that are hard are not the leadership skills, per se. It’s not even the management skills. Here’s some of the things that people I work with and that myself found was really hard. For one thing, you’re giving up coding. I realize you might still get to do some coding, but as a general proposition, you can no longer just call yourself a software engineer or a developer because that’s not what you do. Your core job is no longer to write the software. You don’t build systems of software. You build people and teams. Those are systems of people, okay? And so your job changes.


Marcus: Now, why is this hard? I mean, is it hard for a barista to go work at McDonald’s? No, I doubt it, but maybe. But here’s the thing. For me, being a software engineer was really wrapped up in my self identity. I have wanted to be a software engineer since I was 12 years old. I have spent literally thousands of hours of my own time poring over books. I went to school for this. I self selected into the work, into the program. Like, this is what I love, and so the thought of leaving it to this day still breaks my heart. That’s why, to be completely frank, even though I do not write production software for a living, I still play with software. One of the things I get to do, and you might find this as well, is you get to do more playing and learning and staying sharp that way, rather than being in that production software development cycle.


Marcus: One of the reasons this transition is hard is because we are leaving something we love, feels like, and maybe it’s not absolutely true, but again, it feels like we’re leaving something we love, okay? And when we leave something we love, we may ask ourselves, “What does that mean about me now? What am I? Do I want to be this new thing?” I got a promotion. It was given to me. I took it. I accepted the promotion, and pretty quickly I realized, “What does this mean that I am now? What is my new identity?” Man, the last thing I wanted to be was a manager. I had never had any good experiences with managers my whole life, and the manager that came to mind, the software development technical manager that came to mind when I thought about telling people, “I’m a manager,” was the pointy haired boss from Dilbert. That was kind of the icon. That was the thing. The picture that comes to mind when I think about technical bosses, the clueless boss. I didn’t want to be that.


Marcus: So not only was I leaving something I loved, and okay, now I feel a little lost, but when you think about it like leaving one place and going to another, I was not sure I wanted to go to that other place. I was not sure how far away from technology and software engineering I wanted to be. Now, I hear this from a lot of people who are early in their transition, is they say, “I don’t want to leave it too far behind.”


Marcus: It’s almost like if you said, “Well, I live in Portland, Oregon, but I’m driving my car and I’m going to drive away. I’m not sure I’m going to like Seattle. That’s where I think I’m going, but I don’t want to leave Portland too far behind.” So of course if you’re driving from Portland to Seattle and you really don’t want to leave Portland behind, you’ll probably wander in your driving trip to Seattle, and it will take a lot longer to get outside of Portland and you’ll be constantly looking back in the rear view mirror. “Am I too far? Have I come too far? Can I still go back? Oh, is this a one way highway? Where are the turn offs and the exits? How do I go back if I want to?” That’s fine. That’s how we feel safe when we’re on a journey. We recognize that we have options in front of us, but realizing that you may not actually have any interest in becoming a manager or the kind of manager that you have seen in Dilbert, or unfortunately, even at the company you work at.


Marcus: One of the other hard things about imagining, “Oh, what will it be like to make this transition?” Is if you have never had a good manager, if you have never had a good boss, a great boss, somebody who inspired you, who helped you do the best work of your life, if like me, the boss role models you had were pretty poor, that compounds the problem. You absolutely don’t want to be anything like them, and you can’t really imagine what it would look like to be anything besides them. I suppose in some ways, in kind of a weird analogy, but we learn to be a leader, a manager, by being led and being managed. Now I’m not saying that’s the optimal way, but I think it becomes your default in the same way as you learned to be a parent. How? By the place you grew up, by the way you were parented. So if you are listening to this and you have a very small child, maybe like the ages of between one and five, and you sometimes wonder why your mom or dad’s voice comes out of your mouth, well, that’s why. I certainly noticed it. It’s like this is our default setting, is to be, to model, the people that we worked with essentially.


Marcus: I know that when times especially were stressful, when things were difficult, when I was feeling really insecure, that, boy, when times were rough, that’s when I struggled to be enlightened and my worst boss’s voice would come right out of my mouth, and I would say things and do things that I would then look back and go, “Oh my gosh. I can’t believe I acted just like that guy Paul that I hated.” In the same way today, and I’m a grandfather, I do things with my grandson, and I, in the moment think they’re fine, and I look back and I think, “Why did I do that? “Well that’s the way I thought grandparents should act, or that’s the way my grandfather acted. As you’re probably getting a sense, leaving a place you love — engineering — and going to a place you’re not sure you belong and you’re not sure you even want to be makes for a really hard transition.


Marcus: Now let’s hit on the other thing I just mentioned. You’re not sure you belong there. Imposter syndrome is real. I’m sure you’ve heard of this. If you haven’t, Google it, but the idea that you’re not cut out to be a manager or a leader. Maybe you’ve never been the captain of the football team or the head cheerleader, or these other leadership roles in school. Maybe you didn’t do that, in which case it makes you wonder, “Am I in the right place? When I go behind the velvet rope of management, when they usher me behind the big oak doors into the boardroom, will I be accepted?”


Marcus: I was just talking with somebody yesterday, and this person has all the experience on paper to be a CTO or a vice president of engineering, and I’ve known them for years and they’re considering a new role and they said, “Well, what role do you think I should take?” And I said, “Well, I wouldn’t take anything less than a director, and I think you’d make a great CTO.” They said, “You know, it’s funny you say that, because not that long ago I went to a conference and there was a round table breakout session of other CTOs and I went and sat in there, and you know what I found? They were just like me. They were dressed the same. They were even a little younger. They didn’t have as much gray hair, that they were insecure, and what did they want to talk about? They wanted to talk about, ‘Should we use Rails or Django or Azure or AWS?'” And he said, “I totally love talking about all that stuff. So maybe I do fit in with those people.”


Marcus: What it took for him to recognize that those folks … Maybe there’s only five of them, I don’t know, but whatever it was, it was enough to help him realize, “Oh, I could go there and fit in.” It’s so important for us to belong, and of course this is half the other battle. When you leave the engineering work, you … and I experienced this when I got promoted from within the team of engineers. They used to be my peers, my friends, and now I was their boss. I no longer belonged exactly with them. I couldn’t say, “Oh, I’m just like you.” I really wanted to say, “I was just like you,” because I wanted to be accepted.


Marcus: Unfortunately, I made this mistake, and I’ll just be completely upfront about it. I made the mistake of trying to be a buddy rather than a manager or a leader, and that meant that I found it more comfortable to pretend nothing had changed in the first year, even to the point where my boss got wind of it and he came to me and he said, “The team has said you’re, quote, ‘acting weird’ around them. What’s going on?” And I said, “Well, hey, I’m just being a great boss. Relational leadership. I’m being friendly. I want everybody to like me.” And he said, “No, you’re doing it wrong. You can’t. You can’t just try and win their affection. You can’t be that insecure. Of course, you’ve got to work from the great relationships you already have with them, but recognize that they see you as differently. That’s the truth. You’re more powerful, Marcus. You could fire them.”


Marcus: I didn’t like that. I didn’t like that one bit. I’ll be honest. The idea that I was different was hard enough and then to be handed like a scepter or a sword or some something where it’s like, “You could fire them. You have more power.” I hated that at first, and the analogy I like to use is if you’ve ever seen a little kid try and lift a heavy suitcase, or there’s this movie, there’s a Disney movie from maybe the 80s called Sword in the Stone, and you know, King Arthur pulls the sword out of the stone, and the heavens open, but the sword is so heavy he can barely lift the handle, let alone the blade. He’s like, I don’t know, seven years old or something.


Marcus: And that’s how I felt when I was first wielding any kind of power. It was too heavy for me. It was awkward. It meant that if I needed to swing it, it probably was going to hit the thing I didn’t mean to hit. And maybe it might take off my own foot, or maybe it would really hurt the other person. I was really worried about hurting the other person. After all, I was taught that when you have power, Spiderman, right? “With great power comes great responsibility.” I had to become confident and learn to use any new power I had in very small measures. It was like developing the skills necessary to wield a heavy sword or to lift a heavy suitcase. In time, I could do it, but the reality was that it was really uncomfortable at first, and I was afraid I was going to hurt them or me, and I just couldn’t fathom the idea.


Marcus: This was one of the other reasons it was so hard. I absolutely was terrified of the idea of losing this new job and having to go tell people that I had screwed up. And so in that same way, there was a lot on the line. I had gotten the promotion. I told my parents, my wife, there was more money. “Boy, all that sounds pretty good, except if I’m an imposter, if I don’t fit in, if I’m not accepted behind the velvet rope, I’m going to lose this. They’re going to figure that out.” And all of that caused me a tremendous amount of stress and caused me to try and conform to what these nebulous other people, other managers were doing. After all, if they were doing it, who was I to question it? Right? You just follow along, and after a while, maybe you’ve learned some bad habits. Maybe you’re actually finding that the way you’re leading doesn’t make you as proud as you hoped.


Marcus: Now, if you ever wake up one morning and you find yourself in my position where you look in the mirror and you ask yourself, “Have I become the pointy haired boss? Should I just give this up and go back to engineering, to programming? That’s what I love. That’s what I wish I could do. But what about this money and the prestige? The power, the fame?” Of course, there’s not a lot of power and fame, but it is very hard to ask yourself, “Have I fallen into the habits of doing this in a way that is never what I wanted to be?” That maybe is not just not the best, but maybe it really goes against the kind of boss you ever wanted to be. That makes the transition even harder.


Marcus: So why am I talking about this? What is there to gain from telling you that this transition is hard? Well, the first thing I want you to know is that it’s worth it. Okay? There are so few good engineering managers, and every engineer, every program or every QA person, every designer, they all deserve a good boss. A boss that not only understands the work that they do, but that unleashes them and empowers them to do the work, the best work of their lives. And that’s the kind of boss I want you to be. That’s the kind of boss I wanted to be.


Marcus: Let me tell you, once I finally made the transition, I worked really hard to become the kind of boss that I could be proud of. Not just the kind of boss that had a title. I never wanted to be a power hungry manager. I never wanted to be a leader that was feared. I wanted to be someone who brought out the best in people, and through tremendous hard work, I got there. And so it’s a little bit like somebody who’s jumped into a mountain lake and looks back, and you’re standing on the dock thinking, “Should I jump in too?” Let me tell you, come on in. The water’s fine. It might be kind of a shock to your system at first, but because we do not believe there’s any such thing as these born leaders, because we know that we could become better leaders through learning and effort and intention, we know that, then I’m going to say come on in and join those of us who want to revolutionize what engineering management and leadership looks like, who believe that leadership is what happens when people of all ranks get together, problem solve, and empower each other.


Marcus: That’s the kind of leadership we’re going to talk about on this podcast. I hope, I hope that not only you understand you’re not alone in the uncomfortableness of going from a maker to a manager, but that it is worth the trip. I’m also here, I take your questions on the show. You can attend my workshops. Join my mailing list at If you’ve got a specific problem and you want me to address it on the air, just shoot me an email at and we’ll pick it up in one of the episodes.


Marcus: All right. Well, let’s take one of the questions that came in about our last episode. All right. Josh writes in with this question: “Marcus, my boss appears to have a fixed mindset. Whenever we interview somebody, if he doesn’t feel they’re perfect for the role, he uses the words you mentioned, ‘They’re not cut out for it,’ and he just believes that you hire for the person that you see in front of you, not for anyone they might become. And whenever anyone’s having a problem, the same thing happens, is my boss also just says, ‘Well, we should just get rid of them.’ How do I help my boss to have a growth mindset?”


Marcus: That’s a great question, and when we have a growth mindset and we’re wanting to cultivate that, and this belief that we can learn, that our team can learn, that people can improve, when others around us have a fixed mindset, it can be really frustrating. I think that leaders have to have a growth mindset, because sometimes you have to believe in your team, in the individuals on your team, even more than they believe in themselves. And so here’s my advice. Change your language. Insist on talking about growth and learning and change.


Marcus: For example, my boss used to have this problem and he would say, “Well, we need to get rid of that person. They’re not cut out for it.” And I would say, “Well, where did you learn that we should get rid of people who aren’t cut out for things? And he’d look at me like, “What are you talking about?” And he’d say, “Well, that’s what everybody knows.” And I’d say, “No, you learned that idea somewhere, that if someone is not perfectly cut out for a role, the best thing we can do is to get rid of them.” And that’s just a really simple example, but I kind of became obnoxious. He finally kind of caught onto it. But if you can use a bit of humor and ask the question, “Well, where did you learn that idea?” Always pointing back to the fact that no one comes into this world having these ideas. They’re learned. Most people don’t actually know where they are learned. They’re learned oftentimes in early childhood. They’re learned growing up. For him, he was from another culture, and so he learned things culturally that I hadn’t learned. But whenever I took the time to ask, “Where did you learn that?” And even to this day when I do that, people stop and they reconsider how they got that knowledge.


Marcus: I believe the term is epistemology. “Where did you get that knowledge, and do you have the right to it?” Because if you believe something just is universally true, and I would assert there are very few universal truths, if you believe something that is simply universally true but have no basis for it, that’s faith. I’m okay with faith as long as we call it faith, but when we start to pretend it’s science or that it’s just nature, the way things are, that’s where I get a little uncomfortable, so I like to prod at people. I like to use language that asks them, “Where did they learn that habit? Where did they learn that idea? Oh, has that always been true? Have you ever seen a poor performer improve?” Things like that. I think that that causes people at first maybe to look at you like you’re crazy because you’re not buying into the same belief system that they are, and you’re instead questioning, “Why do we believe that, and is that the only option for our belief?” When you do that, you open up new conversations. You open up new possibilities, and I think that’s really beautiful.


Marcus: Virginia Satir, one of my favorite psychologists and family therapists, she’s the woman who pioneered family therapy, she would talk about how people get into habits about how they treat each other and they get into habits about their thinking, and her whole goal was to help people break out of those habits and see new possibilities. New possibilities are truly lovely for how we work together, for what it means to transition from a programmer to a manager, for what it means to be the boss, and we are living in a time where all ideas about leadership are being tossed up in the air and shaken around, because the old guard of hierarchical command and control leadership is quickly failing and fading. The new guard, that’s us. We are trying to figure out what to put in its place, and in the middle there’s a little bit of chaos.


Marcus: All right, hope that was helpful. Change your language. Challenge them with a smile, with a little bit of humor and a twinkle in your eye, and I think maybe I’ll enter into some interesting conversations.


Announcer: Thank you for listening to Programming Leadership. You can keep up with the latest on the podcast at and on iTunes, Spotify, Google Play, or wherever fine podcasts are distributed. Thanks again for listening and we’ll see you next time.


Announcer: This has been a HumblePod Production. Stay humble.

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