GOTO - Today, Tomorrow and the Future

How to Help Your Boss Help You • Ken Kousen & Trisha Gee

September 16, 2022 Ken Kousen, Trisha Gee & GOTO Season 2 Episode 36
GOTO - Today, Tomorrow and the Future
How to Help Your Boss Help You • Ken Kousen & Trisha Gee
Show Notes Transcript Chapter Markers

This interview was recorded for the GOTO Book Club.

Ken Kousen - Author of "Help Your Boss Help You" & President at Kousen IT
Trisha Gee - Co-Editor of "97 Things Every Java Programmer Should Know" & Java Advocacy Lead at JetBrains

There are tons of books about how to become a manager and how to improve as a manager, but in this Book Club episode, Trisha Gee talks to Ken Kousen about how you can manage your own manager. They explore his book "Help Your Boss Help You," which takes the standpoint of an employee and how you can build a relationship with your boss that helps you get what you want. What drives the dynamic in a professional relationship, and how can you as an employee steer the wheel for your career?
The interview is based on Ken's book "Help Your Boss Help You".

Read the full transcription of the interview here

Ken Kousen • Help Your Boss Help You
Ken Kousen • Kotlin Cookbook
Ken Kousen • Modern Java Recipes
Ken Kousen • Gradle Recipes for Android
Ken Kousen • Making Java Groovy
Robert Axelrod • The Evolution of Cooperation
Kevlin Henney & Trisha Gee • 97 Things Every Java Programmer Should Know
Matthew Skelton & Manuel Pais • Team Topologies


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Trisha Gee: Hello, and welcome to GOTO Book Club. I am Trisha Gee. I'm a Java champion, and I'm interviewing Ken Kousen about his book, which is now Help Your Boss Help You because Ken, it used to have another title, didn't it?

Ken Kousen: That's right. Forever, it was called "Managing Your Manager." That's always been the idea. And then, when the Pragmatic Programmers did a search, they came up with a handful of reasons related to SEO and everything, where they said, "No, you gotta use a different title," and I'm still getting used to it, frankly.

Trisha Gee: So, why don't you just give yourself a quick intro, who you are, and maybe a bit about why you wrote the book?

Ken Kousen: My name's Ken Kousen (like cousin), as you said. Thank you. It's just not spelled that way. [...] My day job normally is teaching software development training classes. I've been in the IT industry, and the engineering industry before that, for roughly 30-some years. During that time, I've had a wide variety of managers. And basically... this book... the material started out as a presentation I made on a conference tour, the "No Fluff Just Stuff" conference tour, where I used to talk about how you can manage your manager, how you can build a relationship with your boss that would help you get what you want, when you want it, in your career.

And the presentation was always very popular, so eventually, I wound up making a video course out of it on the O'Reilly learning platform, and I wound up recording some what they call "Learning Path" over there. I'd always threatened to write a book down out of it. I was always involved with some other book project, and those books were all technical. And that was part of the challenge with this one, you know, there's no spec to write to. It just was whatever occurred to me over the years of my career.

So, eventually, a friend I knew as an editor moved to Pragmatic Programmers. And when I talked to her, she said, "Look, do you finally wanna write that book?" And I said, "Sure." And we went through the process. She was even my editor for a while, and then she wound up leaving, so I wound up with a completely different editor after all that anyway.

It's basically a book that's been several years in development, but it's been seven or eight years in the material, and then it's been decades in preparation and thinking about these issues if you will.

The books before the book

Trisha Gee: You mentioned some of your other books. I wanted to chat a bit about those quickly before we go on to the main book. The first time I came across you, you were talking at JavaOne about Making Java Groovy. I loved that talk because I was struggling a little bit getting to grips with Gradle, which is obviously Groovy-based, and I was also starting to experiment with Spock as a testing framework, which is also Groovy. What I really needed was not an intro to Groovy. I needed just the difference between what I knew as a Java programmer, versus what I needed to know to be effective with Groovy. And so, I loved your presentation for that. And you wrote a book there as well, right?

Ken Kousen: That was my first one, actually. The Making Java Groovy book is a Manning book and that came out in 2013, believe it or not. I had worked on that one from about 2010 to 2013, that timeframe, when Groovy was still really hot and popular, and a really good integration language for Java. The Java developers picked up Groovy very, very quickly, and it was very popular and useful. That's exactly what the whole idea behind the book was: how do you use Groovy and Java together? Because you don't lose anything by adding Groovy, you just add your own capabilities to it.

That was the first one. And then I went from there to, as you mentioned, Gradle. I worked with the O'Reilly people, O'Reilly Media, as well as some of the Gradle people, and the Google people as well, to write Gradle Recipes for Android. And that book was basically given away by Gradle for a number of years. And by the way, you don't want me negotiating any contracts for you, because I agreed to a royalty on a book I knew they were giving away, so probably not the best planning.

So that book was a small recipe book, and I thought, "Well, okay, I've now written a recipe book for O'Reilly. How hard could it be to write another one for the same publisher?" And that's what started the Modern Java Recipes project, which turned out to be way more difficult than I thought it was gonna be. But that's also when I got you involved, again, because you were kind enough to write the foreword on the Modern Java Recipes book. That was very kind of you. Thank you for that.

Trisha Gee: It was nice to be able to do it. You did exactly what's kind of a difficult thing to do, which is, again, bridge the gap between where developers are and where they wanna be. Like, what are the bits of modern Java that they need to know? So, it was my honor to write a foreword for that book.

Ken Kousen: I'm still surprised at how common and popular that information is. A lot of the features I wrote about came out in Java 8, and it's been over five years since that came out. In September Java 17 will come out, a new long-term support version. When I teach functional Java training classes I still get a pretty full room. And in fact, I was teaching a private class just last week on that same information. So, fascinating to me that there's still quite an audience for that. During that time, Kotlin started to rise again. I was always interested in alternative languages on the JVM and the Android people adopted Kotlin wholesale, pretty much.

And then the Gradle people decided to add a Kotlin DSL to the build tool as well. And both of those drove me to getting involved in the Kotlin community. I then went from that one to another O'Reilly book, called Kotlin Cookbook. Although I didn't write specifically about Android, there's some Android stuff in it, that was primarily about how to use Kotlin for anything you would normally use Java for. It just gives you a good sense of the language and works with things like the Spring framework.

That pretty much brings me to the current book. This is the first time I've written anything that wasn't technical, that didn't have a spec. I could put my own twist on it, as you say, but this was all out of my head, and therefore I have lots of uncertainty and doubts of, "Wait a minute. Why should anybody be listening to me?" You know, I wouldn't call it imposter syndrome necessarily, but I could understand the feeling of, "Wow, are you sure you wanna do this?" But again, most people responded really well to the presentations, and therefore I decided to put all those stories and everything in a book.

How to manage your manager: iterated prisoner’s dilemma

Trisha Gee: I really loved the book, because I think the appeal of it is it's something that we all really want to do. How can I have these constructive conversations with my boss? How can I not necessarily turn the relationship on its head, but I understand this is a two-way relationship. It's not just my boss telling me stuff. It depends on who you work for.

And so, I think that's the appeal of the book. A lot of people want to have those conversations going upwards, whereas a lot of, obviously, management books are about having conversations downwards. I get asked a lot when I'm at conferences, "How can I have constructive conversations with my boss? If I'm unhappy or if I've been let down in some way, I don't wanna just tell them I'm unhappy and have then my leverage be ‘I'm gonna leave’.” I really liked what you talked about in the book, particularly using the iterated prisoner’s dilemma. Do you wanna talk a little bit about that?

Ken Kousen: Certainly. The theme you're bringing up is one of the basic concepts of the book: conflict with your manager is kind of inevitable because you want different things. You're evaluated differently in the organization, and compensated differently, and everything. And therefore, sooner or later, there's something they're gonna want that you won't, and vice versa. And the problem is, most employees feel that if they get into a conflict with their manager, they only have two choices, they can either just go along and do whatever the boss says, or they can leave.

And both of those are extreme positions, and neither of them really gets you what you want. So, the basic concept is, how do I make my manager into an ally? How do I express when I'm unhappy? How do I tell them that I don't like a decision they made without provoking a crisis that turns into a big battle, or forcing me to leave, or anything like that? The part about the iterated prisoner’s dilemma that you bring in there is, it is by far the most famous problem in the mathematical theory of games. It shows up everywhere. It shows up in economics, and in politics, and in biodiversity. I mean, it's just all over the place.

And when you turn into the iterated prisoner's dilemma, the key concept, as identified by Robert Axelrod in his classic book The Evolution of Cooperation, is that cooperation can emerge naturally, even in highly confrontational situations, as long as both sides remember you're gonna do this again, and again, and again. And therefore, because you know that this is gonna be a long-term situation, you can train the other side to learn what to expect each time there's a conflict.

Now, I have to be a little careful because I don't wanna think of the employee-manager relationship as a battle, you know, as an actual confrontation. Because if you're actually in a battle, you've already pretty much lost. Even if you win, you lose. You do need your manager to be your ally within the organization, to some degree, to fight the battles where you're not there. You know, things like raises and promotions, etc.

It's more of a nonzero-sum game. It's more of the idea that since both sides want something different, there are strategies where both sides can get what they want. A lot of it is about identifying what does your manager really need from you? What do you really need from your manager? How do you build a professional relationship based on, the term I use is constructive loyalty, meaning you give them the loyalty that they need, but you do it in a way that allows you to still look in the mirror and to still say, "Yes, I stood up for myself, I asked for what I wanted, and I complained when I wasn't happy. But it wasn't a crisis, and I was able to go back to work."

And most of the managers I've talked to actually like that, because they really do, the good managers, especially, want honesty from their employees. They just want it in a way that doesn't threaten the whole relationship and turn everything into a crisis.

Trisha Gee: There are a few things I really wanna pick up on, and I can't decide which one to pick up on first. When I was reading the book, you said quite clearly that your boss does want different things from you. When I was reading that I was like, "Well, whatever. Sure." But when you're talking about the iterated prisoner's dilemma, and a lot of the stuff that happens in the rest of the book, having that in your head, that your boss does want different things from you, and you inevitably have different goals and objectives, I think that was a bit of a lightbulb moment for me. Of course, in order to work together, you're gonna need to find that middle ground where you're both going to agree. But it is also going to lead to conflict at times, when you want something and your boss wants something else.

Ken Kousen: I use a Venn diagram that I showed a couple of times, where you have your agenda for your job, your career and your life. And your boss has an agenda for their job, their career, and their life, as well. And most of the time, we do operate in the overlap. I mean, if there's no overlap, why are we working together in the first place? So there normally is an overlap. We just have to acknowledge that sometimes there are things you want that'll help you personally, that you care about, that the company may not necessarily care about. And of course, sometimes the manager wants things that may help the group and not necessarily you.

If you want an example, I bring up the situation that I've seen in IT, where you learn a new framework or you go to a conference, and you find out about a new system you wanna use on the job. And you know that going to your manager and saying, "Hey, I wanna use this on our current project," that's not likely to get approval, because you're introducing a lot of risks, and you don't know the framework that well. This is your first chance, you may wind up being the only person who can handle it. That's a hard thing to do, so you might consider carving off a piece of the project and doing it on your own, supposedly on your own time, which then of course creeps into work time, but it's a work project.

Eventually, if it does work, you have a meeting with the group and announce, "Hey, look, I took this new technology and applied it to our project, and it was great," and you minimize all the challenges that you faced and all the problems you faced in making it happen. The manager may not react well to that, but if they do, then, of course, they're faced with a different problem in that, as I say, you've introduced a single point of failure into the project: You're now the only person who can maintain that part of the system. And what if you get busy? The manager may say, "Great." and now they've got another capability in the group they can market. But what happens if you're then full, and don't have time to maintain this existing system? Or if you move on to something else, as you've now demonstrated you're likely to do, or even if you're planning to leave?

So the manager decides, "I tell you what. I'm gonna take a junior person or a new person in the group, and have you train that, bring them up to speed on this new technique, so that they can step in when you're not available." Which, of course, to you sounds like, "Hey, they're asking me to train my own lower-cost, more malleable replacement." So that doesn't feel good either. And yet, both sides did things that were very natural, that fit in their own agenda, they just didn't fit in the overlap. We talk about how to handle situations like that in terms of communication, of pushing back, of making plans, etc., overall, in the book.

Find the middle ground

Trisha Gee: I really liked that particular example. Actually, I liked all the examples, because I've seen a lot of them in the real world. I like that example because there's always been tension there, particularly around introducing a new framework or something, because I have seen that there are certain personality types, as individual developers, who are quite happy to go ahead and do that, and win or lose, at least they learnt something. And other personality types who will never take that risk, which means they also don't reap any rewards from that either.

And that's why I think the book is really helpful. I think it really helps move people closer to the middle ground, not everything is binary. With some of this, you can have these constructive conversations up front, to express what you need, hopefully get what you need, but at least get your manager on side, and perhaps also mitigate risks in advance, rather than dump some big surprise on them, which they have to sort of accept or not later on.

Ken Kousen: Part of the concept is that you really do need to have periodic meetings with your boss. Weekly would be ideal, but bi-weekly, if you can get it. It really is foundational because you need to get to know what the boss really wants, what the differences are between what they say and what they mean. They also need to get to know you, to find out that when you're expressing uncertainty, when you sound like you don't know what you're doing, it's just part of your process of learning. It's okay, as opposed to the times when you really do need help.

If you're having these periodic meetings, and they're one-on-one, they're not group meetings or anything, they're about you and your career, you can bring up this idea of, "Hey, I learned this new framework. I really wanna find a place to use it. I think it's gonna be very helpful for us. Can we pick something?" And then the boss could say something like, "Well, let's pick something that's not on the critical path, that's still interesting, and let's build up your expertise because then I could market it. And maybe let's schedule a lunch-and-learn so we could tell everybody."

In other words, now the boss is part of the team and you're planning together. And of course, if they don't help you if they refuse to listen to you, or whatever, now you know that, too. And that goes in the list of, "Did your boss know you were unhappy?" "Yes, I told them this time and this time." It builds up that experience as well. Plus, you know that you stood up for yourself, that you made it clear that you had priorities, and you expressed them in a way that, again, didn't threaten the loyalty relationship, didn't make a challenge into a crisis.

Trisha Gee: I also want to circle back again to the iterated prisoner's dilemma, because I was reading The Expanse at the same time when I was reading your book. And I was super confused. This idea has come up twice, in two books. I'm usually reading a novel and a work-type book at the same time. I'm like, "How is this idea coming up two times in the two different things I'm reading at the same time?" Where did you get that idea from? Because I know that you're a big sci-fi nerd, so I assume you already read that book as well.

Ken Kousen: Oh, of course. Yeah, I've read the whole "Expanse" series, and I'm eagerly waiting for the next season to come out. No, I've seen the prisoner's dilemma in lots of contexts. I don't really remember which one was first. But actually, you know what, now that I think about it, the best manager I ever had was 20-some years ago. He was a really good guy, and happened to be a guy in this particular case. And he's the one who introduced me to Robert Axelrod's book, that The Evolution of Cooperation. That book is a classic. It came out in the '80s or something. It's been through like 9, 10 printings.

When he showed me that book in the late '90s, that's really where even though I'd heard of it earlier than that, that's where I dug in, and it's the source of information, like, on the Christmas Truce in World War I, and many other situations where you have what could be confrontational situations, where both sides wind up winning. By the way, I do point to a very nice iterated prisoner's dilemma simulator on the web. Did you get a chance to try that out?

Trisha Gee: No, I didn't try that. Sorry.

Ken Kousen: The URL is There are many prisoner's dilemma simulators on the web, but this one is really fun because you could tweak the values, you could play with populations of cooperators versus defectors versus other strategies, and watch how they evolve over time. Just one warning, there's sound involved, so you might have to turn off the sound if you're back in the office now. But otherwise, it's a fun way to learn about the ins and outs of the framework.

Inclusive language matters

Trisha Gee: One thing you just said: The best manager you've ever had, and it was a guy in this particular case. One of the things I spotted from the way that you read the book is you do seem to be quite careful to use inclusive language. You are aware that your advice is coming from a White American male point of view. I like the fact that you are careful not to assume that managers are men, for a start. And you put in a number of examples of women struggling with their bosses. As a White woman, I already have a position of privilege, but my experience as a White woman is that you can't always react the same way to a male boss, that perhaps a man might react to a male boss, and vice versa.

So, I like the fact that you were very inclusive. I'm assuming that was intentional because I know that you try very hard to be an ally.

Ken Kousen: It was and I worried about it more than I even expressed in the book. I worried about it the whole time. I don't wanna make the assumption that my experience is universal. I was very clear in the introduction what my background was, so that people, readers, can take that into account and decide whether this has any effect. On the specific issue of women, both employees and in management, that's simple, because every woman I've ever talked to has at least one story that is just awful by any reasonable standard.

I've known that forever. Sometimes all you have to do is be willing to listen, and you find that out. I've had managers both men and women. Another one of the really good ones I had was when I left a major Fortune 500 company and joined a 12-person consulting group. The owner was a woman. And then, even if she didn't have the title of manager, everybody knows who your manager is in a 12-person company. It's the owner.

And for this book, I wanted to make sure that I got as much feedback as possible from people whose backgrounds were as different from mine as I could find. Even though the writing is from my perspective, I can't avoid that. My wife is a strong woman as well. I got to hear her opinions, well I always have for years, and I know many people who are underrepresented minorities, as well as women and some, both.

I tried to make sure I had readers who came from that area. Just as a tiny example, part of the key to the iterated prisoner's dilemma strategy that we take in the book, the whole tit-for-tat strategy, is that when your boss does something you don't like, you have to push back. And you have to push back in a way that doesn't threaten the loyalty relationship. But you have to push back. The problem is, the same exact words coming from a woman or underrepresented minority can be interpreted completely differently than they would be from a man. I mean, from a man, aggression, if you will, is in fact selected for in most organizations. It's viewed as an asset, even if it's arrogance or a problem. Whereas if a woman or a black male or anyone else says something, the same exact things, it can be interpreted very differently.

The real philosophy in the book is you need to push back. How much you do that, how you handle that, that's your judgment. You make the call there. And of course, the truth is that because you're gonna do this multiple times, the strategy and the relationship you build with your manager will also evolve over time. If it doesn't get you what you need in the long term then it's probably time to leave. But at least this gives you something to try to work with.

I tried to find as many readers as I could who were, again, different in background from me. By the way, thank you for being a reader. I also tried to use inclusive language. For example, the plural "they" is increasingly becoming adopted as singular in written literature. Just like the word "you" went through the same evolution in English over time. I simply tried to use "they" in the book. It took a little time to get used to it, but it was actually surprisingly easy once I tried. That's what I tried to do in the book is to make sure that people felt they were, if not included, because again, it's still coming from me, not excluded. That was what I was trying to achieve.

Trisha Gee: From my point of view, I noticed the effort.

Ken Kousen: Oh, good.

Trisha Gee: One of the things you don't notice you do. If you've been working in technology for 20 years, like me, you actually don't always notice the amount of cognitive load you have filtering through the male-dominated language, for example. You just get used to it. And what you do notice after 20 years is when it's not there anymore. Someone is saying "they," and someone is saying "he or she" and putting in examples from women's point of view. So, it's nice. It's not gonna change the whole world, but there will be readers out there, not just men, who'll go, "It doesn't matter. Who cares?" But I can tell you, from my point of view, it does matter, it does make a difference.

Ken Kousen: There is also, by the way, an interesting story I read. This isn't from me. This is from someone else. I was reading an experience of a, I think it was a Black woman. I'm not gonna use a name, because I didn't get permission. But a story I heard from her is she said, "You know that when a company hires an underrepresented minority, and they try to make a real big deal out of the fact that they're working toward diversity and trying to build a more inclusive environment, they'll say, 'Well, what do you want us to change?' And one of the first things that that person may ask for is the acknowledgement of pronouns. Something to keep in mind is that this person knows what they're asking for is a very little thing. They know it's not major. It's not gonna disrupt the whole organization. What they're doing, in a way, at some level, is testing the manager who hired them. They're testing the company. 'Look, you said you cared about diversity. I'm not gonna try to disrupt the whole company overnight. What if I asked for this little thing? Are you gonna do it, or am I gonna immediately get this rebellion, and then I know how you really feel?'"

I figured, look, how hard is it for me to use "they?" and it took, like I say, a little bit of adjustment, because again, I've got all these years of growing up without it. But it wasn't that hard. And it's not that difficult, and it makes people feel a little better. I'm fine with it.

Building a relationship

Trisha Gee: I think one of the — I'm gonna use the word disappointment, but please hear me through to the end — one of the disappointments from the book was it doesn't, of course, have all the answers. The thing you just said, you know, your mileage may vary. The point is about communication, building up a relationship. It's about a bit of push and shove. So I was a little bit disappointed that there were not all the answers for all the problems I had in the past, and all the potential problems I had in the future.

But again, the takeaway point is communication. You have to communicate with your boss! I liked the fact that you were talking about how to have, like I said at the beginning, constructive conversations, constructive pushback, without having to be aggressive. However, the difficulty, of course, is that you as an individual still have to do all of that work. You still have to go to your boss and say, "I need weekly meetings." You have to have those hard conversations with your boss about, "Look, I was not happy with the thing that you did. I understand the thing that you did." Either "I understand it, and why." Or, "Can you please just explain to me what you did and why?"

And those are awkward conversations to have. It is easier to leave a company. But ultimately, like you say, I think building a relationship that's going to grow and improve is kind of worth a large amount of investment because finding a new job is not that easy.

Ken Kousen: Well, there's a couple of things there. First of all I knew I wasn't gonna be able to address everything that people have encountered because this material tends to trigger stories anyway. I get a lot of feedback on interesting stories and what people have gone through is sometimes not very pleasant. But hey, there's a second edition. Who knows?

It's also hard to push back the first time. It's hard to get those meetings when they don't exist. Every decent manager I've ever met wants to have those periodic meetings. They tend to go out of their way to have them. But if a manager has more than, let’s say, 10 direct reports, then they don't have time for all those periodic meetings every week. It takes up all their time and a reorganization is probably coming.

One of the managers I had in my career didn't wanna do that. Then things got sufficiently bad for that person and they established periodic meetings. At first, it felt awkward, but it got much easier when you're at a regular pace. When you're comfortable with it, not every meeting it's a big deal. Many of the times, it's just, "Look, let me tell you what I've identified and let me let you know what's coming up. Here's what I wanna do." We're in and out in 20 minutes. It's not a big deal.

The other part is about pushing back. Everybody feels uncomfortable pushing back because they're on the weaker side of a power dynamic and nobody wants that, that's awkward. But once the manager learns that you can push back without it being a crisis, “I'm not happy, but I'm going back to work," then that helps. Again, over time, they learn that "Okay, I now need to take your wishes and desires into account, because if I do something you don't like, you're gonna be in my office giving me a hard time about it," but then we'll move on. Then maybe they'll learn and maybe they won't, but a lot of times, they will.

It's more a question of establishing the habit, the pattern, and the long game. I often recommend, and this is in the book, because the idea of pushing back against a stronger power is uncomfortable, that you practice this with a friend. Each side takes the opportunity to be the boss and inject some humor in it, give rewards in terms of massive stock, or pay in hundreds of millions of quatloos, or whatever. Just make it entertaining, so that neither side feels so uncomfortable with it. It's only the first couple of times that this is really stressful. Over time, it gets better. Now, of course, it also depends on what decision they made that went against you. If it was simply that you didn't get acknowledgment on a task, that's fairly fixable. But if you got bypassed for a promotion, that's going to take more of a discussion.

Why are there bad managers?

Trisha Gee: You mentioned a few times throughout this interview about good bosses. I think we all know that the people buying this book are not the people with the good bosses. You have a theory about why we run into poor management more often than we run into good management. Do you wanna expand on that?

Ken Kousen: It's very simple, actually. The thing is that management forms a hierarchy, just like technical people have a hierarchy as well. And the problem is that technical people are what I refer to as working professionals, someone who cares more about the details of their job than moving up in the ranks or making another dollar for the company. We're not on the management hierarchy and therefore, the managers we deal with the most are on the lowest rung of that management hierarchy. If they're really good and have a lot of talent, they're always gonna be looking for the next opportunity to move up. They're people who want to achieve the so-called C-level suite, CEO, CIO, etc.

If they've got a lot of talent, they don't tend to stay in one place very long. And therefore, the ones we deal with the most are either the rookies, the ones who are just new at this, or the people who are never gonna be really good. They had their chance and had never moved up, or the technical professionals who were so good at their job, they got promoted into a completely different one for which they have no training, and maybe no temperament or anything. The combination leads us to be dealing with people who just simply aren't good at it. And the thing that makes it even worse is that everybody in an organization has to act like they know what they're doing. I don't mean overselling their own abilities, but you have to show a degree of confidence, or nobody will listen to you, nobody will trust you with a job.

Managers have that even worse. Now you have somebody at the lowest rung of management, with the least amount of power and influence, and they've gotta tell technical people what to do when they know the technical people know more than they do. And yet, the manager has to make a decision and somehow be believed. So they have to act like they know what they're doing and that combination means the technical people tend to wind up with a very low regard for managers in general.

Trisha Gee: When I first read that part of the book, I was like, "This can't be right." I mean, this is true, too. Management generally doesn’t get good levels of training, at all. I've been in team lead positions. I'm currently managing a team. My title is probably manager. I've been a tech lead and I never got any management training at all.

The only management training I got was when I was a graduate at Ford Motor Company, because they hire graduates to go into management. I was 21 at that time, and I don't remember any of that. So, I figured, I thought it was just the lack of training. Since I read your book, which is now about six months ago, I've been thinking and thinking and I'm like, "You're absolutely right about this."

Ken Kousen: Well, that's very validating. Thank you.

Trisha Gee: It's not to say that there aren't good managers out there, at all. But it is to say that, as technical people, why do we seem to run into these people more often than not. And as you said, they're either fairly new to the job, or if they're not new to the job, it's because they haven't progressed. It's a natural selection thing, really.

Ken Kousen: I wanna make another distinction between the role of tech lead and the role of manager. As a tech lead, you often don't need extra advice on how to deal with it, because the job of a tech lead overlaps a lot with the technical job. You both have similar goals. You're trying to make a project happen. The tech lead has additional management responsibilities, but that's not their career. They're a technical person, and they care about and value the same sets of things. When I'm talking about a manager, I'm referring more to a line manager, someone who does raises, promotions, assignments and decision making, on those levels, and hopes to rise through the management ranks as their career.

I find it notable that a lot of, especially large companies, have management training, but it's only after a manager has been promoted through a few levels of management. They call it an "executive management degree" then. They'll send you for an executive MBA, or even just a couple of week courses internally, but they don't do that for the low-level people. That's one of the shocks that technical people getting promoted to management find out, they are suddenly very expendable. As you know, hiring a new technical person is difficult and expensive. It's a real challenge.

But if you want a new low-level technical manager, you can just put out a job request and you'll get 100 resumes tomorrow. Most of them can all do the job, and if they can't, you just get another one. It is different, from the point of view of technical people. That's also, by the way, one of the fear levels that our managers live with all the time. They know they're no longer valued, they know that if they were technical, their technical edge is going away. They're not getting a chance to use it. They know that they don't have a lot of evidence they could point to showing that they're good at their job. They also, again, are at the bottom of the totem pole. There's a lot of issues, and by showing this constructive loyalty you can't take their fear away, but you can avoid making it worse. And a lot of IT people, with their cutting remarks toward management, wind up making their own lives worse as a result.

Trisha Gee: You're right. The way that you point out what your managers fear, that was very, very helpful for me, because one tends to assume that the person above you is more comfortable, is more confident, more settled. You pull back the curtain on that, the fact that these people often have way higher levels of fear, than someone in a senior technical position, who, as you said, is very difficult to replace. Acknowledging that fear is one step closer to empowering yourself in that relationship with your manager.

Change your situation

Ken Kousen: Exactly. A lot of it is based on empathy. Again, there's always the issue of, "Why should I give them loyalty if they don't give it to me?" You know that, "Isn't loyalty earned? Don't we have to do that?" And my attitude, again, is "Well, absolutely." But that's why you're gonna push back, too. That's why it's not gonna be a one-way street. But it's a long-term relationship that you hope to build over time. And if it doesn't work then you can leave. If you already have one foot out the door and you've already decided, "I'm buying this book because I hate my current situation, and I've gotta..."The old cliche is when you're not happy, you change your situation, or you change your situation, right?

If you're in that position what's the harm in then trying the push-back strategy, and that way, you get to calibrate how comfortable you are with it, how much you can push back, and how it's interpreted, all of these things, that if you wind up leaving you were on your way out the door anyway.

Trisha Gee: No, it's a really good time to practice when you don't care as much, because you already have the other option. You're not as afraid. I think one of the other things I liked about the book is that it doesn't give you all the answers. It can't give you all the answers. It also validated, if you like, that there are plenty of circumstances where you are not going to be able to change it. Make the effort, by all means, have the communication, push back, but it's not your failure if you have to move on to something else.

I think this is important, again, for women, underrepresented groups, etc. I haven't worked in these terrible toxic environments at all, I've just worked in environments where I did not thrive and grow. My experience is, if you do hunt around, you will find the environment that you thrive and grow in. So it was kind of nice, with the book, that yes, you have options to help create an environment which might be better for you, but also, you're not going crazy if the best thing for you to do is leave. And that was very validating.

Ken Kousen: You have to realize that if you leave, what's the guarantee that the next place will be fundamentally different? Wherever you wind up, you're going to have a manager. You're going to have to build a relationship with that person that works for both sides. The key is not to see your manager as family. It's not to say, "Oh, this is my friend, and we do friend things.," like it happens on television. They become not just friends, they become parents or caregivers. And that's a completely different relationship, that you don't want. You want to establish a professional relationship so that each side gets what they want at work, and you still get to grow and be productive in your career. And since it's just gonna happen in the next place anyway, moving from one place to another doesn't change who you are. Your next manager may not have any more training than the last one. Each time, it's an opportunity for you to refine the skills.

Again, the whole philosophy is, as you mentioned at the beginning, the whole management literature is written for managers, for leaders, for people who wanna rise in the ranks and become change contributors, and all these things. There's almost nothing written for the working professional, who's still got to deal with managers, but isn't necessarily on a management track, or at least not now. Maybe someday. And they still have to find a way to build that relationship.

Especially things like friends and family, these are mistakes I made so many times in my career. This is why I know this stuff. It's also why I get kind of wired and hyped up on some of them, it's because I'm trying to fix problems that I had when I was early in my career.

Trisha Gee: It's really good.There are two things I wanted to cover. One is I know plenty of people who haven't left a job that is, not just sub-optimal, but one that's making them unhappy, "Because I have friends there. Because I don't wanna let them down." I get that, but it's, in some cases, literally giving you physical health problems. And you don't wanna leave because of why? Because a lot of the people there won't see you the same way at all. You have to put yourself first. As you said, they're not your family, they're not your friends. If you need family and friends, then either go and find other family and friends to have outside of work, or, by all means, keep up these friendships outside of the work relationship, but move your work relationship somewhere else. Don't feel tied in. It's almost like a Stockholm Syndrome type thing, where you feel like you're all in this together, and you have to stay. Have you got a comment on that?

Should your boss be your friend?

Ken Kousen: Just one quick comment that I wanna make a distinction between having friends among your co-workers and friends with your boss. You can have friends with co-workers. That's a team, those are people you see all the time, you have similar goals. You may be competing in a way, but it's not a hostile competition. You're not the ones making the decisions that affect your co-workers' careers, or, if you are, you're hurting yourself in the same process. That's different.

Whereas, your boss is not your friend. That's the key. Early in my career, I thought that by having my boss as my friend would protect me when I made mistakes. There's a big difference between being friendly, which everybody wants to do and having your boss as your friend. And when I say your boss is not your friend, I'm not saying that you have this conversation with your boss and say, "Hey, you're not my friend." It's not like that. You need to protect yourself internally. Because if you think your boss is your friend, there are two traps that you can fall into.

One is that you'll tell your boss things you would only tell friends. You know, "Oh, how'd it go this weekend?" "My spouse was unhappy, I'm not spending enough time with the kids, and I've got this problem and that problem." And your manager's sitting there thinking, "I was thinking of offering them a promotion, but it's only gonna increase the amount of time they spend at work, and I don't wanna do that." You don't want them thinking that at all. You don't want them taking friend issues into account when they're making career decisions for you. That's one.

And the other trap, if you think your boss is your friend, is the first time they make a decision that goes against you, you're not gonna see it as a professional decision. You're gonna be surprised, and you're gonna be hurt. If your initial impulse is to say to your boss, "I thought you were my friend," you've fallen into that trap. Because your boss's response could be, "If you were my friend, you wouldn't have put me in this position." You know, it's really different.

There's nothing wrong with being friendly. And there's nothing wrong with being friends with everybody else at work. That's fine. But now, back to the point you were making, you may feel you don't wanna leave because of your teammates. There's an old saying that you wanna always be the worst player in the band. You wanna be in a situation where you have things to learn and people that can help you, etc. I gotta admit, I don't think I could handle being the worst player in a band, but I don't wanna be necessarily the best player in a band. I get that. But that's different. You can be with your friends and you can help out your friends. But if you are miserable, if you are unhappy, that's gonna hurt your performance, and that's gonna drag everybody down anyway. How are you really benefiting them? They can't fix your relationship with your boss, just as you can't get involved in their relationship with their boss either.

Trisha Gee: For sure. I have a few anecdotes of the "boss is not your friend" thing. I actually was friends with my boss many years back, and everyone in the organization knew that we were friends. We would hang out, go to the pub, we would chat. I really wanted to be promoted, and when it came up for promotion, I didn't get the promotion. And he was like, "How would it look if I put you up for promotion? Because everyone knows we hang out all the time." And I was like, "Man, that totally backfired on me." I mean I want to be friends with him anyway but I had not considered that. It's a real piece of advice, to understand that your boss has to go to bat for you or not. Those boundaries become very difficult to negotiate. "Do I pick my friend? Or do I pick my job?" You know, that kind of thing.

Similarly, right now, I really wanted to disagree with the "boss is not your friend" thing, because, in my team, I am the boss, and they're all my friends. And I love my team so much. Like, we have this really great team. What I want to say, I feel like it makes us stronger that we can be vulnerable and honest with each other because I've never been able to do that with a boss before. I do know problems that happen with some of my teammates because they are open to me. I wanna say, like, "No, of course, you can be friends with your boss." But it does actually make life a little bit tricky, because, as the boss, you are thinking, "Oh, well, I don't know, what should I do?" Like, you say, should I be burdening this person? What should I be doing?

On the other hand, having an open and honest conversation we do, at least, the benefit is that I can usually have open and honest conversations with the team of "These things are coming up. This looks like a good opportunity. This doesn't look like a good opportunity. This might be good for your brand, or it might not be." But I wonder if maybe that's either an anomaly, or I'm gonna run into a problem at some point in the future. Or it might also be a function of the fact that we're all very senior.

Even though I'm not a manager's manager's manager, we all have a lot of experience. I've got 20-odd years’ experience, I'm leading a team of people who are all very experienced people, who have also been managers in the past. I wonder if some of that contributes to a different dynamic. I guess what I'm saying to you, Ken, is please tell me that everything's normal, and everything's fine for me.

Ken Kousen: First of all, I've met a few members of your team, at least online, and you're right, you have a wonderful team. They're great. I have nothing but complimentary things to say about them. Feel free to pass that on. But also, you are the manager, and therefore the dynamic is different. It's different when you're the weaker party in the power relationship. And, again, it's not a question of not being friends, it's a question of protecting yourself, so that when things that would trigger an emotional response from a friend would happen, you recognize it's a professional relationship, and that doesn't mean it can't be a good professional relationship.

But friendship is a different relationship, and you can get that elsewhere. Of course, maybe when you no longer have the power relationship together, that doesn't mean you can't still be friends. Absolutely. But while it's going on, especially if you're the weaker side, if you're the one whose career decisions are being affected by a manager's decisions, at least I need professional distance to be able to handle it when something goes against me.

The thing is a lot of situations work just fine when the company's making money and everything's going well. Almost any situation works then. We've seen lots of Silicon Valley companies that could be massively dysfunctional, but the problems don't show up until something goes wrong. And that's what you're partly preparing for, what happens when bad things happen, when we're under financial constraints, or there are layoffs. Or, maybe a good thing comes in, and there's an opportunity to work on a new project, and you don't get selected.

Another situation you described for me once was that your manager had the wrong title. That your manager turned out to be someone who had a completely different title. I often say that titles could be anything. The person who makes decisions affecting your career, raises, promotions, etc., that's your manager, whether they have the title or not.


Trisha Gee: Exactly. I took a lot from the book and we've already covered a bunch of the things here. We haven't had a chance to touch some of the things I really wanted to talk about. I have already recommended your book to six or seven people before it was even out. I highly recommend it, even if you're not struggling with your boss. And if you are a manager, I think it's a really good idea to read the book. Ken, I just wanted to ask you if there was anything else that you wanted to talk about before we sort of finish up the interview.

Ken Kousen: I just hope the book helps people, honestly. When we were changing titles of the book, and we were looking for a new title, one of my friends suggested that really the title of the book is "How To Be an Employee." It's how to effectively operate that way with a manager. And I liked the title "Help Your Boss Help You." And in fact, I can watch people slowly talk themselves into it, over a period of about five minutes. If you're interested in what I'm doing, or how any of this is going on, or how related issues are happening, I have a free weekly newsletter called Tales From The Jar Side, that I put out every Sunday. I'm also writing a series of Medium articles that are extracts from the book or based on topics in the book, that are available through The Pragmatic Programmers publication. And, of course, feel free to get in touch with me via email, or on Twitter @kenkousen, or whatever you like.

Trisha Gee: I highly recommend the newsletter, because I like the fact that sometimes you can tell the stories that you wouldn't be able to tell, either in the blog post or in the book. And I do skim through it. I sign up to a lot of newsletters, but yours is the one I generally skim every week, apart from the one where you mentioned me, I didn't read it that week.

Ken Kousen: That was a test. Yes.

Trisha Gee: Yes, it was a test. Great. Thank you so much, Ken. I can't recommend the book highly enough. I do think that everyone should read it. And thank you for taking the time to talk to me about the topics in the book.

Ken Kousen: Oh, I always enjoy talking to you. And thank you very much to the GOTO people as well, for giving me the opportunity.

Trisha Gee: Yeah, thank you.

The books before the book
How to manage your manager: iterated prisoner’s dilemma
Find the middle ground
Inclusive language matters
Building a relationship
Why are there bad managers?
Change your situation
Should your boss be your friend?