Managing Your Manager: The Video Course

I’m a regular speaker on the No Fluff, Just Stuff tour (I’m now entering my ninth year, which I can hardly believe), and one of the talks I’ve given there for many years is called “Managing Your Manager”. It’s been one of my most successful talks, and I’ve given several versions of it, including as keynotes at UberConf and DevNexus, the latter of which was recorded on a YouTube video.

Over the past couple of years I’ve been recording video courses for Safari Books Online. Until now they’ve all been developer focused, ranging from a Spring Framework Essentials and Reactive Spring to Understanding Java 8 Generics to Gradle Fundamentals to Practical Android. I have about a dozen courses there, all of which involve technical topics. Those courses normally consist of me preparing materials ahead of time, then going to the O’Reilly Media offices in either Boston, MA or Sebastopol, CA, and talking to a camera for a few days. As a frequent conference speaker and someone who teaches training classes for a living, this is quite natural for me.

Late last year I decided it was finally time to turn my Managing Your Manager talk into a video course, which is now available on Safari. This course is an expanded version of the conference talk, based on what I’ve learned in my roughly 30 years in industry, dealing with big companies and small, working with managers ranging from very good to horrible.

The basic concept is that the vast majority of the literature on management is aimed at managers, trying to show them how to be more successful so that they can ultimately rise to what’s referred to as the “C-level suite”, i.e., CEO, CIO, CTO, and so on. The problem is, there’s very little of quality written for the regular worker who has to deal with management all the time but doesn’t necessarily aspire to line management roles.

This comes up a lot in areas related to I.T., though it applies outside that area as well. Many developers are interested in writing code or other software architecture related tasks, and to them success involves accomplishing their goals with well-written, testable, maintainable code that embodies the latest thinking in software development and architectural patterns. They generally care much more about the details of the project than the interpersonal or financial aspects, though those will influence what they do in a concrete way. They may even take the role of a tech lead and have some limited management responsibilities as a result.

Line managers, however, of the type I discuss in the video, have different goals. They are interested in building successful projects as a way for them to gain more responsibility and experience and use that as a way and rise in the organization or prepare for a move to a new company with greater opportunities. This has a significant impact on how they think, and understanding that directly affects how we deal with managers.

A story I use in the video involves a famous actor during his first experience as a movie director. The other actors on the set knew this person as an actor, so they liked having actor-type discussions with him, like the back-story of a given character, deeper motivations that drive the plot, events occurring outside a given scene, and so on. The director, as an actor, also liked those discussions. But as he said in the article:

The whole time I had a little voice in the back of my head saying, “we’re losing the light, we’re going to have the pay the crew overtime, I’ve got to process the dailies for tomorrow, I have to meet with the financiers, and so on.

In other words, despite the director’s years of training and success as an actor, he knew that he was going to be evaluated based on money. The budget was just as important to the definition of success for him as the artistic aspects of the movie.

(BTW, I would link to that interview, but sadly I don’t remember who it was or where I saw it. From what I gather, that’s a pretty common experience though.)

Managers are strongly focused on the money aspects of any project, and the higher you go in management, the more that dominates their thinking. Knowing that is an important part of building a successful relationship with a manager. You can’t change their focus, but you can take that into account when you work with them, and it often helps to explain their actions, especially when they don’t do what you would like.

Other topics that come up in the video course include:

• The natural reason why so many of our managers so bad
• The crucial question of loyalty
• Strategies you can use from the Iterated Prisoner’s Dilemma problem
• Determining your manager’s communication preferences

That last issue makes use of personality typing techniques, which are controversial at best. The controversy usually arises from applying them incorrectly in industry. When I talk about them, I’m not trying to convince you that they describe reality in any detail, and I’m certainly not trying to get you spend any money. I just use them to help you figure out how to make your arguments in a way that is most likely to be heard by your manager, maximizing the likelihood you will get what you want.

I also have a series of what I call constructive loyalty “How To’s”, like how good enough answers today are much, much better than great answers next week, and understanding that Your Boss Is Not Your Friend, and how to use lessons from Reflective Listening to participate in discussions with your manager when you would rather not, and finally, the Best Way To Tell Your Boss He Or She Is Completely Wrong.

I’m hoping to create a series of blog posts here to describe some of these features in detail, assuming I can free up time from other commitments. Many of the topics I talk about do not appear to be common knowledge, and have come from several bad decisions I made during my career (old saying: “Good judgement comes from experience, but experience comes from bad judgement”), so I want to help others benefit from my thinking and especially from my mistakes.

The inimitable Dan Woods (@danveloper on Twitter and now a manager at Target in Minneapolis) once called a version of this talk the “best talk of the conference” at UberConf, and a friend of mine who is a former Senior Vice President at a Fortune 500 company agreed with many of the recommendations and offered his own advice in several areas. As I say, it’s been one of my most successful talks for years, and now it’s recorded, in expanded form, for anyone to see.

(Okay, anyone with a Safari account, but you can always sign up for the trial, watch the video, and then cancel. I won’t say anything if you won’t. Besides, Safari Books Online has tons of content, from books to videos to training classes. It’s basically the Netflix of technical (and business!) content, so you might like it anyway, especially if you can get your manager to pay for it.)

Since any reputation that I have is based on my work in technical areas, this video might not otherwise be noticed by people outside my direct community. I’m mentioning it here to try to give it a bit more exposure. If you like it, great! Feel free to leave a comment on it. Otherwise, hopefully you’ll find a few ideas to think about in your future career.

Finally, feel free to tell me “that turns out not to be the case” on Twitter (I’m @kenkousen there) if you disagree with everything I said.