Help Your Boss Help You (PragProg)

Craft your dream role at work by guiding your manager to take your priorities into account when making decisions.

Ken Kousen @kenkousen

Edited by Michael Swaine @michaelswaine

Develop more productive habits in dealing with your manager. As a professional in the business world, you care about doing your job the right way. The quality of your work matters to you, both as a professional and as a person. The company you work for cares about making money and your boss is evaluated on that basis. Sometimes those goals overlap, but the different priorities mean conflict is inevitable. Take concrete steps to build a relationship with your manager that helps both sides succeed.

Guide your manager to treat you as a vital member of the team who should be kept as happy and productive as possible.

When your manager insists on a course of action you don’t like, most employees feel they have only two options: you can swallow your objections, or you can leave. Neither option gets you what you want, which is for your manager to consider your interests when making decisions. Challenging your boss directly is risky, but if you understand what really matters to your manager, you can build a balanced relationship that works for both sides.

Provide timely “good enough” answers that satisfy the immediate need of the boss to move forward. Use a productive solution to the Iterated Prisoner’s Dilemma to structure your interactions with management, going along when necessary and pushing back where appropriate, without threatening the loyalty relationship. Send the two most important messages to your boss: “I got this” and “I got your back,” to prove your value to the boss and the organization. Analyze your manager’s communication preferences so you can express your arguments in a way most likely to be heard and understood. Avoid key traps, like thinking of the boss as your friend or violating the chain of command unnecessarily.

Ken Kousen is the author of the Kotlin Cookbook, Modern Java Recipes, Gradle Recipes for Android, and Making Java Groovy, as well as video courses in Android, Groovy, Gradle, Advanced Java, and Spring. A JavaOne Rock Star, he is also a regular speaker on the No Fluff Just Stuff conference tour and has spoken at conferences all over the world. He has taught software development training courses to thousands of students.

His academic background includes BS degrees in both Mechanical Engineering and Mathematics from M.I.T., an MA and Ph.D. in Aerospace Engineering from Princeton, and an MS in Computer Science from R.P.I. He is currently President of Kousen IT, Inc., based in Connecticut.

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Hi all,

Welcome to the forum for my new book, Help Your Boss Help You, currently in Beta. I plan to post here to let you know about updates, relevant blog posts or presentations, or just to answer questions or respond to comments.

For future reference, here are all the ways to contact me (in addition to this forum):

Ken Kousen

One side note: my last name, Kousen, is pronounced as though it was spelled cousin, like the relative. We have no idea why. It was probably an Ellis Island job, i.e., changed at immigration.


Welcome, Ken! I’ll get to reading your book again now that it is in beta. I love my boss though, so I am one of the lucky folks.


Thanks, Margaret. I’m really glad you love your boss, since presumably your boss is at PragProg. :slight_smile: Hopefully you’ll find the advice in the book useful anyway. Please let me know what you think, but there’s no deadline on that, of course.


I was going to say is your boss you yourself Margaret? Although it’s totally understandable if you meant it’s @Dave - he is a lovable guy after all :smiley:

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Congratulations @kenkousen!

I took Kenneth Kousen’s online class Kotlin Fundamentals at Oreilly. Even though I didn’t finish it because of the faulty internet, I liked it a lot. I’m planning to watch the recording in some days.
He also offers a class called Managing your manager. It looked quite interesting from its title. I didn’t have time to watch it, but I still signed up for the class, so that I’m able to watch the recording once I have time.


Thank you very much!

The Managing Your Manager course is based on an earlier version of the material in the book. In reality, my original – naive – plan for the book was simply to write down everything from the training course, which in turn was based on conference presentations I’d made for about seven years. I was astonished at how much the material changed as I wrote the chapters. The writing process itself really caused me to rethink a lot of principles and practices. I also took the opportunity to get feedback from lots of readers as well, and I tried to include as many people as possible whose backgrounds differed from mine.

So thanks for the kind words about the Kotlin course, and I hope you like both the MYM course and the book. Keep in mind that as long as it’s still in beta, any feedback you give me can affect the final form of the text. Plus I can add you to the acknowledgements if you like. :slight_smile:



@AstonJ I guess the boss would be myself in that I am freelance, but yes, I meant @Dave! Note that PragProg is hiring, so if you want a great boss check out Careers. The DE and copyeditor roles are both great if you have some editing experience and want to pick up a few side gigs.


I find it easy to learn technical skills and very difficult to learn how to be confident communicating with the people around me. Punctual good-enough answers appears to be a useful strategy for me to try. My default response is an overly-detailed, thoroughly-researched, check-every-corner answer that is no longer relevant by the time I finish writing the email five-days later. Managing my manger’s expectations is challenging for me.


I understand the need to give complete, detailed answers to questions, mostly because I hate being wrong. As you say, though, that can take a lot of time. The other side-effect I’ve experienced is that if I don’t feel I have enough time to give a thorough answer, I’m reluctant to answer at all, which also doesn’t help. Both problems are why I try to remind myself that a good answer today is better than a great answer next week.

I hope the “good enough answers” approach helps you. Please let me know how it works out, though I should say that a complete, detailed description of your experience isn’t necessary. :slight_smile:


Congratulations to @kenkousen ! On Friday, Help Your Boss Help You (now in print) hit #1 in New Releases on Amazon’s Business Ethics list. Way to go, Ken!

Don’t forget your DevTalk discount: you can get 35% off with your Devtalk discount! Just use the coupon code “" at checkout