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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