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Book Review: “Help Your Boss Help You”

August 13, 2021


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    Geertjan Wielenga

    Geertjan is Senior Director of Open Source Projects at Azul and Apache NetBeans PMC Chair.

Some books were written to be read once and put aside, others to be read thoroughly several times over and then to be placed behind glass to be broken in case of emergency. This book is of the latter kind—once you've read through it a few times, and dipped into the areas that speak to you most, you want to have it nearby both as a PDF and in hard copy format—as a backup just in case you can't find that PDF at the crucial moment when you really need to have a response at hand in times of crisis. You'll also gradually find your hard copy filled with yellow sticky notes at the points in the book that speak to you most, with underlinings of the crucial passages that resonate back to battles long gone but frequently relived in anguish.

The terms "manager management" and "managing upwards" are probably not unfamiliar to most—and most participants in the modern workplace have a random set of tactics available for handling the power imbalance between managers and their staff. In my personal case, as I am sure in most, the arsenal is somewhat intuitive, containing battle hardened standbys such as "never say 'but', always say 'yes, and', at every opportunity tending toward conflict", trying not to respond to things emotionally, at all, and instead always attempting to sound measured and reflective, together with the trusty bromide of counting to ten (slowly) which, in modern technological terminology can be translated to "don't respond to e-mails immediately, take a deep breath, go for a walk, and miraculously upon your return the problem may have resolved itself all on its own".

In that light, modern guru Jordan Peterson frequently refers to child development psychologist Jean Piaget and the games children play, with his understanding that children play multiple games and that winning a game should not come at the expense of not being asked back to play the next game. A precarious balance needs to be maintained for the game universe to be sustained. Such thoughts and considerations of healthy management ecosystems underpin Ken Kousen's truly excellent and heartwarming "Help Your Boss Help You".

Chapter 1, "Making Inevitable Conflict Productive", starts with the great observation that "Conflict with your manager is inevitable because you want different things." In this chapter, you learn why this is (spoiler alert—your manager's job differs from your job and has different priorities to yours), while giving you tips on managing the relationship (avoiding the situation where every disagreement is a crisis), as well as helping you by encouraging you to take a step back in asking why we go to work at all, with references to Office Space (every modern worker's most loved movie) and Maslow's hierarchy of needs. In short, this chapter sets the scene and points the way forward to the book's mission of presenting the long-term process of building a healthy relationship with your manager.

In chapter 2, "Giving Good-Enough Answers", you're immediately given a "quick win" with a truly awesome technique, thoroughly discussed in 10 pages, that I had never thought of and makes perfect sense—when your manager sends you a question out of nowhere, disturbing your train of thought and disrupting the productive flow within which you find yourself, what do you do? It turns out that "good enough answers" (rather than hard won and time consuming perfect answers) are more than good enough. The author arrives at this insight via a thoroughly logical train of thought... and then presents you with a magic question that needs to be inserted at the end of the interaction in this context with your manager. It is an awesome and truly magical question and worth the price of the book itself and which I will therefore not reveal.

In chapter 3, "Creating Constructive Loyalty", using The Caine Mutiny (1954), starring Humphrey Bogart, as the central focus of his analysis, the author argues for the need to play the long game and, regardless of the manager's loyalty to you, you need to establish constructive loyalty with them. "Constructive loyalty is loyalty you can provide that still allows you to push back when necessary and retain your own sense of self-respect. When your manager does something you don’t like, you will push back, but in a way that doesn’t threaten the loyalty relationship." A very important—and unsurprising though frequently broken—insight in this chapter is that, though criticising your job is a time-honoured tradition, criticising your boss where others can hear may feel justified to you, though is not good for anyone, including yourself, those you're sharing your frustrations with, nor the loyalty relationship with your boss regardless of whether they hear of it. Trashing others publicly changes how you feel about them and erodes relationships especially when they're already problematic.

Chapter 4, "Sending the Important Two Messages" looks at the two messages "I Got This: Taking Responsibility" and "I Got Your Back: We’re a Team", since all interactions with a manager are held to send a message and a key takeaway from this chapter is to always plan sending these two specific messages in each interaction with your manager. In parallel with the chapter 2 concept of "good enough answers", these two most important messages to send are not about perfection—but about intention. The hesitancy that an employee might feel about communicating "I got this" and "I got your back" to a manager is connected to a sense that success and perfection are being promised, while all the manager really needs to hear is the enthusiasm and intention in taking on the task at hand. It would be good to, per meeting with a manager, assess how and the extent to which these messages can be communicated with the end goal of establishing and extending a relationship of constructive loyalty in mind.

Chapter 5, "Winning the Prisoner's Dilemma" discusses ways out of the zero-sum game, where "one side has to lose for the other to win, and when problems are cast in that light, rarely is there a face-saving solution available". From game theory, the author proposes, and assesses in detail, the Tit-for-Tat solution, whereby when there is a disagreement, the employee responds to each move made by the manager in like-for-like form, beginning by going along with your manager and immediately pushing back when your manager does something you don't like, followed by a negotiation and, regardless of the outcome, simply going back to work, for the sequence of steps to be repeated at the next interaction. "Pushing back right away," is a strong thread throughout this chapter, coupled with a continual show of loyalty and respect. After all, silently disgruntled compliance doesn't do anyone any good.

In chapter 6, "Communicating More Effectively" provides you with a thorough guide through the Myers-Briggs Type Indicator, which could just as easily be done via the Big Five personality traits (Openness, Conscientiousness, Extraversion, Agreeableness, and Neuroticism), as well as the Keirsey Temperament Sorter (Guardians, Rationals, Idealists, and Artisans), in order to help you make your arguments to your manager in a way that they are most likely to be heard and understood. If, on analysis, the same type of point of difference continues to hamper the relationship with your manager, the reason may be that you're looking at the situation with different lenses and doing a quick assessment of where your manager falls on the basis of these typologies could be the start of a major breakthrough in the relationship: "The goal as employees is to understand enough about your boss’s behavior to help decide how you deal with them."

"Managing the Chain of Command", chapter 7 makes the salient point that you're not alone in having a boss—your boss has one too. The key message here is to be very reluctant in appealing higher up the chain the decisions made by your boss. Never go around your boss. Your boss will find out. That will not be a happy day in your boss's life and therefore also not a happy day in yours. Escalation should happen through your boss, with your boss's knowledge and cooperation, and only as a final resort: "I really believe this is the wrong move, and I want to talk to (the boss’s boss) about it."

Chapter 8, "Your Boss Is Not Your Friend", is an interesting one because in the world of technology, for which this book is primarily written, that is indeed often the case—from within our own network, we find our colleagues, and even our bosses. The dangers of oversharing are discussed in this chapter, as well as the need to maintain emotional distance. Nicely put, at the end, is that though your boss is not your friend, your boss is also not your enemy. The importance of keeping the relationship well balanced and professional, avoiding feeling personally slighted when decisions are made, with a focus on a friendly professional working environment is the key here.

Chapter 9, "Dealing with Special Cases" handles specific scenarios in the common sense approach taken throughout the book—flat organisations, remote work, micromanagers, young managers, and unethical managers. Rare is the employee who hasn't encountered at least two of these special scenarios. As someone who may be approaching, in some working environments, being in the special case of "Older Employees and Younger Managers", I appreciated the insight that "Older employees are generally more consistent than younger ones." And, in the section dealing with "Truly Unethical Managers", the advice to maintain professional distance and keep emotion out of discussions seems smart. In the case of flat organisations, this chapter addresses the interesting conundrum that "just because nobody has the role of manager doesn’t mean managerial tasks don’t have to get done", as well as the lack of internal processes in such organisations, especially when things are not going perfectly, while everything going perfectly is what the flat organisational structure assumes will always be the case.

Wrapping up the book, chapter 10, "Managing Your Manager", brings all the threads together. As pragmatic as all its previous chapters, here the argument is made for pushing for periodic meetings and adopting reflective listening, where what the manager says should be repeated back by the employee to check for understanding, as well as showing constructive loyalty. Here a crucial tip is found for how to "tell your boss they're completely and totally wrong" by means of one magical sentence that will not be revealed in this review!

"Help Your Boss Help You" is all about being heard and understood and about developing a healthy relationship in your work environments. In particular those in technology domains, i.e., in the context of programming, be it developers, testers, etc, will benefit from this book since that is the context from which it is written and where the author has extensive experience in many layers of such organizations.

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  • Avatar photo
    Geertjan Wielenga

    Geertjan is Senior Director of Open Source Projects at Azul and Apache NetBeans PMC Chair.

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