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Making Your Boss Happy Is Not Your Job

Job security is important. Nobody ever wants to worry about where their next bank deposit will come from. One of the most direct ways you might seek to ensure your job security is through making your boss happy. But no matter how this decision is viewed, the underlying logic is fundamentally flawed. If you treat making your boss happy as an end goal in itself, you are jeopardizing your career.

The Motivation to Please

Getting it in your head that pleasing the boss is of top importance can happen in many ways, good and bad. In the worst case scenario, you are just a sycophant, looking to brown-nose your way to the top. On the opposite end of that spectrum, it could be that you are incredibly loyal, and you want to do everything in your power to support your boss’s vision—whatever it may be. Most people probably lie somewhere in-between these two extremes: just a tad paranoid, and assuming that doing whatever the boss wants will reap positive benefits for everyone.

Alternatively, a pressing desire to please could also stem from simple respect for the chain of command. Your boss is higher up the food chain than you, with increased vision of what is happening in the business. Thus, if the boss wants work to head in a certain direction, you take it on faith that it is the right move. Indeed, faith like this is required in business to an extent; think how annoying it would be if no one ever trusted your decisions! But blind faith in leadership is a problem.

Whether your dominant urge to please the boss stems from paranoia, loyalty, or too much faith, the end result is the same: inferior business results.

Tragedy of the Lemonade

Working exactly and exclusively to the vision and specifications brought forth by your boss is great if your boss is infallible. If that is the case, and you have set up a small shrine to your boss’s glory in your living room, then that is terrific. Otherwise, you are creating risks to the business and to your career advancement.

Let’s use a simplified example of a lemonade stand, run by Veronica and her subordinate Betty. Their business goal is to increase lemonade sales from their single location (Veronica’s front lawn), and right now they have 15 dedicated customers (the construction crew across the street). These customers always buy exactly one glass at lunchtime. (They only get short breaks.)

Veronica decides it would be a good idea to delight her customers by selling fun-shaped ice. She wants to send out Betty to buy molds to make dinosaur-shaped ice. Betty thinks it would be a better idea to spend her time putting up fliers on telephone poles around the block to advertise the business. Nonetheless, Betty follows Veronica’s order, and the construction workers are soon drinking dinosaur-themed lemonade. They love the silliness of it, which fulfills Veronica’s goal of increased customer satisfaction, but the construction workers continue to buy exactly one glass of lemonade per day. (Time restraints do not make it convenient to buy more.) Thus, Betty has made her boss happy, and improvement to the business as envisioned by the boss has occurred.

But the “improvement” has not actually added value to the business—sales remain static!

Had Betty stuck to her gut and advertised for the lemonade stand on telephone poles, the potential pool of customers would have expanded beyond their current base. Instead, she followed Veronica’s strategy of trying to squeeze more sales out of the existing base, which is impossible to realize since the construction workers are already buying as much lemonade as they can. Veronica’s noble intentions have amounted to nothing, and Betty’s actions have also amounted to nothing by following her. (Wow, this lemonade stand example went to a dark place.)

Metrics and Outcomes over Smiling Faces

Let’s break down what really happened in the above example:

  • A basic goal was defined: increase lemonade sales.
  • The boss developed a strategy to realize that goal: increase customer satisfaction of the existing base in order to entice them to purchase more.
  • This strategy disagrees with known metrics, namely, that construction workers do not have enough time to conveniently drink more than one glass per day.
  • The subordinate disregards her own strategy for improvement—one that could have worked—in favor of just following her boss’s instruction.
  • Nobody acts selfishly or maliciously. All actions are well-intentioned at every juncture.
  • The final result is that the original goal is never realized.

This example illustrates, among other things, one critical fact: All of your actions as an employee should align with organizational goals, and these actions must agree with available metrics. Ideally, the work your boss gives you will agree with both of these criteria most of the time. But when your boss wants to give you work that misses the mark for achieving a goal, or completely misses the point of the goal altogether—you need to verbalize it.

Any time that you do not see how your work will create business value, you need to seek clarity about it from your boss. You cannot afford to be worried about undermining your boss’s judgement—any good boss will have no problem articulating the importance of a task for you, assuming it exists. But if you actually prove that the task has no value, you might be able to work with your boss to develop an alternative course of action. The business bottom line will benefit from your foresight, and your boss will appreciate your critical thinking.

So in other words, sometimes the best way to make bosses happy is to convince them that everything they want to do is wrong.

The Danger of Only Seeking to Please

What happens when you keep your mouth shut or turn your brain off when no-value-added tasks come along? You contribute to a culture of busy work, business as usual, and stunted innovation. Your boss may not see that. Your boss might even be quite happy with what you are producing, not realizing that the work is ultimately irrelevant. In this way, it is clear how only aiming to please your boss can be damaging to business.

But this attitude is directly damaging to your career as well. Producing trivial work on a regular or semi-regular basis does not contribute in any positive way to making you more hirable in the future. It also does not make you look like a valuable employee to people higher up the food chain than your boss (unless misalignment of objectives and metrics runs rampant up the chain).

Worst of all, if you are actively aware of the fact that you are doing trivial work, it will start to eat away at your dignity. It will negatively affect your performance over time, until busywork becomes the only work you are cut out to do anymore. Is this really the fate you want to risk?

Do everyone a favor and start questioning your boss’s reasoning more often. Your boss will be better for it. The business will be better for it. You will be better for it.

About John Friscia

John Friscia is the Editor of Computer Aid's Accelerating IT Success. He began working for Computer Aid, Inc. in 2013 and continues to provide graphic design support for AITS. He graduated summa cum laude from Shippensburg University with a B.A. in English.

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