3 min read

What Kind of Person Argues With the Boss?

Three reasons why arguing with the boss is a terrible idea - and tips for how to prevail nonetheless
Graffiti of two heads, one saying "Shall we boykott the rent?" and the other answering "Yeah good idea"
These two have a future in politics, I predict | Picture by Author

Greetings friends!

Now that I’m out of the corporate environment, I thought I’d see fewer examples of people behaving in self-destructive ways.

I’ll pause for those of you laughing out loud.

Turns out people are idiots in private life as well. Get into a shouting match with the police officer who pulled you over? Cuss out the harried airline staff when your flight gets delayed? Oh, the pickings are plenty.

Still, nothing conveys futility like picking a public fight with your boss. (Hmmm. How about removing the pins in one’s hand grenades in advance to save time?)

Three Ways You Can Lose

1. You lose if you’re wrong

The chances of you being wrong are not zero. It’s hard to recall at the moment but your boss likely didn’t get there by random chance after demonstrating a complete lack of skills. Unless you are working in politics, in which case all bets are off.

If you are wrong, your boss will think less of you for arguing with him or her.

2. You lose if you’re right

Proving your boss wrong is even worse than being wrong yourself. Your boss will likely thank you for publicly pointing out their error while seething inside with the fire of a fresh volcano.

You won’t be able to point to specific retaliation but, oh, will you experience it. Fully and richly, for months. And it will be deserved.

3. You lose regardless of the merits

Your colleagues watching take note of the sap who just took themselves out of the running for promotion.

The other managers take note of the troublemaker who thinks a public fight with their boss is a good idea. The list of people slated for “alternatively structured ‘work from home’ without pay” just got longer by one.

Blue plastic change purse with the words “Change is Good” printed on it
Act rashly and this will suffice to hold your salary | Picture by Author

How to Correctly Correct Your Boss

I am not at all suggesting that you let your boss’s bad ideas and mistakes go unremarked. Unless you are angling for your boss to fail (or you work in politics … but I repeat myself), in which case all bets are off.

The correct way to point out to your boss an error or raise a potential criticism of any kind is in private and by carefully preserving the boss’s ego:

  • Oh, exalted one. Just last week your nemesis Manager X recommended that idea and the CEO spanked him! It was delicious to watch.
  • Mighty potentate, a moment. (Hastily flipping the pages of your notebook.) Last month you told the board, and I quote, that it would be suicide for the company to pursue that path because it’s illegal, immoral, and worst of all, unprofitable.
  • Your haircut makes your face look positively aquiline in profile, did you know that? Almost noble, I dare say. It is also a noble idea to violate the laws of physics and the pedestrian notion that time only goes in one direction. That’s the kind of revolutionary thinking that demonstrates a true leader.

The Art of Skillful Interpersonal Management

This may surprise younger readers but I can confirm this ill-kept secret: The best idea does not always prevail on the objective merits.

This is both shocking and disturbing, especially for smart employees who have both facts and logic on their side. This leads them to the all-too-common mistake of thinking that if they just explained the facts and logic more clearly, their boss would understand and change their mind.

I’ll pause for those of you laughing out loud.

When most people encounter this phenomenon, they assume that corporations are inefficient and people are stupid. While this is often true, it takes many years more experience to understand an even greater truth: The best idea is often not the right one to pursue.

“Wait, James. That’s an oxymoron. How can the best idea not be the right one to pursue?”

Lots of reasons, dear reader. It may be that we already tried it and failed because it did not fit our culture, didn’t match customer expectations, or required too much time or money, etc.

Because the world is imperfect, imperfect solutions sometimes fit best. Only in a hypothetical world does the “best” solution work best every time. In the real world, there’s a history — both to people and the organizations they’re in.

Thus, when the boss rejects your brilliant and obviously correct idea, take a moment to consider the possibility they’re not an idiot.

Otherwise, you risk demonstrating that you are.

Be well.

By now you know I’ll say you can reduce the chances of being an idiot by reading more of my stories. It’s possible I’m right. But I could be wrong. There’s only one way to find out.