How Smart Employees Trick Their Boss

On Monday, I wrote about How Deceptive Leaders Hurt Employees. I explained that during times of stress, telling someone to “just relax” insults them. IT is shallow and breaks down trust. There is no doubt that those words are often said without ill intent. But they are hurtful nonetheless.

Pithy statements that are grabbed to offer comfort rarely do so. More often than not, they create distance and more sadness. This is why leaders who are pretending to care are deceptive in nature.

I was overwhelmed by the response to the post. Over 50,000 people read it and more than 150 commented. I also received several very nice notes. Here are a few thoughts that people shared:

Losing my sister 5 years ago changed me and it changes you at the core because you see life differently after a great loss. Life is fragile and beautiful but you have to tackle it every day with love and passion.

I agree that a leader needs to be understanding in times of stress. To be dismissive is easier than to be understanding, but a leader usually does not travel the easy path.”

I always appreciate when readers share their own experiences. But this comment caught me off guard and got me thinking:

Those types of managers are lying, deceiving manipulators who are trying to control your emotions, and how you feel about yourself, so they can feel better about themselves.

The comment stood out for me because of its ferocity. It reminded me that deception is often about power and who has it. In these situations, the boss wants to justify his position of strength and reinforce that he is in control. Even when he is not.

But this must work both ways. And of course it does. We all have done our best to deceive our boss, too. When we do it out of selfish desire, it’s destructive, but when we are doing it because it benefits the business, everyone benefits. But when is it okay to deceive your boss?

The best time to trick the boss is when you need to defy his sense of reality because he is clearly wrong. 

You can do this by telling your boss the exact opposite of what he wants to hear. It shocks the system. That will sound deceptive at first because it violates his worldview — but you are actually speaking the truth.

Here is how to take a contrarian position with conviction:

Repeat his false assumptions
Some bosses work on opinion — not fact. Rather than criticize him, unemotionally restate his argument. This shows that you’re listening and willing to work on a solution. It also allows him to reconsider and perhaps self-correct, without further argument.

Examine the facts
Before your meeting with him, spend time researching your argument. Bring facts to the meeting that address his most deeply held theories. Use these to illustrate why your solution makes sense — and always be as objective as possible.

Review the implications
If your boss still refuses to budge, walk through what will happen if you follow his plan. This makes consequences clear, and opens up room to propose a better way. Your boss might not realize what tomorrow will look like if his bad ideas are acted on today.

We all get defensive at work, because ideas are personal. The key is to stay calm, act confident, and be bold in stating what you know.

To an insecure boss, any disagreement can feel like deception. But when something serious is at stake, you are responsible for presenting a firm, reality-based view. Your boss may second-guess your thoughts and argue that you are speaking in falsities — but this can be the best way to shock him into seeing that you’re right.

How have you tricked your boss?

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 product roadmap and marketing planning software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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