Should You Keep Your Boss from Making a Mistake?

What would you do if you knew your boss was making a bad decision?  We’ve all been there.  How did you respond?  Do you sit back and watch it.  Or do you step outside your comfort zone and address it?

My father once told me, “No matter what your official title is, part of your job is to make your boss successful.”  Making your boss successful isn’t about sucking up. It’s about making sure your boss delivers results.  That can include saving your boss from making a mistake.  It’s a tricky area to navigate.  People are often afraid to challenge their boss.  But it doesn’t have to be a challenge.  If you handle it the right way, your boss will see you as supportive.

In his role at the FDIC, my father often worked for a senior level political appointee. Because my Dad was closer to the front line operation, he had institutional knowledge his boss didn’t have.  It gave him a different lens on things.  My father said, “If I see my boss making what I think is a bad decision, I’ll approach him in private, and share my concerns.  I don’t charge in and say ‘You’re making a bad decision.’  Instead I say, ‘Hey boss, I’ve been thinking about this.  Part of my job is to help you be successful, I don’t want this to go down the wrong path.’”

Here are four rules for helping your boss.

1. Do it in private
It’s rude to call the boss out in public, and it’s downright subversive to tell the rest of the staff what a big mistake the boss is making.  This seems like a no brainer, but based on the number of people I see routinely dissing their boss, it merits a mention.

2. Don’t make the boss wrong
Instead of barreling in saying, “You’re making a stupid decision,” frame it as a conversation.  Say, “I’d like to talk to you about X, you know I’ve got your back, I’m concerned this might be perceived wrong, or not be effective, etc.” You’re not there to tell your boss he’s wrong.  You’re there to provide support, a different perspective and intel he might not have.

3. Be concise
Share your concerns, but don’t go on and on.  Be clear about why you’re concerned, even if it’s just a feeling.  That’s OK, simply say, this is why I’m worried.

4. Give the boss space
Don’t try to close the deal and get your boss to change his mind on the spot. Instead, provide him some things to think about.  Then simply say, there are a lot of things to consider, let me know if you’d like to discuss it more after you’ve thought it over.

5. Don’t prove yourself right
If, despite your wise counsel, your boss decides to stick with his earlier course of action, don’t stand on the sidelines waiting for him to fail. Your boss needs to know you have his back, even if he makes a decision you may disagree with. Just as you have one set of information, your boss has a differing perspective.He may know more than you.Even if he is making a mistake, having an unsupportive staffer only makes it worse.

My father used to say, “Put yourself in your boss’s shoes.” You’d want someone to tell you if you were about to make a mistake.

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