How to Talk About Failure to Your Boss

It’s tough enough to talk about failure with people who are closest to you, and it’s even harder to talk about failure with someone who is in charge of your salary. But I have an announcement for you: Nobody benefits from a conversation about failure more than your boss.

Your boss needs you to be brave and talk about failure. She wants you to tell her when things are about to go wrong. The sooner, the better. If you have conversations with your boss about failure early, and often then you’ll set a gold standard in your organization for honesty, transparency and radical candor.

Start with the Stuff You Can Solve

Whether it’s your mistake or something your boss messed up, there’s no bigger win than solving a problem for your boss that’s about to make everybody look stupid.

Intervene Early

Failure spreads throughout an organization like a butterfly effect. There’s a small, initial microfailure that happens in a meeting between two people. Then those two people fail with other two people. Suddenly you’re Lehman Brothers, and you’ve bankrupted America. The sooner you contain your microfailures, the better. Intervene early and get to your boss before she’s swept up in enterprise-level macrofailures.

If Necessary, Wave a Red Flag

Very few things explode at work without notice. What usually happens is that a team makes a choice to ignore signals that a project is about to implode. And if you’re one of the millions of disengaged workers who hate their jobs, why stick your neck out and be the bearer of bad news? You get a paycheck anyway. I’m here to tell you that if you see warning signs of failure, wave a flag and shout from the rooftop. Do what it takes to garner your boss’ attention before things go to hell in a handbasket.

Don’t Be a Snitch

Everybody knows who’s at fault without naming names. So when talking to your boss about failure, don’t be petty. Focus on identifying the risks and overcoming obstacles instead of informing on your colleagues.

Even under the best of circumstances, talking about failure is awkward and off-putting. But while your colleagues are taking a smoke break or ordering a second frappuccino of the day from Starbucks, you could emerge as an organizational hero by talking to your boss about failure.

Talking to your boss about failure is as simple or as hard as you make it. The one thing for certain is that it gets easier with practice. If you’re earnest and helpful, I promise that your boss will trust your good judgment and begin to seek your advice proactively.

Becoming a strategic adviser to your boss? That’s the best outcome of talking to your boss about failure.

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