5 toughest work conversations

'Something shady (or illegal) is going on'
toughest work conversations unethical

Let's hope you never work for a Bernie Madoff type. But if you discover bad deeds are happening in your company, what can you do? Say nothing to your boss, and you risk seeming complicit in the wrongdoing. Speak up and you could earn that dreaded label, "not a team player."

Luckily, you can be a whistleblower without blowing your career, says Grenny. You'll need to be diplomatic, though.

"Start the conversation by sharing your good intentions and stressing that you have the boss's best interest in mind," Grenny suggests. "Explain the negative consequences you think will follow if the behavior continues." After all, bilking customers, deceiving investors, and other dodgy practices have been known to destroy companies, taking thousands of careers straight down the tubes. Remember Enron?

If your boss pooh-poohs your worries ("This is how we've always done it"), or even retaliates against you (goodbye, raise), take your concerns upstairs.

"At that point, it's appropriate to approach your boss's boss," Grenny says. "But, so you don't seem to be going behind your boss's back, suggest that the three of you meet together."

What if the rot seems to go all the way up the organization chart? In that case, start looking for a new job.

  @FortuneMagazine - Last updated August 27 2013 09:43 AM ET
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