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Advice / Succeeding at Work / Work Relationships

Dropping the Bomb: How to Give Your Boss the Bad News

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I remember the time I had to walk into my boss’ office and tell her I’d set the printer on fire, and that it was flashing a message that read, “Ink Burning.”

Thankfully, it was only a ruse so the staff could sing her “Happy Birthday,” but the rather amazing part of the story was her reaction. She did nothing—other than ask me to leave her meeting. It wasn’t until I came back a second time in full-on (fake) panic mode that she finally came down to the break room to see the entire staff standing around a plate of cupcakes.

When I asked her why she hadn’t come down at first—I mean, a fire is pretty serious, right?—she said, “I figured one of two things would happen: Either you’d sort it out, or the smoke alarm would go off and we’d all have to evacuate. But until that happened, I intended to finish my meeting.” Meaning, she came down the second time because I had found something that actually merited her attention—the thought of me throwing a fit in the common area.

Learn from my experience: If you have bad news and actually need your boss’ attention, there are three things you should always take into consideration.

1. Pick Your Moment

We plotted my boss’ surprise during a meeting, because everyone was in on it and it was perfect timing for us. But we had misjudged my boss’ fidelity to her commitments. So first, it’s critical that you find the time that will make the most sense for your supervisor (because, yes, it can vary from when it would work for you) and consider the question of urgency not from your vantage point, but from hers.

For example, say you crash the server. You might think you need to tell your boss right this second—but might it be better to first call tech support and see if there’s an easy fix? Or, maybe you have an ugly run-in with a major client. You might want some time to process and rehash it with a colleague, but if there’s a chance that client will call your supervisor ASAP, you should probably break the news before there are any not-so-pleasant surprises.

If you do need to speak to your boss immediately—especially for personal reasons—do go out of your way to express that these are special circumstances. Begin the conversation by saying, “I know this might not be the best time, but I have something serious I need to discuss.”

2. Choose Your Words (And Tone) Wisely

Now that you’ve found the right time, you need to craft your message. Always tell the end of the story first: “I struggled through the presentation I gave this afternoon, and I could tell our client was not pleased.” Then, apologize (if appropriate) and describe the issues that you think contributed to the snafu. Finish by suggesting your proposed action steps, or by asking for advice.

Remember that the way in which you deliver tough news will guide your boss’ reaction. It’s okay if your tone reflects the gravity of the situation at hand, because people appreciate sincerity. But do resist the temptation to overdramatize an issue that you were able to get under control (no matter how much effort it took). For example, “I realized there was a glitch in the database, and we spent the morning fixing it,” is sufficient. The more measured you are in how you express your news, the more capable you will appear.

If the situation is serious and of a personal nature—e.g., you’re quitting or you have to leave immediately for personal reasons—begin the meeting by taking a less-is-more approach. You can always give more information as the conversation goes along.

3. Lay Out the Next Steps

When there’s an issue at hand, conversations can go one of two ways: They can be problem-focused or solution-focused. And while you can’t control how your boss steers his or her questions—e.g. “How did this happen?” versus, “What do you think we should do about it?”—you can choose how you structure your answers.

Once you’ve covered what went down, shift gears by saying, “Here is what I envision for next steps.” If your boss keeps drawing you back to the issue, use forward-thinking phrases such as, “That’s exactly why I think we should take the following steps so it won’t happen again.”

Tough situations can (usually) be softened when you have a plan for what will happen next. If you don’t know the next steps, at least be able to identify what support you need now or in the future—because, after all, you both want a successful outcome.

Dealing with bad news is tough enough—and sharing it with your boss can be downright painful. But use these tips to have a productive conversation, and you’ll minimize any further damage.