You may have the seen the commercial. A group of IT administrators are gathered around a conference table. The boss, standing at the front, whirls his arms and hands in enthusiastic gestures, laying out his grand e-business plan.

“So, when can we implement it?” he asks. “When do we get started?”

It can’t be implemented, he hears. It’s a nonstarter. In fact, the boss’s great idea is just plain bad. Every employee around the table agrees, and with the power of numbers against him, the crestfallen chief turns sadly to the camera.

In real life, bearing bad news—especially one-on-one—requires a political finesse that no 30-second television spot can accurately depict. In real life, rather than turn to a camera, the boss might turn on the employee or employees who scuttled his great idea. The boss also may blunder ahead and wreck the company—or the current quarter.

So it’s important that bosses hear bad news. The question is—how do you break it to them? We wanted to find out how IT pros can best deliver bad news to a superior, so we put together this simple scenario with two basic questions to ask a panel of workplace experts:

You’re a network administrator or LAN manager. You’ve been invited to a meeting with your boss to hear an idea pitch for a new project.

  • How do you tell your boss—who thought up the idea or who is really gung-ho about the project—that it is not feasible?
  • How do you avoid angering your boss, being labeled a naysayer, or otherwise injuring yourself politically?

Simple rules and subtle tips emerged from the discussion. Read on for suggestions on how you can prepare for and have a productive “bad news” conversation with your boss.

Save bad news for private meetings
The number one rule for delivering bad news is never criticize your superiors or their ideas in public, according to management consultant and professional development coach ArLyne Diamond, Ph.D.

“If you learn about the idea in a meeting, try to get the topic tabled with a suggestion that some research about it might be helpful,” Diamond said. “Take your boss aside privately and share what you know in a friendly, noncondescending manner.”

When you head into that private meeting, you should be fully prepared to have the conversation, said expert Peter Post, a director of the Emily Post Institute and coauthor of The Etiquette Advantage in Business: Personal Skills for Professional Success.

“The more prepared you are, the more confident you will be in your presentation or discussion, which is critical to convincing people that you know what you are talking about and they should listen,” Post said.

Preparing for conversations like these, however, is not always a strong point for technology professionals, according to Impact Innovations Group vice president John Baschab.

Baschab, who is coauthor of The Executive’s Guide to Information Technology, said, “Technology professionals often get a (sometimes deserved) reputation for knee-jerk overreaction to any new plan of action. Proceeding in a deliberate and measured way to gather the full scoop on the proposed project will ensure that you don’t make a fool of yourself.”

Post agreed and said it’s important you have all your facts checked before explaining your position. “Nothing is worse than explaining why you don’t think a project is viable and then discovering you are wrong,” he said.

Emotional rescue
Any bad-news briefing—particularly if it involves a superior—will try your emotions. Organizational psychologist Elizabeth Gibson, Ph.D., suggests that you should prepare yourself by thoroughly examining what you want to gain from the conversation.

“Think it through. Do you want your boss to change her mind and look at things differently, or do you want to let your boss know just how stupid her idea is and how brilliant you are?” asked Gibson,who headed a team of “change consultants” that successfully reorganized retail giant Best Buy.

After mastering your motives, “discharge destructive emotions,” Gibson said. “Naturally, you may be anxious, frustrated, or threatened about the direction your boss is taking. You need to acknowledge and deal with your negative feelings before you meet with him or her.”

Because you can hardly acknowledge every negative thought around the person who controls your career, Gibson advised using surrogates. Let those bad feelings explode into a tape recorder or onto a notebook, or “tell a very trusted friend, who has no personal stake in the situation, but who understands the challenge you are facing.”

Determining what is important to your boss is also a critical part of preparedness planning.

“Step into his shoes,” Gibson advised. “Based on your experience and observations, write down what things seem to be most important to him. These could be things such as having the corner office (status), never being wrong (image), being well liked, or being well respected.”

Engage, don’t enrage
With preparations complete, it’s time to meet—but approach the meeting with the intent to engage, not enrage your superior.

“You engage in a nonthreatening discussion, affirming the possibility of the idea, yet using some open-ended questions that will help influence your superior,” said workplace communications expert Bette Price, a Certified Management Consultant (CMC).

To keep the discussion with your boss nonthreatening, control the tone of your voice by speaking “rationally, not emotionally,” Post said. “The minute emotions start taking over your presentation, your boss is likely to respond to the emotion rather than to the content of what you are saying.”

Instead of blurting the bad news about a bad idea, Price advises using a series of questions that may encourage your boss “to take additional looks at other solutions.”

Questions are important because they “activate the thinking portion of the brain,” said workplace stress expert Janelle Barlow, Ph.D. “People are less likely to get their emotions aroused when they are answering a question.”

Questions come in many colors and tones. They can sound challenging, threatening, cajoling, or reinforcing. Choosing the right colors for your questions makes all the difference in how people receive and answer them. One common mistake people make is asking a question that’s really a suggestion, Barlow said. For example, ”Do you think we will get into trouble with senior management?” is a suggestion—of trouble—made to sound like a question. Genuine questions might be “What are the implications, both positive and negative, of such an IT implementation?” or “Can we look at both sides of this issue?”

Price provided these sample questions you can model to begin difficult conversations about loser projects:

“You know, Mary, that’s certainly a possible solution, yet before we move forward, can we revisit the outcomes we want to achieve? What is the maximum result you see happening with this project? How will it affect our other applications? What possible customer resistance might there be?”

This “question-consider” approach “takes patience, but it is well worth it,” Price said.

Honesty: Still the best policy
“As a professional, you owe it to your boss—and your team—to be open and honest”, said leadership communications consultant John Baldoni.

But delivering the blunt truth does require tact, so preface your truthful comments by saying, “May I speak freely?” advised Phyllis Davis, founder and director of the American Business Ethics and Etiquette Trainers Association. “After this request, you’ve put your boss and other people in the room on notice that your feedback may not be what they expect to hear, but you’re about to take a risk and speak your truth.”

Remember, too, that honesty is not a one-way street.

“It is up to the boss to create conditions where people can bring bad news,” said Baldoni, who cited U.S. Secretary of State Colin Powell’s opinion that if you are not hearing bad news, something must be wrong.

“Managers must create conditions where subordinates can be open and honest and not feel they will be punished for giving an honest critique,” Baldoni said.

“If a person fears their boss or employer, they’ll seldom speak openly,” Davis agreed. “If a boss doesn’t know how to manage and get the best work from his employees then—let’s face it—he or she is a poor manager.”

Navigating office politics
Polish these tidbits of tact—preparation, engagement, and honesty—with a few subtle tricks of diplomacy, and you will be a master office diplomat capable of handling a variety of thorny issues, the experts claim.

Those tricks, according to Davis: Slow down, stay positive, and know when to fold your cards. “Speak slowly—and avoid speaking in negative terms—when delivering ‘bad news’,” Davis said. “Also—blink slightly slower than you normally blink when someone else is speaking, to give the speaker the feeling you’re really listening.”

If your efforts repeatedly fail, and the boss always blunders ahead, remember what Davis said: If the boss is dysfunctional, it’s a dysfunctional office. It’s up to you to become a master of diplomacy or find another job.”