Should We Tell the Boss?

Here are five things your boss always wants to hear -- and five things he hopes you'll never tell him.

As an IT professional, you know the basic rules of office politics, the simple do's and don'ts that govern life at work. Adhering to these standards -- the ones that tell you to be proactive and a team player -- will help you keep your job. If you really want to advance, though, you need to know which types of information your boss relies on you to provide.

More isn't necessarily better, however, and discretion is everything. So, you also need to know the kinds of information your boss never wants to hear from you.

We asked a group of Computerworld's 2008 Premier 100 IT Leaders to talk about the kinds of messages they need to hear loud and clear from their employees and the things they never, ever want to hear. Here's what they said.

Five Things You Should Always Tell Your Boss

1. The real story.

"Sugarcoating problems, holding back information, overpromising and consistently underdelivering are all reasons why IT has a bad reputation. We do this so well, we don't even realize there is a problem," says Robert Strickland, senior vice president and CIO at T-Mobile USA Inc. in Bellevue, Wash. "To lead effectively, I need the complete picture, as do our customers and our suppliers. When information is withheld, you are protecting no one."

Neal Puff, CIO for Arizona's Yuma County, agrees, but with the caveat that this is not a license to vent. "People sometimes confuse the truth with their opinion," he says.

2. Your ideas.

"Bring me ideas to improve the business, even if they're outside of IT," says Kumud Kalia, CIO and executive vice president of customer operations for Toronto-based Direct Energy, an integrated energy company and part of Centrica PLC.

Sounds simple enough, but Kalia says workers are often reluctant to do this, thinking they have to go through established chains of command. But that's not necessarily the case. Bringing ideas straight to the top can help get initiatives going. "I can help get things launched and broker the appropriate conversations," Kalia says.

3. What you want.

Ted Maulucci, CIO at Tridel Corp., a condominium developer in Toronto, tries to shift his workers into the jobs that they would enjoy most. It helps with employee retention, morale and productivity.

He points to one employee who loves working on hardware so much, he'll come in at 3 a.m. to tackle a new project.

That's why Maulucci wants to hear what his staffers want from their jobs and for their futures.

4. No.

It takes courage to tell the boss that you don't agree, but it's better for all involved when you say no to suggested projects, timelines, budgets or technologies that just aren't going to work, says Michael F. Williams, executive director of IT for the Immune Tolerance Network of the Diabetes Center at the University of California, San Francisco, and CIO for the Department of Neurology's Epilepsy Phenome/Genome Project.

But saying no to ill-conceived ideas isn't the same as obstructing an entire project. "After you say no, don't make it impossible," Williams says. "You have to provide various alternatives and let me know the pros and cons."

5. Your successes.

No one wants to spend each day hearing only about project setbacks, failed servers and unexpected downtime. Good news is welcome, too. Yet IT workers seem reluctant to promote the positive, Kalia says.

The thought doesn't occur to them, "or maybe they think that what they're doing isn't that special," he explains.

Whatever the cause of such reticence, Kalia says IT pros should change their mind-sets. He wants to hear about accomplishments so he can recognize them and offer pointers to do even better next time.

"But it's not only about learning what you've done so we can apply best practices," he adds. "It's about celebrating success so everyone can share in that."

Five Things You Should Never Tell Your Boss

1. All about the technology and nothing about the business.

Acting like the business is terra incognita is a no-no. "Never tell me you don't know what the business wants, but you'll build it when they decide," says James E. Schinski, a vice president and CIO at Midwest Independent Transmission System Operator in Carmel, Ind.

Joseph J. Tufano, vice president and CIO at St. John's University in New York, agrees, saying IT workers need to tell him how technology can help the organization and its staffers do their jobs better.

"You bring so much more credibility to the discussion when you're presenting technology in the context of business," he says.

2. That there's only one solution.

"People can sometimes develop a fondness for a certain technology or programming language or manufacturer into almost a religion, but it's never the case that one type of solution is the proper one for all situations," says Yuma County's Puff.

"And when you develop an attitude like this, you're viewed as an obstacle or a roadblock," he adds. "People will assume you're just going to like it this way and you're not going to like it any other way."

3. Negative opinions about your colleagues.

It's a simple rule that can get overlooked when your team is struggling with a missed deadline or a failing project, but think before you point a finger, because bosses generally don't want to hear about it -- especially if you haven't tried to work it out on your own.

"I want a team that works together and not one that's political, and if I see it happening, then I think people are trying to score points," says Kalia.

Of course, there are times when you need to discuss personnel issues with your boss. For example, Kalia wants to know from managers when workers are thinking of leaving.

Just be sure the boss really needs to know about the situation; then be discreet and objective.

4. That there's no way.

Strickland's position: Everything is possible.

"It may be impossible to deliver the exact goal, or it may be impossible to deliver the goal in the way it has been outlined, but before you say it is impossible, tell me some of the challenges you may face, and we can have a conversation about overcoming those challenges," he says. "You may be surprised by what you can accomplish if you let go of your biases."

5. A surprise.

CIOs almost universally say they don't like surprises -- particularly unpleasant ones.

Ian S. Patterson, CIO at Scottrade Inc., a St. Louis-based online brokerage firm, says he always prefers to hear news -- good and bad -- directly from his workers. So when someone comes by and starts with "I want to give you a heads up," it really catches his attention.

Moreover, it's a good bet that your boss prefers to hear that news sooner rather than later, says Gregory B. Morrison, CIO at Cox Enterprises Inc., an Atlanta-based media company and provider of automotive services.

"Getting help early could help keep a small problem from turning into a disaster," he says.

Pratt is a Computerworld contributing writer in Waltham, Mass. Contact her at

Has your own experience been different? Let us know in the article comments.

Copyright © 2008 IDG Communications, Inc.

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