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How to Ask Tough Questions at Work

How to Ask Tough Questions at Work

By Caroline M.L. Potter

Sometimes getting what you want or need is as simple as asking. But when it comes to work matters, asking isn't always that simple. More than courage, career strategist Cynthia Shapiro believes that you must first build trust with your boss -- before you make any of these requests. "You cannot ask for a raise, a promotion, a better desk or shift, or sometimes even help, without a solid foundation in place," she says. "The way you build that foundation is by putting your boss's priorities ahead of your own. Finding out what is most important to him or her and embracing those things are paramount to your success."

Asking for a Raise

If you want a raise, you'll likely have to ask for it. But Shapiro advises being mindful of exactly why you're asking. "People will ask for a raise because of something that's happened in their personal life -- wrong," she says. Or they'll ask for a raise because they 'deserve it' -- also wrong. You need to prove you're worth more to the company."

Shapiro, author of Corporate Confidential: 50 Secrets Your Company Doesn't Want You to Know, suggests doing homework before you ask. Build your case by justifying the added expense of an increase in payroll. Take note of your accomplishments, your increased workload, and when you've increased revenues or cut expenses. Make sure your request is within salary parameters for your region and your level of expertise.

"Pick your timing," Shapiro says. "Wait until the company is feeling flush -- when it just got a big new contract or client, or when you just did something wonderful that the company recognized you for."

When you do ask, be direct and stay on your message. "You are asking for a raise because you are worth more to the company, not because you want one or generally feel you deserve one," she says.

Asking for a Promotion

Asking for a promotion is similar to asking for a raise -- but unlike a raise, which you have to ask for, you should rarely ask for a promotion directly. Assuming that you've built trust with your boss (that is, the gatekeeper to your success), he will view you as an ally, according to Shapiro. "Only allies move up," she says. "Make it known to your boss that you may be interested in other opportunities that come up."

And even if you have a lot to do, make it look easy. "No one will recommend you for advancement if it looks like you can't handle the work you currently have," Shapiro explains. Volunteering for new duties can also send a signal that you're ready to move to the next level.

Asking for a Layoff

If you've heeded Shapiro's advice and established a healthy, respectful bond with your boss, you can probably ask for a layoff and get it. However, she says, "This is the only request that does not require a solid foundation with your gatekeeper. If you really hate your job and have a problem with your boss, you can ask for a layoff, and the boss will most likely give it to you just to get rid of you."

If this is the situation you're in, she recommends, "Let your boss know, confidentially, that you've enjoyed working for the company and the department, but due to a variety of circumstances, you would like to be considered for a layoff if one were to occur."

Leave out the real reasons you want to leave, so you can ensure that your exit occurs on good terms. If you know layoffs are looming, "you should always let the organization know that you'd volunteer," she says. "It will help them make the right decision and may save someone's job." 

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