Seven Questions You MUST Ask Your Boss

Q. I’ve decided that to build more job security I have to step up my support for my boss. I don’t expect a guarantee, but what can I do besides doing my job well? Terry B.

A. That’s a great first step—and a solid base for anything else you do. There are seven key questions most bosses want you to ask that will help you give them support. They’re not in any priority, so ask each one when you think the time is right:

How can I better help you meet your goals? In a good organization, each person’s goals are aligned with the organization’s to assure that everyone is working as a unified team. This starts with your knowing your boss’s goals, so you can adapt or create action steps to help him or her meet them. So ask. But if you’re serious about providing that support, be prepared to take on extra work.

How can I do an even better job? Before you ask this question, review your performance appraisals for the past two or three years and note the actions recommended to you. You must do this first. (If you haven’t accomplished everything suggested, write action steps to make this happen. Include deadline dates and performance measures—which you can present to your boss as a basis for asking how you can do better.) Get confirmation that the behaviors management wanted you to improve are still relevant.

How can I keep you better informed about what I’m doing? Today bosses rarely have the luxury of supervising only 7-8 people—the number that used to be the normal “span of control.” Today, your boss is probably responsible for 15, 20, 30 or more people. Whatever you do, it can’t involve more work for the boss—like reading a long report you send every week. Some managers like to be briefed verbally—even on the short walk to the cafeteria. Others prefer a few bulleted items they can zero in on if needed. But you must keep your boss informed.

What tough problem are you working on that I can help with? Sometimes managers are reluctant to share upper-level problems with subordinates. Worries about confidentiality, an employee’s ability to respect it, or being accused of favoritism are some of the reasons a boss won’t delegate a major problem to solve. If you ask this question, you have to know in advance how you’ll help him or her sidestep those traps.

May I tell you my plans for my career with this company?
Most supervisors appreciate employees who are looking at the long term with the company, and plan their careers accordingly. But your boss won’t know this—and can’t help you get there— if you don’t speak up. Let your boss know that, while you’re happy in your current position, your long-term plans include X, Y and Z, and you want to identify the logical next steps to put you on the right career path.

Then listen carefully. Once the next step has been identified, ask what you need to do to be considered for that position. Request concrete objectives and get them in writing (at the very least, take good notes and recap the list at the end of your discussion). Next, ask when your boss thinks you might be ready. If he or she is hesitant to give a specific date, talk in general terms (“next quarter” or “next year”) to give yourself a workable framework.

How can I help us build better relationships with other departments?
Getting departments to think less of themselves as independent “silos” and more as interdependent players on a larger team is something management struggles with daily. Ask if you might attend other department meetings to get a feel for their needs. Ask if you can contact co-workers and bosses in other departments to ask how your department can provide better support. (But be prepared; some departments may be shocked into silence at the sudden attention; others may already have a list of things they’d like you to do.)

Can I help you cut the meetings you have to attend by sitting in for you? I remember how discouraged I was on the first week of a new job when I was told there were 18 regular meetings I had to attend each month. Sometimes you can’t substitute for your boss—such as in upper management meetings. But there may be many you can attend, then brief the boss when you return. (You may have to be careful about not arousing jealousy among co-workers, who might see you as trying to get up the ladder as fast as you can—even at their expense.)